1 15-0024-cr United States v. Bennett
1 UNITED STATES COURT OF APPEALS 2 FOR THE SECOND CIRCUIT 3 4 August Term, 2015 5 6 (Argued: April 28, 2016 Decided: Octo ber 6, 2016 Amended: October 7, 2016) 7 8 Docket No. 15-0024-cr 9 10 11 UNITED STATES OF AMERICA, 12 13 Appellee
, 14 15

– v. – 16 17 DARRELL BENNETT, also known as Sealed Defendant 1, 18 19 Defendant-Appellant
, 20 21 22 Before: WALKER, CALABRESI, and HALL, Circuit Judges

. 23 24 Defendant-Appellant Darrell Be nnett appeals his below-Guidelines sentence of 84 25 months’ imprisonment after pleading guilty to an information charging him with one count 26 of possession of child pornog raphy under 18 U.S.C. § 2252A(a)(5)(B). Bennett contends that 27 the District Court (Sullivan, J. ) erred by applying in its calculation of the Guidelines range a 28 five-level enhancement under U.S.S.G. § 2G2.2(b)(3)(B) for distribution of child 29 pornography “for the receipt, or expectation of receipt, of a thing of value” based on 30 Bennett’s use of a peer-to-peer file-sharing system to exchange pornography. Although we 31 conclude that Bennett’s specific use of file sharing warranted this enhancement, we hold 32 that the District Court erred in calculating th e Guidelines sentence by failing to recognize 33 that, under U.S.S.G. § 5G1.1(a), where the st atutory maximum falls below what would be 34 the Guidelines range, the statutory ma ximum becomes the Guidelines sentence. 35 Accordingly, we REMAND for resentencing. 36

37 COLLEEN P. CASSIDY, Federal Defenders of New 38 York, Inc., Appeals Bure au, New York, New York, for 39 Defendant-Appellant 40 41 EUN YOUNG CHOI (Adam S. Hickey, on the brief ), 42 Assistant U.S. Attorneys , for , Preet Bharara, United States 432 Attorney for the Southern District of New York , New York, 1 New York, for Appellee 2 3 4 5 CALABRESI, Circuit Judge : 6
Defendant Darrell Bennett appeals his sente nce of 84 months’ imprisonment entered 7

in the United States District Court for the Southern District of New York (Sullivan, J .) after 8
he pled guilty to one count of possession of child pornography under 18 U.S.C. § 9
2252A(a)(5)(B). Bennett argues that the District Court erred in calculating the Guidelines 10
range by imposing a five-level enhancement under U.S.S.G. § 2G2.2(b)(3)(B) for 11
distribution of child pornography “for the rece ipt, or expectation of receipt, of a thing of 12
value” based on his use of a peer-to-peer file -sharing system to trade pornography. While 13
we ultimately conclude that the manner in wh ich Bennett used file sharing warranted this 14
enhancement, we hold that the District Court erred in describing the Guidelines range as 15
above the statutory maximum for the charge. We therefore remand for resentencing. 16

BACKGROUND 17

Bennett pled guilty to an information ch arging him with one count of possession of 18
child pornography under 18 U.S.C. § 2252A(a)(5 )(B). Investigators with the Department of 19
Homeland Security (“DHS”) identified Bennett as part of a larger investigation into the 20
distribution of child pornography via the intern et. In particular, DHS was investigating peer21
to-peer file-sharing services, which allow user s to download files stored on other users’ 22
computers via the internet. On November 15, 2012, an undercover agent contacted Bennett 23
through the file-sharing network GigaTribe an d requested access to the files stored on 24
Bennett’s computer. Bennett provided the pa ssword (which was “fun”), and the agent 253 downloaded six videos from Bennett’s computer that contained child pornography. The 1

undercover officer used software to determine the Internet Protocol address of Bennett’s 2
computer, which was then used to identify Bennett’s residence. 3

