United States v. Hinkel , 837 F.3d 111 ( 2016 )


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  •           United States Court of Appeals
    For the First Circuit
    No. 15-1672
    UNITED STATES OF AMERICA,
    Appellee,
    v.
    PAUL R. HINKEL,
    Defendant, Appellant.
    APPEAL FROM THE UNITED STATES DISTRICT COURT
    FOR THE DISTRICT OF MASSACHUSETTS
    [Hon. William G. Young, U.S. District Judge]
    Before
    Thompson, Selya, and Kayatta,
    Circuit Judges.
    Christine DeMaso, Assistant Federal Public Defender, Federal
    Public Defender Office, District of Massachusetts, for appellant.
    Randall E. Kromm, Assistant United States Attorney, with whom
    Carmen M. Ortiz, United States Attorney, was on brief, for
    appellee.
    September 20, 2016
    KAYATTA, Circuit Judge.        After being ensnared by a law
    enforcement sting operation, Paul Hinkel was charged with using a
    means of interstate commerce (the internet) to entice a minor to
    engage in illegal sexual activity in violation of 18 U.S.C.
    § 2422(b).    He was convicted following a jury trial and sentenced
    to   ten   years'   imprisonment,    to     be   followed   by   five   years'
    supervised release. On appeal, he claims that a variety of alleged
    errors undermined the integrity of the jury's verdict and the
    appropriateness of his sentence.          After careful review, we affirm
    both Hinkel's conviction and the bulk of the sentence imposed by
    the district court, finding cause to alter only two conditions of
    Hinkel's supervised release.
    I.      Background
    At trial, the government relied chiefly on evidence of
    electronic messages exchanged between Hinkel and government agents
    posing as a fifteen-year-old girl and her mother. Because Hinkel's
    challenge trains partly on the sufficiency of the government's
    evidence, we summarize this back-and-forth in considerable detail,
    vulgar and lewd as it is.
    On February 14, 2014, an agent with the Department of
    Homeland Security placed a personal advertisement on the "Casual
    Encounters" online message board, a subsection of the website
    Craigslist frequented by those seeking adult sex partners.              Using
    the name "Lisa Richards," the agent published a post entitled "mom
    - 2 -
    with daughter looking--w4m--38 (Boston)."1       In its entirety, the
    post stated: "open minded mom DDF with daughter looking for male
    that might be interested in taboo relationship, some dom.........
    needs to be discreete though.           if you have an interest in a
    interesting relationship contact me, use intersting in subject
    line.       we will chat off CL."2
    At 12:54 pm that day, Craigslist user "ctautumn," later
    identified as Hinkel, responded to the advertisement via email
    using the subject line "VERY INTERESTING AND INTRIGUING."      Hinkel
    told "Lisa" that he was "an experienced Daddy/Dom and [he] ha[d]
    been looking for this type of scenario."       He then listed some of
    his "taste[s]" and provided graphic descriptions of sexual acts
    that he imagined engaging in with "Lisa" and her daughter.     Forty-
    five minutes later, the agent responded, writing that "she" was
    "trying to introduce [her] daughter to sex" and asking if Hinkel
    "mind[ed] if shes young?"      Prompted by Hinkel's responsive request
    for her daughter's age, "Lisa" informed Hinkel that her daughter
    "Samantha" was "15 but experienced."
    1
    According to trial testimony, the use of "w4m" signified
    that the poster was a "w[oman]" seeking a "m[an]."      Throughout
    this opinion, we reproduce the text of Hinkel and the agents'
    communications warts and all, with minimal editorial revisions for
    clarity.
    2
    Testimony reflected that in the parlance of these online
    postings, "DDF" meant "drug and disease free," "dom" meant
    "dominate," and "CL" meant "Craigslist."
    - 3 -
    Seven    minutes     later,    at    2:05    pm,   Hinkel    responded:
    "Sounds very naughty! I am concerned about her age since legally
    she should be 16 or older."3                He asked whether "Lisa's" daughter
    had "played in this type of scene before" and whether "Mommy and
    daughter play together as well," stating that he found "that kind
    of play so very erotic," and that it was a "big turn on for [him]."
    In response, at 2:10 pm, "Lisa" wrote, "shes not [16 or older] so
    i guess this conversation is over." But Hinkel insisted otherwise,
    replying, one minute later, to say, "Nope..... It is not over!                        I
    want to talk more!           I'm very intrigued by it all.             Such taboo and
    naughty play!!!!"
    Over    the    course   of    roughly      the   next     month,   Hinkel
    corresponded frequently and in lurid detail with "Lisa" and her
    fictitious daughter "Samantha."              In subsequent emails, "Lisa" told
    Hinkel that she was looking for a man to "teach[] her [daughter]"
    and that she wanted "Samantha" "to experience sex with a man the
    right way."      Hinkel frequently expressed eagerness to perform this
    role, describing his own sexual desires in detail.                        From time to
    time,       though,    he    also   expressed      what    he   called    "conflicting
    3
    Hinkel was correct about this as a matter of Massachusetts
    law, see Mass. Gen. Laws ch. 265, § 23; ch. 277, § 39, meaning
    that he would not have been guilty of the crime of conviction had
    he simply responded by stating his intention to wait until
    "Samantha" turned sixteen to engage in the sexual conduct.
