United States Court of Appeals For the First Circuit No. 20-1234

UNITED STATES OF AMERICA,

Appellee,

v.

ROBERT McCULLOCK,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS

[Hon. William G. Young, U.S. District Judge]

Before

Lynch, Lipez, and Thompson, Circuit Judges.

Brendan Kelley, Assistant Federal Public Defender, for appellant. Donald C. Lockhart, Assistant United States Attorney, with whom Andrew E. Lelling, United States Attorney, was on brief, for appellee.

March 18, 2021 THOMPSON, Circuit Judge. We affirm the district judge's

imposition of three special conditions of supervised release. The

how, what, and why behind our decision follows.

How the Case Got Here1

Robert McCullock has spent much of his life on the wrong

side of the law. And his rap sheet is quite disturbing, to say

the least.

First there is his state conviction for two counts of

child molestation: In separate incidents in 1999 and 2000,

McCullock sexually abused five- and nine-year-old girls in

Georgia. And the three-year-old brother of the five-year-old girl

witnessed his sister's molestation. McCullock admitted both

offenses, going so far as to reveal that he had tried to (but could

not) put his penis in the five-year-old girl's vagina. He ended

up with an eight-year prison sentence in 2002.

Then there is his federal conviction for using a computer

to send child pornography: In 2001, while on bond during the

pendency of the molestation case, McCullock participated in a

child-porn file-sharing service. German police downloaded three

child-porn images from his computer located in the United States

(two of the images showed adult men raping girls as young as six).

1 The major background events are undisputed. - 2 - And Georgia police discovered hundreds of kiddie-porn images — and

thousands of erased images — on a computer he had pawned. During

his presentence interview in that case, he told authorities that

he watched child pornography on his computer to lessen his desire

to abuse children and that he "felt he had no cravings for children

anymore at that point" when "he sold his computer" (these are not

direct quotes from McCullock but rather probation's summary of

what he said). After pleading guilty to using a computer to

transport child porn, he got sentenced to ninety-two months in

prison, to run consecutively with the state-prison term, and to

three years of supervised release. His conditions of supervised

release there included bans on committing any state or federal

crime; possessing or viewing sexual materials depicting children

or adults; having any contact with minors unless accompanied by an

adult who is approved by probation and who knows of his child-sex-

abuse history; and using or possessing a computer with internet

access without probation's prior say-so.

And finally there is his state conviction for indecent

assault and battery on a person over the age of fourteen: In 2017,

while on supervised release for the child-porn offense, McCullock

(according to a report by police in Massachusetts) tried to rape

his then-girlfriend. During the violent encounter, he (according

to her) said that "he was going to rape her" and that she had to

- 3 - "'suck[]' and 'fuck him'" — and then he "threw [her] pants across

the room and threw [her] on the bed numerous times." Charged with

"assault to rape," he later pled down to the just-mentioned

indecent-assault-and-battery offense. This time he got two years

in prison.

McCullock's last run-in with the law resulted in the

revocation of his supervised release — the revocation occurred

after his stint in state prison for what he had done to his onetime-

girlfriend and after his civil commitment as a sexual predator.

We will have more to say about the revocation later. But for now

it is enough to note that following a hearing, a district judge

sentenced him to six months in prison plus thirty months (or 2½

years) of supervised release, and imposed a series of special post-

release conditions suggested by probation in its violation report.

Three are relevant here.