The Offense Conduct. On February 22, 2013, DHS agents executed a warrant to 4
search Bennett’s Manhattan apartment for chil d pornography. The agents seized Bennett’s 5
computer, which was later found to contain 208 still images of child pornography and 6
approximately 79 videos of child pornography. These images and videos included graphic 7
depictions of adult men engaging in oral an d anal intercourse with prepubescent boys. 8
Forensic analysis of Bennett’s computer also es tablished that he had shared his password 9
approximately 221 times with approximately 174 different users on GigaTribe. 10
In many cases, Bennett shared his password with other users in exchange for their 11
passwords (password-for-password, or “pass-fo r-pass” exchanges). For instance, Bennett 12
engaged in one such exchange with another user: 13
[Bennett]: whats up? 14
[Bennett]: im in teens boys and stuff. 15
[Bennett]: what about u 16
[Other User]: 3 to 15 b//b, m//b b//g 1 17
[Other User]: pass for pass? 18

1 At sentencing, the Government explained th is portion of the discussion as Bennett

stating that he was interested in pornograph y involving “teens, boys and stuff” and the

other user describing his own interest in pornography involving “people . . . between the

ages of three [and] fifteen” and “boy on boy,” “man on boy,” and “boy on girl”

pornography. App. 229. This characterization was not contested by Bennett’s counsel.4 [Bennett]: yea 1
[Bennett]: mine is fun 2
[Other User]: lol 3
[Other User]: mine is; FFK25 4
[Bennett]: cool 5

... 6
[Bennett]: im trying to dow nload but its not starting 7
[Other User]: because I have a huge amounts of people in que as I have possibly too 8
many files...sorry...be patient s I rarely go offline 9
[Bennett]: ok cool 10

11

1:14-cr-203-1 Doc. 29, Ex. D, at 4. Bennett tr aded passwords with users on other occasions, 12

such as: 13
[Other User]: wanna trade passes? 14
[Bennett]: yea 15
[Bennett]: mine is fun 16
[Bennett]: whats yours 17
[Other User]: thanks 18
[Other User]: t 19

20

Id. at 3. And: 21
[Other User]: would be interested in trading passes if you are 22
[Bennett]: yea I am 235 [Bennett]: yea 1
[Bennett]: mine is fun 2
[Other User]: mines [] 3
[Other User]: thanks for that 4
[Bennett]: thanks 5

6

Id. at 9. 7
Bennett was arrested and charged with the receipt and distribution of child 8
pornography, in violation of 18 U.S.C. § 2252A (a)(2), in addition to possession of child 9
pornography, in violation of 18 U.S.C. § 2252A(a)(5)(B). On March 25, 2014, however, 10
Bennett waived indictment and consented to the filing of an information that charged him 11
solely with the possession count. And, on Sept ember 5, 2014, Bennett pl ed guilty before the 12
District Court (Sullivan, J .) to the possession count of the Information. 13

The PSR. The Presentence Report (“PSR”) prepared by the Probation Office 14
determined the Guidelines range to be 97 months’ to 120 months’ imprisonment. In 15
calculating this range, the PSR found that the base offense level was 18 and applied the 16
following sentencing enhancements: (1) a tw o-level increase because Bennett possessed 17
pornography that “involved a prepubescent mino r or a minor who had not attained the age 18
of 12 years”; (2) a two-level increase because the offense involved “distribution other than 19

distribution described in subsections A thr ough E” of 18 U.S.S.G. § 2G2.2 (b)(3); 2 (3) a four- 20

2 Section 2G2.2.(b)(3) provides for a sentence enhancement where the offense

conduct involves the distribution of material involving sexual exploitation of a minor. The

degree of that enhancement, however, depends on the nature of the distribution at issue.6 level increase because Bennett possessed pornography that “involved material that portrays 1
sadistic or masochistic conduct or other depic tions of violence”; (4) a two-level increase 2

because “the offense involved the use of a computer or an interactive computer service”; 3
and (5) a five-level increase because the offe nse involved 600 or more images. PSR ¶¶ 25–37. 4
This resulted in an adjusted offense leve l of 33, which was reduced by three levels for 5
acceptance of responsibility fo r a total offense level of 30. 6

The total offense level of 30, together with Bennett’s crimin al history category of I, 7
resulted in a Guidelines range of 97 months’ to 121 months’ imprisonment. But, because the 8
Guidelines-range maximum was limited by the statutory maximum of 120 months’ 9
imprisonment, the Probation Office found th at the Guidelines counseled a term of 10
imprisonment of 97 to 120 months. 11

Subsection (A) of that Section prov ides for an enhancement of at least five levels depending

on the retail value of the material at issue where the distribution was “for pecuniary gain.”