    - 4 -
    feelings" regarding the criminal conduct he was preparing to engage
    in.   At one point Hinkel told "Lisa":
    I once placed an ad looking for this very type
    of scenario, but to be honest the ad stated
    that the daughter was to be of legal age. I
    was taken back a bit when you said she wasn't.
    The last thing I want to do to any girl is
    damage her emotionally. I'm very caring. As
    long as she is desires this, I am game.
    On another occasion, Hinkel wrote "Lisa" that when he
    arrived to meet "Samantha" he would "play it by ear and gauge it
    based on Samantha's feelings and comfort level," saying that he
    was "nervous . . . [to] be with such a young girl" and "sooooooooo
    very concerned about her and how she will feel."    "Lisa" reassured
    Hinkel, saying "i think you will love her...and i appreciate the
    way you describe our situation :)," telling him that the planned
    encounter would be "such an amazing experience for us to have
    together."
    Hinkel and "Lisa" formed plans to stage their encounter
    with "Samantha" at "Lisa's home" in Watertown, Massachusetts, on
    March 19, 2014.     A week before, Hinkel exchanged emails directly
    with "Samantha." Referring to her as "sweetheart," Hinkel promised
    to make the experience "fun and enjoyable" for this fifteen-year-
    old girl.      When "Samantha" said that she liked it when she
    "rub[bed] herself," Hinkel asked if she would like him to "touch
    [her] there as well."      In one of his final messages to "Lisa,"
    Hinkel asked whether "Samantha" knew she could never tell anyone
    - 5 -
    about their planned encounter because, in his words, "you and I
    can get into a lot of trouble.        Even years later."
    On the appointed day, Hinkel arrived at the Watertown
    residence where he was greeted by arresting officers. He consented
    to a search of the bag he was carrying and of a lockbox in his
    vehicle.     These searches--and later searches of his home and work
    computers--yielded evidence, ultimately introduced at trial, that
    we will discuss in greater detail later in this opinion.
    II.   Analysis
    A.     Entrapment
    Hinkel does not contest that he was the author of the
    "ctautumn" emails and text messages sent to the government agents.
    His chief defense at trial was entrapment.
    The defense of entrapment "exists to prevent 'abuse[]'
    of the 'processes of detection and enforcement . . . by government
    officials' who might instigate an illegal 'act on the part of
    persons otherwise innocent in order to lure them to its commission
    and to punish them.'"       United States v. Díaz-Maldonado, 
    727 F.3d 130
    ,   137   (1st   Cir.   2013)   (alterations   in   original)    (quoting
    Sorrells v. United States, 
    287 U.S. 435
    , 448 (1932)).              When the
    defense is properly raised, we apply a two-part test.              First, we
    look at the government's conduct to see if it is of the type that
    would cause a person not otherwise predisposed to commit a crime
    to do so.      See 
    id. Examples of
    such "government overreaching"
    - 6 -
    include "excessive pressure by the government upon the defendant
    or the government's taking advantage of an alternative, non-
    criminal type of motive."         United States v. Gendron, 
    18 F.3d 955
    ,
    961–62 (1st Cir. 1994).      If the government does employ "methods of
    persuasion      or   inducement     that     create   a   substantial     risk
    that . . . an offense will be committed by persons other than those
    who are ready to commit it," Model Penal Code § 2.13(1)(b), "we
    proceed to a second step and look at the particular person to see
    if that person was in any event predisposed to commit the crime,"
    
    Díaz-Maldonado, 727 F.3d at 137
    ; accord 
    Gendron, 18 F.3d at 962-63
    .
    In seeking an entrapment jury instruction, a defendant
    must first shoulder the "modest" burden of making a prima facie
    showing that there is some evidence both elements are satisfied in
    his or her case.       United States v. Vasco, 
    564 F.3d 12
    , 18 (1st
    Cir. 2009).      If this "'entry-level burden' of production," Díaz-
    
    Maldonado, 727 F.3d at 139
    (quoting United States v. Coady, 
    809 F.2d 119
    , 122 (1st Cir. 1987)), is satisfied--as it clearly was in
    this case, see, e.g., United States v. Gamache, 
    156 F.3d 1
    , 9–11
    (1st   Cir.    1998)--then   the    defendant    is   entitled   to   a   jury
    instruction explaining the defense.           In addition,
    the burden shifts to the government to prove
    beyond a reasonable doubt one of two things,
    either of which defeats the defense: that the
    government did not wrongfully induce the
    accused to engage in criminal conduct or that
    the accused had a predisposition to engage in
    such conduct absent the inducement.
    - 7 -
    United States v. DePierre, 
    599 F.3d 25
    , 27 (1st Cir. 2010).
