22-178 United States v. Lajeunesse

UNITED STATES COURT OF APPEALS FOR THE SECOND CIRCUIT

August Term 2022

(Argued: March 16, 2023 Decided: November 1, 2023)

Docket No. 22-178 _____________________________________

United States of America,

Appellee,

v.

Terry Lajeunesse,

Defendant-Appellant. _____________________________________

Before:

LEVAL, CHIN, and LEE, Circuit Judges.

Terry Lajeunesse, a defendant in a criminal case, appeals from the judgment of conviction entered by the United States District Court for the Northern District of New York (Glenn T. Suddaby, J.) convicting him on his plea of guilty to possession and receipt of child pornography, under 18 U.S.C. § 2252A(a)(5)(B) and (b)(2) and 18 U.S.C. § 2252A(a)(2)(A) and (b)(1), and obstruction of justice under

(c)(2), contending that his Fourth Amendment rights were violated by a probation officer’s search of his cell phone and a further search by New York State Police, and that the trial court erred in failing to allow him allocution at sentencing. The government contends that his claim as to sentencing allocution is precluded by the appeal waiver he agreed to as a part of his plea agreement. We reject the

1 government’s argument and REMAND for resentencing. We reject the defendant’s other arguments and AFFIRM the conviction.

JAMES P. EGAN, Assistant Federal Public Defender, Federal Public Defender’s Office, Syracuse, NY, for Defendant- Appellant.

PAUL D. SILVER, Assistant U.S. Attorney of Counsel for Carla B. Freedman, United States Attorney for the Northern District of New York, Syracuse, NY, for Appellee.

LEVAL, Circuit Judge:

Terry Lajeunesse, a defendant in a criminal case, appeals from the

judgment of conviction entered by the United States District Court for the

Northern District of New York (Glenn T. Suddaby, J.) 1 convicting him on his

plea of guilty to one count of possession of child pornography, under 18

U.S.C. § 2252A(a)(5)(B) and (b)(2); one count of receipt of child pornography,

under 18 U.S.C. § 2252A(a)(2)(A) and (b)(1); and one count of obstruction of

justice, under

(c)(2). He contends that his Fourth Amendment

1 Judge Norman A. Mordue ruled on Lajeunesse’s motion to suppress. Judge Suddaby presided over Lajeunesse’s plea proceedings and sentencing hearings. 2 rights were violated by a New York probation officer’s search of his cell

phone and a further search by New York State Police, and that the trial court

erred in failing to allow him allocution at sentencing. He was sentenced

primarily to 198 months of imprisonment.

As part of his plea agreement, Lajeunesse retained the right to appeal

the district court’s denial of his motion to suppress the evidence seized in two

searches of his cell phone—one by probation officers, and a second search by

the police—but otherwise waived his rights to appeal any sentence “to a term

of imprisonment of 210 months or less.” App’x at 193–94. In response to

Lajeunesse’s sentencing appeal, the government contends that, as his sentence

was less than 210 months, this claim is barred by his appeal waiver. We reject

the government’s argument and therefore remand for resentencing, at which

Lajeunesse will be afforded the opportunity to address the court. With respect

to the defendant’s Fourth Amendment claims, we reject them and, in that

regard, affirm his convictions.

BACKGROUND

On June 6, 2018, in another case, Lajeunesse was convicted in the courts

of the State of New York on one count of possessing a “sexual performance”

3 by a child—that is, a visual representation of sexual conduct involving a

child—in violation of

. Lajeunesse was placed on

interim probation for one year. Among the terms of his probation, Lajeunesse

was required to comply with over forty general and special conditions. These

conditions included his consent to home visits by his probation officer and to

unannounced examinations of all of his electronics “by the supervising

Probation Officer or designees” including any cell phones to which he had

access. App’x at 155 ¶ 3, 157 ¶ 24. For electronic devices and applications that

were password protected, he was required to provide the passwords to his

probation officer. He was also prohibited from using social media without

permission and from interacting with anybody under the age of 18, whether

in person or online, without supervision. The probation conditions most

relevant to this case are set forth below:

1. Have no deliberate contact with persons under the age of 18 unless supervised by a person approved by your probation officer or the Court and only under circumstances approved by your probation officer or the Court. . . .

9. Permit search of your person, vehicle and place of abode, including any computers or other electronic devices, . . . such search to be conducted by a Probation Officer or a Probation Officer and his agent. . . .

4 12. Shall abide by such curfew as directed by your Probation Officer and shall be at your residence at the hours established in your curfew. (10pm–6am) . . .

14. Not to use/possess/view pornography, erotica, or any other sexually stimulating material/media or items. . . .

19. Not purchase, possess, or indulge in the use of alcohol or products that contain alcohol. . . .

24. You will agree to unannounced examination by the supervising Probation Officer or designees of any and all computer(s) and/or other electronic device(s) to which you have access. This includes access to . . . cell phones, . . . This examination may be conducted where the equipment is located or may be removed and examined in a controlled or laboratory facility. If a device/program is password protected, probationer shall disclose said password to his/her Probation Officer. . . .

36. The Probation Officer shall have the ability to search social networking internet sites and/or programs for probationer information. If the internet site/program is password protected, the probationer shall disclose said password to his/her probation officer.

