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UNITED STATES COURTOF APPEAL S F O R T H E S E C O N D C IR C U IT August Term, 2016 (Argued: Octobe r 6, 2016 De cided: May 31, 2017)

Docket No. 15-1815

UNITED STATES OF AMERICA, Appellee,

— v. — ROSS WILLIAM ULBRI CHT, a/k/ a DREAD PIRAT E ROBERTS, a/k/a S ILK R OAD, a/k/a S EALED DE FENDAN T 1, a/k/a D PR, Defendant-Appellant.

Before : N E W M A N , L Y N C H , and D R O N E Y, Circuit Judges. Ross Will iam Ul

bricht appeals from a judgment of convicti on and sen tence to li fe imprisonment entered in the Un ited States District Court for the S outhern District of New York (Katherine B. For rest, J. ), for drug trafficking and other crimes associated with his creation and operation of an online marketplace known as Silk Road. He argues that (1) the district court err ed in denying his moti on to suppre ss evidence obtained in viol ation of the Fourth Amendment; (2) the district court comm itt ed seve ral err ors that depr ived him of hi s right to afair trial, and i ncorr ectly denied his moti on for a ne w trial; and (3) hi s life

sentenc e is both proce durally and substantivelyunreas onable. For the r easons set forth be low, the judgm ent of the district court is AFFI RMED in allresp ects.

J O S H U A L. D R A T E L , Joshua L. Dr atel, P.C., New York, NY, for defendan t-appellant Ross Wil li am Ulbricht. E U N Y O U N G C H O I , Assistant United States Attorney (Michael D. Ne ff, Tim othy T. Howard, Adam S. Hickey, Assistant United States Attorneys, on the brief ), forPreet Bhar ara, United States Attorney for the SouthernDistrict of New York, New Yor k, NY. Tamar Todd, Jolene Forman, Drug Policy Al li ance, Oakland, CA, for amici curiaeDrug Policy Al li ance, Law Enforce ment Against Prohibition, JustLeadersh ipUSA, and Nancy Gertne r. Joel B. Rudin, Law Offi ces of Joe l B. Rudin, P.C., Ne w York, NY; StevenR. Morrison, Univers ity of North Dakota School of Law, Grand Forks, N D, for amicus curiae National Associati on of Cr iminal Defen se Lawyer s.

G E R A R D E. L Y N C H , Circuit Judge : Defe ndant Ross Will iam Ul bricht appeals from a judgment of convicti on and sente nce to life im prisonment enter ed in the United States District Court for the Souther n District of New York (Kather ine B. Forre st, J. ). A jury convicted Ulbricht of drug trafficking and other crimes associated with his creation and 2operation of Silk Road, an onli ne marketplace whose users primaril y purchase d

and sold il legal goods and services. He challenges seve ral aspects of his conviction and sentence, ar guing that (1) the district court erre d in denying his moti on to suppre ss evidence asser tedly obtained in vi olati on of the Fourth Amendment; (2) the district court comm itt ed numerous e rror s that deprived him of his right to a fair trial, and incorre ctly denied his motion for a new trial; and (3) his li fe sen tence is both pr ocedurally and substantively unreasonable. Be cause we identify no rever sible err or, we AFFIRM Ulbricht’s convicti on and sen tence in allresp ects. BACKGROUND In February 2015, a jury con victed Ross Wil li am Ulbricht on seven counts arising from his creation and oper ation of Sil k Road under the use rname Dr ead Pirate Roberts (“D PR”). Silk Road was a m assive, anonymous criminal 1

The seve n crimes of conviction were: (1) distribution and aidi ng and abetting 1 distributi on of narcotics, 21 U.S.C . § 812, § 841(a)(1), § 841(b)(1)(A) and 18 U.S .C. § 2; (2) using the Internet to distribute narcotics, 21 U.S.C. § 812, § 841( h) and § 841(b)(1)(A); (3) cons piracy to distribute narcotics, 21 U.S.C. § 846; (4) en gaging in a continuing criminalenterp rise, 21 U.S.C . § 848(a); (5) conspiring to obtain unauthorized access to a computer for purpos es of commercial advantage and private financialgain and in furtherance ofother cr iminal and tortious acts, 18 U.S.C. § 1030(a)(2) and § 1030(b); (6) cons piring to traffic in fraudulent identifi cation documents, 18 U.S.C. § 1028(f); and (7) con spiring to lau nder money, 18 U.S.C. § 1956(h ). 3marketplace that operated using the Tor N etwork, which ren ders Inter net traffic

through the Tor b rowser extre mely di fficul t to trace. Silk Road users principally 2 bought and sold drugs, false identificati on documents, and computer hacking software. Tran sactions on Silk Road exclusivel y used Bitcoins, an anonymous but traceable digitalcurre ncy. The site also contained a private message syste m, 3 which all owed user s to send mess ages to each othe r (simil ar to communi cating via emai l), a publi c forum to discuss topics related to SilkRoad, and a “wiki,” which is li ke an encyclopedia that users could access to rece ive advice about using the site. Silk R oad customers and ve ndors could also access a support

Tor is short for the “The Onion Router.” The Tor Network is “a spe cial network 2 on the Interne t designed to make it practi callyimpossible to physical ly l ocate the computers hosting or acce ssing websites on the network.” App’x 53. The Tor Network can b e acces sed via the Tor br owser us ing software that anyone may obtain for fre e on the Intern et. Bitcoi ns allow vendors and customers to mai ntain their anonymity in the same 3 way that cash does, by tr ansfer ring Bitcoi ns be tween anonymous Bitcoin accounts, which do not contain any identifying information about the user of each account. The cur rency is “trace able” in that the transaction history of each indivi dual Bi tcoin i s logged in what i s called the blockchain. The blockchain preve nts a per son from spe nding the same Bitcoin twice, all owing Bit coin to operate s imi larly to a t raditionalform of curre ncy. Bitcoin i s also a completely decentr ali zed curr ency, oper ating free of nation states or ce ntral banks; anyone who downloads the Bitcoin software becomes p art of the Bitcoin network. The blockchain is stored on that network, and the blockchain autom atical ly “selfupdates” when a Bitcoin transaction takes place. Tr. 160. 4section of the webs ite to seek help from the marketplace’s administrators when

an issue aros e. According to the govern ment, between 2011 an d 2013, thousands of vendors used Silk Road to sellapproximately $183 mi ll ion worth of ill egal drugs, as well as other goods and s ervices. Ulbr icht, acting as DPR, ear ned mill ions of dollars in profits from the comm issions collected by Silk R oad on purchas es. In October 2013, the govern ment arres ted Ulbricht, seized the Silk Road server s, and shut down the site. I. Silk Road Investigation After Ulbricht create d Silk Road in 2011, the site attracted the interes t of at least two separate divisions of the Dep artment of Justice: the United States 4 Attorney’s Offices for the District of Maryland and for the S outhern D istrict of New York. Thr oughout the investigati ons, law enforce ment agents knew that the pers on using Dre ad Pirate Roberts as h is or her Silk Road username had cre ated and managed the site, but they did not know DPR’s actual i dentity. In 2012 and 2013, agents from both offices investigated several indivi duals who the The govern ment first learned of Silk Road and began investigating i t in 2011 4 after international packages containing drugs were intercepted at Ch icago’s O’Hare airport. 5government sus pected wer e oper ating Sil k Road as DPR. Those individual s

included Ulbricht, Anand Athavale, and Mark Karpeles. Ultimat ely, the New York office identified Ulbricht as DPR, but the Maryland office had investigated and later abandone d the theory that either Athavale or Karpeles might have been Dre ad Pirate Roberts. Two aspects of the pr e-arr est investigati on into Ulbricht are particularly relevant to this appeal: (1) the pen/ trap orde rs that the gover nment obtained to monitor I nterne t Protocol (“I P”) address traffic to and from various devices associated with Ulbricht; and (2) the cor rupt behavior of two Baltim ore age nts who worked on the Silk Road investigation. A. The Pen/Trap Orders In September 2013, after Ulbricht became a pr imary suspect in the DPR investigati on, the gover nment obtained five “pen/ trap” orde rs. See18 U.S.C. §§ 3121-27 (“Pen/Trap Act”). The order s authorized law enforce ment agents to collect I P address data for Internet traffic to and from Ulbricht’s home wireless router and o ther devices that regularly connected to Ulbricht’s home router. According to the govern ment’s applicati ons for the pen r egister and trap an d trace device, “[e ]very de vice on the Internet is identified by a unique number”

6called an IPaddres s. S.A. 73. “This number is used to route information between 5 devices, for e xample, between two computers.” Id. at 73-74. In other words, an “IP address is analogous to a telephone number ” because “it i ndicates the online identity of the communicating device without revealing the communi cation’s content.” Id. at 74. Ulbricht does not dispute that description of how IP addresses function. The pen/ trap orde rs thus did not permit the government to acces s the content of Ulbricht’s communi cations, nor did the governmen t “seek to obtain[] the contents of an y communi cations.” Id. at 75. According to Ulbricht, the government’s use of his home Internet routing data viol ated the Fourth Amendment because it helped the gove rnment match Ulbricht’s online acti vity with DPR’s use of Silk Road. Ulbricht argues that he has a constitutionalprivacy interest in IP address traffic to and from his home and that the gover nment obtained the pen/ trap orde rs without a warrant, which would have required probab le cause. B. Corrupt Agents Force and B ridges One of the many other tactics that the gover nment used to expo se D PR’s S.A. re fers to the joint sealed appendix in this case. Portions of the sealed 5 appendix quoted in this opi nion are to that extent unse aled. 7identity was to find low-l evel Silk Road adm inistrators who helped D PR

maint ain the site, obtain their cooperation, take over the ir Silk R oad usern ames, and chat with DPR under those identities. The true owner s of the administrator accounts would assist i n the investigation by helping the gover nment chat with DPR and access various aspects of the site. Government agents would also create their own new use rnames and p ose as dr ug dealers or buyers to purchase or sell narcotics and occasionally contact DPR di rectly. One of the gove rnment’s principal tri al wi tnesse s, Spe cial Ag ent Jare d Der -Yeghiayan, used the for mer technique to chat wi th DPR under the n ame Cirrus. C irrus had be en a member of the Silk Road support staff befor e the gover nment took over his account, and Der -Yeghiayan frequently used Silk Road’s messaging system to comm unicate with DPR and other admini strators as Cirrus. C irrus also gave the gover nment access to the s taff chat, a separate p rogram allowing DPR to communi cate only with hi s employees. Two undercover agents involved in the Silk R oad investigati on are of particular im port to this appeal: Secre t Service S pecial Agent Shaun Bridges and Drug Enfor cement Admini stration (“DEA”) Spe cial Ag ent Car l Force, both of whom were ass igned to the Balti more investigati on. Both Force an d Bridges used

8their underco ver acce ss to exp loit the site for their own b enefit in various ways, and they even tuall y pleaded guil ty to crim inal charges in connection with their work on the S il k Road investigat ion. 6 For ex ample, Force and Bridges took over an admini strator account belonging to Curtis Green, who wor ked for S il k Road under the n ame Flush. According to the criminalcomplai nt against Force and Bridges, in Januar y 2013, Bridges used the Flush username to change other use rs’ pass words, empty their Bitcoi n wallets, and keep $350,000 in Bitcoins in offshore b ank accounts, all whi le 7 attempti ng to hide his activi ty through a ser ies of transactions. Specificall y, the 8

Both Force and Br idges pleaded guilty to money laundering and obstruction of 6 justice; Force also pleaded guil ty to extortion. Force was se ntenced to 78 months in prison, and Bridges r eceived a 71-month sente nce. According to the criminalcomplaint against Ulbricht, a Bitcoin wal let is a 7 storage method for Bitcoi ns. The wallet is associated wi th a Bitcoi n addres s, which is “analogous to the account number for a bank acc ount, whil e the ‘wallet’ is analogous to a bank safe wher e the money in the account is physically stored.” App’x 59. Use rs can tr ansact in Bitcoi n by trans ferr ing Bit coins from one “Bitcoin addres s to the Bitcoin address of anothe r user , over the Inter net.” Id. Ulbricht does not dispute that definiti on. As descr ibed below, the gover nment disclosed shortly befor e trial that Force 8 was under inves tigat ion for Silk Road corruption, but said nothi ng about Bridges. Specificall y, the pre trial di sclosure noted that For ce was under investigati on for using the Flush account to steal $350,000, but the criminal com plaint ag ainst the agents alleges that Bridges commit ted that particul ar theft. According to the government, bo th Force and Br idges had access to the Flush account, which 9complai nt against Force and Bridges alleges that Bridges “act[e d] as an

admini strator to re set pins and pass words on var ious Sil k Road vendors ’ accounts,” then ex changed the Bitcoins for U.S . dollars using the Mt. G ox exchan ger. Supp. App’x 180. S hortly after he committed the January 2013 thefts,

9 Bridges asked For ce to chat with DPR as Nob, Force ’s authorized under cover

usern ame, to get advice about how to l iquidate Bi tcoins. He also sought Force’s help in convincing Curtis Green (former ly Fl ush) to help him transfer Bitcoins to other accounts, an d he ultim ately tried to blam e Greenfor the thef t. With the government’s appr oval, Force also posed as a drug dealer and communi cated with DPR as Nob. As par t of his offici al undercover work as Nob , Force agr eed to se llfraudulent identifi cation documents to DPR for $40,000 in Bitcoi ns. According to the cr iminal compl aint agai nst the agents, For ce kept the Bitcoi ns re ceived by his Nob account in connection with that transaction for his pers onal use. On another occasion, again as part of his authorized under cover work, Force advised DPR that he had acces s to informati on about Silk Road from an invented corr upt government employee. DPR paid Force $50,000 in Bitcoins

might explain their init ialsuspicion that Force stole the funds. Mt. Gox was a prominent Bit coin exchange r owned b y Mark Karpeles. 9 10for purpo rted inside law enforcemen t informati on; Force allegedly purloined that

payment as well. Moreover, outside his authorized under cover wor k, Force operated an other account under the name Fren ch Maid, through which he again offere d to sell DPR i nformation about the government’s S il k Road investigation. Acting as French Maid, Force r eceived about $100,000 in Bitcoi ns that he kept for his perso nal use. Force cr eated yet another unauthorized Silk Road account, under the name DeathFr omAbove, which was unknown to law enforce ment untilthe defen se identifi ed it during trial . Force use d the De athFromAbove account to try to extort money from DPR. For ex ample, i n one suchchat that took place on April 16, 2013, DeathFr omAbove told DPR that he knew that DPR’s true identity was Anand Athavale. DeathFr omAbove demanded a payment of $250,000 in exchan ge for which D eathFromAbove would remain silent about DPR’s identity. There is no e vidence that DPR made the requested payment to

10 DeathFr omAbove; indeed, D PR shrugged off the attempted blackmailas

DeathFr omAbove also refe rre d to the $250,000 payment he demanded as 10 “puniti ve damages.” App’x 875. In the gove rnment’s view, the “punitive damages” remark r efer enced the murder of a S il k Road admi nistrator that Ulbricht ordere d and paid for (but that was never carried out). That and other kil li ngs that DPR commi ssioned wil l be descr ibed in more detail below. 11“bogus.”App’x 710.

As willbe ex plained in m ore de tailbelow, the district court prevente d Ulbricht from introduci ng evidence at trial related to Force’s cor ruption because doing so would have expose d the ongoing grand jury investigation i nto Force’s conduct. The district court al so denied Ulbricht discovery r elated to the investigati on and ex cluded certain hears ay statements that arguably revealed Force’s c orruption. Ulbricht contends on ap peal that the district cou rt’s various rulings concerning evidence related to Force de prived him of a fair trial

. Additi onally, Ulbricht did not learn of Bridges’s cor rupt conduct untilafter trial when the cr iminal compl aint agai nst both agents was unsealed. Thus, in his moti on for a ne w trial, he argued that the belated disclosure violated his due proces s rights under Brady v. Maryland, 373 U.S. 83 (1963). Ulbricht contends on appeal that the district court i ncorr ectly denied that mot ion. II. Ulbricht’s Arrest Ulbricht was arres ted in a San Francisco public librar y on October 1, 2013, after the gove rnment had amassed s ignifi cant evidence identifying himas Dr ead Pirate Roberts. The ar rest was s uccessfully orchestr ated to catch Ulbricht in the act of admi nistering Silk Road as DPR. Federal agents obse rved Ulbricht enter

12the public librar y, and a few minutes later Dread Pirate Roberts came online in

the Silk Road staff chat. Der-Ye ghiayan, under the unde rcover admini strator

usern ame Cirrus, initiat ed a chat with DPR, asking himto go to a specific pl ace on the Silk Road site to address some flagged message s from user s. De rYeghiayan reaso ned that this would “force [Ulbricht] to log in under . . . h is Dre ad Pirate Roberts account” in the Silk Road marketplace, as well as i n the staff chat software. Tr. 331-32. Once D er-Ye ghiayan knew that DPR had logged onto the flagged message page in the marketplace, he signaled another agent to effect the ar rest. Ulbricht

was arre sted, and incident to that arrest agen ts seized his laptop. The same chat that Der-Ye ghiayan had initiated wi th Dre ad Pirate Roberts a few minutes ear li er was open onUlbricht’s scree n. Ulbricht also visi ted the flagged post in the marketplace that Der-Ye ghiayan (as Cirrus) h ad asked D PR to l ook at during their chat. While he was chatting wi th Cirrus, more over, Ulbricht had acce ssed Silk Road by using the “Master mind” page. That page was avail able only to Dre ad Pirate Roberts. A great deal of the evidence against Ulbricht cam e from the gover nment’s

searc h of his laptop and his home after the ar rest. Onthe day of Ulbricht’s arre st,

13the govern ment obtained a warrant to seize Ulbricht’s laptop and sear ch it for a

wide variety of informati on related to Silk Road and informati on that would identify Ulbricht as Dr ead Pirate Roberts. Ulbr icht moved to suppress the large quanti ty of evidence obtained fr om his l aptop, challenging the constitu tional ity of that search war rant. Ulbricht argues on ap peal that the district cou rt err ed in denying his moti on to suppre ss. More details concerning the sear ch warran t wil l be des cribed in context b elow. III. The Trial Ulbricht’s trial l asted appro ximatel y three we eks, fro m January 13 through Febr uary 4, 2015. Judge Forr est handled the complex and con tentious trialwith commendable patience and skill . Although Ulbricht does n ot chall enge the sufficiency of the evidence to suppor t the jury’s verdict on any of the counts of conviction, we summ arize the evidence pres ented at trial as context for the issue s raised on appe al. A. The Government’s Case The govern ment prese nted over whelmi ng evidence that Ulbricht created Silk Road in 2011 and continued to operate the site throughout its l ifetim e by maint aining i ts computer infrastructure, interac ting wi th vendors , crafting

14polici es for site users, de ciding whatproducts would be available for sale on the

site, and managing a smal l staff of administrators and sof tware enginee rs. Defe nse couns el conceded in his open ing statement that Ulbricht did in fact create S il k Road. According to Ulbricht’s own words in a 2009 email, Ulbricht originall y conceived of Silk Road as “an online storefr ont that couldn’t be trace d back to [him] . . . where [his] customers co uld buy [his] products” and pay for them “anonymously and securely.” Tr. 991. From 2009 through 2011, Ulbricht worke d to get the site up and running, relying on computer progr amming assistance from others, including his friend Richard Bates. According to one of the journal entries discover ed on his laptop, in 2010 Ulbricht began to grow hallucinogenic mushrooms to sell on the site “for cheap to get pe ople interested.” Tr. 899. As the site began to garne r significant i nteres t in 2011, Ulbricht wrote in his journal that he was “cr eating a year of pros perity and power b eyond what I have ever expe rienced b efore . Silk Road i s going to become a phen omenon and at least one pers on willtell m e about it, unknowing that I was it s cre ator.” Tr. 899-900.

1. Evidence Linking Ulbricht t o Dre ad Pirate Roberts Around January 2012, the Silk Road user who repr esen ted himself as the

15lead admi nistrator of the site adopted the use rname Dr ead Pirate Roberts. The 11 name allu des to the pse udonym of a pirate in the popular novel and fil m The Princess Bridethat is periodical ly passed on fr om one indivi dual to another. In 12 order to assure use rs that posts pur porting to be authored b y DPR were indee d his own, DPR authenticated his posts using an electronic signature known as a PGPkey. Silk Road users had acces s to a public PG P key, and DPR had a

13 private PGP k ey that he alone could use to sign his Silk R oad posts. WhenDPR signed a post using his private key, Silk Road users could run the code in the public key, and if the post was s igned with the correct pr ivate key the user would

rece ive a message that the authentication was successful. The govern ment

recove red D PR’s private PGPkey on Ulbricht’s laptop. Im portantly, the public PGPkey did not change during the site’s life span, meaning that DPR used the same private key to sign his posts throughout the time that he admi nistered S il k Road. The timing of this change cor resp onds to a January 15, 2012 Tor ch at between a 11 user n amed “vj” and Ulbricht, i n which vj advised Ulbricht to change his usern ame from Admi n to Dre ad Pirate Roberts. SeeWil li am Gol dman, The Princess Bride : S. Morgenstern’s Classic Tale of True 12 Love and High Adventure(1973); The Princess Bride(20th Century Fox 1987). PGPstands for “Pr etty Good Pri vacy.” 13 16Additi onal evidence suppor ted the conclusion that Ulbricht was Dread

Pirate Roberts. For example, the instructions that DPR provided to Cirrus (the account that Der-Ye ghiayan lat er use d for under cover wor k) for how to acces s the staff chat and contact DPR directly were found in a file on Ulbricht’s laptop. The govern ment also discovered the following evidence, covering the en tire period during which DPR managed the Silk Road sit e, on Ulbricht’s computer: thousands of pages of chat logs with Silk Road empl oyees; de tail ed journal entries de scribing Ulbricht’s owners hip of the site; a li st that tracked Ulbricht’s tasks and ideas re lated to Sil k Road; a copy of Silk Road’s database; and spre adshee ts cataloguing both the se rver s that hosted Silk Road and expen ses and profits associated with the site. The government se ized approximately $18 mil li on worth of Bitcoins from the wallet on Ulbricht’s laptop and analyzed their transaction history (through blockchain rec ords) to deter mine that about 89% of the Bitcoins on Ulbricht’s comput er came fr om Sil k Road serve rs located in Iceland. A searc h of Ulbricht’s home yielded additi onal evidence linki ng him wi th the site. That evidence included two USB hard drives with vers ions of documents related to Silk Road that were also stor ed on Ulbricht’s laptop. There we re also

17handwritten notes cr umpled i n Ulbricht’s bedr oom trash can about ideas for

improving Sil k Road’s vendor r ating system—an ini tiat ive that Dread Pirate Roberts h ad just revealed through a pos t in a di scussion forum on the site. The govern ment also int roduced other circumstanti al evidence connecting Ulbricht to DPR’s activ ity on Sil k Road, such as evidence matching Ulbricht’s actual t ravel history with DPR’s online discussion of his travel pl ans. As one

concre te example, the gover nment discovered a Tor Chat log on Ulbricht’s 14 laptop mem oriali zing DPR’s chat with a user named H7. On Octobe r 30, 2011, DPR told H7 that he woul d be trave li ng soon. On Ulbr icht’s Gm ailaccount, which uses an email address that incorpor ates his full nam e, the gover nment discovered a tr avel itinerar y from Che apAir that indi cated that Ulbricht woul d be trave li ng on Novembe r 15, 2011. The govern ment introduced sever al additional exampl es of D PR discussing travel plans that m atched up with travel discl osed in Ulbricht’s email and social medi a activi ty. At one point, for example, Ulbricht uploaded photos to his Facebook account in an album entitl ed “Thailand, February 2012.” D PR

Tor Chat is a progr am that al lows “comm unicati on betwee n people on the Tor 14 network.” Tr. 889. 18discussed going to Thail and in a Tor chat on January 27, 2012, indicating that he

was in “Thail and now,” attracted by the “allure of a warm be ach.” Tr. 1300. He also mentioned in a January 26 chat with a user named “vj,” which stood for Variety Jones, that he was in Thail and to expe rience the “beache s and jungles.” Id. at 1298. One of the pho tos in the Thail and Facebook album depicted Ulbricht “in front of what appears to be jungles and beac hes,” b oth of which were refe rence d in DPR’s chats from late January. Id. at 1301.

