United States Court of Appeals 

For the First Circuit 

No. 15-1166 

UNITED STATES OF AMERICA, 

Appellee, 

v. 

JONATHAN FEY, 

Defendant, Appellant. 

APPEAL FROM THE UNITED STATES DISTRICT COURT 

FOR THE DISTRICT OF MASSACHUSETTS 

[Hon. Rya W. Zobel, U.S. District Judge] 

Before 

Howard, Chief Judge, 

Torruella and Barron, Circuit Judges. 

Lisa Aidlin for appellant. 

Kelly Begg Lawrence, Assistant United States Attorney, with 

whom Carmen M. Ortiz, United States Attorney, was on brief, for 

appellee. 

August 16, 2016 
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BARRON, Circuit Judge. Defendant Jonathan Fey was 

convicted for his failure to register as a sex offender under the 

Sex Offender Registration and Notification Act ("SORNA"), 18 

U.S.C. § 2250(a). He now challenges a number of the special 

conditions of supervised release that the District Court imposed 

in connection with the sentence for that conviction. For the 

reasons set forth below, we vacate the condition restricting Fey's 

contact with children but affirm the remaining conditions that he 

challenges. 

I.

Fey's obligation to register pursuant to SORNA stems 

from an incident that took place in 1999. In August of that year, 

Fey -- then 29 years old -- rented a motel room to host a party 

with his co-workers, one of whom was V.P., a 16-year-old girl. 

Fey provided V.P. with alcohol and then raped her after she passed 

out. As a result of that incident, Fey was convicted in 

Massachusetts state court of (1) rape and (2) indecent assault and 

battery on a person over 14 years of age. Fey served nine years 

in prison and was released on June 9, 2010. 

After his release from prison, Fey registered as a sex 

offender on five separate occasions. After June 22, 2011, however, 

he failed to continue to update his registration. In July 2011, 

a warrant was issued for his arrest based on Fey's failure to 

register. Fey was eventually located and arrested in Ohio in May 
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2014. At the time of his arrest, Fey was living with his fiancée 

and her four minor daughters. 

Fey pleaded guilty to the SORNA violation on October 28, 

2014, in the U.S. District Court for the District of Massachusetts. 

At his sentencing, the District Court imposed a period of 

imprisonment of eighteen months, a five-year period of supervised 

release, and a number of conditions of supervised release, three 

of which Fey now challenges on appeal. 

II.

We assess the validity of a special condition of 

supervised release by applying 18 U.S.C. § 3583(d) and §5D1.3(b) 

of the United States Sentencing Guidelines. United States v. 

Pabon, 819 F.3d 26, 30 (1st Cir. 2016). Those provisions "require 

that special conditions cause no greater deprivation of liberty 

than is reasonably necessary to achieve the goals of supervised 

release, and that the conditions be reasonably related both to 

these goals and to the nature and circumstances of the offense and 

the history and characteristics of the defendant." Id. (quoting 

United States v. Del Valle–Cruz, 785 F.3d 48, 58 (1st Cir. 2015)). 

In imposing a special condition, "the district court is 

'required to provide a reasoned and case-specific explanation for 

the conditions it imposes.'" Id. (quoting Del Valle–Cruz, 785 

F.3d at 58). Such an explanation both is required by statute, see 

18 U.S.C. § 3553(c), and facilitates our review on appeal, Pabon, 
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819 F.3d at 31. If the sentencing court does not explicitly 

provide such an explanation, however, we will not automatically 

vacate the condition. Id. Instead, we will attempt to "infer the 

court's reasoning from the record." Id. "In all cases, however, 

the sentence must find 'adequate evidentiary support in the 

record.'" Id. (quoting Del Valle–Cruz, 785 F.3d at 58). 

A.

Fey first challenges a condition restricting his right 

to associate with minors. That condition reads: 

The defendant shall have no direct or indirect contact 

with children under the age of 18, except in the presence 

of a responsible adult who is aware of the nature of the 

defendant's background and current offense, and who has 

been approved by the [probation office]. 

Fey argues that the District Court erred in failing to provide an 

explanation for this condition and that the District Court's 

reasoning cannot be inferred from the record. The parties dispute 

whether Fey objected on this ground below and further dispute the 

standard of review. We need not resolve that dispute, however, as 

we conclude that Fey can meet the more demanding plain-error 

standard that the government asks us to apply. That standard 

requires him to show "(1) that an error occurred (2) which was 

clear or obvious and which not only (3) affected the defendant's 

substantial rights, but also (4) seriously impaired the fairness, 

integrity, or public reputation of judicial proceedings." United 
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States v. Padilla, 415 F.3d 211, 218 (1st Cir. 2005) (en banc) 

(quoting United States v. Duarte, 246 F.3d 56, 60 (1st Cir. 2001)). 