Subsection (B) similarly imposes a five-level enhancement where the distribution was “for

the receipt, or expectation of receipt, of a thing of value, but not for pecuniary gain.”

Subsection (C) provides for a five-level e nhancement where the distribution was “to a

minor.” Subsection (D) requires a six-level enhancement for distribution intended to

“persuade, induce, entice, or coerce” a minor to engage in illegal activity, except where

that illegal activity constitutes “prohibited se xual conduct,” which is subject to a sevenlevel enhancement under Subsection (E). Fi nally, if the offense conduct involved

distribution not described in Subsections (A ) through (E), Subsection (F) provides for a

two-level enhancement. The PSR recommended this two-level enhancement under Section

2G2.2(b)(3)(F).7 The PSR also detailed Bennett’s difficult upbringing. His father physically abused 1
his mother and frequently took Bennett, from about the age of five, to brothels, strip clubs 2
and sex shops in Baltimore. Although Bennett’ s mother left his father when Bennett was 3
five years old, Bennett continued to see his fath er after the divorce. This typically occurred 4
while his father was in the company of women or consuming alcohol. Moreover, when he 5
was seven years old, Bennett was sexually mo lested by a 15-year-old male babysitter. These 6
experiences led him to be focused on (and en gage in) sexual behavior from an extremely 7
early age. Such behavior continued throu ghout high school and college. 8
After finishing law school, during a period of depression, he began to use GigaTribe 9
to view a broad range of pornography, in cluding bestiality, group sex, and child 10
pornography. On this basis, Bennett’s psychiatri c expert concluded that his interest in child 11
pornography was not a product of a real predil ection for minors but rather was “borne out 12
of his own experiences with childhood sexual behavior and represents an unresolved 13
psychological matter that can be addre ssed through psychotherapy.” PSR ¶ 71. 14
Despite this troubled—and, specifically, sexually troubled—background, Bennett was 15
tremendously successful. After high school, Bennett attended Morehouse College, from 16
which he graduated as valedict orian. He then went to the Harvard Law School, graduating 17
in 2010 as a Class Marshal. Bennett was, ho wever, unable to find a legal job after 18
graduating from law school and became severe ly depressed as a result. He briefly sought 19
treatment at Harlem Hospital, where he was di agnosed with depression and bipolar disorder 20
with manic depression and schizophrenia an d was prescribed Seroquel for insomnia. 21
Bennett did find a job as an adjunct professo r of criminal justice at ASA College in 22
Brooklyn, where he worked from early 2011 until late 2013. He then began work as a 238 substitute and adjunct professor at Boroug h of Manhattan Community College. This job 1
continued until his sentencing. 2
The PSR ultimately recommended a Guidelines sentence of 97 months’ 3
imprisonment. This was based, in part, on skepticism toward the conclusions of Bennett’s 4
psychiatric expert that Bennett was not sexually attracted to minors and should not be 5
diagnosed with pedophilia. The recommendation also demonstrated the “serious concerns 6
[of the Probation Office] about [Bennett’s] risk to re-offend and his ability to be safely 7
managed in the community.” Id. at 23. 8
The Sentencing Submissions. On December 5, 2014, Bennett submitted a 9
sentencing letter that requested a sentence of three years’ probation. The submission argued 10
that this sentence was appropriate given (1) Bennett’s unusual promise and success, 11
especially in light of his childhood, (2) Benne tt’s traumatic sexual history, which suggested 12
that Bennett did not pose any danger to the community, and (3) Bennett’s abstention from 13
viewing child pornography after his computer had been seized by agents in February 2013. 14
On this basis, Bennett, and the expert who supported his submission, argued that he was 15
“an excellent candidate for supervision, trea tment and rehabilitation.” App. 108. Bennett 16
did not challenge the PSR’s calcul ation of his Guidelines range. 17
On December 12, 2014, the Government, in its own sentencing submission, agreed 18
that a below-Guidelines sentence was appropriat e for essentially the same reasons advanced 19
by Bennett, but asked for a “significant incarcer atory sentence” given the seriousness of the 20
offense conduct. App. 185. Moreover, as to th e calculation of the Guidelines range, the 21
Government argued that a five-level enhanceme nt under U.S.S.G. § 2G2.2(b)(3)(B), instead 22