    The district court instructed the jury on the parameters
    of the entrapment defense using the pattern jury instructions
    commonly used by district courts in this circuit, declining to
    give a lengthier instruction requested by Hinkel.          The court also
    denied Hinkel's motion for judgment of acquittal premised on the
    government's failure to offer evidence sufficient to remove the
    inference of entrapment from the proceedings.           See Fed. R. Crim.
    P. 29.    Hinkel challenges both of these unfavorable decisions on
    appeal.
    1.     Sufficiency of the Evidence
    Hinkel put a credible entrapment case to the jury by
    arguing that the government's bundling of licit and illicit sex
    into a package deal led him to go where he never would have gone
    but for the government's clever and sophisticated inducement.            The
    government went to lengths to create a dressed-up window of
    opportunity   for   the   crime   to   be   committed   and,   on   numerous
    occasions, downplayed the harm that could be expected to flow from
    the commission of the crime by describing how "amazing" the
    encounter would be, how "excited" "Samantha" was, and how "Lisa"
    "appreciate[d]" how "honest and caring" Hinkel had been in his
    messages.   As in virtually any sting operation, the fictitious co-
    conspirator here also sought to allay concerns about detection by
    - 8 -
    the authorities and to build credibility with the target of the
    investigation         through    frequent,      familiar   communication         that
    undoubtedly took the "edge" off of the reprehensible conduct under
    contemplation.         As for predisposition, Hinkel points out that he
    had never previously been convicted of a crime, had raised two
    adult children and had not been accused of having an inappropriate
    relationship with either of them, and that the government had not
    uncovered any evidence suggesting that he had other underage
    victims.
    The jury, though, was not buying Hinkel's view of the
    evidence.    So the question for the district court, and now us, is
    whether the evidence of both wrongful inducement and lack of
    predisposition was so one-sided that a reasonable jury could not
    have found beyond a reasonable doubt that the government carried
    its burden of negating the entrapment defense.                   This question of
    evidentiary sufficiency is a question of law that we consider de
    novo.   United States v. Prieto, 
    812 F.3d 6
    , 13 (1st Cir. 2016).
    We resolve that question in the government's favor.
    Crucially, the government informed Hinkel at the very outset of
    the exchanges--before rolling out the force of its enticements--
    that the daughter was only fifteen years old.              Promptly thereafter
    (only   about    an     hour    and   fifteen    minutes   after       Hinkel   first
    responded to the advertisement, and just six emails into the
    exchange),      the    agents    pointblank     offered    him    an    unambiguous
    - 9 -
    opportunity to walk away.           The precise words exchanged merit
    attention.      When   told   the   girl's   age   Hinkel   voiced   no   firm
    objection.     Rather, he expressed "concern," and then asked for
    more information about her experience.         A government agent intent
    on inducement might well have simply responded by answering the
    question with assurances about her experience.          Instead, the agent
    treated the expression of concern as a likely objection, and
    volunteered that the "conversation [was] over," thereby giving
    Hinkel an easy out before he crossed the threshold that led to the
    subsequent enticement and assurances that could otherwise be seen
    as creating a disposition where none previously existed.             Equally
    importantly, upon learning the daughter's age and recognizing the
    illegal nature of the proposed relationship, Hinkel explained his
    refusal to walk away by citing the "taboo" nature of the proposal
    as that which made it attractive to him:           "I'm very intrigued by
    it all.   Such taboo and naughty play!!!!"
    Hinkel did thereafter make statements that implied some
    residual conflict concerning the illegality of the proposal, but
    never because he viewed the command of the law as indicative of
    what is right and wrong.      Rather, his concern about the illegality
    of the proposed conduct was one that was assuaged by arrangements
    to minimize detection (i.e., confirming that "Samantha" was told
    to keep their activities secret).        In this respect, he was like a
    putative bank robber who hesitated only to make sure that the
    - 10 -
    bank's security system was down.    He also made clear his position
    that he would do nothing that, in his judgment, harmed "Samantha."
    But, of course, that is a judgment that the law does not allow him
    to make, anymore than it allows a person to kill only those thought
    to deserve death. In this respect, Hinkel's self-serving arrogance
    in relying on his own version of right versus wrong reasonably
    might be seen as an ingredient in his predisposition to commit the
    crime.
    In any event, the important point is that Hinkel was
    offered and declined a clear exit at the outset.    Hinkel was not
    a person who entered a nightclub only to find out several hours
    later that it was a bordello.   Rather, he was more like the person
    who confirmed at the front door the nature of the activity being
    offered, and then entered precisely because its greater than
    expected "taboo" aspects attracted him.   Given such a chronology,
    a jury could easily find beyond a reasonable doubt that the agents'
    subsequent enticements and assurances, much like those of a pimp,4
    were simply reasonable efforts to negotiate the arrangement rather
    than wrongful overreaches aimed at using pressure to create a
    crime.   "This is not a case . . . in which a government agent
    4 It is unfortunately not far-fetched to encounter parents
    pimping their minor children on the internet. See, e.g., Aisha J.
    v. Ariz. Dep't of Econ. Sec., No. 1 CA-JV 11-0161, 
    2012 WL 666573
    ,
    at *2 (Ariz. Ct. App. Feb. 28, 2012).