The government concedes that the District Court "did not 

expound on its reasons" for imposing this associational condition. 

Indeed, the District Court simply stated: "[T]his is a draconian 

order, but I fear that I must impose it." The government contends, 

however, that the District Court's "reasoning is readily inferred 

from the record." We disagree. 

In Pabon, we noted that "we have vacated associational 

conditions where the defendant's prior sex offense occurred in the 

distant past, the intervening time was marked by lawful social 

activity, and the district court did not otherwise explain the 

need for such restrictions." 819 F.3d at 31 (citing Del ValleCruz, 785 F.3d at 59-64). Here, the offense that triggered Fey's 

registration requirement, which occurred in 1999, is a remote one.1 

Cf. Del Valle-Cruz, 785 F.3d at 53, 59 (finding it "troubling" 

that the District Court had imposed associational conditions 

fifteen years after the defendant's underlying sex conviction).2 

 1 We note also that, according to the presentence report, the 

triggering offense occurred at a time when Fey was struggling with 

alcohol abuse. The record indicates that he has been sober since 

1999. 

2 We take the government's point that Fey has spent 

approximately thirteen of the seventeen years since Fey's most 

recent sex offense in prison. But we disagree with the government 

that, as a result, "the temporal connection between Fey's most 

recent prior sex offense and the no contact with minors condition 

is compelling." Although the years of incarceration are relevant 
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In addition, Fey has not committed any sexual or violent crimes in 

the intervening years. According to the record, the only unlawful 

activities in which Fey has engaged between 1999 and today were 

his failures to register as a sex offender and a violation of the 

probation condition restricting him from living with children. 

Cf. id. at 60 & n.10 (vacating a similar condition even though the 

defendant had been convicted four times, including once for 

domestic battery, in the intervening years since his conviction 

for a sex crime); United States v. Mercado, 777 F.3d 532, 534 (1st 

Cir. 2015) (upholding a similar condition in part because the 

sentencing court had noted that "the defendant had what may have 

been one of the most profuse criminal histories the court had ever 

seen"). And, although the condition does not "place an outright 

ban on [Fey's] association with minors," it operates not "in 

limited contexts" but in all contexts. Pabon, 819 F.3d at 31-32. 

Nevertheless, the government argues that other aspects 

of the record make the District Court's unstated reasoning plain. 

See id. at 31 (noting that we have upheld associational conditions 

even when the defendant has not committed a sex offense or 

 

to an analysis of the danger Fey may pose to the public, they do 

not transform an offense that took place seventeen years ago into 

one that took place four years ago. Cf. Del Valle-Cruz, 785 F.3d 

at 52, 59 (focusing on the time between the underlying conviction 

and the imposition of the challenged condition without discounting 

that time based on the years the defendant had spent in jail in 

between). 
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substantial other criminal activity in recent years when the 

defendant's conduct "otherwise indicates an enhanced risk to 

minors"). The government first notes that Fey's triggering offense 

was for rape and that it was not his first sex offense. Rather, 

in 1989, when Fey was 19 years old, he was convicted of sexual 

assault in the third degree on the basis of a relationship he had 

with his 14-year-old girlfriend.3 Next, the government points out 

that the record shows that, in consequence of that conviction, Fey 

was ordered to have no further contact with his 14-year-old 

girlfriend after the 1989 conviction and yet was seen in his car 

with her about a year later. The government further notes that 

the record shows that, as a condition of his probation for his 

1999 rape conviction, Fey was also ordered to "have no unsupervised 

contact with children under the age of 18, other than his own 

child" and was prohibited "from sleeping in a residence in which 

there was a minor, other than his own child, under the age of 18, 

even with an adult present." But, notwithstanding those 

restrictions, Fey admits that he was living with his fiancée and 

her four minor daughters prior to his 2014 arrest. 

In pressing this contention, the government contends 

that our decision in Del Valle-Cruz, in which we vacated a similar, 

unexplained associational condition imposed on another defendant 

 3 This conviction apparently did not trigger any requirement 

to register as a sex offender. 
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who had been convicted of a SORNA violation, is not to the 

contrary. The government rightly points out that Fey has committed 

both more (two as opposed to one) and more serious (rape as opposed 

to sexual battery) sex offenses than had Del Valle-Cruz and that 

Del Valle-Cruz had not violated prior no-contact orders while Fey 

has (by living with his fiancée's daughters in 2014 and by 

contacting his underage girlfriend in 1990). 