of the two-level enhancement under U.S.S.G. § 2G2.2(b)(3)(F), applied. This was because 239 distribution “for the receipt, or expectation of receipt, of a thing of value, but not for 1
pecuniary gain,” instead of simple distribu tion, was involved. The more significant 2
enhancement was appropriate, the Govern ment contended, because Bennett “gave his 3
password to others in anticipa tion of receiving their passwo rds in turn, [so] that Bennett 4
could gain access to other user’s . . . shared folders and the child pornography contained 5
therein.” App. 195. 6
The Sentencing. Bennett was sentenced by the Distri ct Court on December 19, 2014. 7
After summarizing the materials received and confirming that there were no objections to 8
the facts presented in the PSR, the District Co urt turned to the calculation of the Guidelines 9
range. In particular, the District Court found that Bennett’s interact ions with users on the 10
site—where there was an “exchange of passwords, after a brief exchange as to the interests 11
of the users,” App. 231—warranted the impositi on of the five-level enhancement under 12
U.S.S.G. § 2G2.2(b)(3)(B). This resulted in a to tal offense level of 33 an d, based on this, the 13

District Court found: 14
There’s no dispute that Mr. Bennett is in Cr iminal History Category I, so according 15
to the guidelines, the range is 135 to 168. Th at’s about 11 years to 14 years or so. So 16
11 to 14 years, which is a long time. 17

App. 232. 18
After hearing argument from Bennett and the Government, the District Court went 19
on to impose sentence: 20
The maximum here is ten, the guidelines ar e 11 to 14. I’m not moved by that. I think 21 it’s worth noting just because I’m required to note it, but from the moment I read the 22 facts of this case, it seemed to me that eig ht to ten is not inapprop riate, 11 to 14 is not 23 inappropriate. It’s not that I’m callous, it ’s not that I have no sense as to what that 24 time means to a young man like you who has so much promise, but it’s that the 2510 penalty has to send a message of moral o utrage and a message of conviction that 1 children matter. 2
So, look, I have to credit the goodness in you. The fact that I don’t think you’re a 3 predator, you are distinguishable from ma ny other defendants who are charged with 4 crimes like this, I’m prepared to come down below the guidelines, down below the 5 statutory maximum of ten, which would be within the guidelines range, but it seems 6 to me that a sentence of seven years is as low as I can go without insulting the 7 victims in this crime. 8
App. 281. The District Court then imposed a sente nce of seven years’ incarceration, to be 9
followed by five years of supervised releas e. The District Court also ordered special 10

assessment of $100. 11
Bennett appealed. 12

DISCUSSION 13

Bennett’s principal contention on appeal is that the District Court erred in applying a 14

five-level enhancement for distribution “for the receipt, or expectation of receipt, of a thing 15
of value” under U.S.S.G. § 2G2.2(b)(3)(B). We ultimately conclude that this enhancement 16

was warranted in Bennett’s case. But we also hold that the District Court incorrectly 17
calculated the applicable Guidelines range by failing to recognize that the Guidelines range 18
was reduced to the statutory maxi mum under U.S.S.G. § 5G1.1(a). 19

A. 20

We review sentences using a “defere ntial abuse-of-discretion standard.” United States 21

v. Cavera , 550 F.3d 180, 189 (2d Cir. 2008) (en ban c) (internal quotation marks omitted). 22
This review has both procedural and substantive components. Id. First, we scrutinize 23
whether the District Court has committed “signi ficant procedural error, such as failing to 24
calculate (or improperly calculating) the Guid elines range, treating the Guidelines as 2511 mandatory, failing to consider the § 3553(a) fa ctors, selecting a sentence based on clearly 1
erroneous facts, or failing to adequately explain the chosen sentence . . . .” Gall v. United 2

States , 552 U.S. 38, 51 (2007). An error applying the Guidelines is a legal error and, as a 3
result, is reviewed de novo

. United States v. Broxmeyer , 699 F.3d 265, 281 (2d. Cir 2012). Then, 4
if there are no such procedural errors, we proceed to assess whether the sentence was 5
substantively reasonable. Gall , 552 U.S. at 51