37. You are prohibited from using the internet to: access pornographic material and/or any commercial social networking website; communicate with other individuals or groups for the purpose of promoting sexual relations with any person(s) under the age of 18; communicate with a person under the age of 18 when you are over the age of 18.

at 123–26 (emphases added). In the New York State proceeding,

Lajeunesse was read these terms, signed his acknowledgment that he had

read and understood the conditions of his probation, and affirmed his

understanding that, should he violate the terms, his interim probation could

5 be revoked. Warren County Probation Officer Murray was assigned to

supervise Lajeunesse’s probation.

On February 23, 2019, Officer Murray received a tip from Lajeunesse’s

ex-wife, who had known Lajeunesse “for many years.”

. She informed

Officer Murray that Lajeunesse has been: “dating a teenage girl” who is “so

young and vulnerable,” and “staying over at her house frequently overnight

and drinking,” conducting “alarming” activity on Facebook, and “pray[ing]

on [sic]” other teenage girls overseas.

. The informant also

referred Officer Murray to the Facebook page of the supposedly teenage girl

whom Lajeunesse was allegedly dating.

Upon examining the Facebook page, Officer Murray concluded that the

girl appeared to be under the age of 18, but he was unable to determine her

age from that source. He found evidence that Lajeunesse had been

communicating with the girl through a Facebook account that he had not

registered with Officer Murray, as required by the terms of Lajeunesse’s

probation. Officer Murray contacted a Task Force Officer of the Federal

Bureau of Investigation (FBI), asking for assistance to search Lajeunesse’s

6 phone, but was told that the FBI would not review the phone without a

search warrant.

On March 11, 2019, about two weeks after receiving the tip, Officer

Murray conducted a scheduled visit at Lajeunesse’s home to determine

whether he was complying with his probation conditions. He asked to see

Lajeunesse’s cell phone and Lajeunesse handed it to him. When Officer

Murray opened the phone, he saw a picture of the girl from the Facebook

page. Lajeunesse said that he had been in a sexual relationship with her since

November 2018 and that she was 19 years old, nearly 20. Murray later

confirmed that what Lajeunesse said about the young woman’s age was

accurate.

After seeing the photo and hearing about Lajeunesse’s sexual

relationship with the girl who appeared to be underage, Officer Murray

requested assistance from two other probation officers who had more

familiarity with cell phones. One of these probation officers, while conducting

a “cursory search” of the phone, found a file showing what appeared to be

two teenage girls, one of whom was naked and seemed to be about 13 or 14

years old. App’x at 170. The officers also found what they believed to be a

7 media storage application, which they could not open because Lajeunesse

claimed not to know the pin number needed to unlock the application. At this

point, Officer Murray seized the phone in order to conduct “a full forensic

search based on the presence of child pornography, and subject to the

conditions of [d]efendant’s probation.”

Officer Murray again reached out to the FBI Task Force Officer for

assistance with the phone, but she again declined to search the phone without

a warrant. Murray then asked New York State Police Investigator John

Deyette to assist “as an agent of probation.”

. Deyette made a

forensic examination of the phone, which uncovered several images and

videos of sexually explicit conduct involving minors. Lajeunesse was arrested

by New York State authorities on April 2, 2019, at which time the State Police

seized a second phone belonging to Lajeunesse. In June 2019, the FBI began

investigating Lajeunesse’s use of the two cell phones and obtained a warrant

to search the second cell phone. The FBI’s investigation resulted in a federal

indictment on October 16, 2019, for the child pornography offenses. In 2020,

Lajeunesse moved to suppress the material obtained through the searches of

his cell phones. Judge Mordue denied the motion on November 24, 2020.

8 In September 2019, while Lajeunesse was being held on these charges,

he sent two letters to his then 16-year-old son, asking him to claim

responsibility for the pornography so as to “create a little reasonable doubt”

by saying that “you used my phone because yours was broken and you went

on a file sharing site and downloaded some files on accident key word

‘accident’ . . .” and adding that “[y]ou were 14 at the time so they wouldn’t be

able to do Jack Shit to you anyway.”

; 278–79. On the basis of these

letters, on August 12, 2021, Lajeunesse was charged by superseding

information with one count of obstruction of justice, pursuant to

(c)(2), in addition to the child pornography charges.

On the same day, Lajeunesse entered into an agreement to plead guilty,

conditional on preserving his right to appeal the denial of his motion to

suppress. As part of the plea agreement, Lajeunesse waived his right to

“appeal and/or to collaterally attack . . . [a]ny sentence to a term of

imprisonment of 210 months or less; . . . .”

at 193 ¶ 7(d). At Lajeunesse’s

plea hearing, the district court confirmed that Lajeunesse had waived his

right to indictment by a grand jury and understood the consequences of

pleading guilty. The court explicitly asked Lajeunesse if he understood that

9 he would be unable to appeal his sentence, per the plea agreement, if the

court sentenced him to fewer than 210 months of imprisonment and

Lajeunesse responded that he understood.

.

Lajeunesse’s sentencing proceedings were held on January 26, 2022.

Prior to the proceedings, Lajeunesse had written a letter to the court, which

his attorney referenced in his filings. After verifying that Lajeunesse was

present and that there were no remaining objections, the court gave the

government an opportunity to speak. The government rested on its papers.

The court then addressed Lajeunesse’s lawyer, directly.

(“Mr.

Primomo, when you’re ready, sir, you can go ahead.”). Referring to

Lajeunesse’s letter in his statement, Lajeunesse’s lawyer urged the court to

sentence Lajeunesse to no more than the mandatory minimum term of 180

months, emphasizing that Lajeunesse had been in a vulnerable place when he

asked his son to take the blame for the child pornography found on his

phone, that he had had a dysfunctional youth, and that he had accepted the

consequences of his actions.

at 274–76. Defense counsel also asked the

court not to allow the conditional nature of the guilty plea—retaining

Lajeunesse’s right to appeal the motion to suppress—to affect his sentence.