2. Murders Commissioned by Dre ad Pirate Roberts The govern ment also presen ted evidence that DPR commissioned the murders of five pe ople to protect Silk Road’s anonymi ty, although there is no evidence that any of the murder s actuall y occurre d. In March 2013, a Silk Road 15 Ulbricht was not charged in this case with crimes based o n order ing these 15 kil li ngs, although evidence re lati ng to the murders was introduced at trialas actions taken in furtherance of the charge d conspiracies and cr iminal enterpr ise. The kill ings were r efer enced again in connection with Ulbricht’s sentencing. He faces ope n attempted murder-for-h ire charge s in the District of Maryland, however

. United States v. Ulbricht, No. 13-0222-CC B (D. Md.). That indictm ent charges Ulbricht wit

h the attempted murder of C urtis Green (Flush). According to the criminalcomplai nt against the corrupt officers , after Bridges, us ing Flu sh’s account, stole $350,000 in Bi tcoin i n January 2013, D PR recruited Nob (For ce) to kil l Fl ush as punishment for the theft. DPR paid Nob $80,000 to carr y out the murder, which Force faked to make Ulbricht believe that the task was complete. Presumably because the govern ment removed from its trial evi dence an ything that the corrupted age nt Force may have touched, it did not presen t evidence of 19vendor wh ose use rname was FriendlyCh emist threatened to re lease “thousands

of usern ames, ordr [ sic ] amounts, [and] address es” of S il k Road customers and vendors if DPR did not ensure that FriendlyChemist received money fr om another pe rson, Lucydr op. Tr. 1806. Releasing the information woul d have destroye d the affected use rs’ anon ymi ty, undermining the security of the site. In a later chat with another pers on, RealLucyDrop, D PR wrote that it would be “terrible” if the per sonal informati on were to be re leased, and thus he neede d FriendlyChemist’s “real world identity so Ican threatenhim wi th viol ence if he were to r elease any names .” Id. at 1811. The episode e scalated from there. D PR connected with Redandwhite, who was FriendlyChemist’s supplier, and wrote that “FriendlyChe mist i s a liabil ity and I wouldn’t

mind i f he was e xecuted.” Id. at 1822. After negotiating the logi stical detai ls of the murder, Ulbricht agree d to pay Redandwhite $150,000 in Bitcoi ns to killFriendlyChemist. DPR paid Redandwhite, who lat er conf irmed that he had re ceived the payment and carr ied out the murder, and se nt what appeare d to be a photo of the de ad victi m to DPR. DPR replied that he had

the Flush murder-for -hire agre ement, nor did it rely on that mu rder at sentenc ing. 20“rece ived the picture and deleted it,” and thanked Redandwhite for his “swift

action.” Id. at 1892. Around the same time, Ulbricht recorded in a file on his laptop that he “[g]ot word that the blackmai ler was ex ecuted.” Id. at 1887. The government was n ot able to develop any evidence linking these conver sations to an actual m urder . A reason able jury could easilyconclude, however , that the evidence de monstrated that Ulbricht ordere d and paid for the kill ing, and that he believed that it had occurred. Later, DPR orde red four other murder s through Redandwh ite. Dread Pirate Roberts identified another Silk Road user, Tony76, who kne w FriendlyChemist and might compromise the site’s anonymity. Aft er so me negotiati ons, DPR agre ed to pay Redandwhite $500,000 in Bitcoins to killTony76 and three of his associates. DPR then s ent the payment to Redandwhite. On April 6, 2013, Ulbricht wrote in a fil e on his laptop that he “[g]ave angels go ahe ad to find tony76.” Tr. 1900. Two days lat er, Ulbricht re corded that he “[s]ent payment to angels for hit on tony76 and his three associates.” Id. One of the gove rnment’s expe rt witnesses was able to li nk the payments for all five murders to Bitcoin wall ets located on Ulbricht’s laptop. Agai n, while the evidence demonstrate s that Ulbricht ordere d and paid substantial sum s for the murde rs, ther e is no evidence

21that the kil li ngs actuall y took place; the government theor ized that Redandwhite

had tricked Ulbricht into thinking that he actuall y commi tted the murders, b ut that in fact he had not. B. The Defense Case As noted above , Ulbricht conceded at trial that he had created S il k Road, and he was caught r ed-hande d operating the site at the end of the investigati on. His principal defense str ategy at trial —more of an effo rt at mi tigat ion than outright denialof his guil t of the conspiracy and othe r char ges in the indictment—was to admi t his role at the beginning and end of the s ite’s operation, but to contend that he so ld Sil k Road to someone else in 2011 and abandone d his role as its admi nistrator, only to be lured back b y the success or DPR near the end of its operation to take the blame for ope rating the site. The defens e attempted on sever al occasions to im plicate as alternative suspe cts Karpeles and Athavale, both of whom the gover nment had investigated for a possible conne ction to Sil k Road but lat er ab andoned as c andidates for DPR’s real-world identity. As part of his alt ernative-per petrator de fense , Ulbricht theorized that the per son or p erso ns who ope rated as the tr ue Dr ead Pirate Roberts dur ing the purported interim period planted incrimi nating evidence on

22his laptop i n order to frame him. For the most part, the defens e advanced this

theory thro ugh cross- examination of government witnesses. Ulbricht did not testify at tri al. One point in the testimony of Ri chard Bates e xemplifi es the de fense ’s approach an d the govern ment’s res ponse. Bates , Ulbricht’s friend who assisted with com puter progr amming issues whenUlbricht launched Silk R oad, testified for the gove rnment. According to Bates, Ulbricht told himin November 2011 that he had sold Silk Road to someone else, a claim that Bates believed at the time to be true. Mor eover , in a February 2013 Google chat betwee n Bates and Ulbricht, Ulbricht wrote that he was “[g]lad” that Sil k Road was “not [his] problem anymore.” Tr. 1140-41. Bates under stood that to mean that Ulbricht no longer 16 worked on the site. To mi tigate any damage from Bates’s tes tim ony, the gover nment introduced a Dece mber 9, 2011 Tor ch at between Ulbr icht and vj. I n that chat, vj asked Ulbricht whether anyone else knew about his involvement i n Silk Road.

There ar e two versions ofthe trial transcript for January 22, 2015 on the district 16 court docket. The page citations here refe r to the ver sion of the transcr ipt m arked “corre cted,” which is li sted on the district court docket as Do cument No. 208 (14- cr-68). 23Ulbricht responde d: “[U]nfortunately yes. Ther e are two, but they think Isold the

site and got out and they are quit e convinced of it.” Tr. 1191. He furthe r wrote that those two people thought he sold the site “about a month ago,” id. , which roughly corre sponds to the N ovember 2011 c onvers ation between Bates an d Ulbricht. Signifi cantly, i t was shortly after this conver sation that vj suggested that Ulbricht change his online identity to DPR. In vi ew of the fictional character it refe rence d, the govern ment contended that the online moniker DPR was deliberately adopted to support the cove r story that the lead administrator of Silk Road changed over tim e. Thus, although the government elicit ed testimony that Ulbricht told Bates that he sold the site in 2011, it also prese nted evidence that Ulbricht had lied to Bates about that sale and continued to operate the site in secret.

1. Cros s-Examination of G overnment Witnesse s Ulbricht’s defens e depe nded he avily on cross -examination of government witnesses, much of which was designed to supp ort the argument that either Karpeles or Athavale was the r eal DPR, or that mul tipl e people ope rated as Dre ad Pirate Roberts during Silk Road’s li fe span. The district court l imi ted his

cross -examination i n two ways that Ulbricht chall enges on appeal. First, the

24district court prevented Ulbricht from ex ploring several spe cific t opics with DerYeghiayan, the govern ment’s first witness, through whom it i ntroduced much of its evidence. Those topics included, inter alia, Der -Yeghiayan’s prior sus picions that Karpeles was DPR. Sec ond, the district court li mit ed Ulbricht’s ability to

cross examine FBI computer scientist Thom as Kiernan, who testified about evidence that he discover ed on Ulbricht’s laptop, concern ing several spe cific technical i ssues r elated to software on Ulbricht’s computer. More details about those attempted cross -examinations wil l be discussed in context b elow.

2. Hears ay Statements Ulbricht also att empted to introduce two hearsay s tatements in his defense, both of which the district court excluded as inadmissibl e. Those h earsay statements comprise: (1) chats b etween D PR and DeathFromAbove (Force)

concer ning Force’s attempt to extort money from DPR in exch ange for informati on about the gover nment’s investigati on of Silk Road; and (2) the government’s letter de scribing a statement by Andre w Jones, a site administrator,

concer ning one particular convers ation that he had with DPR. The contents o f those he arsay statements and othe r re levant facts wil l be discussed in more detail below.

253. Defe nse Ex pert Witnesse s

Long after the tr ialbegan on J anuary 13, 2015, and sho rtly before the government r ested on Fe bruary 2 an d the defen se re sted on Feb ruary 3, Ulbricht disclosed to the government his intent to call two expe rt witnesses: D r. Steve n Bellovi n and Andre as Antonopoulos. The Antonopoulos disclosure indicated 17 that he would testify on several subjects re levant to Sil k Road, inclu ding “the origins of Bitcoin,” “the various purpos es and use s of Bitcoin,” “the mechanics of Bitcoi n transactions,” “the value of Bitcoin over time since it s inception,” and “the concep ts of Bitcoi n speculating and Bitcoin mini ng,” among other things. App’x 349. The Be ll ovin discl osure followed a simi lar pattern, indicati ng that he would testi fy about “[g]ener al principl es of interne t security and vulnerabilities,” the “import of some li nes of PHP code pr ovided to defense counsel in discovery,” and “[g]e neral principles of public-key cryptography,” among other topics. Id. at 360. Neither disclosure summarized the opinions that the expe rts would offer on those s ubjects, nor did either identify the base s for the e xper ts’ opinions.

Ulbricht noticed his i ntent to callAntonopoulos on January 26 and Be ll ovin on 17 January 30, 2015. 26On January 29 and 31, the government moved to pre clude the testimony of

both proffe red e xper ts. The govern ment argued that the exp ert notices wer e untim ely and did not contai n the information required by Rule 16 of the Federal Rules of CriminalProcedure , including a summary of the opinions that the expe rts would offer on the stand. On Febr uary 1—three days befor e the en d of 18 the trial—the district

court granted the gove rnment’s motions and precluded both exp erts fr om testifying, concluding that the defe ndant’s notices wer e late and that the disclosures wer e subs tantivel y inadequat e under Rule 16. Ulbricht claim s that the district court erred in pr ecluding hi s exp erts fr om testifying. In sum, the defense case was limi ted to cross-e xamining government witnesses, b riefly call ing four character witnesses, having a defe nse investigator authenticate a task li st on Ulbricht’s computer, and re ading a few of DPR’s posts into the record. Ulbr icht contends, however , that his defense was hamstrung by the rulings describe d above.

The govern ment also argued gener all y that some of the topics identifi ed in the 18 disclosures wer e not re levant to Ulbricht’s case or did not require expe rt testimony. 27C. The Verdict and Post-Trial Motion

After deliberating for ab out three and a half hours , the jury return ed a guil ty verdict on allsevencounts in the Indictm ent. As des cribed in more detail below, Ulbricht then moved for a ne w trial u nder Rule 33, Fed. R. C rim. P. The district court denied the moti on, and Ulbricht argues h ere that it err ed in doing

so. IV. Sentencing The United States Probation Office pre pared the Pre-Se ntence Inves tigat ion Report (“PSR”) in March 2015. It describe d the offens e conduct in detailand discussed the five murder s that Ulbricht all egedly hired Redandwhite to commi t. Over Ulbr icht’s objection, the PSR also di scussed s ix drug-related

19 deaths that the gover nment contended, an d the district court found, were connected with Silk Road. Circumstanti al evidence linked each of those fataliti es with varying degrees of ce rtainty to the decedent’s pur chase of dr ugs on Silk Road. For example, one us er died fr om an overdose of hero in combined with other dr ugs. The dece ased individualwas found with a needle and a bag of

The PSR did not refer to the additi onal murder of “Flush” that DPR all egedly 19 paid Force, under his undercove r identity Nob, to commi t. See supra note 15. 28heroin, as we llas a torn-ope n delivery package. Ope n on his computer was a Silk

Road chat in which a vendor descr ibed the package of h eroin that was due to arrive that day, includi ng a tracking number that matched the opene d package. Two other individu als whose deaths the PSR describe d were S il k Road customers who purc hased dr ugs on the site shor tly before their de aths. A fourth pers on died after ingesting a synthetic drug originall y purchase d on Silk Road that he obtained through an intermediary de aler, and a fifth died after leaping from a balcony while high on a psychedelic drug that he bought from the site. A sixth pers on died of pneumonia after placing over thirty order s for he roin and other dr ugs on Silk Road; the autopsy report theor ized that his drug use may have “blunted the dec eased’s perce ption of the sever ity of hi s illness,” thus contributing to hi s pre mature death. PSR ¶ 83. In arguing that the district court should consider the s ix deaths, the gover nment explained that they “ill ustrate the obvious: that drugs can cause s erious harm, including death.” App’x 902. In the first of sever al sentencing submissions, Ulbricht urged the district court not to consider the s ix drug-related deaths an d to strike them from the PSR. In support of that argument, Ulbricht clai med that Sil k Road had harm-reducing effects, meaning that it m ade drug use les s danger ous. Specifically, Ulbricht

29employed Dr. Fer nando Caude vil la (username Doc tor X), a physician who

provided drug-use advice to the site’s customers. Caude vil la spent up to two or three h ours a day on S il k Road discussion fora and sen t over 450 message s providing gui dance about ill egal drug dosage and administration, as wellas informati on about the har ms associated with certain drugs. Caudevilla al so provided weekly re ports to DPR conce rning the advice he gave to the site’s users

. Ulbricht further claimed that Sil k Road all owed for b etter drug quality control because vendors were s ubject to a rating system, buyers were ab le to choose 20 from among many di ffere nt sellers, and the s ite’s anonymity encourage d free dial ogue about drug use that helped mitigat e the stigma accompanyi ng drug addicti on. According to Caudevilla, when the s ite received negative fee dback

21 about the qual ity of the drugs sold by a vendor, that ven dor was r emoved from As the gover nment pointed out in i ts sentenc ing submission, fake vendor 20 reviews wer e commonplace, and vendors sometim es coer ced customers into givi ng them perfe ct ratings. Ulbricht refer enced a s tudy by TimBingham, who resear ched Silk Road users 21 betweenSeptembe r 2012 and August 2013. Bingham int erviewed S il k Road customers and conc luded that the site operated as a “nove l technologi cal drug subculture, potentiall y mi nimi z[ing] drug-related stigma by reinforcing a[] sens e of communi ty.” App’x 905. Thus, Bingham concluded, and Ulbricht argued, that Silk Road encouraged more “r espons ible forms of recr eational drug use.” Id. at 906. 30the site. Finall y, Ulbricht clai med that the site reduced violence asso ciated with

the drug trade b y providing a safe, computer-base d method of purchasing drugs. Ulbricht also submi tted an expe rt repo rt from Dr . Mark Taff, which provided an alternative reas on for e xcluding the six deaths from the PSR. In his repor t, Dr. Taff ex plained that, based on the information avail able, it was impossible to know wi th medicalcertainty that Sil k Road drugs caused the six deaths des cribed in the PSR. Ther e were “gaping holes” in the investigat ions into each death, and s ome were missing autopsy repor ts, toxicology reports, and death cer tifi cates. App’x 911. Mor eover , Dr. Taff claimed that i t was im possible to know the cause of e ach death be cause se veral of the dece ased had ingeste d mul tipl e drugs pr ior to their deaths. Ulbricht argued that, abse nt a clear causal li nk betwee n the deaths an d the offens e conduct, the deaths were n ot relevant to his sentencing at all. The defen se later submitted another se ntencing memorandum, which included 97 l etters fr om friends and family describing Ulbricht’s good char acter as well as academic arti cles about the myriad problems associated with unduly

sever e sen tences for drug crimes. He also urge d the district court not to consider the five murders commissioned by DPR, in part be cause he c lai med only to have

31fantasized about the murders , impl ying that he did not expect them to be carr ied

out. In i ts sentenc ing submission, the government requested that the district court impose a sentence substantiall y above the twen ty-year mandatory mini mum . Ulbricht’s sentencing he aring took place on May 29, 2015. The district 22 court concluded that Ulbricht’s offense level was 43—the h ighest possible offens e level under the Se ntencing Gui delines—and that his crimi nal history category was I. The high offense level largely resulted from the massive quant ity of

23 drugs trafficked using Silk Road, as wellas seve ral enhance ments, including one for directing the use of violence, U.S .S.G. § 2D1.1(b)(2). Ulbricht does not 24 dispute that calcu lati on. Due to the h igh offense level, the Guideli nes advisory At sentencing, the district court vacated Ulbricht’s convicti ons on C ounts One 22 and Three because they were lesser included offenses of C ounts Two and Four resp ectively. Ulbricht was ther efore sentenc ed on C ounts Two, Four, Five, Six, and Seve n. The district court based its Gui delines calcul ation only on those counts. The calculat ed offens e level was actuall y 50, which is higher than the maximum 23 offense level of 43 on the Gui delines senten cing table. The Gui delines provide that “[a]n offense level of more than 43 is to be treated as an offens e level of 43.” U.S.S.G. ch. 5 pt. A, cmt. n.2. Because of the grouping rules, U.S.S.G. ch. 3 pt. D , the lower offen se levels of 24 the computer hacking and fraudulent identifi cation charges did not contribute to Ulbricht’s offense level. 32sentenc e “range ” was life i n prison, and the U.S. Probation Office re commended

that sentence

. At the sentenc ing hearing, the district court resolved se veral disputed issues of fact. For e xample, because Ulbr icht contested his res ponsibili ty for the five commi ssioned murder s for hire , the district court found by a prepon derance of the evidence that Ulbricht did in fact comm ission the murders, b elieving that they would be carr ied out. The district court character ized the evidence of the murders for hire, which included Ulbricht’s journal, chats wi th other Silk Road

users , and the evidence showing that Ulbricht actu all y paid a totalof $650,000 in Bitcoi ns for the kil li ngs, as “ample and unambiguous.” App’x 1465. The court then turne d to the six drug-re lated deaths descr ibed in the PSR. Over Ulbr icht’s objection, the district cou rt found that the deaths wer e “re lated conduct relevant to his senten cing” because the “question as to whether this informati on is proper ly included in the PSR is whether the C ourt finds, by a prepon derance of the evidence[ ,] that the deaths, in some way, related to Silk Road.” Id. at 1472. It w ent on to exp lai n that “the relevant offen se committ ed is the unlawful di stribution of drugs and the runn ing of a criminal drug enterpr ise, . . . [and] base d on the evidence befor e the C ourt, the sale of the dr ugs through

33Silk Road caused harm to the deceden ts.” Id. at 1473. The district court described

the facts associated with five of the deaths and sp ecifical ly found that each was connected to S il k Road, rejecting the defen dant’s argument that but-for causation was required in order for the cour t to consider the deaths as relevant to the offense conduct. Parents of two of the de cedents also made statements at the 25 procee ding, describing the emotional i mpact that the losses had on them and their famil ies. In the course of e xplaining i ts reaso ns for ch oosing Ulbricht’s sentence , the district court di scussed the facts of Ulbricht’s offense , his apparen t character, an d the purpos es of cr iminal punishment. The court describe d Doctor X as “enabling,” App’x 1530, rathe r than re ducing the harms associated with drug use, emphasized the s ocial costs att endant to expan ding the scope of the dr ug market, discussed the five murder s for hire , and stated that the sente nce imposed on Ulbricht could have a powerful gener al deterre nt effect be cause the cas e had

The district court did not specifi callyaddres s one of the six deaths. That 25 decede nt was a frequent Silk Road customer who was found dead in his home with a used syringe and other drug paraph ernalia. The recor d does not indicate why the district court did not di scuss that case, an d neither par ty makes any argument based onthat omi ssion. 34attracted an unusually l arge amount of publici ty. The court then se ntenced

Ulbricht principal ly to l ife im prisonment. This appeal foll owed. DISCUSSION On appeal, Ulbricht raises a number of claim s of er ror. For purpose s of organizationalclarity, we group them int o three categories, and pr esen t them in the orde r in which the issues aros e in the district court. Accordingly, we di scuss first Ulbricht’s clai ms that mu ch of the evidence against himshould have bee n suppre ssed b ecause it was obtained in viol ation of his Fourth Amendment rights; second, h is arguments that the district court’s evidenti ary er rors denied him a fair trial; and thi rd, his objections to his senten ce. I. Fourth Amendment Issues Ulbricht clai ms that the district court err ed in denying his moti on to suppre ss evidence obtained in viol ation of the Fourth Amendment. On appeal from a denial of a suppress ion moti on, “we re view a district court’s findings of fact for clear er ror, an d its resolution of questions of law and mi xed questions of law and fact de novo .” United States v. Bohannon , 824 F.3d 242, 247-48 (2d Cir. 2016). Ulbricht raises two principal arguments. First, he contends that the