. 6

Bennett did not challenge the calculation of the Guidelines range under U.S.S.G. § 7
5G1.1(a) at the District Court. Accordingly, we review any su ch challenges for plain error. 8

Molina-Martinez v. United States , 136 S. Ct. 1338, 1343 (2016). This requires there to be (1) an 9
error, (2) that is “plain—that is to say, clear or obvious,” and (3) which affected “substantial 10
rights.” Id. In turn, for an error to affect substanti al rights, there must be “a reasonable 11
probability that, but for the error, the o utcome of the proceeding would be different.” 12

Id. (internal quotation marks omitted). We then exercise our discretion to correct the error if 13
it “seriously affects the fairness, integrity or public reputation of judicial proceedings.” Id. 14
(internal quotation marks omitted). That said , the plain-error standard is applied less 15
“stringently in the sentencing context, where the cost of correcting an unpreserved error is 16
not as great as in the trial context.” United States v. Gamez , 577 F.3d 394, 397 (2d Cir. 2009) 17
(per curiam). 18

B. 19

Bennett contends that the District Court erred in applying the five-level increase 20
under U.S.S.G. § 2G2.2(b)(3)(B) because Benn ett’s conduct did not amount to anything 2112 “more than simple fire sharing, ” and therefore did not constitute “any particular exchange.” 1
Appellant’s Br. 32. We disagree. 2

Section 2G2.2(b)(3)(B) requires the appl ication of a five-level increase if a 3
defendant’s offense involved “[d]istribution fo r the receipt, or expectation of receipt, of a 4
thing of value, but not for pecuniary gain.” Ap plication Note 1 to that Guideline clarifies 5
that this type of distribution encompasses “any transaction, including bartering or other in6
kind transaction, that is conducted for a thing of value, but not for profit.” U.S.S.G. § 2G2.2 7
cmt. n.1. The Note defines a “thing of value,” in turn, as “anything of valuable 8
consideration,” including “child pornographic ma terial received in exchange for other child 9
pornographic material bartered in cons ideration for the material received.” Id. 10

If a defendant’s conduct involves distribution not for the “receipt, or expectation of 11
receipt, of a thing of value,” and does not ot herwise implicate any of the other forms of 12
aggravated distribution enumerated in U.S.S.G. § 2G2.2(b)(3)(A), (C), (D), or (E), a two13
level increase is applied for simple distri bution under U.S.S.G. § 2G2.2(b)(3)(F). The 14

Government does not contend that Bennett’s conduct implicates an y of these other forms of 15
aggravated distribution. Accordingly, the question before us is whether Bennett’s use of file16
sharing software involves “distribution for the receipt, or expectation of receipt, of” other 17
child pornography. If so, the District Court corr ectly applied a five-level increase; if not, a 18
two-level increase was appropriate. 1913 We have not addressed whethe r the use of file-sharing technology can trigger the 1
enhancement under Section 2G2.2(b)(3)(B), and if so, in what circumstances it is triggered. 3 2
The Fifth and Eighth Circuits have held that an agreement to distribute child pornography 3
in exchange for other child pornography is inherent in the knowing use of file-sharing 4
programs to obtain and make available child pornography. United States v. Groce , 784 F.3d 5
291, 294–95 (5th Cir. 2015); United States v. Griffin , 482 F.3d 1008, 1012–13 (8th Cir. 2007) 6
(“We now hold that § 2G2.2(b)(2 )(B)’s five-level enhancement . . . applies to a defendant 7
who downloads and shares child pornography files via an internet peer-to-peer file-sharing 8
network, as these networks exist . . . for users to share, swap, barter, or trade files between 9
one another.”). 4 Other Circuits have rejected such a per se rule, and instead have looked to 10
the defendant’s particular use of file sharing to determine whether an expectation of receipt 11

existed. United States v. Hernandez , 795 F.3d 1159, 1165 (9th Cir. 2015); United States v. 12

3 We have, however, previously held that file sharing can constitute simple

distribution under U.S.S.G. § 2G2.2(b)(3)(F). United States v. Reingold , 731 F.3d 204, 228–

30 (2d Cir. 2013). There, we found that the le sser enhancement was appropriate given that

the defendant “knew from the start that distri bution was a necessary condition of receipt”

and that, “with that knowledge, [defendant] took deliberate and purposeful actions to effect

that distribution.” Id. at 229.