Special condition 6 says that McCullock "shall not

possess, access, subscribe, or view any videos, magazines,

literature, or Internet websites depicting children or adults in

the nude and/or engaged in sexual activities." Special condition

9 provides that McCullock "must not possess or use any computer or

internet-capable device without prior approval from the Probation

Office" and adds that "[a]ny such device should not be used to

knowingly access or view sexually explicit materials as defined in

- 4 -

(2)(A)." And special condition 12 states that

McCullock "must not knowingly have direct contact, or contact

through a 3rd party, with children under the age of 18, unless

previously approved by the Probation Office, or in the presence of

a responsible adult who has been" preapproved "by the Probation

Office, and who is aware of the nature of [McCullock's] background

and current offense."2

Unhappy with these special conditions, McCullock

appeals.3

What McCullock Argues And Why We Affirm

Reduced to its essence, McCullock argues that the judge

"procedurally" erred by failing to adequately explain the basis

for these special conditions, and then "substantively" erred by

2 We took these quotes from the written judgment, which mimics language in the violation report. McCullock says that the "judgment differs from the [judge's] oral pronouncement" at sentencing "with respect to [special] conditions 6 and 9." But he makes no claim that the differences are "material," noting instead that the judge clearly "included the adult content in [his] prohibitions in both the oral and written conditions." See generally United States v. Fey,

, 6 n.5 (1st Cir. 2016) (mentioning the general rule that when "the conditions imposed orally conflict in a material way with the conditions that ended up on the judgment, the oral conditions control" (quoting United States v. Santiago,

(1st Cir. 2014)). So we need say no more on this subject. 3 For anyone wondering: McCullock completed the six-month prison term and is now on supervised release, subject of course to the complained-of special conditions. - 5 - making them "overly broad" (we will give more specifics shortly)

— in other words, he challenges these special conditions as

"unreasonable." But like the government, we find his arguments

unconvincing.

Standards of Review

We review preserved challenges to the imposition of

special-supervised-release conditions for abuse of discretion and

unpreserved ones for plain error. See, e.g., United States v.

Vega-Rivera,

(1st Cir. 2017).

The abuse-of-discretion standard is multi-dimensional,

however. Within it, we inspect fact findings for clear error,

legal issues de novo (in nonlegalese, with fresh eyes), and

judgment calls with some deference. See, e.g., United States v.

Hood,

(1st Cir. 2019). And we will find an

abuse of discretion only when left with a definite conviction that

"no reasonable person could agree with the judge's decision." See

United States v. Cruz-Ramos,

(1st Cir. 2021)

(internal quotations and citation omitted).

As for plain error, the standard is quite formidable.

The complaining party must show that the judge erred, and glaringly

so (such that the judge should have acted without an objection

from counsel), and that the error affected that party's substantial

rights — typically, because it likely influenced the proceeding's

- 6 - outcome. See United States v. Takesian,

(1st

Cir. 2019). And even if he meets those conditions, we will use

our discretion to fix the error only if he also shows that it

"seriously imperil[s]" the judiciary's public reputation. See

id.; see also Cruz-Ramos,

.

Explanation (The Procedural-Reasonableness Challenges)

We begin with McCullock's procedural-reasonableness

challenges to the sufficiency of the judge's explanation for the

special conditions, starting with conditions 6 and 9 — which (to

borrow McCullock's paraphrase) ban, for 2½ years, "any possession

or access to materials involving adult nudity or sexual activity."4

The parties dispute what standard of review applies to

this aspect of McCullock's procedural-reasonableness claim.

McCullock pushes for abuse of discretion, the government for plain

error. We side with the government.

To save the reader the need to flip back to where we quoted 4

these conditions before: Special condition 6 says that, for 2½ years, McCullock "shall not possess, access, subscribe, or view any videos, magazines, literature, or Internet websites depicting children or adults in the nude and/or engaged in sexual activity." And special condition 9 says that, for 2½ years, he "must not possess or use any computer or internet-capable device without prior approval from the Probation Office" and notes that "[a]ny such device should not be used to knowingly access or view sexually explicit materials as defined in

(2)(A)." - 7 - True, as both sides agree, McCullock objected to special

conditions 6 and 9, telling the judge in his predisposition memo

and at the final revocation hearing that nothing in the record

supported adult-content restrictions. And having read every word

of the hearing transcript, we agree with McCullock that the judge

gave no justifications for their imposition. Nor — as McCullock

also notes, without contradiction from the government — did the

prosecutor or probation give any justifications below.