But while we agree with the government that the record 

here provides greater support for upholding the associational 

condition than did the record in Del Valle-Cruz, the associational 

condition imposed here -- in addition to having a weak temporal 

connection with Fey's sex offense -- is very broad. It prohibits 

Fey from having unapproved "direct or indirect contact" with all 

children: male children, female children, and children of all ages, 

whether or not they are members of Fey's family. Yet, as Fey 

points out, the record reveals no instances in which Fey committed 

a sex offense of any kind against boys, against pre-pubescent 

children, or against members of his family. And the government 

has made no argument that Fey is a danger to such children. Cf. 

United States v. Vélez-Luciano, 814 F.3d 553, 564 (1st Cir. 2016) 

("The record reflects that Vélez–Luciano only poses a threat to 

young girls -- nothing suggests he has any predilection towards 

males."). Thus, given that the District Court did not give any 

explanation, we conclude that the District Court committed a clear 
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or obvious error, thus satisfying the first two prongs of the 

plain-error standard Fey must meet. See United States v. PerazzaMercado, 553 F.3d 65, 78 (1st Cir. 2009). 

And Fey has also satisfied the third and fourth prongs 

of the plain-error test. As we explained in Perazza-Mercado, when 

a District Court provides no explanation for a condition that does 

not find apparent support in the record, "there is a reasonable 

probability that the court might not have imposed the prohibition 

if it had fulfilled its obligation to explain the basis for the 

condition or at least made sure that the record illuminated the 

basis for the condition." Id. And, as we further explained, "[w]e 

cannot endorse the summary imposition of such a significant 

prohibition," unexplained by the District Court and without 

apparent grounding in the record, "without impairing the 

'fairness, integrity, or public reputation of the judicial 

proceedings.'" Id. at 79 (quoting United States v. Wallace, 461 

F.3d 15, 44 (1st Cir. 2006)). Thus, although restrictions on Fey's 

ability to interact with such children might conceivably be 

justifiable under § 3583(d), we conclude this associational 

condition must be vacated.4

 4 Because we conclude that the condition must be vacated on 

this ground, we need not address Fey's contention that the 

condition represents an over-delegation of authority by the 

District Court to the probation office. 
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B.

Fey next challenges a condition that relates to his 

employment. That condition, as orally imposed by the District 

Court at the sentencing hearing,5 is the following. 

[The defendant] shall not be employed in any capacity 

that may cause [him] to come into direct contact with 

children except under circumstances approved in advance 

by the Probation Office and [he] shall not participate 

in any volunteer activity that may cause [him] to come 

in direct contact with children except under 

circumstances approved in advance by the Probation 

Office. 

The District Court again did not provide any 

particularized explanation for this condition. And Fey again 

contends that the record does not support the condition. But we 

do not agree, even assuming (contrary to the government's 

contention) that this challenge is preserved and thus subject to 

review for abuse of discretion. 

Although the District Court did not spell out its 

reasoning, the record here plainly indicates that Fey could pose 

a danger to children in the employment context. Fey's prior sex 

offense involved raping an underage co-worker after providing her 

with alcohol at a party that he was hosting for his co-workers. 

 5 This condition does not appear in the written judgment, but 

Fey makes no argument that it was not actually imposed. And for 

good reason. We have said that, where the conditions imposed 

orally "'conflict in a material way' with the conditions that ended 

up in the judgment," "the oral conditions control." United States 

v. Santiago, 769 F.3d 1, 10 (1st Cir. 2014) (quoting United States 

v. Sepúlveda–Contreras, 466 F.3d 166, 169 (1st Cir. 2006)). 
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Thus, a condition requiring that he seek approval from probation 

before accepting a job or volunteer activity that would bring him 

into direct contact with minors is reasonably related to his 

criminal history. Cf. Del Valle-Cruz, 785 F.3d at 57 ("Because 

Del Valle–Cruz's underlying conviction arose from an incident that 

took place in his workplace, with a minor volunteer, these two 

[employment] restrictions are at least reasonably related to his 

history and characteristics."). 

