Court Opinion

ID: 9892823
Source: CourtListenerOpinion
Date Created: 2023-10-24 22:01:38.182614+00
Date Added: 2024-06-11T08:46:31.337441
License: Public Domain

UNITED STATES DISTRICT COURT
                             FOR THE DISTRICT OF COLUMBIA

 UNITED STATES OF AMERICA
        v.
                                                       Criminal Action No. 21-380 (CKK)
 BRIAN JEFFREY RAYMOND,
             Defendant

                                 MEMORANDUM OPINION
                                    (October 28, 2023)

       Before the Court is Defendant Brian Jeffrey Raymond’s (“Defendant” or “Mr. Raymond”)

[190] Motion to Suppress.      Defendant moves to suppress essentially all documentary and

videographic evidence obtained from his various electronic devices, relying on both the Fourth

Amendment’s and the Fifth Amendment’s exclusionary rules. Defendant’s challenge centers on

the execution of a warrant issued for Defendant’s two iPhones. Defendant argues that law

enforcement exceeded the search and seizure authorized by the warrant in compelling Defendant

to unlock his devices with his passcodes. Insofar as all subsequent warrants rely on the fruits of

this purportedly unlawful conduct, Defendant maintains that these subsequent warrants are so

tainted as to require the suppression of all subsequent evidence. In response, the Government

insists that law enforcement acted lawfully and, even if law enforcement did not, neither

exclusionary rule applies.

        To resolve the particularly complex questions of criminal procedure posed by the Motion,

the Court commenced a five-day suppression hearing on June 1, 2023. The Court heard testimony

from then-Agent Theodore Nelson and Agent Mikel Gajkowski of the Department of State’s

Diplomatic Security Service (“DSS”), the two main law enforcement officers who executed the

warrant for Defendant’s phones. The Court also heard testimony from Raymond White, a digital

                                                1
forensic analyst at the Computer Investigation and Forensics (“CIF”) office in DSS. Additionally,

the Court admitted sixty exhibits into evidence.

       Upon exhaustive review of the record, the pleadings, 1 and the applicable legal authority,

the Court concludes that compelling Defendant to unlock his phones using passcodes exceeded

the scope of an already-executed warrant, and that law enforcement acted in, at best, reckless

disregard of Defendant’s Fourth Amendment rights. Therefore, the Court must exclude the

evidence obtained from Defendant’s phones.             That said, the unconstitutional taint of law

enforcement’s unlawful conduct does not so infect subsequent warrants, which rest on independent

grounds for probable cause, as to require the suppression of documentary and videographic

evidence obtained beyond Defendant’s phones. Lastly, the Court perceives no Fifth Amendment

violation. As such, and in sum, the Court shall GRANT IN PART AND DENY IN PART

Defendant’s [190] Motion to Suppress.

                                    I.     BACKGROUND

       A. Factual Background

       Before turning to the Court’s factual findings, the Court briefly summarizes the factual

and legal background of this case, which the Court has addressed at more length in prior

1
  The Court’s consideration has focused on:
    • Defendant’s Motion to Suppress, ECF No. 190 (“Motion” or “Mot.”);
    • The Government’s Opposition to Defendant’s Motion to Suppress Evidence, ECF No. 198
       (“Opp.”);
    • Defendant’s Reply to Government’s Opposition to Defendant’s Motion to Suppress
       Evidence, ECF No. 204 (“Repl.”);
    • The Government’s Supplemental Briefing on Defendant’s Motion to Suppress Evidence,
       ECF No. 235 (“Gov.’s Supp. Br.”); and
    • Defendant’s Post-Hearing Brief in Support of Motion to Suppress Evidence, ECF No. 236
       (“Def.’s Supp. Br.”).
The Court has also relied on the suppression hearing in this matter and the exhibits admitted into
the hearing record.
                                                   2
opinions. 2

        An investigation of Mr. Raymond was triggered after police responded, on May 31, 2020,

to reports of a naked woman (“AV-1”) 3 screaming on the balcony of Defendant’s residence – a

United States government-leased property in Mexico City, Mexico. When Mr. Raymond was

interviewed in Mexico City by authorities, he indicated that he had met AV-1 online, and the two

had gone to his apartment, had drinks, and engaged in consensual intercourse. See Raymond I, 640

F. Supp. 3d at 15. A June 2, 2020 interview with AV-1 indicated that she had met with Mr.

Raymond outdoors, and he brought wine in a backpack. Id. After going to his apartment, where

they drank more wine and ate light snacks, she could not remember anything––including

intercourse or standing and screaming on his balcony––until she awoke in an ambulance. Id.

When the Federal Bureau of Investigation (“FBI”) ran an analysis on AV-1’s urine sample in

connection with the incident, they found cocaine, methamphetamine, and theophylline (a bronchial

dilator asthma medication) in her system but did not find any evidence of so-called date rape

substances. Id. During her follow-up interview, AV-1 denied ever having used any illegal drugs

and suggested that Mr. Raymond had put the drugs in her drinks. Id. Subsequent searches of

Defendant’s devices (the lawfulness of which is at issue here) revealed a horde of explicit images

and videos reflecting Defendant sexually assaulting scores of sleeping, inert women.

        For example, in exhibits the Court reviewed for the purposes of bail addressed in Raymond

III, Defendant filmed himself lifting and dropping a victim’s limbs, manipulating her eyelids, and

stroking her breasts and genitals with her own hand. 2023 WL 3040453, at *3. When AV-6 face

2
   E.g., United States v. Raymond, 640 F. Supp. 3d 9 (D.D.C. 2022) (“Raymond I”); United States
v. Raymond, --- F. Supp. 3d ---, 2023 WL 2043147 (D.D.C. Feb. 16, 2023) (“Raymond II”);
United States v. Raymond, Crim. A. No. 21-380 (CKK), 2023 WL 3040453 (D.D.C. Apr. 21,
2023) (“Raymond III”).
3
  Alleged victims are denominated by number in the indictment.
                                                 3
flinched, Defendant jumped back, revealing his erect penis. Id. Defendant’s actions are the same

as or similar to those reflected in additional video and/or photographic evidence provided by the

Government for the purposes of resolving other motions filed in this matter. They are also

consistent with the Government’s proffer as to the seventeen other alleged victims arising from

the conduct alleged in the Superseding Indictment. For example, Defendant again captured his

erect penis while kneeling above AV-7’s nude body. Id. Defendant similarly assaulted AV-5,

grabbing her breast and playing with her mouth and tongue as she struggled to breathe. Id. at *6.

Defendant continued his fetish for manipulating his victim’s eyelids with AV-23 and AV-4. Id.

Defendant evidently conducted many internet queries reflecting his intent to and motive for

sexually assaulting his alleged victims, including “Ambien and alcohol and pass out,” “Ambien

and alcohol and side effects,” and “searches for videos of passed out, sleeping, and drunk women.”

Id. This brief discussion of evidence obtained through the warrants at issue is not exhaustive of

the exhibits provided to the Court, and does not begin to cover the Government’s allegations as to

all purported victims, charged and uncharged.