4 The Eighth Circuit has subsequently clarif ied that “whether a defendant qualifies

for the [Section 2G2.2(b)(3)(B)] enhancement must be decided on a case-by-case basis,” but

that this could be established through eviden ce of defendant’s knowledge of “how [file

sharing] worked.” United States v. Stults , 575 F.3d 834, 849 (8th Cir. 2009); see also United

States v. Durham , 618 F.3d 921, 925–26 (8th Cir. 2010).14 McManus , 734 F.3d 315, 320 (4th Cir. 2013); United States v. Spriggs , 666 F.3d 1284, 1288 1
(11th Cir. 2012); United States v. Geiner , 498 F.3d 1104, 1111 (10th Cir. 2007). 2

We decline to adopt the reasoning of those co urts that have found that any use of file 3
sharing triggers the five-level enhancement. Some individuals undoubtedly use file-sharing 4
software to engage in exchanges of illicit pornographic material. Cf. Groce , 784 F.3d at 294 5
(“By using this software as Groce has, the user agrees to distribute the child pornography on 6
his computer in exchange for additional ch ild pornography.”). But individuals need not 7
utilize file sharing as a bargaining platform. Indeed, as the Eleventh Circuit has recognized, 8
“[f]ile-sharing programs exist to promote free a ccess to information” and “[g]enerally . . . do 9
not operate as a forum for bartering.” Spriggs , 666 F.3d at 1288. And, as a technological 10
matter, file-sharing programs facilitate either approach; individuals may or may not restrict 11
access to their files through password protecti on and, even if they do maintain a password, 12
nothing restrains them from making their passwo rd generally available as a gift as opposed 13
to as consideration in an exchange. 14

That many, or perhaps even most, GigaTribe users interact with this service in one 15
way does not imply that other uses should be ignored in evaluating the applicability of the 16
enhancement. Thus, “[ a]lthough a defendant may share files on a file-sharing network with 17
the expectation of receiving other users’ files in return, this is not necessarily true in every 18

case.” Hernandez , 795 F.3d at 1165 (quoting Geiner , 498 F.3d at 1111). 19

Nevertheless, we conclude tha t Bennett’s conduct in the case before us warrants 20
application of the Section 2G2.2(b)(3)(B) enhancement. We have previously held that, to 21
show an exchange, the evidence need not demonstrate a “specific agreement or 2215 understanding between the distributor an d the recipient of child pornography.” United States 1

v. Maneri , 353 F.3d 165, 168 (2d Cir. 2003). Instead, we have stated that evidence of an 2
“expect[ation]—rather than just [a] hope[]—to receive a thing of value,” including child 3
pornography, suffices. Id . Other courts have adopted this logic. For instance, in Hernandez
, 4
the Ninth Circuit concluded that such an expe ctation was supported by evidence of a 5
conversation in which defendant complained th at an undercover officer was “leeching” him 6
by failing to provide defendant with reciprocal access to porn ography. 795 F.3d at 1166. 7

Accordingly, for the enhancement to appl y, the Government must advance specific, 8
individualized evidence that Bennett provided access to his collection of child pornography 9
to another user with the expe ctation that that user would pr ovide similar access to other 10
child-pornography files. That st andard is plainly met here. 11

Bennett repeatedly engaged in “pass-for-pass” exchanges, in which he provided his 12
password to another user with the expectatio n of receiving the other user’s password. 13
Indeed, in one exchange (relied upon by the District Court) Bennett and another user 14
expressly discussed their pornography preferen ces before agreeing to provide each other 15
access to their child-pornography files. Then , upon having trouble downloading the other 16
user’s pornography, Bennett complained of not having received his bargained-for material. 17
And, we agree with the District Court that “[ t]his exchange of passwords, after a brief 18
exchange as to the interests of the users, would seem to be exactly what [Section 19
2G2.2(b)(3)(B) cmt. n.1] has in mind.” App. 231. Moreover, al though the discussions 20
surrounding Bennett’s other exch anges were perhaps not as fulsome, each nevertheless 21
constituted a separate quid pro quo —I’ll give you my password (and therefore access to my 22
child pornography) if you give me yours— that was understood by Bennett to involve an 2316 exchange of child pornography and carried out as such. Thus, Bennett, in carrying out each 1
of these exchanges, did expect to receive access to these indi viduals’ child pornography files 2
in exchange for his own files. 3

We conclude that the District Court proper ly applied a five-level enhancement for 4
distribution for “the receipt, or expectation of receipt, of a thing of value, but not for 5
pecuniary gain” under Section 2G2.2(b)(3)(B). 5 6

5 Bennett contends that the District Court committed procedural error in two other

ways. But neither argument has merit.