    - 11 -
    refused to take 'no' for an answer and persisted in recruiting a
    target."   
    Díaz-Maldonado, 727 F.3d at 137
    .
    This is also not a case like United States v. Poehlman,
    
    217 F.3d 692
    (9th Cir. 2000), where government agents first
    established, over the course of six months, a close relationship
    with a lonely target whom they then enticed by slowly "play[ing]
    on [the target's] obvious need for an adult relationship, for
    acceptance of his sexual proclivities and for a family, to draw
    him ever deeper into a sexual fantasy world involving these
    imaginary girls," 
    id. at 702.
       Similarly, in State v. Canaday, 
    641 N.W.2d 13
    (Neb. 2002), undercover law enforcement agents strung an
    advertisement respondent along for four months before clearly
    establishing that the target was expected to have sex with the
    fictitious pen pal's children as a requirement of any relationship
    with the mother, see 
    id. at 17–20.
    Here,   the   government's    tactics   as   they   played   out
    involved no "psychologically 'graduated' set of responses to [the
    target's] own noncriminal responses, beginning with innocent lures
    and progressing to frank offers."           
    Gendron, 18 F.3d at 963
    .
    Rather, the initial lure was ambiguous (mother and daughter in
    "taboo" and "interesting" arrangement), and the ambiguity was
    thoroughly and promptly eliminated before Hinkel sought to explore
    and act on the further enticements.
    - 12 -
    Because we find that the evidence supported a finding
    that the government did not wrongly induce Hinkel to engage in
    criminal conduct, we need not reach the question of whether the
    government     also   sufficiently    demonstrated    that   Hinkel   was
    predisposed to commit the kind of offense in question absent any
    governmental involvement.     See United States v. Walter, 
    434 F.3d 30
    , 37 (1st Cir. 2006) ("In addressing Walter's primary argument
    that the government failed to carry its burden of proving that no
    entrapment occurred, we again note that the government's burden is
    met if it proves beyond a reasonable doubt that either element of
    the defense, inducement or lack of predisposition, fails."); cf.
    United States v. Nieves-Burgos, 
    62 F.3d 431
    , 434 (1st Cir. 1995)
    ("[W]hen a jury returns a general verdict of guilty on a single
    count charging more than one criminal act, the verdict stands if
    the evidence sufficiently supports any of the acts charged.")
    2.      Instructions
    Hinkel further faults the district court for refusing to
    give his requested entrapment instruction.           Instead, the court
    gave the pattern jury instruction on entrapment commonly used by
    district courts in this jurisdiction.         See Pattern Crim. Jury
    Instr. 1st Cir. § 5.05 (1998).       The chief distinction between the
    two is that Hinkel's version included examples of government
    - 13 -
    activity that might amount to improper inducement to commit a
    crime.5
    We see no abuse of discretion in the court's decision or
    legal error in its instruction.            Arguing otherwise on appeal,
    Hinkel relies principally on United States v. Montañez, 
    105 F.3d 36
    (1st Cir. 1997).        The defendant in Montañez hung his entire
    defense on the theory that he was entrapped by a government agent
    posing as a female friend who repeatedly beseeched him to obtain
    cocaine for her to resell, claiming that she would lose her
    children if he did not help her earn money.         
    Id. at 37–38.
      When
    instructing the jury on entrapment, the district court gave several
    examples of inducement by coercion but refused to include examples
    of entrapment based on appeals to sympathy.        
    Id. at 38
    & n.3.   We
    5   Hinkel had requested that the district court tell jurors
    that:
    Improper inducement may include persuasion,
    false statements, excessive pressure by the
    officer,   an   undue   appeal   to    sympathy,
    psychological     manipulation,     or     other
    governmental conduct that creates a risk of
    causing an otherwise unwilling person to
    commit the crime charged.     Even very subtle
    pressure, if skillfully applied, can amount to
    inducement for purposes of the entrapment
    defense.    Some of the inducement factors
    relevant to enticement of a minor to engage in
    sexual activity may include a) whether the
    government made the initial contact; b)
    whether the government introduced the topics
    of sex and meeting in person; and c) the extent
    to which the government influenced the
    defendant's behavior by portraying the minor
    as sexually precocious.
    - 14 -
    reversed, ruling that by both providing the coercion examples and
    "omitting any 'sympathy' examples, the trial court may well have
    left the jury with the mistaken impression that coercion is a
    necessary   element    of    entrapment       and,    in   this   case,   such   a
    misunderstanding could well have affected the outcome."                   
    Id. at 39.
    Here, the district court did not instruct on entrapment
    by setting out some examples of inducement while leaving out other,
    more pertinent examples. In its discretion, the court simply stuck
    with the standard form, accurately describing the generic defense
    of entrapment, and correctly outlining the elements.                  Unlike in
    Montañez, this instruction "adequately inform[ed] the jury of [the
    defendant's] theory of defense," 
    id. at 40,
    and did not suggest
    that the conduct here was not wrongful by omitting it from a
    description of conduct that was wrongful.