       B. Findings of Fact as to June 3, 2023 Search and Subsequent Warrants

       The Government applied for, and received, a number of warrants to search Defendant’s many

devices. The first warrant, for Defendant’s iPhones (“Phone Warrant”), is most important here and

precipitated the Government’s discovery of the horde of media depicting Defendant abusing

incapacitated women. The probable cause for that warrant was based in part upon AV-1’s law

enforcement interviews, mainly AV-1’s insistence that Defendant had assaulted her, forensic

evidence of sexual assault, and her description of her incapacitation. Gov.’s Hrg. Ex. 4A Aff. ¶¶ 17-

21. The probable cause for the warrant was also predicated upon a June 2, 2020 noncustodial

interview with Defendant. Id. ¶¶ 25-26. The material recovered from the phones formed, in part,

                                                 4
the probable cause for the next warrant for Defendant’s iCloud account (“iCloud Warrant”) and all

subsequent warrants (for, among other things, Defendant’s other electronic devices).

               1. June 2, 2020 Interview

       This interview occurred a day after Defendant’s return from Mexico to the United States.

Hrg. Trans., ECF No. 225 at 101:12 (June 1, 2023) (“6/1/21 Trans.”). At the time, Defendant was

staying at a hotel in Vienna, Virginia. See id. at 151:6-7. During that interview, Defendant told law

enforcement that he had met AV-1 on Tinder. Id. at 18:15-17. He then permitted Agent Gajkowski

to take photos of his Tinder messages, along with messages between AV-1 on WhatsApp, on his

personal iPhone XR. Gov.’s Hrg. Ex. 9-E. Additionally, he presented WhatsApp messages he

exchanged with AV-1 on his iPhone 6 (which the Government claims was government-issued),

Gov.’s Hrg. Exs. 7, 8, and sent screenshots of further messages to law enforcement later that day,

Gov.’s Hrg. Ex. 9-F. Although Defendant indicated he used dating apps only rarely, Agent

Gajkowski was able to observe that Defendant (1) had corresponded with many women on Tinder

and (2) had also downloaded Bumble, another dating application. 6/1/23 Trans. at 115:8-19.

               2. Phone Warrant

       Law enforcement relied in part on this voluntary interview to obtain its first search warrant,

the Phone Warrant. The probable cause rested first on reports by a federal protective squad based at

the United States Embassy, Mexico City. See Gov.’s Hrg. Ex. 4A at 8. Shortly after Mexican law

enforcement responded to Defendant’s apartment in Mexico City during the incident with AV-1, the

federal protective squad observed that “AV-1 was physically unstable and required assistance to

walk, appeared heavily intoxicated, and was later crying in the back of an ambulance.” Id. The

warrant application claimed that AV-1 told those around her that Defendant had “tried to rape [her].”

Id. Law enforcement further alleged that Defendant voluntarily stated to the federal protective squad

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that he had met AV-1 on Tinder and corresponded with her on WhatsApp, as his Tinder and

WhatsApp accounts confirmed to Agent Gajkowski during the June 2, 2020 interview.                 Id.

Defendant also confirmed that AV-1 had indeed claimed that Defendant had tried to sexually assault

AV-1, AV-1 having escaped to the apartment balcony to scream, in Spanish, “help me!” Id. at 8-9.

       In addition to these earlier observations, law enforcement also recounted to the magistrate

judge that American medical personnel “observed visible bruises on AV-1’s forearms, and AV-1

showed them an additional bruise on her shoulder,” after the incident. Id. She further claimed that

she suddenly lost consciousness at Defendant’s apartment, despite drinking relatively little. Id. at

10. Based on these allegations, video evidence of AV-1’s stupor, and Defendant’s June voluntary

interview, law enforcement requested, and a magistrate judge issued, the Phone Warrant to seize and

search the two phones. Id. at 11.

       Specifically, the Phone Warrant authorized the search and seizure of those two phones, “for

the purpose of identifying electronically stored data” reflecting records related to AV-1, sexual

assaults more generally, and records “related to the research, purchase, possession, or use” of date-

rape substances. Id. Attachs. A, B. Law enforcement was further authorized, during the search, to

press Defendant’s fingers to the Touch ID sensors of the two phones and to hold both phones to

Defendant’s face “for the purpose of attempting to unlock the devices via Face ID.” Id. Attach B.

Law enforcement acknowledged in the warrant, however, that these biometrics may not actually

open either phone; sometimes, “a passcode or password must be used instead.” Id. at 4. Agent

Gajkowski offered an example in her affidavit: “when the device has been turned off or restarted.”

Id. Nothing in the warrant authorized law enforcement to obtain passcodes, however––only

biometrics.

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        The warrant affidavit indicated further that the agents would seek to “ruse [Defendant] into

meeting with [them] under the pretext of a brief follow-up interview, whereupon the devices would

be seized in a public setting,” but if Mr. Raymond was unwilling to appear for a second interview,

the agents would approach him at the hotel where he was staying and request that he retrieve the two

phones if he did not have them on his person. Id. at 20. In that event, the agents would escort

Defendant “into his hotel room to ensure there is no destruction of evidence [but] [t]he execution of

the warrant would not involve any further physical intrusion onto a premises.” Id. Before the

execution of the warrant, Agent Gajkowski briefed another DSS agent, Ted Nelson, on the warrant

and their plan to execute it together with two other DSS agents. See Hrg. Trans., ECF No. 266 at

211:11-13 (June 2, 2023) “(6/2/23 Trans.”).

                3. Technical Background on iPhones

        Before addressing the execution of the warrant, the Court must pause to provide a brief

explanation of security settings on iPhones is necessary. Recall that two phones are at issue here:

an iPhone XR and an iPhone 6.          An iPhone XR can be locked by passcode (numeric or

alphanumeric) and Face ID (facial recognition). 6/1/23 Trans. at 45:1-6, 64:11-12. An iPhone 6 can

be locked by passcode (numeric or alphanumeric) or fingerprint, but not Face ID. Id. at 45:7-14,

64:7-10. Both phones require a passcode before changing any settings, including disabling any

locking features. Id. at 68:12-70:14. Additionally, if either iPhone was powered off and then

powered on, if a passcode is enabled, then biometrics are insufficient to unlock the phone (sometimes

termed the “first unlock” stage). Id. at 45:18-20. In this instance, Defendant had enabled passcodes

on both phones, so the iPhone XR could be accessed by Face ID or passcode after first unlock, but

not earlier. Id. at 45:21-23.

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       The stage at which a phone is locked or unlocked also impacts how quickly a phone can be

forensically inventoried. Id. at 47:3-8. If a phone is unlocked, as here, the vast majority, if not the

entirety, of the phone’s contents can be easily inventoried. See id. at 77:21-25. If a phone is

locked, however, it could take, at the time the phones were seized here, up to twenty-five years to

“brute force” entry into the phones, i.e., trying random codes until one works. Id. at 47:14-48:18.

There is also no guarantee that a locked iPhone 6 and iPhone XR can be accessed through the

“brute force” method in the “first unlock” state. Id. at 84:1-8.