But the hearing transcript does reveal that McCullock

never objected to the judge's lack of explanation — despite having

the chance to do so. And had he protested, the judge could have

cured any problem then and there — thus avoiding the need for an

appeal. See, e.g., Puckett v. United States,

(2009) (noting that plain-error review "serves to induce the timely

raising of claims and objections, which gives the district court

the opportunity to consider and resolve them"); United States v.

Dominguez Benitez,

(2004) (stating that the plain-

error standard "encourage[s] timely objections and reduce[s]

wasteful reversals by demanding strenuous exertion to get relief

for unpreserved error"); United States v. Correa-Osorio,

(1st Cir. 2015) (explaining that the plain-error test

"deters unsavory sandbagging by lawyers" — "i.e., their keeping

mum about an error, pocketing it for later just in case" things do

- 8 - not work out in the district court — and "gives judges the chance

to fix" any problem so cases do not needlessly bounce back and

forth between district and circuit courts).

Put bluntly, McCullock's objection to the substantive

constraints imposed by special conditions 6 and 9 does nothing to

preserve a claim that the judge did not sufficiently explain the

reasons for imposing them. See United States v. Hunt,

, 1029 n.2 (D.C. Cir. 2016) (collecting cases from other

circuits). So plain-error review it is.

This hard-to-meet standard puts McCullock in a bind,

however. For even if he has shown error that is plain — after

all, no one "question[s] that a district court is required to

provide a reasoned and case-specific explanation for the sentence

it imposes," see United States v. Gilman,

(1st

Cir. 2007) — he never even tries to carry his burden of showing

both that the error likely changed the case's result and that

enforcing these conditions in these circumstances would seriously

imperil the judiciary's reputation for fairness and integrity.

Which means he has not done enough here to win on plain error.

See Fey,

(1st Cir. 2016); United States v. Mulero-

Díaz,

(1st Cir. 2016); see also Cruz-Ramos,

.

- 9 - We shift then to McCullock's procedural-reasonableness

challenge to special condition 12 — which (as a matter of helpful

repetition) we note says that, for 2½ years, he

must not knowingly have direct contact . . . with children under the age of 18, unless previously approved by the Probation Office, or in the presence of a responsible adult who has been approved by the Probation Office, and who is aware of the nature of [his] background and current offense.

Despite conceding that he must prove plain error to succeed —

because he neither questioned this condition's relevance below,

nor complained about the judge's missing explanation at sentencing

— he has not shown that applying special condition 12 would

jeopardize his substantial rights and the public's perception of

the fairness and integrity of our criminal-justice system. Which

dashes his plain-error hopes on this issue as well. See Fey,

; Mulero-Díaz,

; see also Cruz-Ramos,

.

Looking to turn the tables, McCullock's reply brief

faults the government for not proving with record-based facts that

the judge would unlikely change any of these special conditions on

remand. But it is on McCullock to prove all four plain-error

factors, not on the government to disprove them. See, e.g., United

States v. López,

(1st Cir. 2020). So this

argument does not alter our conclusion.

- 10 - On to the next set of issues.

Overbroadness (The Substantive-Reasonableness Challenges)

We now take up McCullock's substantive-reasonableness

attacks on the contested special conditions, leading off with

special conditions 6 and 9 — which (to copy another of McCullock's

sum-ups) disallows "adult pornography and content" for 2½ years.5

As he sees things, "[n]othing in the record" — not his "child

molestation conviction," not his "child pornography conviction,"

and not his "indecent assault and battery conviction" — links

"viewing adult pornography or adult content containing sexually

explicit scenes" to his criminal conduct. And, his argument

continues, because the facts in no way justify these special

conditions, they are too "broad" and "restrictive" to stand.