10 After defense counsel’s statement, the court gave assurance that it

would not consider the motion to suppress in sentencing and then, without

having asked whether Lajeunesse would like to address the court, declared

itself ready to impose sentence.

. Without specifically mentioning

Lajeunesse’s personal letter to the court, the court stated that it had reviewed

“all pertinent information . . . .”

Having found the guideline sentencing

range to be 180 to 210 months, the court sentenced Lajeunesse to 198 months

in prison followed by 20 years of supervised release.

at 281–82.

The court did not address Lajeunesse directly at any time during the

sentencing hearing, except to ask if he waived a reading of special conditions

that would be applicable during his supervised release. At no time during the

proceeding was Lajeunesse asked whether there was anything he wanted to

say to the court or otherwise given an opportunity for allocution. Neither

Lajeunesse nor his attorney raised any objection to the lack of offer to allocute

during the sentencing hearing.

11 DISCUSSION

I. Motion to Suppress

Lajeunesse argues that the evidence obtained from his cell phone

should be suppressed because the searches were unconstitutional under the

Fourth Amendment. He argues that the evidence from the first search should

be suppressed because: (1) even with Lajeunesse’s diminished privacy

interests as a probationer, the probation officers were required to have

reasonable suspicion for the search of his cell phone; (2) the probation officers

did not have reasonable suspicion that Lajeunesse was in a relationship with

an underage girl or that he possessed illicit images; and (3) therefore, because

Officer Murray had reasonable suspicion only that Lajeunesse was using

Facebook, the probation officers were at most entitled to search his phone for

evidence that he was violating the social media condition of his probation.

Appellant’s Br. at 17 (citing United States v. Chirino,

(2d Cir.

2007));

at 18–20. He contends that the evidence from the later search by the

New York State Police should be suppressed as fruit of the poisoned tree.

at 23 (citing Wong Sun v. United States,

, 484–85 (1962)).

12 The government contends that the probation officers’ search of the cell

phone was “rationally and reasonably related to the performance of Probation

Officer Murray’s duties” such that it was a constitutional search under the

special-needs exception to the Fourth Amendment. In addition, the

government argues that because the search was supported by reasonable

suspicion that the phone contained child pornography and probable cause

that Lajeunesse was violating the social media terms of his probation, it was

reasonable under the totality of the circumstances because of Lajeunesse’s

diminished expectation of privacy as a probationer who had agreed to a

search condition. Appellee’s Br. at 31–33. Even if the search is found to be

unreasonable, the government argues that the exclusionary rule should not

apply.

Judge Mordue denied Lajeunesse’s motion to suppress because Officer

Murray “had reasonable suspicion to believe that [Lajeunesse] was violating

the terms of his probation and/or committing new crimes based on the tip

from Defendant’s ex-wife, [Lajeunesse’s] criminal history, the girl’s Facebook

profile, and [Lajeunesse’s] apparent communications with her via Facebook”

meaning the search was “within the scope of the terms of [his] probation,

13 rationally related to the duties of Officer Murray, and reasonable under the

circumstances.” App’x at 176. The district court also found that “[Lajeunesse]

consented to the initial search of his cell phone, which arguably provided an

independent basis to proceed.”

When reviewing a district court’s denial of a motion to suppress, we

review findings of fact for clear error and legal findings de novo. United States

v. Chandler,

(2d Cir. 2022); see also Chirino,

;

United States v. Bershchansky,

, 108–09 (2d Cir. 2015). We agree

with the district court and affirm the denial of Lajeunesse’s motion to

suppress.

The parties’ briefs focus on the metes and bounds of the special-needs

exception to the Fourth Amendment and whether or not there was reasonable

suspicion to search Lajeunesse’s phone. We find this perplexing because

Judge Mordue noted that Lajeunesse had consented to the initial search of his

cell phone by giving Officer Murray his phone upon the officer’s request. In

addition, Lajeunesse had given his signed agreement to a condition of

probation that he would agree to unannounced searches of his cell phone by

his probation officer and the officer’s designees. It seems likely—although we

14 do not reach a conclusion on the question—that Lajeunesse had thus

consented to the search to which he now objects. 2 Consent is a long-

recognized, well-settled exception to the warrant and probable cause

requirement. See, e.g., Schneckloth v. Bustamonte,

(1973);

United States v. Bracer,

, 524–25 (2d Cir. 1965).

Because the government has not argued that Lajeunesse’s consent alone

was sufficient to legitimate the probation officer’s search, we will examine

also whether the searches were valid in considering the totality of the

circumstances under two standards discussed in Supreme Court opinions.

1. The search was constitutional under the standard articulated by United States v. Knights

The Fourth Amendment protects “[t]he right of the people to be secure

in their persons, houses, papers, and effects, against unreasonable searches

2Lajeunesse possibly consented to a search by handing his cell phone to Officer Murray, at the officer’s request, with the knowledge that he had, as a term of his probation, agreed to searches of all applications on his phone. A typical reasonable person, knowledgeable of this agreement, might infer that Lajeunesse, by handing over his phone to Officer Murray, had agreed to a general search of his phone—as outlined in the terms of his probation—to ensure he was complying with the terms of his probation. See Florida v. Jimeno,

(1991) (explaining that the scope of consent is limited by objective reasonableness). 15 and seizures . . . .” U.S. Const. amend. IV. Typically, for a search to be

reasonable, a warrant must be issued, supported by probable cause. See, e.g.,

Schneckloth,

.