First, Bennett argues that the District Court “disagreed with Dorvee [] . . . and refused

to follow it” in sentencing him to seven ye ars’ imprisonment. Reply Br. 10. Bennett’s

argument here, however, boils down to an asse rtion that his sentence was simply too long

for an offender who is “not a pedophile an d is unlikely to reoffend, and who holds an

advanced education with unusual promise for the future . . . .” Id . 6. Whether or not this is

true, however, Bennett’s claim e ssentially is that his sentence is substantively unreasonable

in light of Dorvee , a claim that we do not reach for reasons mentioned in footnote 9, infra

. Second, Bennett claims that the District Cour t erred by taking into consideration the

fact that Bennett’s offense conduct could ha ve supported a charge under 18 U.S.C. §

2552A(a)(2), which would have been subject to a mandatory minimum of five years. But,

as we have recognized, “[t]he se ntencing court’s discretion is largely unlimited . . . as to the

kind of information it may consid er,” and it is “free to consider . . . evidence of uncharged

crimes, dropped counts of an indictment and cr iminal activity resulting in acquittal in

determining sentence.” United States v. Gomez , 580 F.3d 94, 105 (2d Cir. 2009) (quoting17 C. 1

The District Court, however, erred in calculating Bennett’s Guidelines range in 2
another respect. It failed to take into acco unt the effect of the statutory maximum on the 3
Guidelines as required by U.S.S.G. § 5G1.1(a). 6 4

U.S.S.G. § 5G1.1(a) expressly provides that “[w]here the statutorily authorized 5
maximum sentence is less than the minimum of the applicable guideline range, the 6
statutorily authorized maximum sentence sha ll be the guideline sentence.” Thus, in United 7

States v. Dorvee , 616 F.3d 174, 181 (2d Cir. 2010), we held that it was plain error for a district 8
court to calculate a Guidelines range to be 262 to 327 months’ imprisonment where the 9
statutory maximum of the underlying offens e was 240 months’ imprisonment. Because the 10

district court there “twice stated that the operative Guidelines range was 262 to 327 11

United States v. Sisti , 91 F.3d 305, 312 (2d Cir. 1996)). That Bennett could have been

charged with a more serious crime constitutes da ta similar to this sort of information.

Moreover, while Bennett contends that the Di strict Court wanted to compensate for

Bennett’s having “got[ten] a break” from the Government, Reply Br. 11, there is no basis

for concluding this. Rather, the District Court raised this point in connection with

Bennett’s counsel’s argument that his offe nse conduct was not that serious.

6 Because this argument was not raised below, it is subject to plain-error review.

Additionally, Bennett first made it during or al argument. We neve rtheless exercise our

discretion to consider it. See City of New York v. Mickalis Pawn Shop, LLC , 645 F.3d 114, 137

(2d Cir. 2011). We do so for reasons of judicial economy, as it could be raised in a

collateral proceeding as part of an in effective-assistance-of-counsel claim.18 months” and “never correctly stated that th e operative Guidelines range was 240 months’ 1
imprisonment, either by indicating the Guidelin es range on the record at sentencing or by 2
adopting at sentencing the PSR’s statement of th e applicable Guidelines range,” it “failed to 3
apply section 5G1.1(a) correctly.” Id. Because of this error, it “p lainly erred in its Guidelines 4

calculation.” Id. 5

Here, the District Court made the same error. In calculating the Guidelines range, it 6
specifically stated that “the range is 135 to 168. That’s about 11 years to 14 years or so. So 7
11 to 14 years, which is a long time.” App. 232. It then continued to make reference to the 8
Guidelines range as being 11 to 14 years’ imprisonment. App. 281 (“The maximum here is 9
ten, the guidelines are 11 to 14. . . . [F]rom the moment I read the facts of this case, it 10
seemed to me that eight to ten is not inappr opriate, 11 to 14 is not inappropriate.”). The 11
District Court never corrected this error by indicating that the statutory maximum and the 12
Guidelines range (both the minimum and the maximum) were the same : ten years. 13
Accordingly, the District Court plainly erred in its calculation of the Guidelines range. 7 14