Reviewing for abuse of discretion, as the parties agree

we should, we keep the following checklist in mind:

5 Here we again quote these special conditions, for the reader's convenience: Special condition 6 declares that, for 2½ years, McCullock "shall not possess, access, subscribe, or view any videos, magazines, literature, or Internet websites depicting children or adults in the nude and/or engaged in sexual activity." And special condition 9 declares that, for 2½ years, McCullock "must not possess or use any computer or internet-capable device without prior approval from the Probation Office" and stresses that "[a]ny such device should not be used to knowingly access or view sexually explicit materials as defined in

(2)(A)." - 11 - • Judges have "significant flexibility" in crafting special

conditions. See United States v. Marino,

(1st

Cir. 2016) (quoting United States v. Garrasteguy,

(1st Cir. 2009)).

• A special condition must be "reasonably related" to certain

factors, including "the nature and circumstances of the

offense and the history and characteristics of the

defendant," see

(d)(1), 3553(a)(1) — as well

as three goals of punishment: "deter[ring] and protect[ing]

others and . . . rehabilitat[ing] the defendant," see Marino,

(citing

(a)(2)(B)-(D). Of

note too is that the special condition must "involve[] no

greater deprivation of liberty than is reasonably necessary"

to accomplish those goals, see

(d)(2), and

"be supported by the record," see Marino,

(quoting Garrasteguy,

).

• In applying the abuse-of-discretion standard here, we focus

on the "reasonableness" of the judge's judgment, taking into

account the totality of the circumstances and knowing that

"any one of several sentences may be reasonable in a

particular case." See

(internal quotations and citation

omitted). So, looking to see if the sentence reflects "a

plausible view of the circumstances and culminates in a

- 12 - defensible overall result," see id. at 12 (internal

quotations and citations omitted), we will undo "the judge's

sentencing decision only if it falls outside the expansive

boundaries of the entire range of reasonable sentences," see

id. at 10 (internal quotations and citations omitted).

Ultimately, what "separates" a "permissible" condition from

an "impermissible" one "is whether, given the facts," the

"restriction was 'clearly unnecessary.'" United States v.

Santiago,

(1st Cir. 2014) (quoting United States

v. Brown,

(1st Cir. 2000)).

McCullock cites a quintet of First Circuit cases

striking down supervised-release conditions banning the possession

or viewing of adult sex-related materials where the defendant stood

convicted of child-sex or child-porn crimes. See United States

v. Hinkel,

(1st Cir. 2016); United States v.

Gall,

(1st Cir. 2016); United States v. Medina,

(1st Cir. 2015); United States v. Ramos,

, 63-64 n.28 (1st Cir. 2014); United States v. Perazza-

Mercado,

(1st Cir. 2009). But his case is very

different from those.

Recall McCullock's convictions for two child-molestation

crimes, one involving his admitted attempt to force his penis into

a five year old's vagina. Recall too his possessing and trading

- 13 - child porn on a mind-blowing scale, with at least two images

showing an adult man raping a very young girl. This concatenation

of circumstances justifies an inference — unlike in the quintet of

cases — that porn plays a role in McCullock's sexual misconduct.6

See generally Ramos,

(indicating that the reasonable

inference only has to be that "a ban on adult pornography" is

"reasonably related to" the offense's "nature and circumstances"

and to the defendant's "history and characteristics"). Now recall

his aiming his violent sexual impulses not only at young girls but

also at an adult woman: the revocation-triggering conduct,

remember, involved his viciously attacking his adult girlfriend,

telling her that "he was going to rape" her and that she had to

"suck[] and fuck him" — just before chucking her pants aside and

tossing her on a bed. And given how his perverse interests extend

beyond young girls and to adult women, one can also reasonably

infer that his porn problem in the child context could spill over

into the adult context. Which means that the conditions here —

unlike in the quintet of cases — draw on this lawbreaker's history

and characteristics, providing case-specific reasons to believe

To the extent the judge did not review the presentence 6

report in the child-porn case — a report included in the parties' sealed joint appendix, by the way — we simply point out that we can affirm on any basis supported by the record. See, e.g., United States v. Etienne,

, 923 n.9 (1st Cir. 2006). - 14 - that adult-sexual materials could play a role in his re-offending.