               4. First Meeting

       The following day, June 3, 2020, DSS Agents Gajkowski and Ted Nelson asked Mr.

Raymond to meet with them for a follow-up interview at a Jimmy John’s near the hotel where Mr.

Raymond was staying. The agents recorded their conversation, and a transcript of the interview was

created. See Def.’s Hrg. Ex. 6. The execution of the warrant began, as planned, as a follow-up

interview. Defendant began the interview by alerting Agents Gajkowski and Nelson that he was

“[t]urning [at least one] phone off.” Id. at 2:10-12. During that interview, the agents asked

Defendant if he had his two phones with him and if they could see the phones, and he complied by

handing them over. Id. at 177:15-178:8. In response to an inquiry by the agents as to how the two

phones were secured, Mr. Raymond said, “They’re locked with a PIN.” Id. at 184:2-12. Agent

Nelson indicated then that “DOJ issued a search warrant for both your cell phones, so we’re going

to take both your phones.” Id. at 184:13-18. Mr. Raymond responded. “I can’t, I can’t let you do

that without a lawyer present.” Id. at 184:19-20. Agent Nelson responded by indicating that was

what the search warrant was for, “so we are taking your phones,” and furthermore, he stated that he

was “not asking.” Id. at 184:21-185:4. Law enforcement also asked Defendant to “turn [both

phones] back on.” 6/2/23 Trans. at 47:19-20.

                                                  8
       Mr. Raymond again responded, “I, I’m, I’m serious. I need . . . I can’t authorize that without

a lawyer.” Def.’s Hrg. Ex. 6 at 185:6-10. Agent Nelson replied that it was a “criminal justice

process,” and he would show Mr. Raymond his badge and credentials, and “[n]othing good’s going

to come out of you resisting this.”   Id. at 185:11-19. Mr. Raymond indicated that he was not

resisting. Id. at 185:20. Agent Nelson told Mr. Raymond he could “notify [his] people that we

seized the phones,” but Mr. Raymond indicated that he didn’t “understand how [he was] supposed

to have contact with anybody.” Id. at 185:21-186:9. After Agent Nelson suggested Mr. Raymond

go to a store and get a new cell phone so he could contact people, id. at 186:13-20, Mr. Raymond

indicated that it was “more than an inconvenience” and he was “dead in the water” as he “d[id]n’t

have phone numbers.” Id. at 187:3-12.

       At this point in the conversation, Agent Nelson asked Mr. Raymond if there was “something

we need to know about . . . [b]esides inconvenience,” and Mr. Raymond indicated that there were

“naked photos on [the phones] of women.” Id. at 188:17-22. Agent Nelson then offered to get Mr.

Raymond the contacts he needed but stated that “[w]e need PIN numbers for these phones so we can

access them,” id. at 189:19-21, to which Mr. Raymond responded “I, I have to consult a lawyer

honestly. I can’t - - it’s just something I have to do.” Id. at 189:22-190:1. The dialogue continued

as follows:

       Ms. Gajkowski: Okay.

       Mr. Raymond: You know, I don’t know what my rights are in this situation.

       Ms. Gajkowski: (Inaudible).

       Mr. Nelson: You’re right, but we are seizing the phones. What we need to do though, is
       we need to unlock them and at least put them on airplane mode. Okay?

       Mr. Raymond: I can’t do that until I talk with my lawyer. I just don’t understand what’s
       going on here right now.

                                                 9
       Ms. Gajkowski: So - - so, what we are going to do, because I, I just want to be clear, so
       you’re not willing to voluntarily give us your PIN. Correct?

       Mr. Raymond: No, not until I consult with a lawyer.

       Ms. Gajkowski: Okay, understood.

       Mr. Nelson: Yeah. Okay.

Id. at 190:2-19.

       The agents again told Mr. Raymond they could give him contact numbers from the phones

if he decided to give them the passcode but stated they could not “coerce [him] to give [them] any

PINs.” Id. at 190:22-191:9. They told Mr. Raymond however that “[t]he truth is, one way or another,

we’re getting into the phones.” Id. at 191: 10-17. Mr. Raymond did not provide the PIN codes, and

he stated again that he “just [did not] understand what’s going on.” Id. at 191:21-22. At some point

later, Agent Gajkowski asked if Mr. Raymond could tell her how to “turn this [phone] on airplane

mode” but Mr. Raymond responded that he would “have to unlock it” and did not know if it went

into airplane mode without unlocking it. Id. at 203:3-15. Thereafter, after some additional

conversation and questioning, the agents put Mr. Raymond’s phones in evidence bags and handed

him property receipts, and Agent Gajkowski announced, “The time is 12:26 Saturday, June 6th, and

this concludes our interview and search and seizure warrant execution.” Id. at 220:8-10.

       Despite law enforcement’s announcement that they had executed the warrant, they returned

twice, this time to the lobby of Defendant’s hotel.

               5. Second Meeting

       After their interview, Mr. Raymond returned to his hotel and the agents called Government

counsel to let her know that they had the phones but that Mr. Raymond “declined to provide a

passcode, which he identified as the means for unlocking both devices.” 6/1/23 Trans. at 185:18-19.

                                                 10
Upon receiving that report, the prosecutor directed law enforcement “to go back and compel

[Defendant] to open” his phones, 6/4/23 Trans. at 26:13-16, evidently through biometrics, 6/1/23

Trans. at 186:4-7. Agent Nelson testified, however, that he understood the prosecutor to have

directed law enforcement to use biometrics and, if that method failed, “detain [Defendant] until he

gives [law enforcement] pass[words].” 6/9/23 Trans. at 27:8-12.

       It bears noting at this point that if the prosecutor directed law enforcement to reengage to

compel biometrics, law enforcement undoubtedly would (or should) have understood that effort to

be futile. Through her assistance in the preparation of the warrant, Agent Gajkowski understood that

that the devices could not have been “unlocked through such means,” i.e., biometrics, because they

had been powered off during the earlier interaction that day.

       Nevertheless, approximately one and one-half hours after Mr. Raymond’s phones were

seized, the four agents went to Mr. Raymond’s hotel along with a uniformed and armed police officer

for the Town of Herndon, Virginia. Gov.’s Hrg. Ex. 14. Agent Nelson, Agent Gajkowski, and the

Herndon police officer stationed themselves around the lobby, with two more agents outside, and

one of the agents asked the front desk to summon Mr. Raymond from his room without providing a

reason other than that someone wanted to talk to him. Id. When Mr. Raymond came to the lobby,

Agent Nelson indicated that Mr. Raymond was “not under arrest” but that “[t]he search warrant

compels [him] to open [his] phone” so they had to come back and “get [him] to open his phone.” Id.

Agent Gajkowski indicated that “law enforcement personnel [are] authorized to access fingers,

including thumb onto the device, and further to hold the phone up to [his] face.” Id. When asked if

he could open the phone with a passcode, Mr. Raymond replied, “Yeah. If I’m compelled to do it,

sure.” Id. Feet away from both Defendant and Agent Gajkowski, Agent Nelson responded “you

are,” i.e., Defendant was legally obligated to use passcodes to open the devices. Agent Gajkowski

                                                 11
did not correct Agent Nelson to explain, as they both knew, that the warrant did not compel

Defendant to open his phones with anything other than biometrics.