In United States v. Knights, however, the Supreme Court held that, when

viewing “the totality of the circumstances,” the legitimate expectation of

privacy of a probationer subject to a search condition was so diminished that

a police officer could constitutionally search the probationer’s apartment

based on only reasonable suspicion.

, 118–21 (2001). Because

reasonable suspicion existed in that case, the Court did not clarify whether

reasonable suspicion was necessary or merely sufficient to justify a search

notwithstanding a probationer’s diminished expectation of privacy,

at 120

n.6, and declined to address whether the defendant’s signed agreement to the

probation conditions requiring unannounced searches constituted consent,

thus rendering reasonable suspicion unnecessary.

, 120 n.6; see

also Schneckloth,

(explaining that consent is an exception to the

warrant and probable cause requirement of the Fourth Amendment). The

Court later held in Samson v. California that a search condition can so diminish

a parolee’s expectation of privacy that the Fourth Amendment permits even a

16 suspicionless search by a law enforcement officer, provided the search is not

arbitrary or harassing.

, 847, 850, 856 (2006). This question has not

been squarely addressed in the probationer context, and probationers are

entitled to a greater degree of privacy than are parolees. Id. at 850; see also

United States v. Newton,

(2d Cir. 2004). We need not address

the question of whether a search condition requiring submission to searches

can so diminish the expectation of privacy of a probationer that a

suspicionless search would be constitutional under Knights, because Officer

Murray clearly had reasonable suspicion that contraband or evidence of illicit

activity could be found on Lajeunesse’s phone.

Lajeunesse’s expectation of privacy in his phone was “severely

diminished” due to the fact that he had agreed to unannounced searches of all

his electronics, including his cell phones, as a term of his probation, and

signed a document outlining those terms. See United States v. Reyes,

(2d Cir. 2002). This search condition included a warning that such

searches may take place offsite, indicating that even forensic searches were

within the scope of the provision, and required Lajeunesse to agree to provide

passcodes to his devices and their internal applications. As in Knights, “the

17 probation order clearly expressed the search condition and [Lajeunesse] was

unambiguously informed of it.” Knights,

. Accordingly, as in

Knights, reasonable suspicion is sufficient for a search of Lajeunesse’s phone

to satisfy the Fourth Amendment. See United States v. Lifshitz,

(2d Cir. 2004) (“Probationary searches—whether for law enforcement or

probationary purposes—are acceptable under Knights if based upon

reasonable suspicion (or potentially a lesser standard).”).

Reasonable suspicion exists when there are “specific and articulable

facts which, taken together with rational inferences from those facts,

reasonably warrant the intrusion on a citizen’s liberty interest.” United States

v. Elmore,

, 178–79 (2d Cir. 2007) (alterations adopted) (quoting

Terry v. Ohio,

(1968)). Reasonable suspicion “need not rise to the

level required for probable cause, and . . . falls considerably short of satisfying

a preponderance of the evidence standard.” United States v. Arvizu,

(2002) (citation omitted).

Officer Murray reasonably suspected that Lajeunesse was violating the

terms of his probation and engaging in illegal activity. He had received a tip

that Lajeunesse was breaking multiple terms of his probation, including by

18 drinking, using social media, and breaking curfew, and that, most

importantly, he was in a romantic relationship with a teenager described as

“so young and vulnerable.” App’x at 43. The tip further alleged that

Lajeunesse was interacting with other teenage girls on Facebook.

Officer

Murray had corroborated elements of this tip by investigating the Facebook

page of the teenager with whom Lajeunesse was allegedly in a relationship.

He saw evidence that Lajeunesse had interacted with her Facebook page, and

her page contained pictures of a girl who appeared to be under 18. In

addition, Officer Murray also knew that Lajeunesse was on probation because

he had possessed child pornography. On our review, it appears that the

probation conditions were designed as safeguards to prevent Lajeunesse from

accessing child pornography or having inappropriate interactions with

children. In fact, the same probation condition that forbade Lajeunesse from

using social media also forbade him from accessing pornography websites

and using the internet to contact underage people.

at 40 ¶ 37. Once Officer

Murray had received the tip and confirmed that Lajeunesse was using an

unregistered social media account to interact with at least one girl who

appeared to be underage—and, on the basis of the tip, had reason to believe

19 that he was dating that girl and spending the night at her house—he could

reasonably suspect not only that Lajeunesse was violating terms of his

probation (terms that appeared to be calculated to prevent him from

acquiring child pornography), but also that he was breaking the law by

having a sexual relationship with an underage girl.

Lajeunesse argues that, although Officer Murray had reasonable

suspicion that Lajeunesse was violating the social media term of his

probation, this did not entitle him to a general search of Lajeunesse’s phone,

but only to a search for evidence regarding the social media condition.

Lajeunesse also contends that before searching his phone, Officer Murray

should have conducted an investigation to determine whether or not the

teenager was, in fact, underage. Lajeunesse points to indicia on the Facebook

page that the girl was not underage, such as that the tip had said Lajeunesse

was staying at “her” house (as opposed to her parents’ house), that she was

listed as being from one town but living in another, and that her profile

suggested she was no longer attending high school. Appellant’s Br. at 20. In

Lajeunesse’s view, Officer Murray’s failure to investigate further, combined

20 with the fact that Lajeunesse told Murray that the girl was 19 years old, shows

that the search was harassing or arbitrary.