See generally, e.g., Gall,

(explaining that the

record evidence in Perazza-Mercado and Medina did not "support the

conclusion that pornography had 'contributed to [the defendant's]

offense or would be likely to do so in the future'" (quoting

Perazza-Mercado,

, and Medina, citing

)). At least we cannot say on this record that such a conclusion

amounts to an abuse of discretion, which would require us to hold

that "no reasonable person" could have done what the judge did

here. See, e.g., United States v. Rivera-Carrasquillo,

(1st Cir. 2019), cert. denied,

(2020);

United States v. Maldonado,

(1st Cir. 2013).

McCullock raises several counterarguments, none of which

succeed.

For example, McCullock makes much out of how he pled

guilty to "indecent assault and battery" on his then-girlfriend,

not to the original charge of "assault to rape" her. But he is

still stuck with his threat to "rape" her and his demand that she

"suck[]" and "fuck[]" him, as well as his actions of flinging her

pants across the room and dumping her on the bed. And as to these

threats/demands, he never denies making them, offers no convincing

ground for not crediting them, and gives us no persuasive reason

why we cannot factor them into our analysis.

- 15 - McCullock also protests that "no evidence" shows "that

adult pornography or content played any role" in his "background

. . . , much less in or contemporaneous to any criminal offense."

But our decisions have not "forclos[ed] the imposition of"

conditions like the ones here even if "pornography was not involved

in the offense of conviction and there is no documented history of

the defendant viewing such material" — so long as "a reason to

impose" such conditions is "apparent from the record." See

Perazza-Mercado,

. And as we pointed out three

paragraphs ago, the record justifies the conditions' imposition —

which undermines his suggestion that this is all "post hoc

conjecture."

Still searching for a winning argument, McCullock says

that because German authorities downloaded the child porn from his

computer "some 18 months" after his state child-molestation

conviction, one cannot infer that child porn "likely caused the

molestation conduct." But the record offers no support for the

idea that he began his child-porn file-sharing after the

molestation crimes — do not forget, he had hundreds of images of

child-porn on his computer, with thousands of other images erased

from there as well.

The bottom line is that because in this instance we

cannot say that special conditions 6 and 9 were "clearly

- 16 - unnecessary," see Santiago,

(quoting Brown,

), McCullock's first substantive-unreasonableness challenge

fails.

That leaves us only with McCullock's substantive-

unreasonableness challenge to special condition 12 — which we again

note (one last time) says that, for 2½ years, he

must not knowingly have direct contact . . . with children under the age of 18, unless previously approved by the Probation Office, or in the presence of a responsible adult who has been approved by the Probation Office, and who is aware of the nature of [his] background and current offense.

Conceding that our review is for plain error — which again requires

him "to show error; plainness; an adverse effect on his substantial

rights; and a serious compromise of the fairness, integrity, or

reputation of" the sentencing process, see Cruz-Ramos,

— he offers many reasons why we should vacate this special

condition. But while we respect his effort, we cannot do what he

asks us to do.

McCullock, for instance, complains that special

condition 12 bans any "incidental" contact with minors even if

"unexpected" or not "purposeful." But the special condition says

(emphasis ours) that he "must not knowingly have direct contact

. . . with children under the age of 18," language that limits the

condition to intentional contacts with minors. Also and

- 17 - importantly, the special condition is not a flat ban on knowing

contacts with minors. And we know this because such contacts

simply require preapproval from probation. See United States v.

Cabrera-Rivera,

(1st Cir. 2018) (placing some

weight on the condition's preapproval component); United States v.

Pabon,

(1st Cir. 2016) (same, adding that

"associational restrictions" work "to protect the public,

especially children, from the defendant, as well as to promote the

defendant's rehabilitation," and noting that such restrictions

"are usually read to exclude incidental encounters").

Moving on, McCullock objects that special condition 12

does not distinguish between girls and boys. Admittedly, as he

emphasizes, his two molestation crimes involved very young girls.