       The agents discussed changing the passcodes, and while Agent Gajkowski looked at the first

phone, they handed Mr. Raymond the second phone and asked him to open it, which he did. Agent

Gajkowski then attempted to change the settings/passcodes on one of the phones, but she noted that

it required an additional ID or code. She told Mr. Raymond, “So, it’s up to you, if you want to enter

the password, you don’t have to.” Id. Mr. Raymond responded, “I don’t understand. Aren’t I

compelled to - - ?” Id. Agent Gajkowski said, “You are not compelled to give us the code, only the

thumbprint, so I want to be clear on that.” Id. Mr. Raymond replied, “Well, I’d rather - - I mean,

just for privacy reasons . . . I’d rather not.” Id. Agent Nelson asked Agent Gajkowski if she had

changed the passcode on the first phone, but she said she was unable to do so without Mr. Raymond’s

password [to his Apple account]. The agents told Mr. Raymond that was all they needed and thanked

him, and he left to go back to his hotel room. This interaction, like the next, took place in a public,

hotel lobby, in calm and conversational tones. See Gov.’s Hrg. Exs. 14, 15.

               6. Third and Final Meeting

       Approximately one hour after their second encounter with Defendant, law enforcement

returned again. The phones had re-locked again, so law enforcement asked Defendant whether he

would change his password so as to permit law enforcement to remove the password settings and

establish permanent access to the phones. Gov.’s Hrg. Ex. 15. Without this last interaction, Agent

Nelson said, law enforcement was “dead in the water.” 6/2/23 Trans. at 122:3-4. At this point,

Defendant finally relented, entered his passcodes again, and then changed the settings to ensure law

enforcement would retain access. Gov.’s Hrg. Ex. 15.

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               7. Phones’ Contents and Subsequent Warrants

       After the June 2, 2020 interview that precipitated the Phone Warrant, Agent Gajkowski

sought assistance from the prosecutor and fellow law enforcement to submit requests to Match

(parent company of Tinder and Bumble), Facebook (parent company of WhatsApp), and Apple to

preserve all data linked to any accounts Defendant may have then maintained with these companies

(termed “preservation requests”). 6/2/23 Trans. at 36:3-19 Shortly after the execution of the Phone

Warrant, the prosecutor advised law enforcement to submit these preservation requests as soon as

possible. Id. These preservation requests were coterminous with law enforcement’s intention to

eventually seek a warrant for Defendant’s iCloud account. 6/8/23 Trans. at 85:21-25, 86:1-4. 4

       At the same time, law enforcement worked to forensically image the two phones. During

June 2020, law enforcement recovered one explicit photograph depicting a nude, unconscious

woman. 6/1/23 Trans. at 55:11-19. Law enforcement also recovered data reflecting thirty other

similar media on the iPhone XR. Id. at 58:3-9. The iPhone 6 revealed WhatsApp messages with

multiple women that the indictment claims Defendant sexually abused. Id. at 18:9. It also contained

an internet search for “deep sleep.” Id. at 23:2-4.

4
  Defendant insists that Agent Gajkowski offered conflicting testimony as to whether, and when,
law enforcement intended to seek a warrant for Defendant’s iCloud account. Defendant’s
briefing mischaracterizes Agent Gajkowski’s testimony. Defendant argues that Agent
Gajkowksi said “she did not know whether she ‘plan[ned] to get a warrant for Mr. Raymond’s
iCloud’ prior to July 24, 2020.” Def.’s Supp. Br. at 32 n.8. That interaction proceeded as
follows:

       Q: Prior to July 24, 2020, you didn’t have a plan to get a warrant for Mr. Raymond’s
       iCloud; right?

       A: I don’t know if that’s accurate.

6/5/23 Trans. at 59:3-5. In other words, defense counsel’s assertion that there was no plan for
the iCloud Warrant prior to July 24, 2020 was inaccurate.

                                                  13
       These revelations formed, in part, the probable cause for the next key warrant, the iCloud

Warrant. 5 Gov.’s Hrg. Ex. 4C Aff. ¶¶ 17-22. The iCloud Warrant’s probable-cause also relied on

the same information used for the Phone Warrant. See id. ¶¶ 6-15. That said, the affidavit in support

of the warrant, prepared again by Agent Gajkowski added additional, somewhat exculpatory

information as to AV-1: a subsequent forensic analysis of AV-1’s urine reflected that her “alcohol

concentration was likely 320 ml/dL (0.32%) at the time of the incident.” Id. ¶ 15. Agent Gajkowski

also opined that “perpetrators of drug or alcohol-facilitated sexual assault frequently store photos,

conversations, and other digital ‘keepsakes’ of their criminal activities” on, among other things,

digital accounts stored in the cloud. Id. ¶ 24. Based on this affidavit, the iCloud Warrant issued on

August 14, 2020. Id. Warrant at 1. The iCloud Warrant revealed a horde of images and videos

depicting Defendant assaulting passed-out women, and this material constitutes the Government’s

key trial evidence. It also formed the vast majority of the probable cause for subsequent warrants.

See, e.g., Gov.’s Hrg. Ex. 4K Aff. at ¶ 19.

       C. Procedural Background to Date

       Based upon this particularly inculpatory evidence, 6 recovered in large part from

Defendant’s iCloud account, the Government filed a one-count Complaint charging Defendant with

enticing or coercing another “to travel in interstate or foreign commerce . . . to engage in . . . any

sexual activity for which any person can be charged with a criminal offense,” in violation of 18

U.S.C. § 2422(a). See ECF No. 1 (Oct. 8, 2020). On December 31, 2020, the Government filed a

5
  Though not relevant for present purposes, to be precise, the iCloud Warrant was the third of
seventeen warrants issued over the course of the investigation. The second covered Defendant’s
residence in Mexico City. Gov.’s Hrg. Ex. 4B.
6
  The Court reiterates that the adjudication of guilt or innocence is exclusively the province of
the jury. At present time, Defendant must be presumed innocent until proven guilty. To the
extent the Court offers any particular editorialization, it is only to provide context for the
resolution of the legal issues before it.
                                                 14
superseding complaint, charging Defendant with sexual abuse in violation 18 U.S.C. § 2242(2) and

abusive sexual contact in violation of 18 U.S.C. § 2244(a)(2). In accordance with a plea agreement,

the Government then filed a superseding Information, alleging two counts of sexual abuse in

violation of 18 U.S.C. § 2242(2) and one count of transportation of obscene material (the photos and

videos of unconscious women) in violation of 18 U.S.C. § 1462. ECF No. 59 at 1-4 (May 28, 2021).

On July 23, 2021, Defendant entered, and the Court accepted, a plea of “guilty” as to the charges in

the superseding Information. See Minute Entry (July 23, 2021); Statement of Offense, ECF No. 68;

Plea Agreement, ECF No. 69.