35pen/ trap orde rs that the gover nment used to monitor IPaddres s traffic to and

from his home router violated the Fourth Amendment because the govern ment obtained the orde rs without a warrant. Sec ond, he claims that the warr ants authorizing the government to searc h his laptop as well as hi s Google and Facebook accounts violated the Fourth Amendment’s particularity requi rement. We reject those contentions and affirm the den ialof Ulbricht’s moti on to suppre ss. A. Pen/Trap Orders Pursuant to orders issued by United States magistrate judges in the SouthernDistrict of New York, the gove rnment used five pe n register s and trap and trace de vices to monit or IP addresse s associated with Internet traffic to and from Ulbricht’s wireless home router and devices that re gularly connected to that router. The government ob tained the order s pursuant to the Pen/ Trap Act, which provides that a govern ment attorney “may make [an] appli cation for an order

. . . authorizing or approving the install ation and use of a pen r egister or a tr ap and trace device . . . to a court of competen t jurisdi ction.” 18 U.S.C. § 3122(a)(1). A “pen r egister” is defined as a “de vice or proce ss which re cords or decodes dial ing, routing, addressing, or signaling i nformation transmitt ed by an

36instrument or facili ty from which a wi re or electronic communi cation i s

transmitted,” and “shall not include the contents of any communicati on.” Id. § 3127(3). A “trap and trace ” device means “a device or proces s which captures the incoming el ectronic or othe r impul ses which identify the originati ng number or other dial ing, routing, addressing, and signaling i nformation reasonab ly l ikely to identify the sour ce of a wire or electronic communi cation.” Id. § 3127(4). Like pen r egisters, trap an d trace devices may not capture the “contents of any communi cation.” Id. The statute does not re qui re a se arch warr ant for the use of a pen r egister or tr ap and trace de vice, nor does it demand the ki nd of showing required to obtain such a warran t. Rather, the statute requires only that the applicati on contain a “certificati on . . . that the information l ikely t o be ob tained is relevant to an ongoing criminalinvestigati on.” Id. § 3122(b)(2). The orde rs in this case authorized the gove rnment to “use a pe n register and trap and trace device to identify the sour ce and des tinati on [IP] addresse s, along with the dates, times, durations, ports of tran smission, and any Transmission Control Protocol (‘TCP’) connection data, associated with any 26

Data are tr ansmitt ed on the Intern et via discrete packets, rathe r than in a 26 continuous stream. TCP is a “comm unicati ons pro tocol used to process such data packets assoc iated wi th popular Internet applicati ons,” such as browse r and e37electronic communi cations sent to or from” various devices, including Ulbricht’s

home wireless router and his laptop. S.A. 93. In each or der, the gove rnment 27 specified that it di d not seek to obtain the conten ts of any communi cations. Instead, it sought authorization to col lect only “di ali ng, routing, address ing, and signali ng information” that was akin to data captured by “traditionaltelephonic pen r egisters and tr ap and trace de vices.” Id. at 130. Ulbricht cl aims thatthe pen/ trap orde rs violated the Fourth Amendment because he had a r easonab le expe ctation of privacy i n the IP address r outing i nformation that the orders all owed the gover nment to coll ect. 28

mailapplicati ons. S.A. 97. Like IP address data, the TCP data that the orders permitted the government to acquire do not include the contents of communi cations, and Ulbricht has not expr esse d any independe nt concernover the govern ment’s collecti on of TCP conne ction data. Some of the pe n/trap o rder s phras ed the scop e of the or der slightly di ffere ntly. 27 For ex ample, one order authorized install ing “a trap and trace device to identify the source [IP] address of any Intern et communi cations directed to, and a pen register to de termine the destination IPaddres ses of an y Internet communi cations originating from,” the re levant devices. S.A. 67. In other wor ds, not every or der so ught TCP connection data as well as I P address infor mati on. Neither par ty has suggested that the differe nces among the pe n/trap o rder s are material t o any issue pre sented b y this appeal. In the district court, Ulbricht made the same arguments con cerning his Fourth 28 Amendment privacy interest in the information captured by the pen r egisters and trap and trace devices. The district court ruled gener all y that the “type of informati on sought [in the order s] was entirely appro priate for that type of 38The Fourth Amendment to the United States Con stitution provides that:

“The right of the people to be secure in their person s, houses , papers , and effects, against unreasonab le search es and s eizures, sh allnot be violated, and no Warrants s hall i ssue, b ut upon probable cause , supported b y Oath or affirmation, and particularly describing the place to be sear ched, and the p erso ns or things to be se ized.” The “corne rstone ofthe modern law of sear ches is the pr incipl e that, to mount a successful Fourth Amendment chall enge, a de fendant must demonstrate that he pe rsonally has an ex pectation of privacy in the place

searc hed.” United States v. Haqq , 278 F.3d 44, 47 (2d Cir. 2002) (internal quotati on marks omitt ed). Thus, a “Fourth Amendment ‘sear ch[]’ . . . does n ot occur unless the sear ch invades an objec t or area [in which] one has a subjective ex pectation of privacy that society i s pre pared to acce pt as objectively reasonab le.” United States v. Hayes , 551 F.3d 138, 143 (2d Cir. 2008). The Supre me Court has long he ld that a “person has n o legiti mate expe ctation of privacy i n information he voluntari ly turns over to third parties,”

order .” App’x 208. The cour t declined to address Ulbricht’s “nove l Fourth Amendment arguments” regar ding the pen/tr ap devices be cause he h ad “not established the r equisi te privacy interest . . . to” demonstrate h is standing to challenge the order s. Id. The govern ment has agree d that Ulbricht has standing to pursue his Fourth Amendment ar guments on appeal. 39including phone n umbers dialed in making a telephone call and captured by a

pen r egister. Smith v. Maryland, 442 U.S. 735, 743-44 (1979). This is so because phone use rs “typicall y know that they must convey numerical information to the phone company; that the phon e company has facilit ies for re cording this informati on; and that the phone company does in fact recor d this informati on for a variety of legit imat e business purpose s.” Id. at 743. Simi larly, “e-mai l and Internet user s . . . rely on third-par ty equi pment in order to en gage in communi cation.” United States v. Forrester , 512 F.3d 500, 510 (9th Cir. 2008). Internet user s thus “should know that this i nformation is provided to and used by Internet se rvice provider s for the s pecific purpose of direc ting the routing of informati on.” Id. Moreover , “IP addresses are not mere ly passively conveyed through third party equipment, but rather are voluntaril y turned over in order to direct the third party’s se rver s.” United States v. Christie, 624 F.3d 558, 574 (3d Cir. 2010) (internal quot ation marks omi tted). Ulbricht notes that questi ons have b een r aised about whether some aspects of modern techn ology, which entrust great quanti ties of signifi cant pers onal informati on to third party vendors , arguably maki ng exten sive government surveillance possible, call for a re-evaluation of the third-party disclosure

40doctrine established by Smith

. See, e.g. , United States v. Jones , 565 U.S. 400, 417-18

(2012) (Sotomayor, J., concurr ing); American Civil Liberties Union v. Clapper , 785 F.3d 787, 824 (2d Cir. 2015). We re main bound, however, b y that rule unti l and unless it is overruled by the S upreme C ourt. See United States v. Gomez, 580 F.3d 94, 104 (2d Cir. 2009); see also United States v. Wheelock , 772 F.3d 825, 829 (8th Cir. 2014). Moreover , whatever n ovel or more intrusive surve il lance techniques mi ght pres ent future questions concer ning the appropr iate scope of the third-par ty disclosure doctrine, the or ders in this case do n ot prese nt such issues. The

recor ding of IPaddres s information and sim il ar routing data, which reveal the existence of connections be tween communicati ons devices without disclosi ng the content of the communicati ons, are precisely analogous to the capture of telephone number s at issue in Smith . That is why the orders here fit com fortably withi n the language of a statute drafted with the earlier technology in mind. The substituti on of electronic methods of communicati on for telephon e calls does not alone create a r easonab le expectation of privacy in the identiti es of devices with whom one communi cates. Nor does it raise novel issues distinct from those long since re solved in the context of telephone communi cation, wi th which society has

41li ved for the nearly forty year s since Smith was decided. Like telephone

companies, Internet ser vice providers r equire that i dentifying i nformation be disclosed in order to make communicat ion among electronic devices possible. In li ght of the Smith rule, no re asonable pe rson could maintai n a privacy interest in that sort of information. We there fore join the other circuits that have considered this narr ow question and hold that coll ecting IPaddres s information devoid of content is “constituti onally indistingui shable fr om the use of a pen r egister.” Forrester , 512 F.3d at 510; see, e.g. , Wheelock , 772 F.3d at 828 (holdi ng that the defendan t “cannot claima reaso nable exp ectation of privacy in [the] government’s acquisition of his subscr iber information, incl uding his I P address an d name,” because it had been “reve aled to a third party” (internal quotati on marks omitt ed)); Christie, 624 F.3d at 573 (holdi ng that there is no e xpectation of privacy in “subscribe r information provided to an internet pr ovider,” such as an IP addre ss (internal quotati on marks omitt ed)); see also Guest v. Leis , 255 F.3d 325, 336 (6th Cir. 2001) (holding that “computer users do n ot have a legiti mate expectation of privacy in their [bulleti n board] subscr iber information because the y have conveye d it to another pers on”); United States v. Graham , 824 F.3d 421, 432 (4th Cir. 2016) (en b anc)

42(noting that “thi rd-party information relating to the se nding and routing of

electronic communi cations does not re ceive Fourth Amendment protection”); United States v. Carpenter , 819 F.3d 880, 887 (6th Cir. 2016) (“[C] ourts have not (yet, at least) extended [Four th Amendment] protections to the internet analogue to envelope markings, namely the metadata used to route internet communi cations, li ke . . . IP addresse s.”). Wher e, as he re, the gove rnment did not access the contents of any of Ulbricht’s communicati ons, it did not need to obtain a warrant to collect IPaddres s routing informati on in which Ulbricht di d not have a legiti mate privacy interest. We ther efore reject Ulbricht’s contention that the issuance of suchorder s violat ed his Fourth Amendment rights. 29

The issue pre sented in this case is nar rowly confined to order s that are limi ted 29 to the capture of IP address es, TCP conn ection data, and simi lar routing informati on. Our holding therefor e does n ot address other, more invasive surveillance techniques that capture more information (such as content), which may requi re a war rant issued on pr obable cause o r an or der pur suant to Tit le II I of the Omnibus Cr ime Control and Safe S treets Act of 1968, codified as amended at 18 U.S.C. §§ 2510-22. See generally In the Matter of a Warrant for All Content & Other Info. Associated with the Email Account xxxxxxx@gmail.com Maintained at Premises Controlled by Google, Inc ., 33 F. Supp. 3d 386, 393-96 (S.D .N.Y. 2014), as amended (Aug. 7, 2014) (descr ibing the avail able caselaw concer ning search warrants of e mailaccounts). Simil arly, to the extent that some of the out-of-circuit cases cited in the text also addre ss the Fourth Amendmen t status of other types of evidence, s uch as historical cell -site locati on information, we expre ss no views on such issues, wh ich are not pre sented in this case. 43Ulbricht’s additi onal arguments are not pe rsuasive. Ulbricht contends

gener ally that pen/trap order s may monit or a communicat ion’s content by tracking metadata, but he does not identify what m etadata the government might have collected or ex plain how the pen/trap order s in this case gave the government information concern ing the content of his communi cations. He also claim s that the order s violat ed the Fourth Amendment by impermissibly monitori ng activi ty wit hin his home, relying on Kyllo v. United States , 533 U.S. 27 (2001). In Kyllo , the Cour t held that using t hermal-imag ing technology from outside the home to discern whethe r a per son was gro wing mari juana in the home might reveal innocent, non-criminalinformati on in which a resident has a privacy interest. Id. at 38. Ulbricht contends that monit oring IP address traffic through his router is simi lar to the thermal-im aging technology because it mi ght

reve al when and how Ulbricht used his computer whenhe was at home. The same can be said, however, of anordinary telephone pen r egister, which can

reve al i f, when, and ho w a pers on uses h is or her home phone to make calls. See Smith , 442 U.S. at 743. IP address traffic simil arly reveals whe ther an Inter net subscr iber (or , more pre cisely, a person who us es the s ubscribe r’s Interne t connection) is home and using the Internet. N othing in Kyllo suggests that

44government monitoring of data discl osed to an outside telephone o r Interne t

provider for ordinary busines s purpos es be comes constituti onally suspect when investigators use that informati on to draw infere nces ab out whether someon e is maki ng telephone calls or acces sing websites from inside his or he r home. We theref ore s ee no con stitutional di ffere nce be tween monitoring home phone dial ing informati on and IP address r outing data. Thus, we conclude that the pen register an d trap and trace order s did not viol ate the Fourth Amendment. 30 B. Search Warrants Ulbricht also contends that the warran ts authorizing the search and s eizure of his laptop as wellas his Facebook an d Google accounts vi olated the Fourth

Ulbricht’s alternative argument, that the pen/trap or ders violated the Pen/ Trap 30 Act and the Store d Communicati ons Act (“SC A”) because they sought prospe ctive data, i s without m erit. Ulbricht clai ms that the orders were o btained both through the Pen/Trap Act, 18 U.S.C . §§ 3121-27, and the SC A, 18 U.S.C. § 2703(d). To the contrary, e ach pen/ trap orde r (and the unde rlying requests for such orde rs) r elied exclusively on the Pen/Trap Act, not the SC A. The fact that one of the gove rnment’s goals was to monitor IPaddres s traffic to match Ulbricht’s Internet activity with DPR’s does not undermine the validity of the order s. The orde rs themse lves did not al low the government to track the location of the router and other e qui pment to which the trap and trace de vice was attached. Thus, they were not “geo-locating” devices, as Ulbricht suggests, any more than subpo enas for hotel registers, p arking tickets, and credit card rec eipts, or any other methods by which the gover nment obtains informati on that can be used to identify a suspect’s location at parti cular points in ti me. 45Amendment’s particularity requirement. The Fourth Amendment explicitl y

commands that warrants must be base d on prob able cause and must “particularlydescr ib[e] the place to be s earche d, and the per sons or things to be seized.” U.S. C onst. amend. IV. “It i s famil iar history that indi scriminate searche s and seizures conducted under the authority of ‘general warr ants’ were the imm ediate evils that m otivated the framing and adopti on of the Fourth Amendment.” Payton v. New York , 445 U.S. 573, 583 (1980). Those ge neral warrants “s pecified only an offense,” leaving “to the discretion of the ex ecuting official s the decision as to which per sons sh ould be arre sted and which places should be se arched.” Steagald v. United States , 451 U.S. 204, 220 (1981). The principal defect in such a warrant was that it permitt ed a “gene ral, exploratory rummagi ng in a person ’s belongings,” Andresen v. Maryland, 427 U.S. 463, 480 (1976) (internal quot ation marks omi tted), a problem that the Fourth Amendment attempted to resolve by re qui ring the warran t to “set out wi th particulari ty” the “scope of the authorized sear ch,” Kentucky v. King, 563 U.S. 452, 459 (2011). 31

In addition to preventing gener al searche s, the par ticul arity requirement serves 31 two other purpos es not re levant to thi s appeal: “pre venting the seizure of ob jects upon the mistaken assumption that they fall wi thin the magi strate’s authorizati on, and pre venting the issuance of warr ants without a substanti al factual basis.” United States v. Young, 745 F.2d 733, 759 (2d Cir. 1984). 46To be sufficiently particul ar under the Fourth Amendment, a warran t must

satisfy three r equirements. First, “a warrant must identifythe specific offense for which the police have established prob able cause.” United States v. Galpin , 720 F.3d 436, 445 (2d Cir. 2013). Se cond, “a warr ant must describe the place to be

searc hed.” Id. at 445-46. Finall y, the “warran t must specify the it ems to be se ized by their re lati on to designated crimes.” Id. at 446 (internal qu otation m arks omit ted). “Where , as her e, the pr operty to be searc hed is a computer hard dr ive, the particularity requirement assumes eve n greater importance.” Id. A gener al search of electronic data is an especially potent threat to privacy because har d drives and e-mail accounts m ay be “akin to a residenc e in terms of the scop e and quanti ty of private informati on [they] may contain.” Id. The “seizure of a computer hard dr ive, and its subsequent retention by the gove rnment, can [there fore] give the gove rnment poss ession of a vast trove of pers onal informati on about the per son to whom the drive be longs, much of which m ay be entirely irrelevant to the criminalinvestigati on that led to the seizure.” United States v. Ganias , 824 F.3d 199, 217 (2d Cir. 2016) (enbanc). Suchsensitive recor ds might inclu de “[t]ax re cords, diaries, pe rsonal photograph s, electronic books,

47electronic media, medi cal data, records of inter net sear ches, [an d] banking and

shopping information.” Id. at 218. Because of the n ature of digitalstorage, it is not always feasible to “extract and segr egate re sponsive data from non-r espons ive data,” id. at 213, creating a “serious risk that ever y warrant for electronic informati on willbecome, in effe ct, a general warr ant,” Galpin , 720 F.3d at 447 (internal quot ation marks omi tted). Thus, we have he ld that warrants that failto “li nk [the evidence sought] to the criminalactivi ty supported by pr obable cause” do not satisfy the particularity requirement because they “lack[] meaningful parameters on an other wise li mitless sear ch” of a defe ndant’s electronic media. United States v. Rosa , 626 F.3d 56, 62 (2d Cir. 2010). The Fourth Amendment does n ot require a perfe ct description of the data to be se arched an d seized, howeve r. Se arch warr ants covering digitaldata may contain “some ambigui ty . . . so long as law enforcement agents h ave done the best that could reasonab ly be expe cted under the circumstances, have acquired allthe descr ipti ve facts which a reas onable investigati on could be exp ected to cover, and h ave insured that all those facts were included i n the warr ant.” Galpin , 720 F.3d at 446 (internal quotati on marks omitt ed).

48Moreover , it i s important to bear in mind that a searc h warran t does not

neces sarily lack parti cularitysimpl y because it i s bro ad. Since a sear ch of a computer is “akin to [a search of] a r esidence,” id. , searc hes of computers may sometim es ne ed to be as broad as searc hes of r esidences pursuant to warran ts. Simi larly, tradi tionalsearc hes for paper r ecords , li ke sear ches for electronic

recor ds, have always entailed the expos ure of r ecords that are not the objec ts of the sear ch to at least superficial exami nation in order to identify and seize those

recor ds that are. And in many cases , the volume of records proper ly subject to seizure be cause of their e videntiary valu e may be vast. None of these consequences neces sarily turns a searc h warran t into a prohibit ed gene ral warrant. 1. Laptop Sear ch Warr ant The warran t authorizi ng the sear ch and seizure of Ulbricht’s laptop (the “Laptop Warran t”) explicitly i ncorpor ated by re fere nce an affidavit li sting the crimes charged , which at the tim e included narcotics trafficking, com puter hacking, money laundering, and murder-for-h ire offens es in violat ion of 21 U.S.C. § 846, 18 U.S .C. §§ 1030, 1956, and 1958. See In re 650 Fifth Ave. & Related Properties , 830 F.3d 66, 101 (2d Cir. 2016) (des cribing the requirements for a

49criminalsearc h warran t’s incorporation of an affidavit by refere nce). The 32 affidavit also described the workings of Silk Road and the role of Dr ead Pirate Roberts in ope rating the site and included a wealth of information supporting a finding thatthere was probab le cause to believe that Ulbricht and DPR were the same pers on. Based onthat informati on, the Laptop Warr ant all eged that Ulbricht “use[d] [the laptop] in connection with hi s oper ation of Sil k Road,” and that there was “pr obable cause to b elieve that evidence, fruits, and instrumentali ties of the [charge d offense s]” would be found on the laptop. S.A. 246. 33 Generally speaking, the Laptop Warran t divi ded the information to be

searc hed for an d seized into two categories. The first cover ed evidence

concer ning Silk R oad that was located on the computer, including, inter alia , “data associated with the Sil k Road website, such as we b content, se rver code, or database r ecords ”; any evidence con cerning se rver s or computer e qui pment connected with Silk Road; e-mai ls, private messages, and for um postings or

Because the warrant incorpor ated the affidavit by refere nce, we r efer to the 32 documents together as the Laptop Warran t for the sake o f simpl icity. Ulbricht does not challenge the ex istence of prob able cause to be li eve both that 33 he commit ted these off ense s and that the laptop would contain evidence of the m. 50“other communicati ons conce rning Silk Road i n any way”; evidence conce rning

“funds used to facilit ate or pr oceeds derived fro m Sil k Road,” inclu ding Bit coin wall et files and transactions with Bit coin exchange rs, or “informati on concer ning any financial account s . . . wher e Silk Road funds may be stored”; and “an y evidence conce rning any ill egal activi ty associated with Sil k Road.” Id. at 246-48. The secon d category of information in the Laptop Warrant included “evidence r elevant to corrob orating the identifi cation of Ulbricht as the Silk R oad user ‘D read Pirate Rober ts.’” Id . at 248. In order to conn ect Ulbricht with DPR, the Laptop Warr ant authorized agents to sear ch for: “any communicati ons or writings by Ulbricht, whi ch may reflect lingui stic patterns or idiosyncra[s]ies associated with ‘Dread Pirate Rober ts,’ or politi cal/economic views associated with [DPR] . . .”; “any evidence concer ning any computer equipm ent, software,

or user names used b y Ulbricht, to al low comparison wi th” computer equipm ent used by D PR; “any evidence concer ning Ulbricht’s travel or patterns of movement, to al low comparison wi th patterns of online activity of [DPR]”; “any evidence conce rning Ulbricht’s technical exper tise concern ing Tor, Bitcoins,” and other computer pr ogramming i ssues; an y evidence conce rning Ulbricht’s attempts to “obtai n fake identificati on documents,” use aliases, or othe rwise

51evade law enfor cement; and “any other evidence impli cating Ulbricht in the

subject offens es.” Id . at 248-49 (footnote omit ted). After care ful consideration of the warrant, the s upporting affidavi t, and Ulbricht’s arguments, we conclude that the Laptop Warr ant did not vi olate the Fourth Amendment’s particularityrequirement. We note, at the outset of our 34 review, that the warr ant plainl y satisfies the basic elements of the par ticul arity requirement as traditional ly understood. By incorporating the affidavit by refe rence , the Laptop Warr ant li sts the char ged crimes, desc ribes the place to be

searc hed, and de signates the information to be seized in connection with the specified offense s. Each categor y of informati on sought is relevant to Silk Road, DPR’s oper ation thereof, or identifying Ulbricht as DPR. We do not unders tand Ulbricht’s arguments to contest the Laptop Warr ant’s basic compliance wi th those re qui rements. 35

