          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
              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


                                         - 2 -
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,


                                     - 3 -
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




                                     - 4 -
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 Valle-

Cruz, 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.
       2We 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


                                           - 5 -
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).


                                       - 6 -
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.


                                       - 7 -
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


                                    - 8 -
or obvious error, thus satisfying the first two prongs of the

plain-error standard Fey must meet.                   See United States v. Perazza-

Mercado, 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.


                                              - 9 -
                                         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.


      5This 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)).


                                    - 10 -
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




                               - 11 -
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 plain-

error 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 plain-

error 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




                                      - 12 -
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).


                                  - 13 -
      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 re-

examination of that condition.




      7For 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.


                                       - 14 -