We do not find these arguments convincing. The violation of the social

media term did not happen in isolation and must be considered in context,

including, most importantly, that it supported Officer Murray’s reasonable

suspicion that Lajeunesse was dating an underage girl, and that Officer

Murray knew about Lajeunesse’s past child pornography possession

conviction. It was proper in these circumstances for Officer Murray to search

the phone, after he had confirmed the violation of the social media term and

that Lajeunesse was interacting with the girl. Cf. United States v. Massey,

(2d Cir. 2006) (explaining that once a parole officer found a

machete, she had reasonable suspicion to search for additional contraband).

Nor does the fact that Lajeunesse told Officer Murray that his girlfriend was

19 years old or the fact that her Facebook page contained details that could be

read to suggest she was of age mean that Murray was bound to take

Lajeunesse at his word, particularly when Murray had seen evidence to the

contrary—the photos on the Facebook page—suggesting she was underage.

Just as an officer conducting an arrest is not required to consider every

21 alternative explanation of innocence, Murray was not obligated to accept

Lajeunesse’s self-serving contention that she was of age. See, e.g., Ricciuti v.

N.Y.C. Transit Auth.,

(2d Cir. 1997); see also Martinsky v. City

of Bridgeport,

(2d Cir. 2012) (summary order). To conclude

otherwise would allow any probationer to evade detection by lying.

Finally, Lajeunesse argues that this search is “particularly troubling”

because it was a search of a cell phone, Appellant’s Br. at 22, noting that the

Supreme Court ruled in Riley v. California that the search of a cell phone

incident to arrest was not permissible under the Fourth Amendment.

, 401–02 (2014). 3 Notwithstanding that Riley gave cell phones a broader

scope of protection under the Fourth Amendment than physical space,

at

3Lajeunesse also cites to United States v. Fletcher as additional support that phones should be treated differently in these circumstances. In that case, however, the search at issue was unreasonable because the probationer’s cell phone was not subject to a search condition and, therefore, the search of his phone fell outside of the regulation authorizing probation searches and was not a special-needs search.

(6th Cir. 2020). The search in that case was also found to be unreasonable under the totality of the circumstances, applying the United States v. Knights framework, because “[the defendant’s] probation agreement could have but did not authorize the search of his cell phones or digital devices.”

. Here, Lajeunesse’s probation conditions explicitly include a search condition for all electronics, including his cell phone, and any storage application on those electronics. 22 386, we do not construe that ruling as implying that these circumstances

would not justify Murray’s search of Lajeunesse’s cell phone.

Because Officer Murray reasonably suspected that Lajeunesse’s phone

would show violations of the terms of his probation and/or illegal activity,

and because Lajeunesse’s expectation of privacy was further steeply

diminished on account of the terms of his probation, we conclude that the

search of his phone was reasonable under the Fourth Amendment.

2. The search was also constitutional under the “special-needs” exception of Griffin v. Wisconsin

We also examine the search under the special-needs analysis of Griffin

v. Wisconsin.

In Griffin, the Supreme Court identified an exception to the warrant and

probable cause requirement of the Fourth Amendment, ruling that the

“special need” of a state operating a probation system “permit[s] a degree of

impingement upon privacy that would not be constitutional if applied to the

public at large.”

(1987). In Griffin, the warrantless search of a

probationer’s home by a probation officer was held reasonable because “it

was conducted pursuant to a valid regulation governing probationers.”

. As we have previously explained, the “special-needs” framework

23 espoused in Griffin rests on the “rehabilitative relationship between the

[probationer] and the [probation] officer, and thus [does] not extend[] to other

law enforcement officers unless they are acting under the direction of the

[probation] officer.” United States v. Braggs,

(2d Cir. 2021)

(quoting United States v. Freeman,

(10th Cir. 2007)).

Otherwise, the special-needs framework is more deferential to the needs of

the probation system than the Knights framework and requires only that the

search be “conducted pursuant to a valid regulation governing probationers.”

Griffin,

;

(“The search of Griffin's home satisfied the

demands of the Fourth Amendment because it was carried out pursuant to a

regulation that itself satisfies the Fourth Amendment's reasonableness

requirement under well-established principles.”); Braggs,

n.4

(citing United States v. Quinones,

, 69 n.1 (2d Cir. 2012)

(summary order)). We find that this requirement was met.

The search of Lajeunesse’s phone was pursuant to a court-ordered

probationary condition, which “carries as much if not more constitutional

weight” as a regulation applicable to all probationers. People v. Hale,

(N.Y. 1999); see also United States v. Grimes,

, 258

24 n.3 (2d Cir. 2000) (per curiam) (“The critical question, for Fourth Amendment

purposes, is whether the regulation contains a reasonableness requirement (or

some more stringent standard); it is not which branch of Government

generated the rule.”); United States v. Giannetta,

(1st Cir.