The district court ruled that Ulbricht did not have standing to raise his Fourth 34 Amendment challenges because he did not establish that he had a per sonal expe ctation of privacy i n the laptop or his Facebook an d Google accounts. We expr ess no view on that issue, since the district court also reached the mer its of the motion to suppress and the government has agreed that Ulbricht has standing to chall enge the warrants an d accompanying searche s. It i s worth noting that Ulbricht does not challenge the validi ty of the searc h 35 warrant cove ring his home, although that warrant is quite sim il ar to the Laptop 52Rather, Ulbricht’s arguments turn onthe special problems asso ciated with

searc hes of computers which, as we have acknowledged in pr ior cases, Galpin , 720 F.3d at 447; Ganias , 824 F.3d at 217-18, can be par ticul arly intrusive. These arguments merit careful attention. For example, Ulbricht qu estions the appropr iateness of the pr otocols that the Laptop Warrant instructed officers to use in exe cuting the search. Those procedur es included opening or “curs orily reading the first few” page s of files to “determine their pre cise contents,”

searc hing for deliberately hidden files, using “key word sear ches thr ough all electronic storage ar eas,” and r eviewing fil e “directories” to dete rmine what was relevant. S.A. 253. Ulbricht, supported b y amicus the National Associati on of Criminal Defense Lawyers (“N ACDL”) , argues that the war rant was insuffici ently particul ar be cause the gove rnment and the magistrate judge failed to specify the sear ch terms and pr otocols ex antein the warrant. We cannot agre e. As illu strated by the facts of this very case , it wi lloften be impossible to identi fy in advance the words or phr ases that willsepar ate relevant files or documents be fore the searc h takes place, be cause officers cannot Warrant and ap pears to be just as broad . Specificall y, the home sear ch warran t all ows the gover nment to search f or and se ize evidence conce rning Ulbricht’s travel or patterns of movement and any of his communi cations or writings. 53readily antici pate how a suspe ct wil l store information related to the charged

crimes. Files and documents can easily be given misl eading or coded n ames, and words that might be expec ted to occur in pertinent documents can b e encr ypted;

even ve ry simple codes can defe at a pre-planned wor d searc h. For ex ample, at least one of the folders on Ulbricht’s computer had a name with the misspell ing “ali aces.” App’x 309. For a more challenging example, Ulbricht also kept records of certain Tor chats in a file on his laptop thatwas labeled “mbsobzvkhwx4h mjt .” Id. at 398. 36 The agents r easonab ly anti cipated that they woul d face such pr oblems in this case. Oper ating Sil k Road invol ved using sophisticated technology to m ask its users’ identities. Accordingly, al though we acknowledge the NAC DL’s suggestions in its amicus submission for lim iti ng the scope of such sear ch terms, the abse nce of the pr oposed limi tati ons does not viol ate the particularity

We note that Ulbricht and amicus NACD L somewhat exagger ate the novelty of 36 computer sear ches in this regar d. A traditi onal physical search for p aper “dr ug recor ds” or “tax r ecords ” may entaila simi lar examination of al l sorts of files and papers to determine whether such re cords ar e hidden in files with innocuous or misl eading names or wr itt en in coded ter ms to mask their content. For obvious reaso ns, sear ch warran ts authorizing the seizure of such evidence have not traditi onally specifi ed that agents may look only at file fol ders labe led “drug recor ds” or may seize only paper s containing the word “cocaine”—the equival ent of the ex ante“searc h terms” demanded b y Ulbricht. 54requirement on the facts of this case. We theref ore con clude that, i n pre paring the

Laptop Warran t, “law enforcement agents [did] the best that could reasonab ly be expe cted under the circumstances, [had] acquired all the des criptive facts which

a reaso nable investigati on could be exp ected to cover , and [had] insured that all those facts wer e included in the warrant.” Galpin , 720 F.3d at 446 (internal quotation marks omi tted). The fundamental flaw in Ulbricht’s (and the NAC DL’s) ar gument is that i t confuses a war rant’s br eadth with a lack of parti cularity . As noted above , bre adth and particularity are r elated but distinct concepts. A warrant may be b road, in that it authorizes the gover nment to search anidentifi ed location or object for a wide range of poten tial ly relevant material, withoutviol ating the particul arity requirement. For ex ample, a warrant may all ow the govern ment to search a suspected dr ug dealer’s en tire home where there is pr obable cause to b elieve that evidence r elevant to that acti vity m ay be found anywhe re in the r esidence. Simi larly, “[w]hen the criminalactivi ty pervades [an] entire b usiness, se izure of allrecor ds of the bus iness is appropr iate, and broad language used in warr ants wil l not offend the particularity requi rements.” U.S. Postal Serv. v. C.E.C. Servs ., 869 F.2d 184, 187 (2d Cir. 1989). Ulbricht used his laptop to comm it the char ged

55offense s by cre ating and continuing to operate S il k Road. Thus, a broad warr ant

all owing the government to sear ch his laptop for potentiall y extens ive evidence of those cr imes does not offend the Fourth Amendment, as long as that warrant meets the thre e particularity crit eria outli ned above

. It i s also true that allow ing law enforcement to searchhis writings for li nguisti c simi lariti es with DPR authorizes a broad searc h of written materials on Ulbricht’s hard drive. That fact, however , does not mean that the warr ants viol ated the Fourth Amendment. The Laptop War rant clearly explained that the government planned to compare Ulbricht’s writings to DPR’s posts to confirm that they were the same pers on, by identifying both linguisti c patterns and disti nctive shared p olitical or economic vi ews. Ulbricht and the NAC DL simil arly claimthat searching for all evidence of his trave l patterns and movement violat es the Fourth Amendment’s particularity requi rement. Again, the warr ant explained that it sought information about Ulbricht’s travel “to al low comparison with patt erns of online activi ty of ‘Dread Pirate Robe rts’ and any information known about his locati on at particular ti mes.” S.A. 248. Thus, the Laptop War rant

56connects the informati on sought to the crimes charge d and, more spe cifical ly, i ts

relevance to identifying Ulbricht as the per petrator of thos e crimes. 37 We re main sensiti ve to the difficul ties associated with preser ving a criminaldefendan t’s privacy while searching through his electronic data and computer hard dr ives. In the course of s earching for informati on related to Silk Road and DPR, the gover nment may indeed h ave come acros s per sonal documents that were unr elated to Ulbricht’s crimes. Such an invasion of a criminaldefendan t’s privacy is inevit able, however , in alm ost any warran ted

searc h because in “searche s for pape rs, it is certain that some innocuous documents wil l be examined, at least cursorily, in order to deter mine whether

Evidence re vealing a suspect’s past movements is often highly relevant to a 37 criminalinvestigati on. Such evidenc e might be used to establish—or r ule out—the suspect’s pr esen ce at a crime scene or other pertinent location at a particular ti me. It m ay also disclose other, unre lated informati on about the suspect’s no n-criminalassociations, interests, and b ehavior, and may be dr awn from a wide variety of sources. Gover nment efforts to deve lop such informati on, including by sear ch warran ts authorizing i ts seizure, ar e not inhere ntly questionable under the Fourth Amendment. Using piecemeal or laborious investigati ve techniques, it m ight take l aw enforce ment officers a gre at deal of tim e and effor t to compi le a comprehens ive recor d of a suspect’s tr avel or other movements. The fact that extensive trave l records ar e store d on a digit al device and may be acces sed re adily via a keystroke or quick search doe s not imm unize those re cords fr om seizure. Indeed, the s eizure of a pape r journal or calendar in a conventional search will often all ow officers to map out a defendant’s trave l history with sim il ar ease . 57they are, in fact, among those pape rs authorized to be seized.” Ganias , 824 F.3d at

211, quoting Andresen , 427 U.S. at 482 n.11. The Fourth Amendment limi ts such “unwarranted intrusions upon privacy,” id. (internal quot ation marks omi tted), by re qui ring a warrant to des cribe its scope with particularity. The Laptop Warrant satisfied that requirement. Ulbricht has challenged only the facial vali dity of the Laptop Warrant and not its execution. Because we have no r eason to doubt that the officers faithfull y executed the warrant, its exe cution di d not result in an undue invasion of Ulbricht’s privacy. Finall y, we note that the crimes char ged in this case were somewhat unusual. Thi s case doe s not involve a more typicalsituati on in which officers

searc hed for e vidence of a physician’s ill egal distributi on of pain medicati ons, to use the NAC DL’s e xample, which may have electronicall y-stored data ass ociated with the all eged cr imes on a hard drive that largely contains non-criminal informati on. Her e the cr imes under investigation were commi tted largely through computers that ther e was pr obable cause to b elieve inclu ded the laptop at issue, and the sear ch warran t appli cation gave ampl e basis for the issuing magi strate judge to conclude that evidence re lated to Sil k Road and Ulbricht’s use of the D PR username likely permeated Ulbricht’s computer. Thus, given the

58nature of Ulbricht’s crimes and their s ymbioti c connection to his digi tal devices,

we decline to rethink the well-settled Fourth Amendment principl es that the Laptop Warran t may i mpli cate. A future case may re qui re this Cour t to articul ate special li mit ations on digi tal searches to effectuate the Fourth Amendment’s particularity or re asonablene ss re qui rements. S uch a case is not be fore us.

2. The Google and Facebook Warr ants Ulbricht also chall enges the warran ts that all owed the gover nment to

searc h his Google and Facebook accounts, although he does n ot prese nt any specific arguments related to those war rants. Both warr ants, through affidavits incorporated b y refe rence , set forth the b asis for pro bable cause to se arch those accounts for evidenc e of Ulbricht’s involvement in Sil k Road. The warrants also authorized the govern ment to search his Google and Facebook acc ounts for “evidence, fr uits, and instrumental iti es” of the s pecified offense s, including, inter alia : “any communi cations or writings by Ulbricht”; “any evidence concer ning any computer equipm ent, software, o r user names used b y Ulbricht”; “any evidence conce rning Ulbricht’s travel or patterns of movement”; and any “other evidence of the” c rimes charged. S .A. 334-35, 393-94. The scope of the Google and Facebook warr ants thus substantiallyparalleled that of the Laptop Warrant.

59The Google and Facebook warr ants were constituti onal for the same

reaso ns that the Laptop Warr ant was valid. They satisfied all three of the particularity requirements becaus e they listed the subject offens es, des cribed the things to be sear ched, and identified the information to be seized in relation to the charge d crimes. Ulbricht does not advance an y additi onal arguments specific to the Google and Facebook warran ts, nor have we identifi ed any indepen dent

reaso n to find them unconstitu tional ly l acking in specifici ty.

3. Conclusion In sum, the issuance of the pen/ trap orde rs and the three s earch war rants that Ulbricht chall enges in this appeal di d not viol ate the Fourth Amendment. 38 Thus, we affirm the district court’s denial of Ulbricht’s suppr ession motion. II. The District Court’s Trial Rulings and Ulbricht’s Rule 33 Motion Ulbricht contends that he did not rece ive a fair trialfor se veral reas ons: (1) the district court’s rulings surrounding corrupt agen ts Force and Br idges The govern ment also contends that, even if the warr ants were invali d, the good 38 faith exception preve nts the applicati on of the ex clusionary rule. In general, the “exclusion of evidence is inappropr iate when the gover nment acts in objectively reaso nable re li ance on a s earch war rant, evenwhen the war rant is subse quently invali dated.” Ganias , 824 F.3d at 221 (internal quotati on marks omitt ed). Because we conclude that allthree o f the warr ants were vali d, we nee d not address the government’s altern ative argument. 60viol ated his due proce ss rights; (2) the district court err oneously precluded two

defens e exp erts fr om testifying; (3) the district court abused its discretion when it curtailed Ulbricht’s cros s-examination of two government witnesses; and ( 4) the district court erred whe n it ruled that certain hearsay statements wer e inadmi ssible. He also contends that, even if each individualerr or is harmless, the cumul ative effect of those e rror s prejudiced himto the extent that his trial was fundamentall y unfair. We detect no er ror in the district court’s rulings on any of those issues an d theref ore con clude that Ulbricht was not depr ived of his right to a fair trial. A. Corrupt Agents Force and Bridges Ulbricht’s principal fai r trial argument is that the district court erre d in numerous ways by pr eventing him from relying on i nformation related to the corruption of two feder al agents, Force and Br idges, involved in the investigation of the Silk Road sit e. Befor e trial, the district court (1) pre cluded Ulbricht from refe rring at trial to the se cret gran d jury procee ding against Force; (2) denied Ulbricht discovery related to the Force investigati on; and (3) denied Ulbr icht an adjournment of the trial unti l the Force investigation was compl ete. Dur ing trial, the district court excluded as hear say certain chats that re lated to Force’s ill icit

61use of Silk Road. Final ly, Ulbricht learned afte r trial that the gover nment was

investigating a second c orrupt agen t, Bridges. Ulbricht contends that the failure to disclose Bridges’s corr uption unti l after the trial vi olated Brady v. Maryland, 373 U.S. 83 (1963) , and that the district court errone ously denied his moti on for a ne w trial on that g round. Without q

uestion, the shocking per sonal corruption of these two government agen ts disgraced the age ncies for which they wor ked and embarr assed the many honorable men and women wor king in those age ncies to investigate serious criminalwrongdoing. Even more importantly, when law enforc ement officers ab use their offices for pers onal gain, com mit other cr iminal acts, violat e the rights of citizens, or lie under oath, they unde rmine the public’s vitaltrust in the integrity of l aw enforce ment. They may al so compromise the investigati ons and pr osecutions on which they work. At the same tim e, the ven ali ty of indi vidualagents does not neces sarily affect the re li abili ty of the government’s e vidence in a particular case or be come relevant to the adjudicati on of ever y case in which the agents par tici pated. Cour ts are ob li gated to ensure that probative evidence is disclosed to the defe nse, carefully evaluat ed by the cour t for its material ity t o the case, an d submitt ed for

62the jury’s consider ation where admissible. But courts must al so take care that

wrongdoing by investigators that has no be aring on the matter befor e the court not be use d as a diversion from fairly assess ing the prosec ution’s case. Like any other poten tialevidence, information about poli ce corr uption m ust be evaluated by re fere nce to the or dinary rules of criminal procedure and e vidence, a task to which we now turn.

1. Background: Pretr ialDisclosure of the For ce Investigation The govern ment disclosed it s investigati on into Force’s cor ruption to the defens e about six weeks befor e trial. I niti all y, on Novembe r 21, 2014, the government wro te a sealed ex parteletter to the district court seeking permission to disclose to the defense informati on about the Force grand jury investigation subject to a protective orde r. The district court granted the applicati on. On 39 Dece mber 1, the gove rnment provided a copy of the November 21 letter, which otherwise r emained sealed, to defens e counse l. According to the lett er, For ce leaked information t o DPR in exchange for payment and “cor ruptly obtain[ed]

The govern ment required such an ord er b ecause gr and jury procee dings are 39 secr et and a govern ment attorney “must not discl ose a matter occurr ing before the grand jury,” Rule 6(e)(2)(B)(vi), Fed. R. Cr im. P ., withouta court order, Rule 6(e)(3)(E), subject to li mit ed exc eptions not relevant he re. 63procee ds from the Silk Road website and conver t[ed] them to his personal

use.”App’x 649. The government thenundertook to purge its trial evidence of anything arguably traceable to Force. Ulbricht moved to unseal the entire Novembe r 21 letter so that he could rely on the information in the lett er that re lated to Force’s corr uption at t rial, arguing that the letter incl uded Brady informati on and that he ther efore had a particularized need to disclose the information thatoutweighed the pres umpti on of grand jury se crecy. He also requested discovery an d subpoen as under Rules 16 and 17, Fed. R. Cr im. P ., to learn more about the sc ope of Force ’s corr uption. I n the alternative, Ulbricht sought an adjournment of the trial unt ilthe Force investigati on concluded and information about his corruption mi ght become public through the fil ing of charges against him. On Dece mber 15, the district court held a sealed hear ing on that i ssue and invited further written submissions, including a particularized l ist of Ulbricht’s di scover y requests. One week later, the district court issued a sealed and partiallyredacted op inion denying all of 40 Portions of the district court opini on were redacted b ecause the y refe rence d the 40 defendan t’s ex partesubmissions explaining how he would use informati on related to the Force investigati on at trial. This Court has r eviewed an unre dacted version of the district court opinion in connection with this appeal, but not the ex parteletters that the opinion refer ences . 64Ulbricht’s requests. The cour t did i ndicate, however, that througho ut the trialit

would “entertain specific requests to use information from the November 21, 2014 Letter on cr oss-ex aminat ion.” App’x 700. Moreover , the court exp lai ned that it woul d “entertain a re newed application” for a “particulari zed disclosure” of facts relevant to Force ’s corr uption i f the govern ment’s trial t actics or evidence “open[e d] the door” to such fac ts. Id.

2. Preclusion of Force Investigation Evi dence: Rule 6(e) On appeal, Ulbricht claim s that the district court erred in den ying his moti on to unseal the Novembe r 21 letter be cause he de monstrated a particularized need that rebutted the pr esumption of secrec y that attaches to grand jury investigations. We disagree. “[T]he prop er functioning of our grand jury sys tem depends uponthe

secr ecy of grand jury pr oceedings.” Douglas Oil Co. of California v. Petrol Stops Nw. , 441 U.S. 211, 218 (1979). We have descr ibed five rationales for such se crecy:

(1) To preve nt the escape of those whose indictment may be contemplated; (2) to insure the utmost freedom to the grand jury in its deliber ations, and to prevent pers ons subject to indictment or their friends fro m importuni ng the grand juror s; (3) to preve nt suborn ation of perjury or tampering with the witnesses who may testify before the gr and jury and later appear

65at the trial of those indicted by it; (4) to encourage fr ee and untrammeled discl osures by per sons who h ave informati on with respec t to the commi ssion of crimes; (5) to protect the innocent accuse d who is exone rated from disclosure of the fact that he has b een unde r investigati on, and from the e xpens e of standing trial where there was no prob abili ty of guil t. In re Grand Jury Subpoena , 103 F.3d 234, 237 (2d Cir. 1996). Rule 6(e)(6) of the Feder al Rul es of C riminal Procedure implements this poli cy of secr ecy by requiring that “al l records, o rder s, and subpo enas relating to grand jury procee dings [must] be sealed.” In re Grand Jury Subpoena , 103 F.3d at 237 (emphasis in original ). Informati on falling withi n Rule 6(e)’s protections is entitled to a “pres umpti on of secr ecy and closure.” Id. at 239. To rebut the pre sumption of

secr ecy, the par ty “seeking disclosure [must] show a particularized need that outweighs the need for secr ecy.” Id. (internal quot ation marks omi tted). To prove a particularized need, parties se eking disclosure must show that the “material they see k is needed to avoid a possible injustice i n another judici al proceeding, that the need for disclosure is greater than the nee d for continued secr ecy, and that their request is structured to cover only mat erial so neede d.” Id. (internal quotation marks omi tted). “A district court’s decisi on as to whether the burde n of

66showing a particularized i nteres t has bee n met wil l be overturn ed only if the

court has abuse d its discretion.” Id. We cannot say that the district court abused its discretion when it denied Ulbricht’s request to unseal the Novembe r 21 letter discussing the Force grand jury investigati on. It i s undisputed that the letter contained informati on related to a grand jury proc eeding that, if made publi c, would di sclose matters occurr ing befor e the gran d jury. Ulbricht did not dem onstrate a par ticul arized nee d for disclosure because he did not show that the nee d for disclosure was gr eater than the nee d for continued secr ecy or that a poss ible inj ustice would result i f the grand jury investigation was not di sclosed. Spe cifical ly, the district court did not

err in concludi ng that revealing the entire letter could have compromised the Force gr and jury investigati on in a number of ways. For example, potential coconspirators might have learne d of the investigati on and attempted to inti midat e witnesses or destroy e vidence. The investigation was also l ikely t o garner signifi cant media attention, a fact that mi ght influ ence witness es or grand jurors

. And, although Force knew of the investigati on, reve ali ng its existence to the public m ight have harmed him if the allegati ons had ultim ately proved untrue. Finall y, Ulbricht’s request was not structured to cove r only the information

67neede d to avoid any possible inju stice; instead, he sought to unseal the entire

November 21 letter and did not propose a more narro wly tai lored disclosure. In redacted por tions of its opi nion, the district court al so consider ed ex parte arguments concer ning how the Force inves tigat ion mi ght be re levant to Ulbricht’s defens e. In gener al terms, Ulbricht argued that the agents’ corr uption was criticalto his defense because it woul d reve al the agents’ abili ty to falsi fy evidence against him and demonstrate their motive to do so. According to the district court’s characterization of his ex parte letters, Ulbricht speculated that Force may have use d Curtis Green ’s (Flush) admini strative capabili ties to impersonate DPR; Force ’s corr upt conduct mi ght have demonstrated te chnical vulnerabilities in the site that woul d rende r it susceptible to hacking; and learning that Force had good information about the Silk Road investigation m ight have caused the true DPR to recr uit Ulbricht as his succes sor. 41

As noted above , see note 5, we have c arefully considered to what exten t itis 41 appropr iate to refer to por tions of the recor d that remain under seal. We have beenespe ciall y careful in describing the por tions of the district court’s opini on that remain redacted and ther efore are still not avai lable to the government or to the public. We appreciate that charge s against Ulbricht remain pending in Maryland and that the redacted information descr ibes what would have beenhis trial strategy had he bee n able to refe rence Force’s c orruption. We have thus descr ibed the defe nse’s r edacted arguments at a fairly high level of generality. We are confident that any exper ienced pros ecutor could antici pate those 68The district court reasone d that much of the informati on that mi ght have

arguably supported any ofthose theor ies was made availabl e to the defe nse in discovery. The only new information in the November 21 letter concer ned the investigati on of Force ’s corr uption; the fact of that i nvestigation and it s scope does not bolster any of the defe nse theo ries that Ulbricht described befor e the district court or on appeal. That Force was pe rsonally corrupt and use d his undercove r identity to stealmoney from Silk Road and DPR does not suggest either a motive or an ability on his part to frame Ulbricht as DPR. Abse nt any explanation of how Force could have or chestrate d a massive plant of incriminating informat ion on Ulbricht’s person al l aptop, his larcenous be havior does not advance the claimthat such a frame-up was poss ible beyond mere

arguments, and that in any event the information is largely stat ed or impli ed in Ulbricht’s own publicl y fil ed br iefs on appeal. Particularl y given that our descr ipti on relates to how the For ce information mi ght have bee n used at a trial that is now compl eted, and that we now hold that Ulbricht is not entit led to a new trial, we conclude that the publi c’s nee d to understand and e valuate Ulbricht’s arguments that he was unfairly prejudiced by the district court’s rulings, as well as our reasons for rejecting those arguments, outweighs any mini mal interes t that Ulbricht might have in wi thholding hi s contentions from the govern ment. 69speculation. Thus, Ulbricht was equ all y capable of pre senting his various defens e

theories to the jury with or without the November 21 letter. 42 The govern ment’s commi tment to eli minating allevidence that came from Force’s wor k on the Silk Road investi gation further unde rmines Ulbricht’s claim 43 that he neede d the information to avoi d a possible injusti ce. Had Forc e bee n called as a government witness, or h ad any of the gover nment’s evidence r elied on his credibility, his character for truthfulness would have be en at issue during the trial, and informati on that im peached h is credibili ty woul d have be come highly relevant. Ulbricht’s reliance on the gener al fact of cooperation among different gover nment agencies and differ ent U.S. Attorney’s Offices does n ot undermine the gover nment’s explicit repres entations that none of the evidence pres ented at trial derived from Force, and nothing in the record s uggests that