       Despite the plea, this case did not proceed to sentencing. Rather, Defendant moved to

withdraw his plea, based mainly on ineffective assistance of counsel. Raymond I, 640 F. Supp. 3d

at 21. After substantial briefing, the Court granted the motion on those grounds. Id. at 34. The

Government then sought, and a grand jury returned, the first indictment, comprising eleven counts

similar to those charged in the prior charging instruments. United States v. Raymond, Crim. A. No.

21-380 (CKK), 2023 WL 3040453, at *3 (D.D.C. Apr. 21, 2023) (“Raymond III”). That indictment

alleged: two counts of sexual abuse in violation of 18 U.S.C. §§ 2242(2), 7(9); one count of

aggravated sexual abuse in violation of 18 U.S.C. §§ 2241(b), 7(9); seven counts of abusive sexual

contact, in violation of 18 U.S.C. §§ 2244(a)(2) and 7(9); and one count of coercion and enticement

to travel to engage in unlawful sexual activity, in violation of 18 U.S.C. § 2442(a); two counts of

sexual abuse in violation of 18 U.S.C. §§ 2242(2), 7(9); one count of aggravated sexual abuse in

violation of 18 U.S.C. §§ 2241(b), 7(9); seven counts of abusive sexual contact, in violation of 18

U.S.C. §§ 2244(a)(2) and 7(9); and one count of coercion and enticement to travel to engage in

unlawful sexual activity, in violation of 18 U.S.C. § 2442(a). Raymond III, 2023 WL 3040453, at

*3. Based on the allegations in that indictment and the substantial litigation this case has incurred,

                                                 15
the Court tolled all Speedy Trial time until trial, set for November 8, 2023. Raymond II, 2023 WL

2043147 at *4.

       A battery of pretrial motions are pending before the Court, including the instant Motion to

Suppress. The Court now turns to its resolution.

                                       II.   DISCUSSION

   A. Fourth Amendment

             1. Lawfulness of Search

       “It is a cardinal rule that, in seizing goods and articles, law enforcement must secure and

use search warrants where reasonably practicable.” 5 Orfield’s Criminal Procedure Under the

Federal Rules § 41:2 (West 2023). This warrant requirement extends to a person’s smartphone.

See Carpenter v. United States, 138 S.Ct. 2206, 2214 (2018). The Government does not

maintain that exceptional circumstances permitted a warrantless search. Rather, the Government

argues that the Phone Warrant’s authority extended to the second and third seizures of

Defendant.

       To the contrary. Because the warrant expired at the conclusion of the first search, the

second and third seizure of Defendant to effect law enforcement’s intended search was unlawful.

And because the record does not establish that either iPhone in fact belonged to anyone other

than Defendant, the contents of both phones are therefore presumptively subject to suppression.

These facts, plus the fact that law enforcement would have had to have known that their return

efforts to re-execute an expired warrant would be futile, require the suppression of the phones’

contents.

                                                   16
               i.      Privacy Interest

       Through its briefing, the Government has maintained that Defendant had no privacy

interest in the contents of the iPhone 6, because that phone was government-issued and

Defendant’s employer warned him that the phone may be subject to search. Gov.’s Supp. Br. at

21. Were the factual premise accurate, Defendant would have no privacy interest in that phone’s

contents. See United States v. Hill, 319 F. Supp. 3d 44, 50 (D.D.C. 2018). Yet the evidentiary

record is devoid any of indication that the iPhone 6 was, in fact, government-issued. Defendant

characterized the iPhone 6 as his “Mexican number phone.” Gov.’s Hrg. Ex. 9. Although he

appeared at one point to agree that he had a “personal” phone and a “work” phone, Defendant

later stated that the phone “belongs to Mexico,” as if it is a phone he maintains in Mexico

because he works there. Id. Although it might be reasonable to infer that the phone was issued

by Defendant’s government employer, the Government adduced neither witness testimony nor

documentary evidence supporting this assertion––either during the suppression hearing or in its

papers. Accordingly, the Court cannot find by a preponderance of the evidence that the iPhone 6

was not, as Defendant maintains, a personal phone.

               ii.     Temporal Applicability of Phone Warrant

       A search warrant, like a pumpkin carriage, retains its magical properties only for a certain

period of time. For example, after fourteen days, midnight strikes, and the search warrant loses

its validity. Fed. R. Crim. P. 41(e)(2)(A)(i). Similarly, a warrant’s authority to search a person

or premises expires when “the items described in the warrant h[ave] been seized.” See, e.g.,

Creamer v. porter, 754 F.2d 1311, 1319 (5th Cir. 1985). A warrant permits but one search, and

when it is completed, “the prevailing guidance . . . is simple: get another warrant.” In re Search

                                                17
of Twenty-Six (26) Digital Devices, Search Warrant No. 21-233 (BAH/GMH), 2022 WL 998896,

at *9 (D.D.C. Mar. 14, 2022) (Howell, C.J.) (collecting cases).

       Some jurisdictions, however, have blessed a limited gloss on this rule, permitting law

enforcement to “pause” the execution of a search, even after discovering the material to be

seized, and to return to the execution of the warrant at some later point. 7 This gloss, not yet

recognized by this Circuit, is termed the “reasonable continuation” doctrine. Shamaeizadeh v.

Cunigan, 338 F.3d 535, 547 n.5 (6th Cir. 2003). Under this “reasonable continuation” doctrine,

law enforcement may pause the execution of a warrant and return to it later so long as the

suspension of the search is (1) reasonable under the totality of the circumstances and (2) not, in

fact, a new search. United States v. Keszthelyi, 308 F.3d 557, 571-72 (6th Cir. 2002). The basis

for this doctrine is understandable. So long as law enforcement otherwise complies with a

warrant’s requirements, law enforcement is due some deference in how to execute it. See Dalia

v. United States, 441 U.S. 238, 257 (1979). Sometimes, law enforcement will encounter

unforeseen challenges that will prevent them from fully executing the warrant and will want to

confer with others on the challenge before them. See United States v. Hendley, Crim. Case No.

14-353-ODE-JSA, 2015 WL 13736219, at *8 (N.D. Ga. Oct. 19, 2015); cf. also United States v.

Whitfield, 629 F.3d 136, 141 (D.C. Cir. 1980) (in context of exigent search of automobile,

holding that exigency does not necessarily “disappear[] when the police decide in good faith to

delay their search for a more opportune time or place”).

       The Government contends that this is such a case. Agent Gajkowski did not actually

force Defendant to apply his biometrics to the phones before concluding the first interaction, and

7
  See, e.g., United States v. Bowling, 351 F.2d 236 (6th Cir. 1965) cert. denied 383 U.S. 908
(1966); United States v. Carter, 854 F.2d 1102, 1107 (8th Cir. 1988); United States v. Kaplan,
895 F.2d 618, 623 (9th Cir. 1990).
                                                 18
the prosecutor was evidently surprised to learn that Agent Gajkowski concluded that biometrics

would fail given Defendant’s use of passcodes on both phones. So, the argument goes, law

enforcement was due another shot at executing the biometrics provision of the warrant.