    B.    Evidentiary Issues
    On   appeal,    Hinkel   renews     his    objections    to   several
    unfavorable evidentiary judgment calls made by the district court
    during the course of the trial.                Hinkel challenges: (1) the
    admission of seventeen photographs and five sexually explicit
    cartoons discovered on his work computer; (2) the admission of
    evidence of sexual paraphernalia and children's clothing found in
    the trunk of his car on the day of his arrest; (3) the exclusion
    of evidence of a prior sexually-tinged electronic conversation
    - 15 -
    with an adult he met online; and (4) the exclusion of certain text
    messages    Hinkel   sent   to    "Lisa"   that,    he    argues,   would   have
    "contextualized the government's facially inculpatory evidence."
    We address each evidentiary challenge in turn.
    1.     The Photographs and Cartoon Evidence
    A post-arrest forensic examination of Hinkel's computer
    yielded twenty-two electronic images that were later introduced at
    trial.     Seventeen are photographs of Hinkel, apparently self-
    taken.    The remaining five are drawings of anime characters.              Once
    the district court ruled that Hinkel was entitled to a jury
    instruction on entrapment, the government offered and the district
    court admitted, over Hinkel's objection, both sets of evidence as
    probative   of   Hinkel's   predisposition         to    commit   the   crime   of
    conviction.6     The images, the court reasoned, were probative of
    Hinkel's predisposition to commit a sex crime involving a minor
    because they demonstrated Hinkel's interest in "playing out a role
    of a hypersexualized child in need of chastisement," a fantasy
    that he later sought to actualize through his communications with
    "Lisa" and "Samantha."           The government briefly discussed these
    images at trial in the course of its examination of the forensic
    6 Much of this evidentiary contest played out in advance of
    trial, with the district court informing the parties how it would
    rule were the entrapment issue to arise at trial, as it ultimately
    did. Hinkel objected when the images were introduced, dooming the
    government's appellate argument that the dispute has not been
    properly preserved.
    - 16 -
    technician and again during closing arguments.                 Jurors were, of
    course, free to peruse the contents of the entire report.
    Evidence of another act is ordinarily impermissible "to
    show that on a particular occasion the person acted in accordance
    with"   the    character    manifest      in   the     other   act,     Fed.     R.
    Evid. 404(b)(1), but such evidence may be introduced "for another
    purpose, such as proving motive, opportunity, intent, preparation,
    plan,   knowledge,     identity,   absence       of    mistake,    or   lack     of
    accident," 
    id. 404(b)(2). "[I]n
    situations where the defendant
    employs entrapment as a defense to criminal liability, prior bad
    acts relevant to a defendant's predisposition to commit a crime
    are highly probative."      United States v. Van Horn, 
    277 F.3d 48
    , 57
    (1st Cir. 2002); cf. United States v. Thomas, 
    134 F.3d 975
    , 980
    (9th Cir.), as amended on denial of reh'g (Apr. 10, 1998) ("For
    the jury to find predisposition beyond a reasonable doubt, it must
    consider the defendant's character.").           But even if evidence of a
    defendant's prior acts or his or her character has "special
    relevance"    to   a   disputed   issue   such    as    predisposition,        such
    evidence "may not be admitted if . . . its probative value is
    'substantially outweighed by the danger of . . . unfair prejudice,
    confusion of the issues, or misleading the jury.'"                Van 
    Horn, 277 F.3d at 57
    (quoting Fed. R. Evid. 403).
    We review the court's decision to admit this evidence
    for abuse of discretion.      
    Id. at 56.
          Because the "balancing act"
    - 17 -
    demanded by Rule 403 is a "fact-sensitive enterprise" best left to
    the trial judge, "[o]nly rarely and in extraordinarily compelling
    circumstances will we, from the vista of a cold appellate record,
    reverse a district court's on-the-spot judgment concerning the
    relative weighing of probative value and unfair effect."        United
    States v. Vizcarrondo-Casanova, 
    763 F.3d 89
    , 94 (1st Cir 2014)
    (alteration in original) (quoting Freeman v. Package Mach. Co.,
    
    865 F.2d 1331
    , 1340 (1988)); see also United States v. Majeroni,
    
    784 F.3d 72
    , 76 (1st Cir. 2015) ("In exercising their broad
    discretion under Rule 403, trial judges have a feel for the
    evidence and the courtroom that is difficult to replicate on the
    pages of a transcript, so our deference to judgment calls of this
    type is great.").
    We consider first the five cartoons, which consist of
    detailed anime drawings of adults and minors engaged in sex acts,
    sometimes in bondage.       It was well within the trial court's
    discretion to admit these cartoons found on Hinkel's computer
    depicting    sex    with   children    as   probative   of     Hinkel's
    predisposition.    Cf. United States v. Chambers, 
    642 F.3d 588
    , 595–
    96 (7th Cir. 2011) (images of child pornography possessed by
    defendant    admissible    to   show   "sexual   inclination   towards
    children"); United States v. Brand, 
    467 F.3d 179
    , 199-201 (2d Cir.