1990). Under New York law, a probation officer may search a probationer

pursuant to a search condition, if the scope of the search condition is

“circumscribed to specified types of searches by probation officers acting

within the scope of their supervisory duty and in the context of the

probationary goal of rehabilitation.” Hale,

. 4 The New

York Court of Appeals has explained that this standard is “essentially” the

same as the limitation on searches by parole officers, which is that a search

must be rationally and reasonably related to the parole officer’s duties. People

v. Jackson,

(N.Y. 1978); People v. Huntley,

(N.Y. 1977). 5 With respect to parolees, we have long held that a requirement

4 Absent a search condition, the state imposes further limitations on the search of a probationer.

; Hale,

. 5 In People v. Jackson, the New York Court of Appeals explained that a

requirement that a search be “consistent with the duty to supervise adherence to the conditions of probation or parole and the duty to influence the offender

25 that a search be “rationally and reasonably related to the performance of [a]

parole officer’s duty” is a valid rule governing special-needs searches. United

States v. Grimes,

, 258–59, 259 n.4 (2d Cir. 2000) (quoting Huntley,

). By the same logic, a state law requirement that a search

must be rationally and reasonably related to a probation officer’s duties is

also consistent with the requirements of the Fourth Amendment.

As in Griffin, therefore, the search of Lajeunesse’s phone was pursuant

to a valid rule, because it was authorized by a search condition that contained

an acceptable court-made reasonableness limitation comporting with the

Fourth Amendment. See Grimes,

n.3. 6 We next assess whether

to refrain from unlawful conduct” is “essentially” the same as the limitations on parole officers,

, which is that a search must be “rationally and reasonably related to the performance of the parole officer’s duty,” Huntley,

. 6 Certain search conditions may be too restrictive, too burdensome, or too

intrusive to pass muster under the Fourth Amendment. See Lifshitz,

(finding that a probation requirement that the defendant install software that continuously monitored his computer usage may be an unconstitutional intrusion); United States v. Sofsky,

, 126–27 (2d Cir. 2002) (finding unconstitutional a probation condition that banned a defendant from using any computers and noting that a better approach would be unannounced inspections of the defendant’s computer). However, Lajeunesse has not challenged the conditions of his probation. 26 the search was permissible under that rule: was the probation officers’ search

of Lajeunesse’s phone rationally and reasonably related to their roles as

probation officers? It is clear that it was.

There can be no question that a search is rationally and reasonably

related to a probation officer’s duties if the probation officer reasonably

suspects that the probationer is violating a term of probation or is otherwise

engaged in criminal behavior. See Griffin,

(explaining that

restrictions placed on probationers “are meant to assure that probation serves

as a period of genuine rehabilitation and that the community is not harmed

by the probationer's being at large.”); Newton,

(explaining that

“the obligation to detect and prevent parole violations . . . is part of a parole

officer’s duty” (citation and quotation marks omitted)). Because we have

already concluded that Officer Murray had reasonable suspicion to conduct

this search, the search of Lajeunesse’s phone by Officer Murray (and the other

probation officers acting under his direction) was rationally and reasonably

related to Officer Murray’s duties as a probation officer. As such, it was

27 pursuant to a valid rule governing probationers and constitutional under the

special-needs exception to the Fourth Amendment. 7

3. The second search of Lajeunesse’s phone was not fruit of the poisoned tree

Lajeunesse’s sole argument regarding a later search of his phone by the

New York State Police is that it is the fruit of a poisoned tree because it was

justified by the findings on the earlier cell phone search, which violated the

Fourth Amendment. The argument has no validity because we have

concluded that the initial search of Lajeunesse’s phone was reasonable under

the Fourth Amendment. Because the initial search was constitutional, the

subsequent search by the New York State Police, based in part on the earlier

findings, was not the fruit of a poisoned tree. See Wong Sun v. United States,

(1962). The district court properly denied Lajeunesse’s motion to

suppress.

7Needless to say, if Lajeunesse’s agreement to the conditions of probation requiring his assent to searches of his phone, coupled with his turning over his phone to Officer Murray upon his request, constituted consent to the search (a question on which we express no opinion), the Fourth Amendment would not require reasonable suspicion to justify the search. See, e.g., Knights,

, 120 n.6; Schneckloth,

; Florida v. Jimeno,

. 28 II. Failure to Allow Allocution at Sentencing

Lajeunesse argues that the district court’s failure to provide him an

opportunity for allocution at his sentencing requires that we vacate his

sentence and remand for resentencing, notwithstanding his waiver of his

rights to appeal a sentence to a term of imprisonment of less than 210 months

or his failure to object at sentencing. The government argues principally that

Lajeunesse’s appeal waiver is broad and bars him from appealing his

sentence, especially given this court’s presumption of enforceability of

appellate waivers. Lajeunesse argues that the language in his waiver was

narrower than the type of language we have previously upheld and that it

should not be enforced in this instance.

We first assess whether Lajeunesse’s waiver bars him from appealing

this alleged error, and second, whether this allocution error, to which no

objection was made during the sentencing proceeding, requires that the

sentence be vacated. We hold that the appeal waiver does not bar this appeal

and that resentencing is required.

29 1. The appeal waiver does not bar this appeal

Lajeunesse’s plea agreement waived his right to appeal “any sentence

to a term of imprisonment of 210 months or less.” App’x at 193. Because

Lajeunesse was sentenced to a prison term of 198 months, the government

asserts that he waived the right to appeal. Lajeunesse argues that his appeal

waiver does not cover a procedural error such as allocution. Considering the

appellate waiver in the context of the full plea agreement and in light of the

importance of the right to allocution, we conclude that his broad general

waiver should be construed as not contemplating a scenario in which the

district court failed to invite allocution and therefore does not cover it.

“We review plea agreements, including waivers of the right to appeal,

de novo and in accordance with general principles of the law of contract.”

United States v. Green,

(2d Cir. 2018); see also United States v.