And, as he also implies, we have no clue on this record if his

stash of child porn had images of boys. But even he concedes that

the record shows that when he tried to sexually penetrate the five-

year-old girl, her three-year-old brother was "present" (to quote

McCullock's brief) — viewing so much that he could tell his mother

what had happened. From all this one could infer that McCullock

either wanted the boy to see the crime or was indifferent to his

seeing it. Which makes the boy another one of McCullock's victims.

McCullock also protests that special condition 12

applies to minors "irrespective of age" and covers contacts with

- 18 - "older minors." Again, the molestation crimes and the specific

child-porn images in the record involved prepubescent minors. But

there is no reason to think that his appetite for sexual violence

is limited to that age group. And there is reason to think the

opposite, given his revocation-triggering acts — e.g., his "rape"

threat and demands for sex directed at his then-girlfriend.

Lastly, McCullock stresses that the molestations

occurred about twenty years ago and that he has no child-sex-crime

convictions since then. But he spent the bulk of that intervening

stretch locked up in prison and away from children. So any

suggestion by him that this "time was marked by lawful social

activity" is off base. See Pabon,

.

As for the plain-error standard, knowing that "[t]he

simplest way to decide [an issue] is often the best," see

Stor/Gard, Inc. v. Strathmore Ins. Co.,

(1st

Cir. 2013) (quoting Chambers v. Bowersox,

, 564 n.4

(8th Cir. 1998)), we jump straight to the plainness prong — which

requires McCullock to show that the judge flouted "controlling

precedent" in imposing special condition 12, see United States v.

Morosco,

(1st Cir. 2016) (quoting Correa-Osorio,

). McCullock does say that the judge "clear[ly] and

obvious[ly] err[ed]" here. But he never convincingly explains how

binding authority makes this so, given the key particulars

- 19 - highlighted in the last four paragraphs — that (a) the special

condition is textually limited to intentional contacts with minors

and is not a flat ban because of the probation-preapproval option;

that (b) a boy was a casualty of his horrific conduct; that

(c) there is no clear prepubescent/postpubescent demarcation line

when it comes to his violent-sexual inclinations; and that (d) he

sat in prison for many years between the molestations and the

revocation-triggering behavior. See, e.g., United States v.

López,

(1st Cir. 2020) (stating that the truism

that "[t]he proponent of plain error must carry the burden of

establishing each" facet of the plain-error test).

Perhaps McCullock thinks that his discussion of Fey

fills in the blanks. If so, he is wrong. Fey got convicted under

state law for raping a sixteen-year-old girl in 1999. See Fey,

. He later pled guilty in 2014 to failing to register

as a sex offender under federal law. See

Applying plain-

error review, we vacated a supervised-release condition barring

"direct" and "indirect" contact with all children. See

at 3-

6. But unfortunately for McCullock, Fey's case is readily

distinguishable from his. Fey — unlike McCullock — "ha[d] not

committed any sexual or violent crimes in the [roughly fifteen]

intervening years." See

(noting that Fey had only failed

to register and violated a condition banning him from living with

- 20 - children). Fey's condition — unlike McCullock's — also lacked a

"knowingly" requirement and forbade "indirect contact" (again,

McCullock's forbids him from "knowingly hav[ing] direct contact").

And the government in Fey — unlike the government here — "made no

argument" based on "a danger" to boys. See

. So Fey does

not help McCullock.

If more were needed, we point out that McCullock is free

to ask the judge to modify the special condition under

(e)(2). See, e.g., United States v. Mercado,

(1st Cir. 2015).7

The net result is that because McCullock has failed to

prove the judge plainly erred in imposing special condition 12,

his second substantive-unreasonableness challenge fails too.

Final Words

For the reasons recorded above, we affirm the judgment

entered below.

7 McCullock is right that caselaw says that "[t]o approve problematic conditions because a judge or a probation officer might, in her or his discretion, relax them in the future, undermines the command to sentencing courts to not deprive offenders of more liberty than is necessary to carry out the goals of supervised release." See Ramos,

. The difficulty for him is that his special-condition-12-is-problematic thesis necessarily depends on his establishing plain error — which he has not done. - 21 -