Even on appe al, moreover, after the disclosure of additionalinformati on in the 42 prose cutions of Bridges and Force , Ulbricht does not provide any conc rete explanation of how the techniques used by the corrupt agen ts to steal money from Silk Road coul d have be en used, b y them or by other s, to plant the massive amounts of incrim inating information found on Ulbricht’s l aptop and in his house. For ex ample, the government declined to pres ent evidence of D PR’s attempt t o 43 commi ssion an additionalmurder be cause that conduct involved Force acting as Nob. 70those re pres entations were false . Ulbricht had no need to r ely on the grand jury

investigati on of Force to attack the credibili ty of the actual government witnesse s or the integrity of its other evidence. In sum, Ulbricht has not sh own that the district court abused its discretion in maintaining the se crecy of the Force gr and jury investigati on. He did not demonstrate to the district court, and has not demonstr ated on appeal, that keeping the Nove mber 21 letter unde r seal re sulted in any i njustice, or that his need for disclosing the investigation was greater than the n eed for continued

secr ecy. 44 3. Denial of Discover y Related to Force Ulbricht clai ms that the district court err ed in denying him di scover y, including requested s ubpoenas , related to the Force investigati on. Rule 16(a)(1)(E), Fed. R. Cr im. P ., requires the gover nment to disclose informati on withi n its control if the information is “m aterial to preparing the defe nse” or wil l

Moreover, the district court specifical ly ruled that i t would entertain Ulbricht’s 44 applicati ons to rely on spe cific parts of the letter at trialif doing so woul d be neces sary for effective cros s-examination. Thus, Ulbricht was gi ven the opportunity to show particul arized nee d in the context of spe cific t rial evidence. Ulbricht has not identifi ed any point in the trial where he attempted to show that Force’s b ehavior had be come relevant to challenging the credibili ty of particul ar aspects of the prose cution’s case. 71be a par t of the government’s c ase-in-chief. Evidence is material if i t “could be

used to counter the government’s cas e or to bolster a defens e.” United States v. Stevens , 985 F.2d 1175, 1180 (2d Cir. 1993). “An appe ll ate court, in assess ing the materiali ty of withheld information, considers not only the logicalrelationship betweenthe information and the issues in the case, b ut also the im portance of the informati on in li ght of the evidence as a whole.” Id. To justi fy a new trial, there “must be some indicati on that the pretr ialdisclosure of the disputed evidence would have enabled the de fendant significantl y to alt er the quantum of proof in his favor.” Id. (internal quot ation marks omi tted). Rule 17(c), Fed. R. Crim. P., al lows parties to subpoena documents an d objects to be introduced at cr iminal trial s. A subpoe na must meet three criteria: “(1) relevancy; (2) admissibili ty; [and] (3) specificity.” United States v. Nixon , 418 U.S. 683, 700 (1974). The par ty requesting the subpoena must also show that the informati on sought is “not otherwise pr ocurable re asonably in advance of trial by

exer cise of due dili gence,” that “the par ty cannot proper ly prepare for trial withoutsuch production,” and that “the applicati on is made in good faith and is not intended as a gene ral ‘fishing expedition.’” Id. at 699-700. We review the

72district court’s discovery rulings for abuse of discr etion. United States v. Rigas , 583

F.3d 108, 125 (2d Cir. 2009). The district court did not abuse its di scre tion when it denied Ulbricht’s discovery re quests related to the Force inves tigat ion. Ulbricht submi tted 28 indivi dual di scover y requests in connection with the Force disclosure. Those ranged fr om the reason ably specific, such as “recor ds from any and all Bit coin accounts” used by For ce, to the ver y broad, suchas “any spe nding, net worth, or other financial analysi s conducted with respe ct to former SA For ce,” “any and all phone r ecords relating to former SA Force ,” and “bank account re cords fr om any and all bank accounts mai ntained by former S A Force or his spouse.” App’x 669- 70. The district court concluded that those r equests were too broad and unfocused, and that the information requested was not material in the Rul e 16

sense because the defen se “has n ot articul ated a coher ent and particular reaso n why” the Force investigati on could “counter the gover nment’s case or bolster a defens e.” Id. at 697. Next, the district court concluded that the Rule 17 subpoenas were p art of the same over allfishing expedition and that the issuance of such subpoen as could compromi se the For ce grand jury investigation.

73There was no abuse o f discretion in those rulings. Ulbricht has not shown

that, had the governmen t produced eve ry piece of r equested information, he would have been ab le to alt er the quantum of proof in his favor at trial. That is so because there is no indication, beyond Ulbricht’s spec ulati on, that Force manufactured any of the evidence on which the govern ment relied at trial, let alone the most damning evidence discovered on the hard dr ive on Ulbricht’s laptop and at his apartment. Because Force did not testify at trial, information related to his corruption would not have bee n relevant to attack the credibility of any testimony he would have given. Moreover, Ulbr icht has not identifi ed any specific aspect of the trial evidence that he could have under mined using the requested information. Thus, even if the district court erre d in not granting at least some of Ulbricht’s discovery re quests, any such er ror doe s not justify a new trial. 4. Ulbricht’s Moti on to Adjourn the Trial Ulbricht contends that the district court erre d in denying his request to adjourn the trial unti l the Force investigation was compl ete. “[A] district court has a gre at deal of lat itude i n scheduling trials.” United States v. Griffiths , 750 F.3d 237, 241 (2d Cir. 2014) (internal quotati on marks omitt ed). Thus, “trial courts

74enjoy very b road discretion in granting or denying trial continuances.” United

States v. Stringer

, 730 F.3d 120, 127 (2d Cir. 2013). A decision to grant or de ny a request for an adjournment is reviewed for ab use of discre tion, and we “wil l find no such abuse unless the den ialwas an arb itrary action that substantial ly impai red the d efens e.” Id. (internal quot ation marks omi tted). Thus, the party seeking a continuance has the burdenof showing “both arb itrariness and prejudice in order to obtain rever sal” based on a de nial of an adjou rnment. Id. at 128 (internal quot ation marks omi tted). The district court did not abuse its di scre tion i n denying Ulbricht’s request for an adjournment of the tr ial . In a sealed portion of the proc eedings on the f irst day of trial, the district court explained its reasons f or denying the adjournment. The court ruled that because none of the evidence r evealed by the gove rnment

concer ning Force’s cor ruption was exculpatory, there was no re ason to believe that delayi ng the trial woul d assist Ulbricht’s defens e. That analysis was not irrational or arbitrary. Moreo ver, as e xplained in more detailboth above an d below, Ulbricht has not shown how information related to Force’s corruption was either ex culpatory or material t o his defens e. Thus, he h as not shown that the

75district court’s refusal to adjourn the trial was prejudici al, l et alone substantiall y

so. 5. Preclusion of the DeathFr omAbove Chats As already desc ribed, Forc e used D eathFromAbove as an unauthorized Silk Road username through which he attempted to extort money fr om DPR. The government only learne d of Force’s activi ty as DeathFr omAbove during trial, when the de fense attempted to i ntroduce a r edacted chat be tween DPR and DeathFr omAbove. In the chat at issue, DeathFr omAbove impl ied that he knew that DPR’s real identity w as Anand Athavale. De athFromAbove then attempted to blackmai l DPR by saying that, i f DPR gave him $250,000, he would not “gi ve you [ sic ] identityto law enforcement.” App’x 712. The govern ment objected to admit ting the chat on three gr ounds: (1) it was hears ay; (2) its probative value was substantiall y outweighed by unfair prejudice under Rule 403, Fed. R. Evid.; and (3) it was a “back-door attempt to re-inject” Force’s c orruption into the defens e’s trial evidence. App’x 707. The district court excluded the chat as h earsay. At trial, Ulbricht cl aimed that the chat was not being offer ed for its truth, but instead to show its effect on D PR; that i s, if DPR was actuall y Athavale, one would expect DPR to take certain steps to protect his

76identity. The district court disagreed and ruled that the De athFromAbove chat

was hear say becaus e it was offered for the truth of the matter asse rted therein—that govern ment agents at one time thought that A thavale was DPR—and it di d not fallinto any hearsay ex ceptions. In the alternative, the district court found that the Athavale-as-DPR theor y lacked suffici ent suppor t, was speculative, and risked jury confusion. In general, hear say is not admi ssible unless an ex ception applies. See Fed. R. Evid. 802. “The Federal Rules of Evidence define he arsay as a de clarant’s out-of-court statement offered in evidence to prove the tr uth of the matter

asser ted in the statement.” United States v. Dupree, 706 F.3d 131, 136 (2d Cir. 2013) (internal quot ation marks and alterations omi tted). If “the signifi cance of an offere d statement li es solely in the fact that it was made, no issue is raised as to the truth of anything asser ted, and the statement is not hears ay.” Id. (internal quotation marks omi tted). “The trial court’s ul tim ate decisions as to the admission or exclusion of evidence are reviewed for abuse of discr etion.” Davis v. Velez , 797 F.3d 192, 201 (2d Cir. 2015). The district court concluded that the De athFromAbove chat was he arsay because it was an out-of-court statement being offered for the truth of the matter

77asser ted there in. That ruling was not an abuse of discretion. Contrar y to

Ulbricht’s asser tions on appeal, the district court di d not rest its decision on the need for grand jury sec recy to pr otect the Force inves tigation. Instead, the decision was a straightforward application of the rule against hearsay. Ulbricht does not provide any de tail ed arguments to the contr ary that are specific to the DeathFromAbove chat; instead, he discusses the district court’s preclusion of all of the evidence related to the Forc e investigati on collecti vely. At trial, however, he claimed that the statement was offered on ly to demonstrate “the fact that it w as communi cated to DPR . . . in that thi s particular piece of evidence communicates to DPR the name and profile of the per son [D]eath[F]r om[A]bove believes is D PR.” Tr. 1866. Ulbricht cl aimed that the statement was “offere d for the fact that DPR was getting informati on about people who wer e suppose d to be DPR,” and “one of these p eople is [Athavale].” Id. at 1867. Once the district court expr esse d skepticism about hi s argument, Ulbricht clai med that he sought to admi t the chat to demonstrate its effect on DPR: “if you’re DPR and you get a name . . . this Anand Athavale and a profile and details . . . and you’re put on notice that it ’s you, you’re going to take steps.” Id. at 1867-68. In other words, Ulbr icht clai med that he did not offer it for the

78truth of the matter asser ted in the chat: that agents in the Balti more investigati on,

including Force, b elieved that Athaval e was the r eal Dre ad Pirate Roberts, or that Athavale was in fact the real DPR. Ulbricht’s propose d non-hear say use of the ch at—to show its effect on DPR—is not suffici ently probative that the evidence’s e xclusion prejudiced him. The statement does not appe ar to have had aneffect on D PR that woul d bolster Ulbricht’s defens e. DPR did not alter his behavior in res ponse to the e xtortion attempt. I ndeed, h e re ferr ed to it as “bogus” in one of the journal entries discovered onUlbricht’s laptop. App’x 710. If Athaval e had be en the r eal Dre ad Pirate Roberts, he li kely woul d have had a differe nt reaction to the threaten ed expos ure of his identity. DPR’s reactions to other attempts to destroy the s ite’s anonymity w ere dramatic, and i ncluded hiring people to kil l the users who threatene d to compromise Sil k Road. Therefor e, evenif Ulbricht did not offer the chat for its truth, any relevance of the arguably non-he arsay use of the statement was entirely too remote to outweigh the possible jury confusion that would result from the injection of Force into the trial or the li kelihood that the jury would confuse the h earsay an d non-hear say significance of the evidence.

796. Ulbricht’s Rule 33 Mot ion: Brady v. Maryland

Ulbricht moved for a new trial under Rule 33, Fed. R. Crim. P., raising

sever al i ssues co ncern ing the unfairness of the asser tedly belated disclosures of the investigati ons into Force and Br idges. The only argument that he pursues in 45 this appeal is that the be lated discl osures viol ated his due proce ss rights under Bradybecause the information was both materialand exculpatory. Rule 33(a) provides that, on “the defe ndant’s motion, the court may vacate any judgment and grant a new trial i f the interest of justice so re qui res.” We have advised district courts to “exercise Rule 33 authority sparingly and in the most extraor dinary circumstances.” United States v. Coté , 544 F.3d 88, 101 (2d Cir. 2008) (internal quot ation marks omi tted). “Where a defendan t’s Bradyclaimwas raised in a moti on for a ne w trial pursuant to Ru le 33[,] . . . we review the de nial of the moti on for ab use of discre tion.” United States v. Douglas , 525 F.3d 225, 245 (2d Cir. 2008) (internal quot ation marks omi tted). In the context of denying a Rule 33 moti on, a “district court abuses . . . the discre tion accorded to it when (1) its

Ulbricht fil ed his Rule 33 moti on on March 6, 2015. The criminalcomplai nt 45 against Force and Bridges was unsealed on March30, which is the first ti me that Ulbricht learned that Bridges was cor rupt and was involved in the case.

80decision rests onan err or of law . . . or a clearly err oneous factual finding, or (2)

its decision—though not necessarily the product of a legal error or a clearly

err oneous factual finding—cannot be located within the range ofpermissible decisions.” United States v. Forbes , 790 F.3d 403, 406 (2d Cir. 2015) (internal quotation marks omi tted). There ar e three components of a Bradyviol ation: “(1) The evidence at issue must be favorable to the accuse d, either be cause it is exculpatory or becaus e it is impeaching; (2) that evi dence must have b een s uppres sed by the [government], either will full y or inadverten tly; and (3) prejudice must have ensued.” United States v. Certified Envtl. Servs., Inc ., 753 F.3d 72, 91 (2d Cir. 2014) (internal quotation marks omi tted). Informati on is exculpatory if it relat es to the defendan t’s guil t or innocence. United States v. Avellino , 136 F.3d 249, 255 (2d Cir. 1998). In order to sh ow that he has be en pr ejudiced, a defendant must demonstrate “a re asonable pr obability that, had the evidence b een disclosed, the result of the proc eeding would have bee n different, suchthat the fail ure to disclose undermines confidence in the verdict.” Certified Envtl. Servs., Inc. , 753 F.3d at 91 (internal quotati on marks and alterations omitted). Thus, the prose cution “m ust disclose . . . exculpatory and impeachment informati on no

81later than the point at which a reasonable pr obability wil l exist that the outcom e

would have been differ ent if an earlier disclosure had b een made.” Id. at 92 (internal quot ation marks omi tted). In general, a “pruden t prosecutor will err on the side of transp arency, r esolving doubtful q uestions in favor of disclosure.” Cone v. Bell , 556 U.S. 449, 470 n.15 (2009). Although the agents’ ill egal behavior in connection with the Silk Road investigati on is deeply troubling, the government’s D ecember 2014 disclosure of the Force investigati on and the pos t-trialdisclosure of Bridges’s cor ruption did not viol ate Ulbricht’s due proce ss rights. Evidence con cerning the age nts’ corruption is not Bradyinformati on becaus e it is not exculpatory or impeaching of the gover nment’s trial evidence. For this reas on, the gover nment’s failure to

reve al the fullextent of the inves tigat ions untilafter Ulbricht’s trial did not prejudice him. As already explained, the fact that Force pur loined Bit coins from Silk Road and att empted to blackmai l DPR does not relate to Ulbricht’s guil t or innocence; the same logic appl ies to Bridges’s simil ar be havior. The agents’ corruption has nothing to do with whether Ulbricht oper ated the site as Dr ead Pirate Roberts. Ulbricht has not r aised any credible doubts ab out the reliabil ity of the evidence that the gove rnment pre sented at trial, nor has he explained why

82the agents’ illegalactions relate to his guil t at al l. Indeed, the governmen t

removed fr om it s exh ibit l ist the it ems relevant to Force , including communi cations between N ob (his authorized under cover use rname) and D PR. Those communicati ons included an instance in which DPR hired Nob to kill Curtis Green ( Flush) as punishment for using his admini strator status to steal Bitcoi ns from Silk Road users. Ulbricht does n ot identify any parti cular evidence introduced by the gover nment at trialthat is traceable to either Force or Bridges, or the admissibili ty of which depends on e ither agent’s integrity. Ulbricht’s arguments to the contrar y largely rest on spe culati on. First, Ulbricht contends that the Silk Road investi gations occurring in Balt imore and New York we re “[c]oor dinated and [c]ombined,” suggesting that Force’s corruption may have somehow infected the evidence that the Ne w York office used in its prosecution. Appellant Br. 40. Ulbricht explains that the offices communi cated frequently and share d informati on through emails and repor ts. Assuming that Ulbricht is corre ct, the fact that the Silk R oad investigati on took place in several offices, one of which employed two corrupt agents, does not alter our analysis. Ulbricht stil l has not shown how the age nts’ corr upt behavior is exculpatory as to him, even if Force and Br idges at tim es shar ed their work

83product with New York and that work pr oduct infl uenced the large r

investigati on. The re levant qu estion, on which none of Ulbr icht’s arguments casts any light or raises any doubt, is whether an y particular i tem of evidence was tainted i n some way by the misconduct of Bridges or For ce. Next, Ulbricht surmises that the agen ts may have fabricated evidence suggesting that Ulbricht was DPR. I n so arguing, Ulbricht im plies that Force and Bridges may have had sufficiently high-l evel admini strator acce ss to Silk Road to manipul ate the “financial, t ransactional, and communi cations infrastructure of the Silk Road sit e.” Reply Br. 14. Nothing in the govern ment’s disclosures, and nothing that Ulbricht identifi es in the re cord or h as produce d from any independen t source, sugges ts that either Bridges or Force had s uch capacity. Absen t further de tailor evidence that Force and Br idges were ab le to infi ltrate DPR’s communi cations or transactions, Ulbricht’s argument is simply t oo speculative to warrant a new trial. Ulbricht further claim s that Bridges used sophisticated techniqu es to try to place blame on others for his corr upt conduct, reflecting a pattern of fr aming others for his own crimes. That fact alone does not suggest that Bridges fabr icated any evidence against Ulbricht or attempted to frame him. That Bridges undertook to deflect blame for things he had done doe s

84not suggest any re ason why Bridges would be motivated to frame Ulbricht for

things that DPR had done. Nor do es Ulbricht explain how Bridges’s actions should undermine our confidence in any of the specific evidence on which the government r elied at trial

. 46 Finall y, Ulbricht submit ted a supplemental appendix that incl uded a newly-discovered, unr edacted re port from the Joint Automated Booki ng System (“JABS”). In that report, under the heading “Arr ested or Received Information,”

47 Force is listed as the officer on the case, and the Balti more DEA is listed as the relevant agency. Ulbr icht apparently means to suggest that this report sho ws that Force played a more p ervasive r ole in the investigat ion than the government has acknowledged. In resp onse, the government ar gues that Force was s impl y the

In a footnote, Ulbricht clai ms that fail ing to di sclose the full extent of the 46 agents’ corr uption deprived him of an opportunity t o “attack[] the investigati on as shoddy.” Kyles v. Whitley, 514 U.S. 419, 442 n.13 (1995). Now that he has all of the relevant information, he stilldoes not ex plain how he mi ght have demonstrated deficiencies in the gover nment’s investigati on of his or one of the other initialsuspects’ con duct that woul d undermine our confidence in the verdict. As the gover nment explains, and Ulbricht does not dispute, JABS is a database 47 maint ained by the United States Mars hals Service that catalogues information regar ding all eged offe nders who have be en arr ested and b ooked by fed eral, state, or local lawenforc ement agencies. 85most recent pe rson to make change s to the JABS r eport by updating it to i nclude

informati on about Ulbricht’s famil y members and the pending charge s in Maryland. In any event, the JABS r eport be aring Force’s n ame does not show how information related to Force’s corr uption exculpates Ulbricht. It merely confirms that Force was a par tici pant in the Balti more Silk Road i nvestigation and that he continued to be involved in the case after Ulbricht was arres ted. In the face of the e ntire recor d of the trial, i n which the prove nance of the government’s e vidence was ex haustively di splayed without indicati on that Force

was res ponsible for any of it, this single report has littl e or no p robative value. In sum, we conclude that the Force and Bridges co mplaint did not contain Bradyinformati on becaus e the agen ts’ corruption does n ot bear onUlbricht’s guil t or innocence. Thus , any delay in the government’s disclosure of the ir corruption did not viol ate Ulbricht’s due proce ss rights. B. Preclusion of Defense Experts The district court precluded both of Ulbricht’s prop osed ex pert witnesse s from testifying because he did not timel y or adequately discl ose his intent to call them under Rule 16, Fed. R. Cr im. P . In general, the “defe ndant must, at the government’s r equest, give to the government a written summary of any [expe rt]

86testimony that a defendan t intends to use. . . . This summary m ust describe the witness’s opinions, the base s and re asons for those opinions, and the witness’s qual ifications.” Fed. R. Cr im. P . 16(b)(1)(C ). The purpos e of the ex pert 48 disclosure requirement is to “mi nimi ze surpr ise that often res ults from unexpe cted expe rt testimony, reduce the ne ed for con tinuances, and to provide the oppone nt with a fai r oppor tunityto test the merit of the expe rt’s testimony through focused cr oss-ex aminat ion.” Fed. R. Crim. P. 16, advi sory committ ee’s note to 1993 amendment. Indeed, “[w]ith increased use of both scientific and nonscientific expert tes tim ony, one of couns el’s most basic discovery nee ds is to learn that an expe rt is expec ted to testify.” Id. If a party fail s to comply wi th Rule 16, the district court has “br oad discretion in fashioning a remedy,” which may i nclude granting a continuance or “order ing the exclusion of evidence.” United States v. Lee, 834 F.3d 145, 158 (2d Cir. 2016) (internal quotati on marks omitt ed); seeFed. R. Cr im. P . 16(d)(2)(A)-(D) (a district court m ay order “any other [r emedy] that is just u nder the circumstances”). We thus r eview the district court’s choice of remedy for abuse of

It i s undisputed that the government r equested such disclosure on D ecember 48 29, 2014, two weeks be fore trial began. 87discretion. “In considering whether the district court abused its discretion, we

look to the reasons wh y disclosure was not made, the ex tent of the prejudice, i f any, to the opposing party, the fe asibili ty of rectifying that prejudi ce by a continuance, and any other relevant circumstances.” Lee, 834 F.3d at 159 (internal quotation marks omi tted). The district court did not abuse its di scre tion i n pre cludi ng the defe nse from calling its proposed e xper ts. Not only were the disclosure s late, more importantl y, they were plainl y inadequat e. Both disclosures mer ely li sted gene ral and in some cases e xtremely broad topics on which the e xper ts might opine. For example, the disclosures indicated that the expe rts would testify on general topics, incl uding: “the origins of Bit coin,” “the various purpose s and uses of Bitcoi n,” “the mechanics of Bitcoin transactions,” “the value of Bitcoin over time since its inception,” “the concepts of Bitcoin speculati ng and Bitcoin m ining,” “[g]ener al principl es of interne t security and vulnerabilities,” the “import of some lines of PHP code provided to defen se counse l i n discovery,” and “[g]ener al principl es of public-key cryptograph y,” among others. App’x 349, 360. They did not summ arize the ex perts’ opinions about those topics, let al one descr ibe the base s for the e xper ts’ opinions.