       To bolster the point, the Government relies mainly on two sets of cases. The first holds

that law enforcement may return when they realize they inadvertently had not seized all items

that they were obligated to seize under the terms of the warrant. See, e.g., Kaplan, 895 F.2d at

623. The second involves logistical challenges. See United States v. Gerber, 994 F.2d 1556,

1557-59 (11th Cir. 1993). In Gerber, a warrant issued directing law enforcement to search the

interior of a car. Id. at 1557. Law enforcement searched some of the car, but stopped when they

arrived at the car’s engine block. Id. The hood would not open without a crowbar, so law

enforcement returned three days later, thinking the subsequent search of the engine block lawful

even though the warrant had expired three days earlier. Id. This second visit was a continuation

of the first, the Eleventh Circuit held, because law enforcement announced that they purposefully

intended to pause the search and they believed, evidently in good faith, that the warrant was still

active at the time of the second visit. Id. at 1561.

       Assuming arguendo that the continuation doctrine is good law in this Circuit, neither

category of cases applies here. First and foremost, Agent Gajkowski affirmatively announced

that the warrant had been executed at the conclusion of law enforcement’s first interaction with

Defendant. June 6, 2020 Interview of Brian Raymond (“Interview Tr.”), Ex. E, ECF No. 119-5 at

220:8-10. Agent Gajkowski was correct in saying so––law enforcement had finished seizing all

items described in the warrant. The plain text of the warrant was also clear that it had been

executed. Law enforcement was “authorized to [use biometrics]” “[d]uring the execution of the

                                                  19
search of” the phones. Gov.’s Ex. 4B Attach. B at 2. The “search” to be executed was “the

seizure” of the phones, which would later be subject to forensic examination. Id. Attach. A at 2.

       Moreover, unlike in Gerber, law enforcement was not met by an unexpected,

surmountable challenge. They were faced with passcodes that they anticipated Defendant might

have activated, and acknowledged that their form of crowbar, biometrics, would not work under

that circumstance. Nevertheless, despite understanding that they had executed the warrant and

that a return trip would be futile, Agents Gajkowski and Nelson went one step further to compel

not just biometrics but also Defendant’s entry of his passcodes, decidedly beyond the scope of

the warrant and contrary to explicit instructions from the prosecutor to Agent Gajkowski before

the execution of the warrant. That is not a reasonable, good faith extension of a half-executed

warrant. That is a futile, illegal attempt to reanimate a warrant whose authority had already

lapsed. Accordingly, the second and third interactions with Defendant were warrantless.

           2. Exclusionary Rule

       As explained further above, the Fourth Amendment’s exclusionary rule usually applies to

the fruits of an unconstitutional search or seizure. Wong Sun v. United States, 371 U.S. 471, 484

(1963). This “fruit of a poisonous tree” doctrine encompasses both the primary evidence obtained

and evidence later obtained as a derivative of the original illegality. Id. at 488. Because of the

high social costs associated with excluding evidence, however, the Supreme Court has recognized

a number of exceptions to the exclusionary rule. See Brown v. Illinois, 422 U.S. 597, 95 S. Ct.

2254, 45 L. Ed. 2d 416 (1975). Here, the Government relies on just two: (1) the “good faith”

exception and (2) the “inevitable discovery” doctrine. First, the Court cannot conclude on this

evidentiary record that the law enforcement officers that executed the Phone Warrant behaved in

good faith. Rather, the Court finds that law enforcement acted in reckless disregard of the Fourth

                                                20
Amendment’s warrant requirement. Second, the Court concludes that the Government confuses

the “inevitable discovery” doctrine for the similar “independent source” doctrine, and that the latter

requires suppression of only the contents of the phones. At bottom, the phones’ contents seized

must be suppressed, but material seized pursuant to the iCloud Warrant and all subsequent warrants

is not subject to suppression.

                       i.        Good Faith

       Not all unlawful conduct requires suppression. The Fourth Amendment’s exclusionary

rule does not provide “a personal constitutional right of the party aggrieved.” Leon, 468 U.S. at

906. Rather, the exclusionary rule is a “prudential doctrine” meant solely to “deter future Fourth

Amendment violations.” Davis v. United States, 564 U.S. 229, 236-37 (2011) (internal quotation

marks omitted). As such, where law enforcement act with a “reasonable good-faith belief that

their conduct is lawful,” a reviewing court may not exclude unlawfully-seized evidence. Id. In

light of this precedent, it is incumbent upon the moving party to demonstrate that law enforcement

“violate[d] [a defendant’s] Fourth Amendment rights deliberately, recklessly, or with gross

negligence.”   Id. at 240.       Otherwise, the reviewing court must excuse law enforcement’s

unconstitutional conduct.

       That said, cases involving good-faith constitutional violations are innocuous indeed. Most

common, police rely on a warrant rendered defective by a magistrate’s inadvertent, earlier mistake.

See, e.g., United States v. Thorne, 548 F. Supp. 3d 70, 130-32 (D.D.C. 2021) (Howell, C.J.)

(collecting cases). In other words, “good faith” cases tend to revolve around a defective warrant,

not defective execution of a valid warrant. See, e.g., United States v. Ginyard, 628 F. Supp. 3d 31,

49-50 (D.D.C. 2022) (CKK). To be sure, the “good faith” exception can also apply to minor,

“technical violation of the terms of the warrant,” but these cases tend to involve how and when a

                                                 21
warrant is executed. See, e.g., United States v. Squillacote, 221 F.3d 542, 557 (4th Cir. 2000)

(concluding the law enforcement’s continuation of a search into the evening, even though the

warrant required a daytime search, was a “technical violation[]” “motivated by considerations of

practicality rather than by a desire to engage in indiscriminate ‘fishing’” (cleaned up)).

       Here, law enforcement’s violation of the Phone Warrant was far more than “minor” or

“technical.” Most importantly, the record utterly belies the Government’s assertion that Agents

Gajkowski and Nelson “did not know that the phones could be unlocked using more than one

method.” Opp. at 35-36. Days earlier in her affidavit in support of the Phone Warrant, Agent

Gajkowski wrote, under oath, that she did know that each phone could be locked with both

biometrics and an alphanumeric passcode. See 6/8/23 Trans. at 69:2-15. By the conclusion of the

first interaction with Defendant both Agents Gajkowski and Nelson had learned that each phone

was in fact secured using both measures. See id. at 59:20-22. And Agent Gajkowski knew, based

on her sworn affidavit, that any attempt to use only biometrics to unlock the phones, which were

in “first unlock” state, would have been futile. Because Agent Gajkowski had both been trained

in the execution of search warrants and was accompanied with a more experienced Agent Nelson,

both Agent Gajkowski and Agent Nelson must have known that a fully-executed warrant cannot

be executed a second time, much as they might have liked a second go at Mr. Raymond. Supra

at 6. Nevertheless, they returned not just once, but twice, to execute a dead warrant.