Fey argues that the condition should be vacated because 

it, like the general associational condition discussed above, does 

not differentiate between types of children to whom Fey arguably 

poses some risk and others -- like boys and young children -- to 

whom he apparently does not. But this condition is less sweeping 

than the more general associational condition. It operates only 

in the "limited context[]" of employment. See Pabon, 819 F.3d at 

31-32. In addition, Fey must seek that approval only before 

accepting a job that would put him in "direct," rather than "direct 

or indirect" contact with children. There is thus no reason to 

believe that such a requirement will impose the kind of significant 

restriction on Fey's liberty that the more general associational 

condition (which uses the "direct or indirect" formulation) would. 

Accordingly, because the District Court's reasoning for imposing 

this condition can be inferred from the record, we conclude that 
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the District Court did not abuse its discretion in imposing the 

condition without an express explanation. 

Fey also makes a number of arguments based on 18 U.S.C. 

§ 3563(b)(5) and §5F1.5 of the United States Sentencing Guidelines. 

These arguments, which he unmistakably did not raise below, fail 

as well. Even if Fey is correct that this condition is an 

occupational restriction subject to § 3563(b)(5) and §5F1.5 and 

that the District Court failed to abide by the terms of those 

sections in imposing that condition, he cannot show plain error, 

as he must to prevail on this newly pressed challenge. See 

Padilla, 415 F.3d at 218. As set forth above, to meet the plainerror standard, Fey must show "(1) that an error occurred (2) which 

was clear or obvious and which not only (3) affected the 

defendant's substantial rights, but also (4) seriously impaired 

the fairness, integrity, or public reputation of judicial 

proceedings." Id. (quoting Duarte, 246 F.3d at 60). But Fey has 

made no argument that any error the District Court committed in 

imposing this condition affected his substantial rights or 

seriously impaired the fairness, integrity, or public reputation 

of judicial proceedings. Thus, he has not met his burden on plainerror review and we have no basis on which to vacate the condition. 

See United States v. Olano, 507 U.S. 725, 734 (1993) (explaining 

that, on plain-error review, "[i]t is the defendant rather than 
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the Government who bears the burden of persuasion with respect to 

prejudice.").6

C.

Fey's final challenge is to the condition that reads, in 

pertinent part: "The defendant shall participate in a sexual 

specific evaluation or sex offender specific treatment, conducted 

by a sex offender treatment provider, as directed and approved by 

the Probation Office." On appeal, Fey appears to challenge the 

imposition of both sexual specific evaluation and sex offender 

specific treatment. But the government argues that he 

affirmatively waived his objection to both aspects of this 

condition in the course of a colloquy with the District Court. We 

agree. 

The relevant colloquy proceeded as follows. 

Fey's Counsel: I would ask . . . that the Court allow 

Probation to have Mr. Fey go under a sex offender 

evaluation, and I've had that on other occasions, and 

the reason I like the evaluation is if they have an 

evaluation and they have information that comes back 

saying this doctor says this man needs treatment, they 

can come back to the Court. However, when you attach 

the horse to the cart, the cart tends to get pulled along 

because it's all one in the same, meaning that the 

treatment -- 

The Court: But Probation doesn't have to direct it and 

Probation -- it is as directed and approved by Probation. 

 6 Fey briefly adverts to an argument that the District Court 

erred by delegating authority to probation to oversee his 

employment, but he has not developed that argument and so we deem 

it waived. See United States v. Zannino, 895 F.2d 1, 17 (1st Cir. 

1990). 
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Probation doesn't require it in every sentence. 

Probation tailors it to the situation as they see it. 

So, this is not a mandatory thing. It is something that 

Probation may ask for and if it does, he can object. 

Fey's Counsel: Fine. I'll cross that bridge. I would 

object, though, to [other conditions] . . . . 

Through this exchange, Fey disclaimed any objection to 

the imposition of a sexual specific evaluation by requesting that 

such an evaluation take place. He then affirmatively abandoned 

any objection to the sex offender treatment portion of the 

condition upon being told that he could object at a later date if 

probation does in fact direct such treatment. Having 

"intentional[ly] relinquish[ed] . . . [his] known right" to object 

to either aspect of the condition, Fey cannot now re-assert that 

right on appeal. Id. at 725, 733.7 As the District Court 

instructed him at sentencing, he is free to object at a later date 

if he is in fact ordered to undergo sex offender treatment. 

III.

For the reasons set forth above, we vacate the condition 

restricting Fey's "direct or indirect contact with children under 

the age of 18" and remand for re-sentencing limited to a reexamination of that condition. 

 7 For the same reason, Fey waived any argument that, as he 

now asserts, this condition represented an improper delegation of 

authority by the District Court to the probation office.