88Indeed, although the listed topi cs cer tainl y pertained gene rally to Si lk

Road, the disclosures wer e so vague that it is di fficul t to discern whether the proffer ed exp ert testimony would have been at all relevant under Rules 401 and 702(a), Fed. R. Evid. In his oppositi on to the govern ment’s moti on to preclude 49 Antonopoulos, Ulbricht described the expe rt’s prop osed testimony in more detail, buthe stilldid not di sclose the opinions that the exp ert intended to offer

. For ex ample, that suppl emental discl osure indicated that an “[i]ndepende nt defens e investigati on has uncove red that” the gover nment’s claimthat over 700,000 Bitcoi ns wer e transfe rre d to Ulbricht’s Bit coin wall et “is im plausible,” and the ex pert would “dispute this fi nding.” App’x 382. Although that i s more specific, it i s not a summary of Antonopoulos’s opinion, nor does it identify the basis for that opinion. Thus, to this day Ulbricht has not des cribed what opinions

In particul ar, Ulbricht’s disclosures did not discuss, and he has not desc ribed 49 on appeal, how one e xper t’s propose d testimony on “[g]eneral principles of internet sec urity and vul nerab il iti es” would have linked to the defense claimthat the damning documentary evidence of Ulbricht’s guilt found on his laptop was or could have be en fabr icated or planted. The jury was aware fr om other evidence, and indee d it i s within ordinary lay experience, that var ious forms of hacking are poss ible. What was lacking, what the defen se ex pert disclosures did not purport to addre ss, and what Ulbricht stillhas not provided on ap peal, is any explanation, let al one a cre dible explanation, of how the bre adth and variety of informati on, from the laptop and other s ources, co uld have been p lanted. 89the exp erts would offer or explained the methods they use d to arrive at any of

those conclusions. The district court also di d not abuse its discretion in finding that the government would be pr ejudiced by the belated and inadequate disclosures, in part becaus e the gover nment was due to res t the following day, providing it with no time to prepare to re spond to the ex perts. Mor eover , the district court considere d intermediate sanctions short of pr eclusion but found them to be inadequate. I n rejecting a continuance as a pos sible remedy, the district court emphasized the “known issues with a conti nuance,” es peciall y in a lengthy trial

. Id. at 369. Two of the jurors had time constraints, and a continuance might have caused the cour t to lose one or both of thos e jurors, e specially i f the continuance was lengthy. If it

were to gr ant a continuance, the court would also need to perfor m it s function as a gatekeepe r of ex pert testimony under Daubert v. Merrell Dow Pharm., Inc. , 509 U.S. 579, 592-93 (1993), which requires the district court to make a “preliminary ass essment of whe ther the r easoning or methodology underlying the [expe rt] testimony i s scientifical ly val id” and “can be applied to

90the facts in issue.” The district court cannot perfor m that com plex evaluation of 50 an expe rt’s prop osed methodology without a clear articulati on of what the expe rt’s opinions are an d, even more importantl y, of the base s for those opinions. In li ght of the risk of losing jurors and the lack of a sufficiently com pelli ng reas on for the de fense ’s clear violati on of Rule 16, the district court was wi thin it s discretion when it determined that a continuance was not practical and that the appropr iate remedy was to preclude the witness es altogether. Ulbricht’s arguments to the contrar y are not pe rsuasive. First, Ulbricht argues that the two ex perts we re ne cessar y to rebut portions of the gove rnment’s case that he was p recluded from addre ssing during cross- examination, as wellas the testimony of Ilhwan Yum, a government witness who analyzed trans actions

We have e xplained that a Daubert reliabili ty assess ment requires a district court 50 to consider the “e xtent to which [the expe rt’s theor y] has be en subjecte d to peer review and publication,” whether the techn ique is “subject to standards controlli ng the technique’s oper ation,” the “known or potential rate of err or,” and the “degr ee of acce ptance within the relevant scientific com munity.” United States v. Romano , 794 F.3d 317, 330 (2d Cir. 2015) (internal quotati on marks omit ted). That inquiry is a “fl exible one,” ho wever, an d Daubertis not a “definiti ve checklist or test” for the reliabili ty of exper t testim ony. Id. (internal quotation marks omi tted). Thus, “[w]hether Daubert ’s specific factors are , or are not, reason able measures of reliabili ty in a particul ar case is a matt er that the law grants the trial judge broad latitude to determine.” Id. at 331 (internal qu otation marks omitt ed). 91associated with Bi tcoin wal lets found on Ulbricht’s laptop. Ulbricht now

contends that por tions of Yum’s testi mony were incorr ect, including his descr ipti on of what a “hot” Bitcoi n wallet i s. Ulbricht does not, however , 51 explain how Yum’s testim ony was incorre ct, what contrary evidence his exper ts would have provided had they be en allowed to testify, or how any purported

corre ction of Yum ’s testimony woul d have affecte d the case against Ulbricht. Nor has he p roduced any s umm aries of his pro posed e xper t testim ony or des cribed how that testim ony would have beenmaterial t o Ulbricht’s guil t or innocence. In other wor ds, Ulbricht has not shown that pr ecluding Bell ovin and Antonopoulos from testifying prejudiced him . Ulbricht’s alternative argument that the disclosures wer e in fact adequate is i ncorr ect for the r easons already explained. Ulbricht next argues that preclusion was an unduly harsh re medy under the circumstances. Along those lines, he claims that certain exhibits, such as the summary chart on which Yum relied, were not produce d untilmid-t rial. Thus,

“The terms hot wallet and cold wal let derive from the more gen eral terms hot 51 storage, meaning online storage, and c old storage, meaning offline storage. A hot wall et is a Bitcoin wallet for which the private keys are s tored on a ne tworkconnected machine ( i.e. [,] in hot storage). By contras t, for a cold wall et the private keys are stored offline.” Steve n Goldfeder et al. , Securing Bitcoin Wallets via a New DSA/ECDSA Threshold Signature Scheme, Princeton University 10, available at http://www.cs.pr inceton.edu/~ste venag/thr eshold_sigs.pdf. 92according to Ulbricht, he could not have known about his need fo r ex pert

witnesses to counter specific trialexhibits untilit was al ready too late to comply with Rul e 16. In his view, the district court shoul d not have held him so strictly t o Rule 16’s requirements because he could not have known until Yumtestified that he would need to call an exper t. While Ulbricht is corre ct that excluding hi s exp erts was a h arsh s anction and was not to be imposed lightl y, the district court considered the pos sibili ty of granting a continuance or a more limi ted sanction and found those r emedies to be inapprop riate under the c ircumstances. Such car eful consideration of a range of possible sanctions shor t of preclusion is especially i mportant in the atypi cal case whe re a cr iminal defendant, rathe r than the gove rnment, is prec luded from putti ng on his case b ecause of a Rule 16 violati on. Limi ting the defense ’s pres entation of his case impl icates the fundamental right of “an accused to pres ent witnesses in his own def ense .” Chambers v. Mississippi, 410 U.S. 284, 302 (1973). However , the defen dant must sti ll“comply wi th established rules of procedur e and evidence designed to assur e both fairne ss and r eliabil ity in the

ascer tainm ent of guilt

and innocence.” Id. Here , Ulbricht did not com ply wi th the procedur al requi rements as sociated with expert disclosures. The district court

93gave the issue due con sideration and appropr iatelyexer cised its discretion in

remedying the defe nse’s Rule 16 violati on. Finall y, Ulbricht cannot credibly argue that Yum’s testim ony was the first notice he had about the pos sible need for an expe rt witness to testify as part of his affirmati ve case. The Silk Road prosecution was uniquely laden wi th issues related to technology, computer ser vers, fo rens ics, cyber s ecurity, digi tal

curre ncy, and myriad other issues that are indisputably “beyond the ken of the average juror .” United States v. Mejia, 545 F.3d 179, 191 (2d Cir. 2008) (internal quotation marks omi tted). Ulbricht surely knew from the outset that, in order to mount a m eaningful att ack on the gover nment’s voluminous and technically complex evidence, he would need to callhis own expe rt. Indeed, in his opening statement, Ulbricht’s counsel clai med that he would show that the Bit coins in Ulbricht’s wall et were from innocent transactions ass ociated with Bitcoin speculation, rather than, as the government conte nded, re lated to Sil k Road. 52

No evidence about the source of those Bitcoins was in fact presen ted by 52 Ulbricht, and neither the e xper t disclosures pre sented to the district court nor Ulbricht’s arguments on appeal suggest that either Be ll ovin or Antonopoulos would have provided an analysis or exp lanati on of Ulbricht’s Bitcoin t ransactions that woul d have re vealed a non-Silk Road source for Ulbricht’s Bitcoins. 94Ulbricht’s opening statement also im plied that Bi tTorrent’s security deficiencies 53 could have all owed the true D PR to pl ant incriminating evidence on his laptop. It is diffi cult t o fathom how he planned to advance thos e theor ies without relying on expe rt testimony. In short, Ulbricht argues that the district court’s pre clusion of his proffere d expe rt witnesses de nied him a fai r oppor tunityto prese nt his defense . But the same failings that rende r Ulbricht’s exp ert disclosures inadequate under Rule 16 preclude us fr om findi ng the kind of prejudice he as serts. Ulbr icht di d not disclose to the district court, and has not prese nted on appe al, any explanation of what the propos ed exp erts would have said that would have supported a nonspeculative basis for doubting the prob ative val ue of evidence fr om a variety of electronic and other s ources identifying Ulbricht as DPR throughout the li fe of Silk Road. Thus, we cannot conclude that he was pr ejudiced by the exp erts’ exclusion.

BitTorrent is a peer -to-peer file sharing service that is used to transfe r large files 53 withoutdisrupting I nterne t serve rs. It has both legitim ate and ill icit purpose s. See Next Phase Distribution, Inc. v. John Does 1-27, 284 F.R.D. 165, 167 (S.D .N.Y. 2012). 95C. Curtailing Cross-Examination

Ulbricht contends that the district court erre d in li miting his abil ity t o

cross -examine two government witnesse s: De r-Yeghiayan and Kiernan. “We review a trial court’s decision to l imi t the scope of cr oss-ex aminat ion for abuse of discretion.” United States v. Cedeno , 644 F.3d 79, 81 (2d Cir. 2011). “A district court is accorded br oad discretion in controlling the scope and exten t of crossexamination.” United States v. James , 712 F.3d 79, 103 (2d Cir. 2013) (internal quotation marks omi tted); see Fed. R. Evid. 611(a). Thus, “a district court may impose reasonab le li mit s on cros s-examination to protect against, e.g ., harass ment, prejudice, confusion, and waste.” James , 712 F.3d at 103 (internal quotation marks omi tted). In general, however , a “district court should afford wide lat itude to a defendant in a criminal case to cross -examine govern ment witnesses.” Id. (internal quot ation marks omi tted). That is so because the Confr ontation Clause gives “a defendant the r ight not onlyto cross-e xaminati on, but to effective cross -examination.” Id. “[I]t does not follow, of course , that the Confr ontation Clause preven ts a trial j udge from imposing anyli mit s” on defe nse counsel’s cros s-examination of government witnesses

. Id. (emphasis in original ).

961. Agent Der -Yeghiayan

Ulbricht argues that the district court erre d when it struck portions of De rYeghiayan’s testimony that referen ced his prior b elief that K arpeles might be Dre ad Pirate Roberts. Ulbricht also challenges the striking of a simi lar but analyti callydisti nct piece of testimony: Der-Ye ghiayan’s statement that Karpeles’s attorne y had offere d informati on about Silk Road in exch ange for Karpeles re ceiving i mmu nity from prosecution. Ulbricht wanted the jury to infer that Karpeles had some criminal involvement in Sil k Road that motivated himto pursue a coop eration agree ment with the gover nment. Der -Yeghiayan answer ed the defe ndant’s initi al questions about those topics, and the governmen t did not object to them untila later side bar. D uring the side bar , the district court expre ssed its initi al vi ew that the questions were proper , but requested written br iefing on the subject. After r eviewing the parties’ submissions, the district court agreed with the government that neither Der

Yeghiayan’s prior opinions about whethe r Karpeles was D PR nor Karpeles’s offer of infor mati on about Silk Road was relevant to Ulbricht’s case. The court thus directed the gover nment to identifyportions of De r-Yeghiayan’s testimony

97to strike. After the gover nment identifi ed the improper testimony, the distri ct

court gave a gene ral li miting instructi on to the jury:

You heard tes tim ony while Mr. Der- Yeghiayan was on the stand re garding pers onal beliefs or suspicions he may have had about particular indi vidual s at various points during his investig ation. And I instruct you that what the agent suspe cted about others isn’t evidence and should be disre garded. N ow, consistent with allof the instructions I’mgoing to gi ve you at the end of the case, ther e was other testimony that Mr. De r-Yeghiayan provided which you may consider during your deliberations and give it the weight that you deem that it deserves . So it’s the suspicions, all ri ght? Tr. 974. Ulbricht contends on app eal that the district court err ed in striking the testimony. We disagree . The district court did not err in concludi ng that Der

Yeghiayan’s prior be li efs about Karpeles as a possible DPR suspe ct were not relevant to the char ges against Ulbricht. In order to elicit t estimony im plicat ing an alternative perpe trator, a defe ndant “must show that his proffere d evidence on the alleged alternative perpetr ator is sufficient, on it s own or in combination with other evidence in the re cord, to show a ne xus be tween the cr ime charged and the asse rted alternative per petrator.” Wade v. Mantello , 333 F.3d 51, 61-62 (2d Cir. 2003) (internal quotati on marks omitt ed). Thus, to avoid a “grave risk of jury

98confusion,” a defendan t must offer more than “unsuppor ted speculation that

another pe rson may have don e the cr ime.” Id. at 62 (internal qu otation m arks omit ted). An “agent’s state of mind as the investigation progress ed is ordinarily of lit tle or no relevance to the question of the defendant[’s] guilt.” United States v. Johnson , 529 F.3d 493, 501 (2d Cir. 2008). Thus, striking Der -Yeghiayan’s testimony and i nstructing the jury to disregard his ear li er opinions about Karpeles’s pos sible guil t was not err or. 54 Further, an y arguable er ror that occurr ed was har mless. Defe nse couns el continued to cross-e xamine Der -Yeghiayan and elicit ed admissible testim ony about the earlier investigation i nto Karpeles; indeed, the district court took over

cross -examination at several points to assist the defense in asking proper questions. Cf. Cotto v. Herbert, 331 F.3d 217, 254 (2d Cir. 2003) (in considering

Ulbricht also contends on appeal that the gover nment’s objection to the 54 testimony, whi ch occurr ed at a later sidebar, was untim ely. He cites no law in support of that argument. In gener al, an “objection should be made after the question has been as ked but befor e an answe r has b een given.” Hutchinson v. Groskin , 927 F.2d 722, 725 (2d Cir. 1991). That “rule is not inflexible,” id. , however, and we do not “nece ssarily find [a]n objection affirmat ively wai ved bec ause it might have be en interpos ed a few questions earlier,” United States v. Pujana-Mena , 949 F.2d 24, 33 (2d Cir. 1991). Thus, although a contemporaneous objection is prefer able, the district court was within its discretion to sustain the later objection and strike the testimony. 99whether a Confr ontation Clause viol ation i s harmless, we co nsider, inter alia , “the

extent of cr oss-ex amination otherwise per mit ted”). Moreove r, Ulbricht discussed the investigati on of Karpeles in his summati on without objecti on. What was relevant at trial was any actualevidence pointing to Karpeles as the true D read Pirate Roberts. The district court did not li mit Ulbricht’s cross-e xaminati on of Der -Yeghiayan as to his knowledge of such evidence . The district court directed the jury to disregard only testimony as to the agent’s “suspicions,” Tr. 974, a subject of “litt le or no re levance to . . . the defe ndant[’s] guilt ,” Johnson , 529 F.3d at 501. We simil arly reject Ulbricht’s contention that striking Der-Yeghiayan’s testimony concerning Karpeles’s offe r to provide information about SilkRoad in exchan ge for immuni ty was an abuse of discr etion. Absent other evidence in the

recor d regar ding Karpeles, it was proper to ex clude wholly speculative suggestions of an alternative per petrator de fense based onKarpeles’s attorne y’s offer of infor mati on in exchange for his client’s im munity. And even as suming, arguendo , that the district court erred in striking the testimony, any error was harmless. To the ex tent this testim ony was stricken fr om the trialrecor d, that ruling occurred outside the pre sence of the jury. All the jury was told was to

100disregard tes tim ony about “what the agent suspe cted about others ,” Tr. 974, a

category that hardly would be unders tood by the jury to encompass tes tim ony about the actions of Karpeles’s attorne y. As explained in detail above, moreover, the evidence identifying Ulbricht as Dread Pirate Robe rts was over whelmi ng and largely unchall enged. That Karpeles may have h ad informati on about Silk Road does not imply that he was D PR, only that he had some knowledge ofor involvement wi th the site. Particul arly given that K arpeles likely had some knowledge about Silk Road sim ply because of his ope ration of Mt. Gox, a prominent Bitcoi n exch anger, an y marginal probative val ue in the fact that he claim ed to have such kn owledge, and offer ed to provide it to the government, could not have meaningful ly affected the balance of evidenc e available to the jury regar ding the identity of DPR.

2. Agent Kiernan Defe nse couns el cross-e xamined Ki ernanextens ively, and Ulbricht contends on ap peal that the district cou rt err ed in preve nting himfrom exploring certain topics during that cross-ex aminat ion. Those excluded topics include: the

101meaning of various acronyms, the significance of a certain line of PHP code, 55

whether the FBI all owed Kiernan to run BitTorrent on h is work computer despite its l ack of security, and whether the Linux kerne l that Ki ernanused on his work 56 computer was the same as the one that Ulbricht install ed on his laptop. Ulbricht explains that he was attempting to show that Kiernan’s con clusions about Ulbricht’s laptop were inaccurate be cause they wer e base d on unreliable informati on. The district court sustained objections to those questions because, in its view, they were outside the s cope of Kiernan’s dire ct testim ony. SeeFed. R. Evid. 611(b) (“Cr oss-ex amination should not go beyond the subjec t matt er of the direct examination and mat ters affe cting the witness’s credibility.”); Baker v. Goldman Sachs & Co. , 669 F.3d 105, 110 (2d Cir. 2012) (“Once any direct examination i s concluded, cross -examination wi thin the scope of the dire ct foll ows.”). On appeal, Ulbricht claim s that, because Ki ernantestified about the operation of Tor C hat and other for ensic computer issues dur ing his direct

PHP is a comm on computer progr amming language that i s used pr imari ly i n 55 website deve lopment. A kerne l i s an oper ating system’s core, and it “is an essen tialpart of the Linux 56 operating system.” Tr. 1070. 102testimony, the precluded questions were within that testi mony’s scope and

should have bee n allowed. Even assuming that Ulbricht is corre ct, any err or is harmless. Ulbricht was per mitted to questi on Kiernan about whether Linux was customi zable, and Kiernan admitt ed during cross that he did not know whether he used the same vers ion of Tor Chat that Ulbricht had install ed on his laptop. Ulbricht’s counsel also asked seve ral questi ons about the se curity vul nerab il iti es of BitTorrent, conveying to the jury that using BitTorren t mi ght have re ndere d Ulbricht’s computer susceptible to hacking. Thus, Ulbricht was able to eli cit testimony supporting his proposed infer ence that Kiernan’s con clusions based on the Tor Ch at evidence wer e flawed. Ulbricht does not exp lai n how he was prejudiced when the district court prohibited himfrom asking Ki ernancertain other questions. We there fore identify no reve rsible er ror in the district court’s li mit ations on Ki ernan ’s cross examination. D. Andrew Jones Hearsay Statement The district court excluded a statement all egedly made by Andre w Jones, who was a Silk Road administrator under the user name Inigo. Jones cooper ated with the government and was on the government’s witness li st untilthe middl e of trial, when the government de cided not to callhim. Defense counsel explore d

103the possibility of calling Jones as a witness, but Jones’s attorney advised Ulbricht

that Jones would invoke the Fifth Am endment and re fuse to testify if com pelled to appear. In light of Jones’s unavailabil ity, Ulbricht sought to admit a Dece mber 29, 2014 letter from the gover nment to defense counsel that describe d a statement that Jones made during one of h is interviews. The relevant por tion of the 57 government’s letter is as follows:

At some point i n or about August or S eptember 2013, Jones tried to authenticate that the Silk Road user “Dre ad Pirate Roberts” whom he was talking to at the tim e . . . was the same pe rson with whom he had be en communi cating i n the past with this username. Previously, . . . Jones and “Dr ead Pirate Roberts” h ad agreed upon a “handshake ” to use for authentication, in which Jones would provide a cer tain prompt and “Dre ad Pirate Roberts” would provide a cer tain resp onse. Whe n, during the 2013 chat in question, Jones provided what he b elieved to be the des ignated prompt, “Dre ad Pirate Roberts” was unab le to provide the resp onse Jon es thought they had agre ed on. Howeve r, later in the chat, Jones aske d “Dre ad Pirate Roberts” to vali date himself by specifying the first job that “Dread Pirate Roberts” ass igned to him(running the “DPR Book Club”), which “Dre ad Pirate Roberts” was ab le to do.