       In doing so, they also ignored the clear terms of the warrant, a warrant that Agent

Gajkowski had prepared herself and on which she had briefed Agent Nelson in advance of the

warrant’s execution. Id. Both Agents Gajkowski and Nelson must have known, then, that the

warrant permitted only compelled biometrics, not compelled passcodes. Agent Gajkowski must

have known the warrant’s ambits not just because she prepared it, but because she had also had a

                                                 22
conversation with the prosecutor days prior in which she was reminded that law enforcement may

not, under any circumstances, compel passcodes. Def.’s Hrg. Ex. 50. Yet Agent Nelson, standing

only few feet away from Defendant and Agent Gajkowski, did just that during the second

interaction with Defendant, falsely stating to Defendant that “[t]he [Phone] [W]arrant compels you

[Defendant] to open your [Defendant’s] phone” using a passcode. Agent Gajkowski undoubtedly

herad Agent Nelson’s reckless misstatement, yet she did nothing.

       There is no good-faith explanation for this conduct. To reiterate, Agents Gajkowski and

Nelson knew that they had fully executed the Phone Warrant at the end of their first meeting with

Defendant. Agent Gajkowski knew that any further interaction to unlock either phone would be

futile, unless she somehow convinced or ordered Defendant to take a step not permitted by the

warrant––passcodes. She knew that Defendant refused to voluntarily provide or enter them at the

first interaction. Yet she returned with Agent Nelson, and permitted, by an act of omission, Agent

Nelson to unlawfully compel Defendant to enter a passcode against Defendant’s will. Either law

enforcement’s conduct here was intentional or grossly negligence. In either case, law enforcement

did not act in good faith in compelling Defendant’s passcodes.

                      ii.     Inevitable Discovery/Independent Source

       Second, as to both the Phone Warrant and the iCloud Warrant, the Government relies on

the “inevitable discovery” doctrine. Opp. at 47. This exception to the exclusionary rule applies

where the Government demonstrates “that the information [at issue] ultimately or inevitably would

have been discovered by lawful means.” Nix v. Williams, 467 U.S. 431, 444 (1984). As the

Supreme Court explained in Nix, this doctrine is closely related to the very similar “independent

source” doctrine. Id. at 441-43. They are, however, distinct. On the one hand, the “inevitable

discovery” doctrine asks whether “evidence found because of an earlier [Fourth Amendment]

                                                23
violation would inevitably have been discovered lawfully,” while the “independent source”

doctrine, on the other hand, asks “whether [law enforcement] did in fact acquire certain evidence

by reliance upon an untainted source.”        LaFave et al., 3 Crim. Proc. § 9.3(e) (West 2023)

(collecting cases). In effect, the “inevitable discovery” doctrine applies where law enforcement

obtained evidence without a warrant, whereas the “independent source” applies where law

enforcement obtained evidence pursuant to a warrant that may or may not be tainted by an earlier

Fourth Amendment violation. See Murray v. United States, 487 U.S. 533, 538 (1988). Here,

therefore, the “inevitable discovery” applies to the contents of the iPhones, and the “independent

source” doctrine applies to the evidence found on Defendant’s iCloud account.

       Inevitable Discovery. The inevitable discovery doctrine applies, when, by a preponderance

of the evidence, that even without the unlawful conduct, the evidence sought to be admitted would

have been discovered anyway. Nix, 467 U.S. at 444. However, the doctrine is limited to

inevitability that “involves no speculative elements but focuses on demonstrated historical facts

capable of ready verification or impeachment and does not require a departure from the usual

burden of proof at suppression hearings.” Id. The D.C. Circuit has also expressed significant

doubt as to whether the inevitable discovery doctrine may ever be applied to “primary evidence,”

as opposed to mere “derivative evidence.” See United States v. $639,558.00 in U.S. Currency, 955

F.2d 712, 718-21 (D.C. Cir. 1992).

       Because, under this doctrine, the Government must engage in hypothetical reasoning, it is

usually quite difficult to demonstrate that law enforcement truly would have inevitably discovered

the contested evidence. In this regard, United States v. Holmes, 505 F.3d 1288, 1293 (D.C. Cir.

2007) is particularly instructive. In that case, officers conducted a Terry stop and frisk of a suspect

who was acting suspicious, was in an alleyway late at night, and fled as the officers approached.

                                                  24
Id. at 1292. While there were no issues with the initial Terry stop, the officers unlawfully exceeded

the scope of the Terry search when they removed keys to the suspect’s car from the suspect’s

pocket. Id. at 1293. Exceeding the bounds of their authority to execute a traffic stop, the officers

then used the keys to open the suspect’s car and found an illegal gun and ammunition. Id. Under

those circumstances, the Government could not demonstrate that law enforcement would have

inevitably discovered the illegal gun and ammunition. Id. For the keys to be discovered absent

the unlawful expansion of the Terry patdown, the officers would have had to ask the suspect about

the keys, and then, the suspect would have had to answer honestly and lead the officers to his car.

Id. at 1294. Whether, as a counterfactual, those circumstances might have come to pass had law

enforcement behaved lawfully was too speculative. Id.

       In this instance, there were no separate avenues of investigation that were occurring at the

same time when the officers illegally searched Defendant’s phones. In the alternative where the

officers did not compel Defendant to turnover his passcodes, the agents testified that they would

have used the CIF to break into the phone. 6/2/23 Trans. at 22:5-9. The evidentiary record

establishes that it is indeed wholly speculative that CIF would have ever gained access to either

phone’s contents, and even then precisely what would have been forensically imageable. The

“brute force” method CIF would have employed has high variance; using brute force can take

moments to open a phone, but it can also take years. 6/1/23 Trans. at 47:16-18. In some instances,

the phone never unlocks. Id. at 48:18. This step alone injects enough uncertainty into this separate,

hypothetical line of investigation to vitiate the Government’s invocation of the inevitable

discovery doctrine. With no exception to the exclusionary rule on point, the Court must suppress

the contents of both phones.

                                                 25
       Independent Source. Having concluded that the exclusionary rule applies to the compelled

unlocking of Defendant’s phones, the Court turns to whether law enforcement’s unconstitutional

seizure of Defendant compels the suppression of evidence obtained from the iCloud account. On

the one hand, so long as law enforcement had a separate, independence source for probable cause

as to the iCloud warrant, the evidence obtained therefrom is not subject to the exclusionary rule.

See Murray, 487 U.S. at 2532. On the other hand, there can be no independent source if “the

officers’ decision to seek the warrant was prompted by what they had seen [through an unlawful

search or seizure], or if the information obtained during the illegal search or seizure was presented

to the judge and affected their decision to issue the warrant.” Id. at 35-36.

       Defendant correctly observes that the affidavit in support of the iCloud relied extensively

on the materials and information obtained from the phones. Supra at 13. Defendant also

emphasizes that the government only sought the iCloud warrant until more than two months after

the illegal seizures once the phones had been fully analyzed. Repl. at 20-21.