Yemitan,

(2d Cir. 1995). But plea agreements are not ordinary

contracts. Rather, we “temper the application of ordinary contract principles

with ‘special due process concerns for fairness and the adequacy of

procedural safeguards.’” United States v. Granik,

(2d Cir.

2004) (quoting United States v. Altro,

(2d Cir. 1999)). Further,

30 recognizing the government’s “awesome advantages in bargaining power” in

construing such agreements, we tend to favor the defendants in cases of

doubt. United States v. Ready,

(2d Cir. 1996), superseded on other

grounds as stated in United States v. Cook,

(2d Cir. 2013); see

also United States v. Woltmann,

(2d Cir. 2010) (“Such contracts

are narrowly construed.”).

A plea agreement that waives the right to appeal a sentence is

“presumptively enforceable” if it has been entered into “knowingly,

voluntarily, and competently.” United States v. Riggi,

(2d Cir.

2011) (first quoting United States v. Arevalo,

(2d Cir. 2010); and

then quoting United States v. Gomez–Perez,

(2d Cir. 2000)).

Exceptions to this presumption “occupy a very circumscribed area of our

jurisprudence.” Riggi,

(quoting Gomez-Perez,

).

In part, this has been to preserve the value of an appellate waiver as a

“bargaining chip” for the defendant. Yemitan,

.

Nonetheless, not all appellate waivers are enforceable. Prior rulings

have shed some light on what sorts of errors may be found to fall outside the

scope of a general appeal waiver. We have explained that “‘a defendant may

31 be deemed incapable of waiving a right that has an overriding impact on

public interests,’ . . . as such a waiver may ‘irreparably discredit[] the federal

courts.’” Riggi,

(alteration in original) (quoting Ready, 82 F.3d

at 555–56). For example, we have suggested that “a sentence tainted by racial

bias could not be supported on contract principles, since neither party can be

deemed to have accepted such a risk or be entitled to such a result as a benefit

of the bargain.” Yemitan,

; see also United States v. Jacobson,

, 22–23 (2d Cir. 1994) (holding that an appellate waiver did not extend

to “an arguably unconstitutional use of naturalized status as the basis for a

sentence.”). We have also found that an appellate waiver did not extend to

cover scenarios in which the district court rooted its decision in mistakes of

fact. United States v. Liriano-Blanco,

, 174–75 (2d Cir. 2007) (finding

that the appellate waiver did not cover court’s sentence when based on the

mistaken belief that the defendant had retained the right to appeal a relevant

legal question).

We have enforced general appellate waivers as to claims of more

clerical procedural errors. For example, we have construed general appellate

waivers to cover instances in which a judge failed to provide a rationale for

32 the particular sentence, in contravention to

(c)(1), although

noting that, “[a]t some point, . . . an arbitrary practice of sentencing without

proffered reasons would amount to an abdication of judicial responsibility

subject to mandamus . . . .” Yemitan,

. Similarly, we have upheld

general appellate waivers in cases where the district court failed to rule on

objections to the Presentencing Report (PSR) and on requests for a downward

departure, did not adopt the findings of the PSR, did not explain its analysis

of the sentencing factors, and did not calculate a sentencing range. United

States v. Buissereth,

, 117–18 (2d Cir. 2011). In so doing, however,

we recognized that “it is apparent from the transcript . . . that the District

Court gave due consideration to [the defendant’s] sentencing arguments.”

; see also Arevalo,

(upholding an appellate waiver when the

district court failed to make an explicit determination on facts in the PSR, but

recognizing that the district court had “heard the parties’ objection” and

“ultimately agreed . . . that the lower Guidelines range should apply”).

The nub of the appeal waiver analysis is “the nature of the right at issue

and whether the sentence ‘was reached in a manner that the plea agreement

did not anticipate.’” Riggi,

(quoting Liriano-Blanco,

174). Applying this framework, we now assess the nature of the right to

allocution at sentencing and whether Lajeunesse’s plea agreement could have

anticipated that his sentence would be reached without him having had an

opportunity to address the court.

Although the right to allocution is not a constitutional right, this court

has described it as an “absolute right.” United States v. Li,

, 132–33

(2d Cir. 1997) (quoting United States v. Sparrow,

(5th Cir.

1982)). The right has been codified in the Federal Rules of Criminal Procedure

for over 80 years, and its history extends back much further. See Fed. R. Crim.

P. 32(i)(4)(A)(ii) (“Before imposing sentence, the court must: . . . address the

defendant personally in order to permit the defendant to speak or present any

information to mitigate the sentence.”). The leading resource on the history of

allocution describes the practice as “of such ancientness that it is difficult, if

not impossible, to discover its historical origin.” See Paul W. Barrett,

Allocution, 9 MO. L. R. 115, 115 (1944). Allocution has its roots in common law,

dating back to at least 1689. Id. at 121; see also Schwab v. Berggren,

(1892) (tracing allocution to common law); Green v. United States,

(1961) (same); see also Rex v. Royce, 4 Burr. 2073, 2086, 98 Eng. Rep. 81

34 (K.B. 1767) (summarizing an allocution that occurred at sentencing). At

common law, a bill of attainder—which prevented the family of the

defendant from inheriting property or titles—could be reversed if allocution

had not been offered. Barrett, Allocution at 129–30; see Anonymous, 3 Mod. 265,

266, 87 Eng. Rep. 175 (K.B. 1689) (reversing a bill of attainder because the

defendant was not given an opportunity to say “why sentence of death shall

not pass upon him”); The King v. Speke, 90 Eng. Rep. 1047 (K.B. 1689–1712)

(same); Rex & Regina v. Geary, 2 Salk. 630, 91 Eng. Rep. 532 (K.B. 1689–1712)

(same).