The govern ment did not concede that the statement was Bradyinformati on, but 57 disclosed it “in an abundance of caution.” App’x 398. 104App’x 398. Ulbricht argues that the Jon es statement supports his theor y that 58 more than one p erso n acted as D read Pirate Rober ts, because at one point DPR could authenti cate his identityto Jones, but at another tim e he could not. When it became clear that Jone s was unavailable to testi fy, Ulbricht asked the govern ment to stipul ate that the Jones s tatement could be read to the jury. The govern ment ini tial ly agreed, but then ch anged its mi nd and oppose d admit ting the Jones statement. The defe nse acknowledged that the s tatement was hears ay, but clai med that it was admissible under two hearsay e xceptions: under Rule 804(b)(3), Fed. R. Evid., as a statement against i nteres t, and under Rule 807’s residual exception. The district court ruled that the statement was inadmi ssible, specificall y address ing only Ru le 804(b)(3). On appe al, Ulbricht continues to argue that the statement was admissible under either e xception. Neither of his theories is per suasive. 59 What Ulbricht sought to i ntroduce was the government’s letter p araphr asing a 58 statement made by Jones dur ing an interview, not a verbatim transcript of what Jones had said. We refe r to it as the “Jones s tatement” for the sake of s impl icity. We note that the Jone s statement is double hears ay, in that the defense s ought 59 to admi t the government’s s ubsequent characte rization of Jones’s interview, and both the gover nment’s letter and Jone s’s statement to the agents we re out of court statements offer ed for the ir truth. When confr onted with “hearsay within hears ay, or double hear say,” courts must determine that “each par t of the 105A district court’s “ul tim ate decisions as to the admission or exclusion of

evidence ar e re viewed for abuse of discretion, and willnot be disturbe d unless they are manifestly err oneous.” Davis , 797 F.3d at 201 (internal quotati on marks and citati ons omitted). To invoke the 804(b )(3) exce ption for a statement against interest, the pr oponent of the s tatement “must show (1) that the declarant is unavail able as a witness, (2) that the statement is sufficiently reli able to warrant an inferen ce that a reas onable man in [the declarant’s] position would not have made the statement unless he b elieved it t o be true , and (3) that corrob orating circumstances clearly indicat e the trustworthines s of the statement.” United States v. Wexler , 522 F.3d 194, 202 (2d Cir. 2008) (internal quotati on marks omitt ed). The

exce ption appli es “only if the district court determines that a reasonab le person in the declarant’s shoe s would perceive the s tatement as detrimental t o his or her own penal interest.” United States v. Saget, 377 F.3d 223, 231 (2d Cir. 2004). The key to this inquiry is whether the statement is sufficiently “self-i nculpatory,”

combined statement[]” is independently admissibl e. United States v. Williams , 927 F.2d 95, 100 (2d Cir. 1991). Because we conclude that no hear say exce ption applied to the Jones statement at all, we nee d not address the double hear say issue. 106which the district court m ust evaluate on a “case-by-cas e basis.” United States v.

Williams , 506 F.3d 151, 155 (2d Cir. 2007). The district court did not err in concludi ng that the Jones s tatement did not fall w ithi n Rule 804(b)(3)’s hear say exce ption. There is no dispute that Jones was unavail able to testify because he planned to invoke his Fifth Am endment privil ege. The cour t ruled that the Rul e 804(b)(3) e xception did not apply because Jones was un der a coope ration agreement at the time that he made the relevant statement to the government and the chat did not have any particular im pact on Jones’s penal interests. Onappeal, Ulbricht clai ms that the extent of Jone s’s criminalli abili ty was unknown when he made the statement because he could stil l be vulnerable to pros ecution in other jurisdicti ons, and he had not yet bee n sentenc ed when h e made the statement to the gover nment. See Mitchell v. United States , 526 U.S. 314, 326 (1999) (in the Fifth Amendment context, there can be a “legit imate fear of advers e conse quences from further testimony” where a sentenc e has not yet b een imposed). We are not pers uaded that Jones’s s tatement was against his penal interests. Given the cooper ation agreement, the gover nment’s role at Jones ’s future sente ncing, and the penalties for lying to the government, it is far from

107clear that it was agai nst Jones’s interest to disclose details of his crim inal act ivi ties

at the tim e the statement in question was made. Moreover, e ven to the ex tent that Jones’s disclosures taken as a whole con stitut ed inculpatory admi ssions, the particular statement i n question had li ttl e adver se effe ct on Jones. Jon es’s inculpat ory admissions to the government conce rn whethe r he committed crim es connected to S il k Road. His description of his “handshake” with DPR pres upposes that he had already discussed h is own crimes with the government. Whether DPR did or did not recognize Jones ’s identifying prompt does not b ear on Jones ’s guil t of any crime associated with the site, since he had already confirmed his role working for D PR. The detail s of this convers ation wi th DPR thus do not inculpat e Jones ; instead, they either he lp or hurt Ulbricht. Accordingly, the district cou rt did not abuse its discretion in holding that Rul e 804(b)(3) does not apply. Rule 807 provides for a limi ted, res idualexce ption to the rule against hears ay where no other e xception applies. A hears ay statement may be admissibl e under Rule 807 i f: “(i) it is particul arly trustworthy; (ii) i t bears on a material fact; (iii ) it i s the most probative evidence addres sing that fact; (i v) its admission i s consistent with the rules of evidence and advances the interests of

108justice; and (v) it s proffe r follows adequate noti ce to the adver se par ty.” United

States v. Morgan , 385 F.3d 196, 208 (2d Cir. 2004) (internal quotati on marks omit ted). The “re sidual hearsay exce ption[] wil l be used ver y rare ly, and only i n

exce ptional ci rcumstances.” Parsons v. Honeywell, Inc ., 929 F.2d 901, 907 (2d Cir. 1991) (internal quot ation marks omi tted). The district court did not specifi callyaddres s Ulbricht’s request to admit the statement under Rule 807, but we conclude that the limi ted res idualexce ption does not ass ist Ulbricht. We are loath to assume that a stat ement made by a criminalin debriefings to the gover nment pursuant to a cooper ation agreement is categorically“particularlytrustworthy,” as Rule 807 requires. But even if Jones ’s statement meets that criterion, and was offer ed “as evidence of a material fact ,” we cannot say that it is “m ore pr obative on the point for which it i s offer ed than any other e vidence that the propon ent can obtain through re asonable eff orts.” Fed. R. Evid. 807(a)(2)-(3). Ulbricht has not attempted to explain how the Jones statement satisfies this requi rement. Finall y, even if the district court erre d in excluding the statement under either hear say exce ption, any error was certainly harmless. The conve rsation betweenJones and DPR in it s totali ty was not actual ly helpfulto Ulbricht. As

109explained, during the chat in question, DPR was at one point unable to provide

the designated re sponse , but later he identified him self to Jones’s s atisfacti on. The statement thus contains the see ds of its own refutation. Since DPR’s alleged failu re to ver ify his i dentity and his subsequent remedy of that failure occurre d during the same online chat, the interaction provides litt le or no suppor t for the defens e theor y that different indivi duals acted as DPR at different times. E. Cumulative Erro r Ulbricht argues that the cumulat ive effect of the district court’s evidentiary rulings deprived him of a fair trial

. See United States v. Al-Moayad, 545 F.3d 139, 178 (2d Cir. 2008). We h ave exh austively reviewed his contentions of trial error and have concluded that none of those conten tions has merit. The challenged trial rul ings were we llwithi n the district court’s discretion, and the various exclusions did not preven t the defens e from offer ing evidence prob ative of innocence. At the trial in thi s case, the government pr esen ted overwhe lming evidence that Ulbricht was indeed Dr ead Pirate Roberts. The evidence that the defens e was pr ecluded from offering to re fute that proof was ex cluded because it was speculative, unreliable, offered in contrave ntion of the Federal Rules of Evidence or of C rimi nal Procedure, or otherwise inadmissible. The few instances

110in which the district court’s rulings may be questioned, where we noted the relevance of the harmless e rror rule, involved minor and marginal points. Accordingly, whether cons idered se parately or cumulati vely, none of Ulbricht’s evidentiary arguments lead us to doubt that he was found guilty after a fair trial. III. Sentencing “[A] district court has broad latitu de to impose either a Guidelines sentenc e or a non -Gui delines senten ce.” Rigas , 583 F.3d at 114 (internal q uotati on marks omitt ed). “Accordingly, the role of the C ourt of Appeals is lim ited to examining a sentence for reaso nablenes s, which is akin to review under an ‘abuse-of-discr etion’ standard.” Id. “This standard applies both to the [substantive reas onablenes s of the] se ntence itself and to the proce dures employed in arriving at the se ntence.” Id. (internal quot ation marks omi tted). Ulbricht and amici challenge his li fe sen tence as b oth procedur all y and 60 substantively unreasonab le.

The amiciwho join Ulbricht’s challenge to his life sentence include: the Dr ug 60 Poli cy All iance, Law Enforce ment Against Prohibition, JustLeadersh ipUSA, and retired D istrict Judge Nancy Gertner. 111A. Procedural Reasonableness

“A sentenc e is proced urally unreasonable if the district court fail s to calcul ate (or improper ly cal culates) the Senten cing Gui delines range, tr eats the Senten cing Gui delines as mandatory, fails to consider the § 3553(a) factors, s elects a sentenc e base d on clearly err oneous facts, or fails adequ ately to explain the chosensentenc e.” United States v. Jesurum , 819 F.3d 667, 670 (2d Cir. 2016) (internal quot ation marks and emphasis omit ted). To “hold that a factualfinding is ‘clearly errone ous,’ we must be left with the definit e and firm conviction that a mistak e has b een committed.” United States v. DeSilva , 613 F.3d 352, 356 (2d Cir. 2010). Where “there ar e two permissible views of the evidence, the factfinder’s choice betwee n them cannot be clear ly errone ous.” United States v. Norman , 776 F.3d 67, 76 (2d Cir. 2015) (internal quotati on marks omitt ed). In gener al, a “sentenc ing court has discretion to consider a wide range of information i n arriving at an appropriate se ntence.” United States v. Prescott, 920 F.2d 139, 143 (2d Cir. 1990). “The district court’s factual findings at senten cing need be supported on ly by a preponde rance ofthe evidence.” Norman , 776 F.3d at 76. “Where we identify procedural err or in a senten ce, but the re cord indicates clearly that the district

court would have im posed the s ame sentence in any

112event, the e rror may be deemed har mless, avoidi ng the nee d to vacate the

sentenc e and to re mand the case for rese ntencing.” United States v. Jass , 569 F.3d 47, 68 (2d Cir 2009) (internal quotati on marks omitt ed); see also United States v. Cavera , 550 F.3d 180, 197 (2d Cir. 2008) (enbanc) (dec li ning to reach claim that district court erred in re lyi ng on vague conce rn about gun violence be cause it was clear that the “district court woul d have imposed the same se ntence had it relied solely on” the permissible concer n about deterr ence). Ulbricht’s only clai m of procedural er ror is that it was im proper for the district court to consider six drug-related deaths as relevant to his senten ce because there was insuffici ent information connecting them wi th drugs purchase d on Silk Road. I n terms of our s entencing jurisprudenc e, Ulbricht claim s that the district court relied on clearly errone ous facts in im posing sentenc e. We ar e not per suaded. Ulbricht submit ted an exp ert re port in which Dr. Mark Taff wro te that the

recor ds associated with the six deaths wer e subs tantial ly i ncomplete. For example, many did not i nclude fullautopsies, rende ring it di fficul t to discern the precise c ause of death to a re asonable degr ee of medical certainty in fi ve of the

113cases. Equal ly i mportantly, Dr. Taff wrote that he could not conclusively 61 connect the s pecific drugs that the deceden ts consumed with Sil k Road, because it i s impossible to “correlate the time of purchase/ acqui siti on from an alleged Silk Road vendor” and the “tim e of usage of the all eged Silk road purchas e” with the deaths. S.A. 446. We ass ume for purpose s of this opinion that Dr. Taff’s

62 conclusions are sufficiently sound to raise a genuine question about whether the deaths des cribed in the PSR wer e caused b y drugs purch ased on S il k Road. As explained above, h owever, Ulbr icht was not being prosec uted or punished for homici de on a theor y that he pers onally caused those deaths. No r did the fact of the deaths incre ase his offen se level under the Gui delines. The question before the district court was whether the sale of large quanti ties of drugs on Silk Road

In the sixth case, D r. Taff concluded that the cause of de ath was ingesting 61 mul tipl e drugs coupled with a pre-e xisting heart condition. The origi nal forensic repor ts concer ning that death did not factor in the pre sence of drugs other than synthetic mariju ana (obtained via Silk R oad) and did not include the hear t condition as a contributi ng cause. Senten cing amicimake a simi lar argument, clai ming that a complex array of 62 causes ar e re sponsible for dr ug-related deaths, including societalfailu res. Assuming that i s corr ect, the increas ed availabil ity of drugs is certainly one of the causes of ove rdose and other dr ug-related accidental deaths. Thus, the district court did not err in concluding that Sil k Road, which was by all account s a market-expanding drug e nterpr ise, contributed to the gene ral social costs of drug trafficking. Those harms are n umerous and include the risk of death. 114created a s uffici ent risk of death to per mit the district court to take the deaths into account in assessing the s eriousnes s of Ulbricht’s crimes when it considere d the factors listed in 18 U.S.C. § 3553(a). As with other facts re levant to sentencing, that questi on is for the district court to answer, b ased on the prepon derance of the evidence. Norman , 776 F.3d at 76. Contrar y to Ulbricht’s clai ms, the district court di d not summarily reject Dr

. Taff’s conclusions. Rather, it addresse d his repor t carefully and acknowledged the evidentiary challenges of conne cting the deaths to Silk Road. The court concluded that Dr. Taff’s pr oposed “r easonab le degree of medical certainty” standard was s impl y too high an evidentiary standard for pur poses o f including the deaths in the PSR. The cour t reasone d that it was “not asking whether the but for cause o f death is drugs purch ased on S il k Road,” but rather “whe ther ther e is a connection betwee n the purch ase of dr ugs on Silk Road and [the] death” in the

sense that the sale of those dr ugs created a r isk of death. App’x 1476. For those limi ted purpose s and judged by that standard, the circumstanti al evidence conn ecting the drug-related deaths to Silk R oad was sufficient to consider them at Ulbricht’s sente ncing. To take the stronges t example, one decede nt was found in his apartment with a package torn open. His computer

115had the Silk Road site open, with chat m essage s from the ven dor des cribing the

heroin and pr escr ipti on drug purch ase as we llas the package tr acking informati on. The tracking number matched the infor mati on on the tornpackage in the apartment. A toxicology report determined that he died of an ove rdose of heroin combined with other pr escr ipti on drugs. The fac ts connecting the other five deaths to Silk Road varied i n stren gth. The availabl e evidence was sufficient, however , to all ow the district court find by a preponder ance of the e vidence that the deaths wer e conne cted to Silk Road; there fore, the court could consider the risk of death that the site create d. Nothing in the sentencing trans cript suggests that the court considere d the information for any other pur pose. We are sensitive to the possibili ty that the evidence of the six de aths was emotional ly i nflamm atory and risked impli citly escalating Ulbricht’s resp onsibili ty from facil itating the sale of drugs to causing the deaths of s ever al drug user s. But there is no indicati on that the deaths in question played such a

63 role in the district court’s sentencing deter mination. In urging the court to

Ulbricht does not argue that the e vidence re lated to the accidentaloverdos e 63 deaths should have b een e xcluded due to its emoti onal nature; his argument is based s olely on the clai m that the evidence was irrelevant be cause the de aths were n ot sufficientl y li nked to Silk Road. 116consider e vidence of the de aths, the gover nment explained that the deaths

“il lustrate the obvious: that drugs can cause s erious harm, including death.” App’x 902. See United States v. Pacheco, 489 F.3d 40, 48 n.5 (1st Cir. 2007) (obser ving that a defendant who “engaged in the commercial trade of potent substances . . . must have known [that such trade] could have dire consequences ”). Of course , to the extent that the har ms of the drug trade we re ob vious, there was no nee d to introduce evidence of thes e particular incidents, let al one to hammer the point home with unavoi dably emoti onal victim i mpact statements by pare nts of two of the deced ents. No fede ral judge needs to be reminded of 64 the tragic consequences of the traffic in dangerous s ubstances o n the lives of

users and addicts, or of the risks of ove rdose and other r amifi cations of the most dangerous o f ill egal drugs. Those con sequences ar e among the re asons why il legal drugs are proh ibited and constitu te a principal ju stification advanced for the extr emely lengthy sentences provided by fe deral statutes and sen tencing guidelines for trafficking i n ill icit substances . Absen t reason to b elieve that a drug Ulbricht does not challenge the pro priety of those statements apar t from his 64 gener al argument that i t was procedur all y unreason able to consider the s ix deaths as r elevant to his sentence

. 117dealer’s methods we re unusually reckless, in that they enhan ced the r isk of death

from drugs he sold beyond those already inhere nt in the trade, we do not think that the fact that the ever-pr esen t risk of tragedy came to fruition i n a particular instance should enhance those se ntences , or that the inabili ty of the government to li nk a particular dealer’s pro duct to a specific death should m iti gate them. The government’s insistence on proce eding with thi s evidence ge nerated anappellate issue that has taken on a disprop ortionate focus in relation to the reasons actuall y advanced by the district court i n its lengthy and careful statement of the reaso ns for the se ntence it imposed. App’x 1509-41. We are not pers uaded, however, that the introducti on of the evidence in this case was er ror, although it may have been incautious for the govern ment to insist on prese nting it

to the district court. As already explained, it was certainly appropr iate for the district court to consider the risk of death fr om use of drugs in assessing the s eriousnes s of the offe nse con duct, one of the factors that a judge must consider in im posing sentenc e. See 18 U.S.C. § 3553(a)(2) (A). That appears to be the only way the judge in this case used the e vidence of the dr ug-related deaths. Emotionall y wrenching as the statements of the dece dents’ pare nts were , we cannot and do not ass ume that federal judges are unab le to put their

118sympathies for particular victi ms to one side and asse ss the e vidence for its

rational relati onship to the sen tencing decision. And here , the rec ord makes clear that the district court di d not use the evidence of the drug-re lated deaths to enhance Ulbricht’s sentence , either as a for mal m atter under the Gui delines or otherwise. For allthe exten sive litigati on of the pr opriety of including this informati on in the PSR, in im posing sentenc e the district court did not refer to the drug-related deaths as an aggravating factor. Indeed, the on ly m ention of that evidence at all was a passing refer ence to “facts b rought out in connection with [those] death[s ]” that “provide evidence of firs t-tim e and ex panded [dr ug] usage.” App’x 1521-22. This re fere nce occurr ed in the entirely appropr iate context of a lengthy discussion of the gene ral social harms of Ulbricht’s massive drug-trading marketplace. Id . at 1522-28. That discussion was particul arly germane to this case for sever al reasons. First, Ulbricht clai med that Sil k Road reduced the harms associated with the drug trade in seve ral ways. For ex ample, he argued that trafficking in drugs over the Internet re duced violence associated with hand-to-hand transactions and the societal sti gma of drug use, and Silk Road’s vendor r ating system ensured that customers had acce ss to better qual ity drugs and more information about the

119drugs that they were purchasing. Those ar guments prompted the district court to

reflect br oadly on the costs of the dr ug trade and discuss Silk Road’s participati on in those harms. Reas onable people may and do disagree about the social ut il ity of harsh sen tences for the distribution of controll ed subs tances, or even of cr iminal prohibiti on of their sale and use at all . It i s very p ossible that, at some future point, we willcome to regard the se policies as tragic mi stakes and adopt less punitive and more effective methods of re ducing the inci dence an d costs of drug use

. At this point

in our history, however, the democratically-elected repr esen tati ves of the pe ople have opted for a policy of prohibition, backed by

sever e punishment. That poli cy results in the routine incarcer ation of many traffickers for extende d periods of time. This case involves a defendant who stood at one re move from the trade, who did not for the most part dirty his hands with the actual possession and sale of dr ugs and other co ntraband that his site offered. B ut he did take a cut of the proceeds , in exchange f or making it easier for such drugs to be purchase d and sold, in a way that m ay well have expande d the market by allowi ng more peop le access to drugs in gr eater quanti ties than mi ght otherwise have b een available to them. In the routine

120instances of se ntencing drug sellers, the dangerous as pects of the trade are close

to the surface an d require lit tle emphasis. In thi s case, a r eminder of the consequences of facili tating such trans actions was perhap s more ne cessar y, particularlybecause Ulbricht clai med that his sit e actuall y made the drug trade safer , and he appe ared to contes t the legit imacy of the laws he violated. 65 In a footnote in his reply brief, Ulbricht raises for the first tim e an additional 65 argument: that the district court i mproperly gave him a li fe sen tence be cause of the politi cal and phil osophical beliefs that led himto start Silk Road in the first instance. Ulbricht argues that re li ance on politicalbeliefs at sentenc ing is prohibited by the Guideli nes, U.S .S.G. § 5H1.10, and the First Amendment. The district court reflected on Ulbricht’s philosophy, however , only in the course of discussing his character an d his reason s for committ ing the offense

. See18 U.S.C. § 3553(a)(1). That discussion was relevant to senten cing. Ulbricht, as the district court concluded,“viewed Silk Road both as above the law and the laws didn’t apply.” App’x 1515. He appe ared to be li eve that his per sonal views about the propr iety of the drug laws and the paramount role of indivi dual l iberty entitled him t o violate democratically-enacted cr iminal prohibiti ons. For e xample, some of his Silk Road posts “discuss the laws as the oppre ssor” an d proclaim that “each trans action i s a victory over the op pres sor.” Id. at 1516. That Ulbricht believes that drug use s hould be legali zed is not relevant to sen tencing; that he believes he is e ntitl ed to bre ak the laws that prohibit certain substances is relevant to his likel ihood of recidivism, a mandated sentencing cons ideration. 18 U.S.C. § 3553(a)(2) (C). The district court there fore did not sen tence Ulbricht base d on any proh ibited characteristic, nor did the court place more weight on that factor than the facts war ranted. Cf. United States v. Jenkins , —F.3d.—, 2017 WL 1371399 (2d Cir. Apr. 17, 2017) ( vacating a sentence as substantively unreas onable wher e the district court relied exclusively on the defendant’s “disdain for the law” in “dramat icall y increasing” a defen dant’s senten ce for child pornography offe nses) . Ulbricht’s disrespe ct for the law was simplyone factor that the district court considered in imposing sentence, along with many 121Finall y, we need look no further than the district court’s expre ss re asons

for imposing sentence to conc lude that drug-related deaths played little part in dictating the sen tence imposed. As tragic as they ar e, and as for esee able in li ght of the volume of dangerous dr ugs trafficked through Silk Road, those deaths

were ac cidents. In li ght of the overwh elmi ng evidence, discusse d below, that Ulbricht was prepar ed, like other drug kingpins, to protect his profits by paying large sums of money to have individu als who threatene d his enterp rise murdered, it would be plainl y wrong to conclude that he was se ntenced for accidental deaths that the districtcourt discussed only in passing in im posing sentenc e. Even we re we to con clude that the evidence of the S il k Road-related deaths should not have b een r eceived, any er ror would be har mless, because the

recor d is absolutely cl ear that the district court, after finding that Ulbricht commi ssioned five murders , would have im posed the s ame sentence if the evidence of the d rug-related deaths had bee n excluded. The sente ncing amiciadvance one additi onal argument: that the district court’s consider ation of the drug-related deaths violated the Fifth and Sixth Amendments because the fact of those de aths was not charge d in the Indictment others, an d was not accorde d undue weight in determini ng the sen tence. 122and prove n to the jury. “While we are not re qui red to addre ss arguments r aised

only by an amicus ,” Am. Atheists, Inc. v. Port Auth. of N.Y. & New Jersey, 760 F.3d 227, 237 n.11 (2d Cir. 2014), we do s o here in an exces s of caution. The argument is without merit under Apprendi v. New Jersey, 530 U.S. 466 (2000), and its progeny. A district court m ay consider as p art of its sentencing deter minat ion uncharged co nduct proven b y a prepon derance of the evidence as long as that conduct does not increas e either the statutory mi nimumor maximumavail able punishment. See United States v. Stevenson , 834 F.3d 80, 85 (2d Cir. 2016); United States v. Ryan , 806 F.3d 691, 693-94 (2d Cir. 2015). The S upreme C ourt has “long recognized that br oad senten cing discretion, informed by judi cial fact finding, does not violate the Sixth Amendment.” Alleyne v. United States , 133 S. Ct. 2151, 2163 (2013). Here , the six drug-re lated deaths (and more importantly, Ulbricht’s attempted mu rder s for hire ) were uncharged fac ts that did not increas e either the statutory twenty-year minimum or the maximu m li fe sen tence applicable to the crimes of which he was found guilty, beyond a reas onable doubt, by the jury. Thus, the district court did not vi olate the Constituti on when it found by a prepon derance of the evidence that the s ix deaths were connected to S il k Road