       The Court is not so troubled. As a threshold matter, an affidavit merely incorporating

information obtained lawfully does not defeat the “independent source” doctrine so long as the

affidavit also incorporates information legally obtained. United States v. Redrick, 48 F. Supp. 3d

91, 107 (D.D.C. 2014) (RJL). To illustrate this point, consider United States v. Halliman, 923

F.2d 873 (D.C. Cir. 1991) (Thomas, J.). There, exigent circumstances permitted law enforcement

to search a portion of a suspect’s hotel room. Id. at 880. Law enforcement went further, however,

in searching other areas for which there existed neither exigent circumstances nor a warrant. Id.

Although the evidence recovered served as a basis for a later warrant, police did not seek that later

warrant but for the unlawfully-seized evidence, nor did the unlawfully-seized evidence play a

dispositive role in the magistrate’s decision to issue the later warrant. Id. at 881-82. Accordingly,

                                                 26
the evidence obtained from the later warrant was not subject to suppression where the warrant

therefore relied on evidentiary bases independent from the tainted evidence. Id. at 882. Halliman

therefore envisions two questions under such circumstances: (1) would law enforcement have

sought the later warrant regardless of the tainted evidence, and (2) was there probable cause for

the later warrant absent the tainted evidence. See id.

       As to the first question, the officers’ actions and testimony here support the counterfactual

that they would have sought the subsequent warrant for the iCloud account irrespective of the

information found on the iPhones. When asked the question directly, Special Agent Gajkowski

explicitly answered that she would have applied for the iCloud Warrant absent the information

obtained in the iPhones. 6/8/23 Trans. at 85:25-86:1-4. Her actions also signaled that there was

already a plan in place to get a warrant to search the iCloud account before the officers discovered

what was on the phone. On the same day that investigators seized the two iPhones from the

defendant, which had clearly not yet been searched, law enforcement also submitted a preservation

request to Apple for the defendant’s iCloud account before the iPhones had been analyzed. Supra

at 13. As such, it is eminently clear from the factual record that it is the mere existence of the

phones, and not their contents, that prompted law enforcement to seek the preservation request

and, ultimately, the warrant for Defendant’s iCloud account.

       When asked why she waited as long as she did to actually seek the search warrant after

submitting the preservation request, Agent Gajkowski indicated that there were more pressing

matters ongoing in the investigation. 6/8/23 Trans. at 86:7-15. Once the preservation request was

filed, the information sought to be preserved must be retained for 90 days before a new renewed

request to retain the specific records. 18 U.S.C. § 2703(f). Given that Agent Gajkowski sought the

                                                27
iCloud Warrant well within the bounds of those 90 days, the two-month delay in applying for the

iCloud Warrant is not particularly suspect, and her explanation fairly reasonable.

       As to whether the magistrate would have found probable cause to search the iCloud account

absent the phones’ contents, it is evident that the probable cause for the Phone Warrant, which

Defendant does not contest, carried over to the iCloud Warrant. Indeed, the affidavit in support of

the iCloud Warrant copies those portions of the Phone Warrant verbatim. Compare Gov.’s Hrg.

Ex. 4A with Gov.’s Hrg. Ex. 4C. As explained further above, each affidavit recounts AV-1’s

report of sexual assault, AV-1’s demeanor on the day she reported, and Defendant’s statements

from voluntary interviews that indicated that he had iPhones that had relevant messages and

information that would have been backed up to the iCloud. Supra at 12-13. Additionally, each

warrant notes that Defendant admitted that he corresponded with AV-1 on his iPhones, and that

iPhones are necessarily linked to iCloud storage. It further explained that iCloud storage often

contains data associated with the use of iCloud-connected services, including email, images and

videos, and other files. Id. iCloud could also be used to store iOS device backups, which could

contain a user’s photos and videos, messages, voicemail messages, call history, contacts, calendar

events, reminders, notes, app data and settings, and other data. Id. at 25. So, there was a substantial

basis to conclude that there was evidence of unlawful interactions between Defendant and AV-1

on Defendant’s iCloud account. Cf. United States v. Griffith, 867 F.3d 1265, 1274 (D.C. Cir. 2017)

(concluding that there is probable cause for a warrant as to a suspect’s phone where the

Government establishes that the suspect likely owns a phone and there is reason to believe that

there is evidence on the phone).

       To be sure, the iCloud Warrant also relies on the phones’ contents. For example, the

affidavit in support of the iCloud Warrant references video fragments and photos of several

                                                  28
different victims and Defendant’s internet search history.      Supra at 12-13.      The contents

influenced how the affidavit is structured––they are presented after the information that is also

included in the Phone Warrant affidavit. Id. at 13. Yet, even omitting these additions, the earlier

sections of the affidavit provide probable cause to search Defendant’s iCloud account. As such,

the contents of Defendant’s phones could not have had a dispositive impact on the magistrate’s

decision to issue the warrant. Without that dispositive impact, the iCloud Warrant, and all

subsequent warrants, remain valid. As such, the evidence seized pursuant to those warrants is not

subject to suppression.

                                         *      *       *

       In sum, the Court concludes that the Phone Warrant was finally executed at the end of law

enforcement’s first interaction with Defendant. Each time law enforcement reengaged Defendant,

they acted beyond the scope of the warrant, either in grossly negligent or intentional violation of

law. Because the Government cannot show on this record that it would have inevitably discovered

either phone’s contents, the contents of both phones must be suppressed. Each subsequent warrant

remains untainted by this earlier Fourth Amendment violation, however, so their fruits are not

subject to suppression.

   B. Fifth Amendment

       Defendant also argues that on the Due Process Clause and Self-Incrimination Clause

require suppression of the fruits of each of the Government’s searches. These arguments merit

far less consideration.

       As to the former, Defendant cannot establish a violation of the Due Process Clause, because

he cannot come close to demonstrating that the police engaged in the sort of “egregious” behavior

necessary to render a statement involuntary. See United States v. Mohammed, 693 F.3d 192, 198

                                                29
(D.C. Cir. 2012) (suggesting that, at a minimum, a defendant must show the law enforcement

threatened or injured the defendant during questioning); Mincey v. Arizona, 437 U.S. 385, 398-

400 (1978) (confession involuntary where defendant had been wounded a few hours before

question, was in hospital bed in an intensive care unit encumbered by tubes and needles, was

complaining of intense pain, and gave confused and incoherent responses). Here, each interaction

took place in a public, hotel lobby, in calm and conversational tones. Supra at 12. As to the latter,

it suffices to note that Miranda’s prophylactic rule applies only to testimonial statements, not

tangible evidence. United States v. Patane, 542 U.S. 630, 637 (2004).

       As such, Defendant’s Fifth Amendment challenge fails.

                                     III.    CONCLUSION

       Having emerged from the thicket of these complex questions of criminal procedure, the

Court’s conclusion is nevertheless straightforward. The phones’ contents must be suppressed, but

the remainder of the Government’s evidence survives. As such, the Court GRANTS IN PART

AND DENIES IN PART Defendant’s [190] Motion to Suppress.                     An appropriate order

accompanies this Memorandum Opinion.

       Dated: October 28, 2023

                                                        /s/
                                                      COLLEEN KOLLAR-KOTELLY
                                                      United States District Judge

                                                 30