    2006) (evidence of "possession of images of child pornography and
    child erotica" admissible to show defendant predisposed to commit
    - 18 -
    "sexual     offenses   against   children").         Hinkel    could   hardly
    challenge the government to prove his predisposition to engage in
    sex with a minor while simultaneously barring the government from
    presenting proof that he possessed depictions of adults having sex
    with minors.
    The   seventeen   photos   of   Hinkel   require    a   different
    analysis.    None involve children.     Rather, thirteen pictures show
    Hinkel wearing women's underwear,7 sometimes with his genitalia
    visible, one shows him prepared to punish himself, two show his
    erect penis, and two present views of his spread buttocks.              What
    properly probative role these pictures had in this case is a
    mystery.    The government forthrightly confesses that "they played
    virtually no role in the government's case or its response to
    Hinkel's entrapment defense."      Egged on less frankly by government
    counsel at trial, the district court hypothesized that the pictures
    were all relevant to the entrapment defense.           The reasoning seems
    to be that in one of the pictures Hinkel appears to wear a child's
    tutu, so if Hinkel fantasized himself as a child, that reasonably
    suggests he was predisposed to have sex with a child.            No evidence
    at all supported this hypothesized nexus.              Nor does the nexus
    apply, even by its own terms, to sixteen of the seventeen pictures.
    7 Trial testimony indicated that some of the items of clothing
    worn by Hinkel in these photos appeared to be among those found in
    Hinkel's vehicle at the time of his arrest. See infra Part II.B.2.
    - 19 -
    The Supreme Court has cautioned that "evidence that
    merely indicates a generic inclination to act within a broad range,
    not all of which is criminal, is of little probative value in
    establishing predisposition."      Jacobson v. United States, 
    503 U.S. 540
    , 550 (1992).     Our own court has rejected as impermissible "the
    inference . . . that the tendency to engage in unusual, albeit
    legal, sexual activity with an adult indicates a predisposition
    toward pedophilia."     
    Gamache, 156 F.3d at 11
    .      In sum, the photos
    had virtually no probative force on any issue properly before the
    jury.
    We turn therefore to the issue of prejudice.           In most
    circumstances, the prejudicial impact of these photos would be
    patent and substantial.      Knowledge of Hinkel's licit but unusual
    sexual practices and his attitude toward sex might cause some
    jurors to think that his proclivities knew no bounds, licit or
    otherwise.     In this case, though, this prejudicial potential was
    largely cumulative, or redundant, because of the email exchanges
    put   before   the   jury.   In   these    properly   admitted   exchanges
    evidencing both the crime and the facts relevant to the entrapment
    defense, Hinkel repeatedly and lewdly described his preferred
    sexual practices, including practices likely viewed by some jurors
    as more unusual than what the pictures showed.             Also properly
    admitted were the graphic anime pictures, the relevant prejudicial
    impact of which went much more directly to the heart of the case.
    - 20 -
    The risk of incremental prejudice from the photos was further
    blunted by the district court's prophylactic statement to the jury
    earlier in the trial that it was not to act as "the bedroom police"
    and that "if we get evidence in this case of cross-dressing or
    bondage and discipline or, within limits, sadomasochism, that
    whatever    you   may   think   about   that   conduct,   among   consenting
    adults . . . .     That's not criminal."
    All in all, we have evidence of very little probative
    value that was nevertheless highly unlikely to have caused any
    incremental prejudice in the context of this particular record
    already replete with evidence of Hinkel's sexual behavior and
    plans.     Whether that means that, net-net, the district court did
    not abuse its discretion, or that error exists, but it is harmless,
    we need not decide. In either event, Hinkel loses.8
    2.    Other Evidentiary Challenges
    Law enforcement officers found a lockbox in the truck
    Hinkel drove to the scene where he intended to consummate the
    8For this same reason, it was not plain error for the district
    court to have failed to repeat without request its earlier
    instruction that the jurors were not "bedroom police."        Trial
    counsel, too, may have had perfectly rational tactical reasons to
    refrain from seeking the repetitive instruction. See United States
    v. Fanfan, 
    468 F.3d 7
    , 12–13 (1st Cir. 2006) ("[M]any defense
    lawyers would shrink from an instruction that the jury should not
    count [a defendant's] propensity for [a particular crime] against
    him. Rather than erasing the risk that the jury would misuse the
    bad act evidence, such an instruction could easily invite the
    jury's attention to a quite natural inference.").
    - 21 -
    crime.    After securing Hinkel's consent, they searched the lockbox
    and discovered a cache of sexual paraphernalia, including women's
    clothing and underwear, children’s underwear, and sex toys among
    other    objects.   Over   objection,    the   district   court   admitted
    evidence of this material, finding it "probative of [Hinkel's]
    then present intent."      See Fed. R. Evid. 803(3).       Hinkel argues
    that this evidence was both irrelevant and unfairly prejudicial.