123and that they were relevant to Ulbricht’s senten ce be cause they wer e part of the

harm that the site caused. In sum, we mi ght not, in the prosecutors ’ shoes , have chose n to offer this evidence at sen tencing, or have admitted it as district ju dges. We con clude, however , (1) that the district court di d not clearly err whe n it found by a prepon derance of the evidence that the s ix deaths were connected to S il k Road; (2) that itdid not abuse its discretion in determini ng that it w as approp riate to consider those acts as bear ing on the ser iousness of the n arcotics offense s of which Ulbricht was convicted, one of many factors the district court was required to consider in exe rcising its di scre tion under § 3553(a); and (3) that the evidence in qu estion in fact played a m inim al role, if any, i n the actual sentencing, and that in li ght of the reas ons given by the district court for its senten cing decision, we can be ab solutely certain thatthe same sen tence would have be en imposed if the evidence had n ot been r eceived. Ulbricht’s sen tence was the refor e not procedur all y unreason able. B. Substantive Unreasonableness “We will. . . set aside a district court’s substantive [senten cing] determination only in exce ptional cases where the trial court’s decision cannot be

124located within the range ofpermissible decisions.” Cavera, 550 F.3d at 189

(emphasis and internal quotat ion marks omi tted). Our re view is “deferen tial,” and this Court does “not consider what weight we would ourselves have given a particular factor.” Rigas , 583 F.3d at 122. “Rather, we consider whether the factor, as exp lai ned by the district court, can bear the we ight assigned it u nder the totali ty of the circumstances in the case.” Id. Our role in “patrolling the boundaries of r easonab leness” is modest. United States v. Broxmeyer , 699 F.3d 265, 289 (2d Cir. 2012) (alterations and internal quotati on marks omitt ed). Accordingly, we “wil l set aside only those outli er se ntences that reflect actual abuse of a district court’s consider able senten cing discretion.” United States v. Messina , 806 F.3d 55, 66 (2d Cir. 2015). In li ght of the defer ential standard of review, we canno t say that Ulbricht’s li fe sen tence was s ubstantively unreasonable. The district court identifi ed numerous facts that made Ulbricht’s case ex traordinary, in its view render ing a li fe sen tence “sufficient, but not greater than neces sary, to comply wi th the purpose s” of sen tencing. 18 U.S.C. § 3553(a). The court descr ibed the crime as a “planned, comprehe nsive, and deliberate s cheme . . . which posed s erious danger to public health and to our communities.” App’x 1511-12. Silk Road was a

125“worldwide criminal drug enterpr ise with a m assive geograp hic scope.” Id. at

1512. The fact that Ulbricht operated the site from be hind a computer, rather than in person like a more pr ototypicaldrug kingpin, does not make his crime less serious or less danger ous. Moreover , Silk Road uni quely expanded the drug market by providing an easy aven ue for pe ople to become first-time drug users and dealers. B ecause dr ugs were shipped to customers in the mail, Sil k Road brought “drugs to communiti es that pre viously m ay have had no acce ss to such drugs . . . in such quantit ies.” Id. at 1522. The quanti ty and nature of the dr ugs sold on Silk Road are staggering. According to the PSR, from 2011 through 2013, Silk Road customers transacted in approximately $183 mi ll ion worth of ill egal drugs. At the tim e the gover nment shut down Silk Road on October 2, 2013, ther e were approximately 13,802 li stings for controlled substance s on the web site. Of those listi ngs, ther e were 643 li stings for cocaine-bas ed products, 305 for LSD pr oducts, and 261 for methamphetamine products. The dr ugs were sold mostl y for individu al, personal use, b ut some drugs such as heroin and cocaine we re also available in “m ulti -kil ogram quanti ties.” PSR ¶ 26. The available drugs were not limi ted to heroin, nar cotics, synthetic mariju ana, and other dangerous b ut recre ationalsubstances . For

126example, after be ing tol d that cyanide was “the most wellknown assass inati on

suicide [ sic ] poison out there,” Ulbricht allowed vendors to se llit on Sil k Road despite its singul ar, deadly purpose . App’x 1519. As the district court noted, despite earlier pr otestations that Sil k Road would not al low the sale of products that could be used to infli ct deliberate harm on other s, it took Ul bricht all of si x minut es to decide “that it i s okay to sell cyanide,” id ., in exchange f or the customary cut of the procee ds. The drug offen ses alone—ignoring all other ill icit materials sold on the site —yielded a calcul ated offense level of 50. Of that calcu lati on, only two levels 66 As explained, Silk Road also trafficked i n ill egal goods such as counter feit 66 identifi cation documents and computer hacking tool s and se rvices. Whenthe government sh ut down Silk R oad, there were 156 listings for forge d identity documents on the site. The spe cific com puter hacking tools avail able included software for compromising u sern ames and passwor ds of electronic accounts, including emailand Facebook; Re mote Access Tools (“RATs”) that all ow hackers to obtain remote access to a victim’ s computer, including turning on and using the computer’s web cam; keyloggers, which all ow a user to monitor keystrokes inputted by a victi m to di scer n their passwor ds and other sensitive informati on; and Distributed De nial of Service (“DD oS”) tools, which all ow hackers to disable websites by flooding networks with mali cious Internet traffic. Silk R oad also offere d money laundering services thr ough vendors who sold U.S. curre ncy and anonymous debit cards. Bec ause the adjusted offen se levels for thos e groups of offense s were substantiall y lower than the offen se level for the dr ug group, they did not contribute to Ulbricht’s over alloffense level. In assessing the subs tantive reaso nablenes s of the se ntence imposed, howe ver, it is wellto remember that the sentenc e encompass ed Ulbricht’s role not only in the distributi on of controlled 127are attributable to Ulbricht’s “credible threats ofdirected violence” associated

with the mu rder s for hire . PSR ¶ 94. Thus, even without considering that enhance ment, the drug convictions yiel ded an offen se level of 48, which is higher than the maximumoffense level recognized by the Guidelines, for which a sentenc e of life im prisonment is recommended e ven for s omeone who, like Ulbricht, has no prior cr iminal convicti ons. Ulbricht does not challenge the accuracy of the Guideli nes calculati on or of the f act-findings on which i t is based. That the sentence imposed accorded with the Guidel ines rec ommendati on does not automatical ly render it reasonable. See United States v. Dorvee, 616 F.3d 174, 182 (2d Cir. 2010). The Guideli nes ar e, howeve r, themselves a factor that Congr ess has directed district courts to consider. 18 U.S.C . § 3553(a)(4)(A). Moreover , as the cons idered judgment of the United States Se ntencing Commission, they bear on the other factors that Congre ss has r equired courts to evaluate, incl uding the need to re flect the seriousne ss of the offe nse, id. § 3553(a)(2)(A), to provide adequate deterr ence, id. § 3553(a)(2)(B), and, be cause they are co nsidered b y alljudges throughout the feder al system, the need to

substances , but in a wi de variety of other c rimi nal offenses as well.

128“avoid unwarranted se ntence dispar iti es among defen dants with sim il ar re cords

who have be en found guilty of si mil ar conduct,” id. § 3553(a)(6). Accordingly, whil e a life sentence for se ll ing drugs alone would gi ve pause, we would be har d put to find such a sentence b eyond the b ounds of

reaso n for dr ug crimes of this magni tude. But the facts of this case involve much 67 more than simply faci li tati ng the sale of nar cotics. The district court found by a prepon derance of the evidence that Ulbricht commissioned at l east five murders in the course of p rotecting Silk Road’s anonymi ty, a findi ng that Ulbricht does not challenge in thi s appeal. Ulbricht discussed those anticipated murders 68 callou sly and casuall y in his journal and i n his communi cations with the

Note that such a sen tence is mandatoryunder fe deral law for selling j ust five 67 kil ograms of cocaine after two pr ior convicti ons for anyfelony narcotics offens e, see21 U.S.C. § 841(b )(1)(A), and the Supr eme Cour t has upheld against constituti onal chall enge a mandatory se ntence of life imprisonment for selling 650 grams of cocaine, Harmelin v. Michigan , 501 U.S. 957 (1991). Ulbricht does not mention his orders for the commission of those murders until 68 his reply brief. Eve n there , he does not argue that the district court erre d in concluding that

he deliberately commissioned those murders; r ather, he claim s instead only that the mu rder s did not support a life sentence b ecause the y did not actuall y take place. But in evaluating Ulbricht’s char acter and dange rousne ss, the most relevant points are that he wan ted the murders to be commit ted, he paid for them, and he be li eved that they had b een car ried out. The fact that his hired assas sin may have defrauded h im does not reflect positivel y on Ulbricht’s character . Commissioni ng the murders signifi cantly ju stified the li fe sen tence. 129purported assassin Redand white. For example, in connection with the first hit, he

wrote to Redandwhite that “FriendlyChemist is a l iabil ity and Iwouldn’t m ind if he was ex ecuted.” Tr. 1822. In the cours e of negotiating the price for the killing, DPR claim ed that “[n]ot long ago, I had a cl ean hit done for $80k,” id. at 1883, but that he had “only ever commi ssioned the one other hit, so I’m sti lllearning this market,” id

. at 1884. He then paid $150,000 in Bitcoi ns for the murder, and he

rece ived what purported to be photographic documentation i f its compl etion. Ulbricht then wrote in his journal that he “[g]ot word that the blackmai ler was

exec uted,” id. at 1887, before returning quickl y to other tasks ass ociated with running the site. In negotiating the other four kill ings, Ulbricht ini tial ly resisted mult iple murders. He instructed Redandwhite to “just hit Andrew [use rnames Tony76 and nipplesuckcanuck] and leave it at that.” Id. at 1897. Redandwhite said he could do i t for “150 just li ke last ti me,” but that he would not be able to recover any of DPR’s money if he kill ed only one per son be cause he would have to commi t the murder outside of the victim ’s home or office whe re he stored his funds. Id. If Ulbricht wanted himto recover money, the self-prof esse d assass in claim ed, he would have to killnot only Tony76, but al so his three associates. DPR

130resp onded that he would “defer to [Redandwhite’s] better judgment and hope [d]

[to] recover some assets” f rom the hit. Id. at 1899. He then se nt $500,000 in Bitcoi ns, the agr eed-upon pr ice for four killings, to Redandwhite. As the district court stated in discussing Ulbricht’s journal entries concern ing these projec ted murders, his wor ds are “the words of a man who is callous as to the consequences or the har m and suffering that [his actions] may cause others.” App’x 1521. The rec ord was more thansufficient to support the district court’s reliance on those attempted murders in sentencing Ulbricht to li fe in prison. The attempted mu rder s for hire separ ate this case from that of an ordinary dr ug dealer, re gardless of the quantity of drugs involved i n the offen se, and lend further s upport to the district court’s finding that Ulbricht’s conduct and character were e xceptionally destructive. That he was able to distance him self from the actual vi olence he p aid for by using a computer to order the kill ings is not mitigating. Indeed, the cr uelty that he displ ayed in his casual and confident negotiati ons for the hits is unnerving. We thus cannot say that a life sentence was outside the “range of pe rmissible decisions” under the circumstances. Cavera , 550 F.3d at 189.

131Ulbricht’s arguments on appeal have r hetorical power be cause of the s heer

magnitude of his senten ce, but they do not pr ovide a legal basis for vacating that sentenc e as sub stantively u nreas onable. He con tends that the district court ignored the letters s ubmit ted on his beh alf, thus fail ing to consider his positive contributions to his fami ly and society as wellas his potential producti vity should he be r eleased fr om prison. To the contrary, however , the district court “read e ach and eve ry one of [ the letters] with care,” some “more than once.” App’x 1534. Recognizing that the letters were “beautiful” and “profoundly moving,” the district court obser ved that they reve al Ulbricht’s human complexity. Id. at 1534-35. Nothing in the record s upports the claim that the district court fai led to recognize the importance of the letters , incorrectly discounted Ulbricht’s more favorable ch aracteristics, or other wise inappropriately dismi ssed the ir role in its sentencing determination. Simi larly, Ulbricht’s argument that the district court ignored his contention that SilkRoad reduced the harmful effects of drug cr imes must be rejected. The district court thoroughly di scussed D octor X’s role at Silk Road and Ulbricht’s claim s that the site reduced violence, ove rdose s, and other harms associated with drug trafficking, and concluded that they were unpe rsuasive. We s ee no e rror in

132its analysi s, and Ulbricht’s arguments conce rning harm re duction do not render

his sentence substantively unreasonab le. Ulbricht also cl aims thatthere is an unwar ranted disparity betwee n his sentenc e and the appr oximatel y 17-month sentence that Peter Nash, a S il k Road admini strator, r eceived. Again, however, the district court consider ed the arguments concer ning Nash’s se ntence and f ound them to be irrelevant to Ulbricht’s crime because N ash was a low-level site administrator who pleaded guil ty and cooperated with the gover nment. Along those same lines, Ulbricht notes that Silk Road drug dealers re ceived lower sen tences than h e did. For example, one such d rug dealer r eceived a ten-ye ar sen tence. The fact that different peo ple involved wi th the site rece ived dramatical ly l ower se ntences does not mean that Ulbricht’s own sen tence was s ubstantively unreasonable on the indivi dual facts of his case. Ulbricht was the creator and head administrator 69 of the site. That fact alone distinguishes his case f rom that of any indivi dual sell er or employee who use d or worke d for the site. Ulbricht profited from eve ry sale

In his reply, Ulbricht refer ences other instances in which people involv ed with 69 Silk Road (and i ts apparen t reincarnation, Silk Road 2.0) received significantl y lower senten ces. Ulbricht does n ot provide sufficient detailabout those indivi duals’ conduct, however, to per mit meaningful com parisons with his case. 133on Silk Road, and he facili tated the acts of each dr ug dealer and drug

organization that used it . Moreover , he attempted to commi ssion at least five murders to pr otect his crimi nal enterpr ise. Those facts r ender his case disti nguishable from those who committ ed other crimes using Silk R oad or otherwise facilit ated its operation. Ulbricht next reiterate s his argument that he was more like someone running a crack house than like a drug ki ngpin because he cre ated the online platform that others used to sell drugs and was not himself a drug dealer. That 70 argument also understates the vast extent of S il k Road’s drug market, which had thousands of customers and trafficked in about $183 mi ll ion in i ll egal drugs. People may differ about whether “r espe ctable” people who, acting as prope rty

owners , money launderer s, or other facili tators of crime for pe rsonal gain are less guil ty than those who per sonally handle the narcotics. We cannot fault the district court for rejecting the argument that Ulbricht’s contribution to the narcotics trade was inhe rently less culpable than that of the dealers wh o paid him to use Silk Road to com plete their transactions.

Ulbricht did selldrugs on S il k Road for at least some brief pe riod of tim e, when 70 he gre w and sold hallu cinogenic mushrooms to drum up i nteres t in the site. 134Both the sente ncing amici and Ulbricht further con tend that the district

court placed too much weight on the notion of general deterr ence in meting out the life sentence. S pecificall y, Ulbricht fears that re sorting to “gener al deterre nce withoutany confining principles . . . guarantees that [the se ntence] will create disparity.” Appell ant Br. 139. Amicialso obser ve that academic studi es counse l against placi ng too much emphasis on gener al deterre nce in sente ncing because

sever e criminalpunishments do not actuall y decre ase either supply or demand for ill egal drugs. Further , according to amici, the threat of a long sen tence does not deter cr iminal conduct more effectively than the threat of a shor ter se ntence. In his reply, Ulbricht identi fies sever al l ucrative dark markets that have emer ged since Silk Road’s demise in 2013. I n his view, the existence of mul tipl e copycat Tor-base d il legal m arketplaces pr oves that gene ral deterr ence is illu sory and that the district court placed too m uch weight on that factor. Although those arguments have some s upport among scholars and

rese archer s, the abilityof a senten ce to “afford ade quate deterren ce to criminal conduct” is a factor that district courts are requiredby Congr ess to cons ider in arriving at the appropr iate sentence. 18 U.S .C. § 3553(a)(2)(B); see United States v. Tran , 519 F.3d 98, 107 (2d Cir. 2008). Co ngres s, moreover , has not concluded that

135the per sistence of nar cotics crimes is a reason to abandonthe effor ts to deter

them by lengthy sentence s. The district court obser ved that “gener al deterre nce plays a particul arly im portant role” in Ulbricht’s case be cause Silk Road is “withoutserious pr ecede nt” and gener ated an unusually l arge amount of public interest. App’x 1532-33. The court thus carefully analyzed the role that gener al deterr ence played in Ulbricht’s indivi dual case. At the same tim e, it is evident from the sen tencing transcript that gener al deterre nce was “just one e lement in the [district court’s] analysis,” id. at 1533, and the district court considered many other factors befor e sen tencing Ulbricht to l ife in prison. Thus, the factor of gener al deterre nce, “as e xplained by the district court, can bear the weight assigned it under the totality of circumstances in this case.” Rigas , 583 F.3d at 122. Finall y, Ulbricht and amicipoint out that li fe sen tences ar e rar e in the feder al system, typi callyrese rved for egregious violent crimes, thus rende ring Ulbricht’s sentence substantively unreasonab le. Moreover , according to amici, 71 li fe sen tences ar e normally i mposed in cases whe re that is the district judge’s only sentencing option. Thus, they claimthat Ulbricht’s li fe sen tence is

Amicialso clai m that Ulbricht’s life sentence viol ates the Eighth Amendment’s 71 ban on cr uel and unusual puni shment. That argument is plai nly incorrect in li ght of binding Supreme C ourt prece dent to the contrar y. See Harmelin , 501 U.S. 957. 136substantively unreasonab le in the context of the fede ral system, where li fe

sentenc es are particularlyrare for those with no criminal history who are convicted of drug crimes. 72 We agree with Ulbricht that li fe sen tences ar e extr aordinary and infrequent, which is as itshould be. But the rar ity of l ife sentence s does n ot mean that the im position of such a sentence in this case is substantively unreasonable under our law. Each case must be consider ed on its own facts and in light of all of the circumstances of a par ticul ar offen se as we llas other r elevant conduct, which, in this case, includes five att empted murders for hire. As we h ave descr ibed, the district court carefull y considere d Ulbricht’s offense , his perso nal characteristics, and the contex t for his crimes, rec ognizing that only exceptional cases justify such a seve re se ntence. Although we might not have im posed the s ame sentence

In his reply, Ulbricht raises a distinct but related argument for the first tim e. He 72 argues that “concur rence s from Supr eme Cour t opinions and dissents from denials of certiorari suggest[] that judici al factfi nding viol ates a defe ndant’s constituti onal right to a j ury trial where the factfinding rende rs r easonab le an otherwise sub stantively u nreas onable sen tence.” Reply Br. 60. For that proposition, he cites United States v. Hebert, 813 F.3d 551, 563 (5th Cir. 2015), cert. denied, 137 S. Ct. 37 (2016), Jones v. United States , 135 S. Ct. 8 (2014) (S calia, J., dissenting from denial of certiorari), and United States v. White, 551 F.3d 381, 386 (6th Cir. 2008) (Merr itt

, J., dissenting). His argument, however , has no suppor t in existing law. 137ourselves in the first instance, onthe facts of this case a life senten ce was “within

the range of permissible decisions” that the district court coul d have re ached. Rigas , 583 F.3d at 122. We do not re ach our conclusion light ly. A li fe sen tence is the se cond most 73

sever e penalty that may be im posed in the fe deral criminaljustice system. “The size of [Ulbricht’s] senten ce alone [ther efore ] counsels our car eful, searching review of it.” United States v. Brown , 843 F.3d 74, 85 (2d Cir. 2016) (Sack., J., concurring). C ourts have the power to conde mn a young man to di e in prison, and judges must exer cise that power only in a smallnumber of cas es after the deepe st thought and reflection. Of course , any “senten cing proceeding is a solemn occasion at which the judge has the weighty duty of determini ng the fate

The life sentence is par ticul arly sever e bec ause, as in all federal cases, Ulbricht 73 wil l never b e eligibl e for par ole. Unli ke state sen tences in jurisdicti ons per mit ting a sentenc e of, for e xample, “25 years to life,” there is no automatic recons ideration of this sentence, or of whether an offende r has r eformed, after any lengthy period of incarcer ation. We note that, particul arly in the case of a young offender , the prisone r willallbut certainly change (for b etter or wor se) after many years of incarceration. In a system without parole, however, a sentenc ing court is forced to exe rcise its best judgment to predict whether a sentenc e of life im prisonment or one of 25, 30, or 50 year s is required to serve the purpose s of sen tencing, without the option of defer ring that judgm ent to a point at which the effects of incarce ration, and the passage of tim e, willbe more apparen t. 138of another h uman being.” United States v. Alcantara , 396 F.3d 189, 199 (2d Cir.

2005). We must be es peciall y sensitive to that dutywhere the most sever e sentenc es are in qu estion. The district court gave Ulbricht’s sentence the thorough consider ation that i t required, reviewing the voluminous sen tencing submissions, analyzing the factors required by law, and carefully weighing Ulbricht’s mi tigat ing arguments. The extraor dinarilydetailed sentencing transcr ipt shows that the district court appreciated its i mportant respon sibili ty in considering a sen tence of suchmagnitude and carr ied out that responsibili ty with care and p rudence . Under the law, we cannot say that it s decision was substantively unreasonab le. CONCLUSION For the for egoing reason s, we AFFIRM the judgm ent of the district court in allresp ects.

139