7 At oral argument, the Government argu ed that the following statement by the

District Court indicated that it correctly calcul ated the Guidelines sentence to be 10 years’

imprisonment:

I’m prepared to come do wn below the guidelines, down below the statutory maximum

of ten, which would be within the guidelines range

. . . .19 Moreover, the District Court’s error affe cted Bennett’s substantial rights. As the 1
Supreme Court recently recognized, “[i]n most cases a defendant who has shown that the 2
district court mistakenly deemed applicable an incorrect, higher Guidelines range has 3
demonstrated a reasonable probability of a different outcome.” Molina-Martinez , 136 S. Ct. 4

at 1346. This is because the “Guidelines are no t only the starting point for most federal 5
sentencing proceedings b ut also the lodestar.” Id. Indeed, “[e]ven if the sentencing judge 6
sees a reason to vary from the Guidelines, if the judge uses the sentencing range as the 7
beginning point to explain the decision to deviate from it, then the Guidelines are in a real sense 8
the basis for the sentence .” Id. at 1345 (emphasis in original) (internal quotation marks 9
omitted); see also Dorvee , 616 F.3d at 181 (finding that miscal culation of Guidelines affected 10
substantial rights where the “district court cont inued to treat [the miscalculated range] as 11
though it were the benchmark for any variance”). 8 12

Oral Arg. Recording at 1:39:30–:48:00 (q uoting App. 281 (emphasis added)). The

Government contends that the clause “which wo uld be within the guidelines range” should

be read to equate the Guidelines range and the statutory maximum. This interpretation of

the statement, however, is dubious. The statutory maximum would not be within the

Guidelines “range” if the District Court had calculated the Guidelines sentence correctly.

That maximum would be the Guidelines.

8 This conclusion, moreover, accords wi th contemporary research on judicial

decision making, which indicates that anchorin g and other “contextual factors” can affect

the exact sentence imposed. See Jeffrey J. Rachlinski, Andrew J. Wistrich & Chris Guthrie,20 Here, the miscalculated Guidelines rang e may well have anchored the District 1
Court’s thinking as to what an appropriat e sentence would be. Thus, even though the 2

District Court asserted it was “not moved by” the Guidelines, it returned multiple times to 3
the “11 to 14” range in framing its choice of a seven-year below-Gu idelines sentence. App. 4
281. And, to the extent that the District Cour t concluded that this sentence was necessary 5
“to send a message of moral outrage,” id. , the strength of such a message is necessarily 6
reflective of the Guidelines range, which, itse lf, “is based on the seriousness of a defendant’s 7
offense,” Molina-Martinez , 136 S.Ct. at 1342. 8

In these circumstances, and given the less stringent application of the plain-error 9
standard in sentencing, Gamez , 577 F.3d at 397, we hold that the District Court’s error 10
affected Bennett’s substantial rights and seri ously affected the fairness of the judicial 11
proceedings. See Molina-Martinez , 136 S. Ct. at 1343. Bennett therefore has met the 12
requirements of plain error review. 9 13

14

15

Can Judges Make Reliable Numeric Judgment s? Distorted Damages and Skewed Sentences , 90 Ind.

L. J. 695, 706 (2015).

9 Because we conclude that the District Court committed procedural error in

imposing Bennett’s original sentence, we do not proceed to review the sentence for

substantive reasonableness. See Cavera , 550 F.3d at 190. In doing this we emphasize that we

are taking no position, at this time, on Bennett’s substantive Dorvee contention.21 CONCLUSION 1

The District Court properly applied the five-level enhancement under U.S.S.G. § 2
2G2.2(b)(3)(B), but miscalculated the Guidelin es sentence applicable to Bennett’s conduct 3
because it referenced a Guidelines range above the statutory maximum sentence. That 4

miscalculation affected Bennett’s substanti al rights. Accordin gly, we REMAND for 5
resentencing. 6