    We disagree:   it was no abuse of discretion to let the
    jury learn of the sex-related objects Hinkel brought with him from
    Connecticut to Massachusetts for the encounter with "Lisa" and
    "Samantha."    All of this evidence went to helping the government
    prove its affirmative case that Hinkel was not all talk and no
    action.     In short, the objects were relevant--and highly so--
    because Hinkel brought them to the scene of the meeting with Lisa,
    evidencing that sex was the purpose of that meeting. Hinkel argues
    that he only intended to use what he carried out of the truck.
    But a jury could reasonably find that he brought all of the items
    as possible objects to use with "Samantha."          After all, he had
    told "Lisa" that he would "play it by ear" and "see how it went"
    with "Samantha."    To the extent the objects also ran the risk of
    eliciting juror disgust, and thus prejudice, the balance here was
    one that the trial judge had ample discretion to weigh.
    Hinkel also challenges two decisions by the district
    court excluding evidence he sought to admit. One piece of evidence
    - 22 -
    was a fragment of a 2010 online chat exchange recovered from
    Hinkel's work computer.         The exchange occurred between two users,
    "fun2day07" (Hinkel, by his own assertion) and "purpleangel1219,"
    that apparently took place in March 2010.                 At one point in the
    chat transcript, "purpleangel1219" asked Hinkel (assuming he is,
    indeed, "fun2day07") if he ever "want[ed] to play with [his
    daughter]"    and     Hinkel   said   he   had   not   and    "would   never   do
    any[thing] like that."         Counsel for Hinkel sought to introduce the
    chat transcript as evidence of lack of predisposition and the
    district court ruled the exchange irrelevant. For several reasons,
    this is a judgment we will not disturb.                For one, the exchange
    occurred several years before the events in question.                    Second,
    there was no suggestion in Hinkel's prosecution that he abused his
    own   children.        Leaving    aside    questions      about   authenticity,
    hearsay, and completeness, excluding this evidence on relevance
    grounds   was     a   decision    well     within   the      judge's   range   of
    discretionary authority.
    Hinkel also sought to admit certain text messages sent
    by him, which he says provided context for two other messages that
    were read aloud by a government witness at trial.9                     The text
    9These text messages sent by Hinkel to "Lisa" read, "I'm glad
    and eager to hear her response. Makes me aroused to think of her
    like this," and, "Very hot, I could even use a toy on her, while
    in that position, and make her cum several times before I take
    her."
    - 23 -
    messages read aloud related to Hinkel sending "Lisa" an explicit
    photograph.   Defense counsel objected to the text messages in the
    first instance but then, on cross examination, sought to introduce
    other parts of the conversation to place the messages in context.
    The district court ruled that this was impermissible since the
    defense was objecting to the messages' admissibility.         On appeal,
    Hinkel claims he would have used the opportunity to highlight a
    text message wherein he wrote, "Too bad, looks like I scared you
    with that photo.    Take care."
    The district court's treatment of this evidence was
    inconsistent at best. But we fail to see how this lost opportunity
    to introduce evidence of Hinkel apologizing for sending an explicit
    photograph would have had any bearing at all on the strength,
    completeness, or relevance of the government's evidence.              Even
    assuming   that   the   district   court's   puzzling   explanation   for
    excluding the text evidence was error, there is nothing remotely
    exculpatory about the text message conversation that could have
    materially benefitted Hinkel.       Any error was harmless.   See United
    States v. Shea, 
    159 F.3d 37
    , 40 (1st Cir. 1998); United States v.
    Rose, 
    104 F.3d 1408
    , 1414 (1st Cir. 1997).
    C.   Supervised Release
    After serving his ten-year prison sentence--the minimum
    term of imprisonment for conviction under this statute, see 18
    U.S.C. § 2422(b)--Hinkel will be subject to a five-year term of
    - 24 -
    supervised release.      At Hinkel's sentencing hearing, the district
    court imposed all of the Special Conditions ("Conditions") of
    supervised    release    proposed    by   the   Probation   Office   in   its
    Presentence Report ("PSR").         Hinkel has preserved objections to
    four of the thirteen Conditions, excerpted in relevant part below:
    Condition 4: The defendant shall not possess
    or use a computer or have access to any online
    service without the prior approval of the
    Probation Office.
    Condition 7: The defendant is not to use a
    computer, internet-capable device, or similar
    electronic device to access child pornography
    or to communicate with any individual or group
    for the purpose of promoting sexual relations
    with children.   The defendant is prohibited
    from entering chat rooms to send or receive
    'instant messages,' or to send or receive
    email with attached electronic files through
    any electronic medium unless required for an
    express class assignment in an accredited
    educational institution or as an express job
    requirement for legal, outside employment.
    The defendant shall not utilize any sex-
    related adult telephone services, websites, or
    electronic bulletin boards.
    Condition 9: The defendant shall provide the
    probation officer with access to any requested
    financial   information    for   purposes   of
    monitoring their compliance with the imposed
    computer     access/monitoring     conditions,
    including, but not limited to, credit card
    bills, telephone bills, and cable/satellite
    television bills.
    Condition   13: The defendant shall be subject
    to search    and seizure of his residence and
    elsewhere    with reasonable suspicion by the
    Probation   Office.