Allocution is “designed to enable our system of justice to mete out

punishment in the most equitable fashion possible, [and] to help ensure that

sentencing is particularized and reflects individual circumstances.” Li,

(quoting United States v. Barnes,

(7th Cir. 1991)).

Given that about 98% of criminal convictions adjudicated in a U.S. district

court are the result of a plea agreement, for nearly all convicted defendants, a

defendant’s sole opportunity to address the court and share his or her story is

during allocution at sentencing. See Mark Motivans, Bureau of Justice

35 Statistics, Federal Justice Statistics, 2020 at 10 (May 2022). 8 We have observed

that allocution humanizes the sentencing process, providing a defendant with

an opportunity to be heard and reducing the appearance of “assembly-line

justice.” Li,

(quoting Barnes,

).

In sum, while allocution is not a constitutional right, the right is a

weighty one that is essential to the sentencing process and that carries

important public policy implications. Furthermore, deprivation of allocution

is a far more substantial error than the clerical, non-prejudicial procedural

errors for which we have enforced appellate waivers. See, e.g., Buissereth,

; Arevalo,

. Here, the nature of the error meant that the

district court lacked access to important information—the defendant’s

attitude towards his commission of the crime 9—and is therefore more akin to

8 Table 6 of this report shows that, in FY 2020, 90.9% of criminal cases in a U.S. district court resulted in convictions following a guilty plea. In comparison, 1.7% of criminal cases resulted in convictions following a trial. This means that of the 92.6% of federal criminal cases that resulted in a conviction, 98.1% of those convictions were the result of a guilty plea. See also Mark Motivans, Bureau of Justice Statistics, Federal Justice Statistics, 2019 at 10 (Oct. 2021). 9 Lajeunesse’s letter to the court cannot, alone, provide this information. A

face-to-face communication gives the court an infinitely better opportunity to evaluate the sincerity of claims of contrition and remorse than a letter.

36 a case where the district court rooted its decision in mistaken fact. Liriano-

Blanco,

. The guideline sentencing range was 180 to 210 months

imprisonment and surely, the defendant’s remorsefulness—or lack thereof—

could have impacted the district court’s sentencing decision.

We next consider whether Lajeunesse’s plea agreement should be

construed as including an agreement on Lajeunesse’s part to give up his right

to this statutorily-guaranteed opportunity to address the court as to his

sentence, in the event the court erroneously failed to accord him the right.

Lajeunesse’s plea agreement waived his right to appeal “[a]ny sentence to a

term of imprisonment of 210 months or less.” App’x at 193. This waiver is

broad on its face, but when viewed in the context of the entire contract and

against the backdrop of the magnitude of the right to allocution, we find it

cannot be reasonably read to have contemplated this scenario, in which

Lajeunesse would be deprived of his right to allocution. The agreement seems

to take Lajeunesse’s allocution as a given. For example, the agreement

explains, “The defendant understands that the sentencing court may consider

Furthermore, some people, perhaps including Lajeunesse, may lack resources to communicate such sentiments in writing. 37 any statement that the defendant has made or makes in this Plea Agreement,

during the guilty plea, to the Probation Office, and at sentencing when imposing

sentence.”

at 197–98 (emphasis added). Similarly, should Lajeunesse breach

the agreement, in future proceedings against him, the government may

“utilize any information, statement, or testimony provided by the defendant

in any proceeding, including at sentencing . . . .”

(emphasis added).

It also seems to us that a circumstance, such as this one, where the

district court fails to invite the defendant to speak at sentencing and no

objection is made, such that the district court’s error is not called to its

attention prior to pronouncing a sentence, is likely a rarity. It therefore seems

unlikely to be the type of error that one would anticipate in drafting an

appellate waiver.

Given the magnitude and character of the right to allocution, its

longstanding history, and our perception that this type of error is uncommon,

we do not think Lajeunesse’s plea agreement can reasonably be construed as

anticipating a sentencing proceeding that omitted allocution. We decline to

enforce the appeal waiver and proceed to the merits.

38 2. Resentencing is required because Lajeunesse was not afforded an opportunity to speak at sentencing

On the merits of the question, Lajeunesse argues that resentencing is

required because he was not afforded his right to allocute. He argues that the

court’s failure to provide allocution calls for automatic resentencing, even

under plain error review, given that he made no objection during the

sentencing proceeding. The government’s brief focuses on enforcement of his

waiver of appeal and advances no argument against ordering resentencing in

the event we do not enforce the appeal waiver. We conclude that we should

remand for resentencing, as the defendant has made a reasonable argument

that he is entitled to resentencing and the government has made no argument

to the contrary. See, e.g., United States v. Gonzalez,

(2d Cir.

2008). Because the government makes no argument to the contrary, we do so

without ruling as to the appropriate standard of review for an unpreserved

claim of failure to grant allocution. Accordingly, we remand to the district

court with instructions to vacate his sentence and resentence, affording him

the right of allocution.

39 CONCLUSION

For the foregoing reasons, we affirm the district court’s denial of

Lajeunesse’s motion to suppress, but remand the case to the district court

with instructions to vacate the sentence and resentence, affording the

defendant the right of allocution in conformance with Rule 32.

40