    - 25 -
    We   review   preserved   challenges    to    conditions    of
    supervised release for abuse of the sentencing judge's discretion.
    United States v. Perazza-Mercado, 
    553 F.3d 65
    , 69 (1st Cir. 2009).
    "Although district courts have significant discretion to impose
    special conditions of supervised release, that discretion is not
    unlimited."     United States v. Medina, 
    779 F.3d 55
    , 60 (1st Cir.
    2015).   A special condition of release may only be imposed if the
    sentencing court determines that the condition:
    (1) is reasonably related to the factors set
    forth in [18 U.S.C. § ]3553(a)(1), (a)(2)(B),
    (a)(2)(C), and (a)(2)(D);
    (2) involves no greater deprivation of liberty
    than is reasonably necessary for the purposes
    set forth in [18 U.S.C. § ]3553(a)(2)(B),
    (a)(2)(C), and (a)(2)(D); and
    (3) is consistent with any pertinent policy
    statements issued by the Sentencing Commission
    pursuant to 28 U.S.C. [§ ]994(a).
    18 U.S.C. § 3583(d); see generally 
    Medina, 779 F.3d at 60
    .            The
    rationale for imposing the condition must also "have adequate
    evidentiary support in the record."         United States v. Roy, 
    438 F.3d 140
    , 144 (1st Cir. 2006).
    Applying   these   principles,   we   find   that   the   first
    sentence of Condition 4, excerpted above, sweeps too broadly in
    banning Hinkel from, essentially, all internet access without the
    - 26 -
    prior approval of his probation officer.10              This kind of broad-
    brush,    untailored    approach   to       sculpting   the    conditions   of
    supervised release imposes "a greater deprivation of liberty than
    is reasonably necessary" to achieve the penal goals Congress has
    identified.   18 U.S.C. § 3583(2).
    We have upheld broad restrictions on internet access as
    a condition of supervised release "where (1) the defendant used
    the internet in the underlying offense; (2) the defendant had a
    history of improperly using the internet to engage in illegal
    conduct; or (3) particular and identifiable characteristics of the
    defendant   suggested    that   such    a    restriction      was   warranted."
    
    Perazza-Mercado, 553 F.3d at 70
    . Here, Hinkel did use the internet
    in committing the crime but we are reluctant to rely on that use
    alone where it is largely collateral to the offense in question,
    much like how using his truck to arrive to meet "Lisa" and
    "Samantha" would differ from using his truck to drive recklessly.
    As we have previously observed, "[a]n undue restriction
    on internet use 'renders modern life--in which, for example, the
    government strongly encourages taxpayers to file their returns
    electronically, where more and more commerce is conducted on-line,
    and where vast amounts of government information are communicated
    10 Condition 4 also requires that Hinkel cooperate with
    Probation to install software on his computer to monitor his
    activities. He does not object to this requirement.
    - 27 -
    via website--exceptionally difficult.'"                 
    Id. at 72
    (quoting United
    States   v.    Holm,      
    326 F.3d 872
    ,    878    (7th      Cir.   2003)).        That
    observation, made some seven years ago, has only more force today.
    And it takes no leap of faith to predict that in roughly nine
    years, when Hinkel is released, internet connectivity is likely to
    be even closer to a prerequisite to normal functioning in modern
    society.      See generally Riley v. California, 
    134 S. Ct. 2473
    , 2484
    (2014) (observing two years ago that internet-enabled smart phones
    "are now such a pervasive and insistent part of daily life that
    the proverbial visitor from Mars might conclude they were an
    important feature of human anatomy").
    Hinkel's     internet     usage        will    also      be   subject    to
    electronic monitoring per the unobjected-to additional provisions
    of Condition 4.        Given these restrictions, further banning Hinkel
    from even monitored internet access provides too little benefit to
    outweigh      what   we    increasingly       view    as    a   serious     and   severe
    imposition.
    Nor do we take solace, as we have in a previous case, in
    the presence in Condition 4 of a safety valve permitting the
    defendant to seek approval from the Probation Office and, if
    necessary, the district court, in order to use the internet for
    educational or vocational purposes. See United States v. Stergios,
    
    659 F.3d 127
    , 134 (1st Cir. 2011) ("Should Stergios find [the
    internet ban] unduly restrictive upon his release, he need only
    - 28 -
    speak with his supervising officer and, if that does not succeed,
    raise the issue with the district court.").                 Stergios, unlike
    Hinkel, was a "repeat offender" with "a history of improperly using
    the internet to engage in fraud."              
    Id. at 135.
            Importantly,
    Stergios had previously proven himself unable or unwilling to
    refrain from using a computer to commit fraud while on supervised
    release following a conviction arising out of a similar use of
    computers to commit fraud.       There is no contention that Hinkel has
    such   a   recidivist   history    or   that    he    has   already    violated
    conditions of release.     Our obligation to ensure that the special
    conditions of supervised release work no "greater deprivation of
    liberty than is reasonably necessary," 18 U.S.C. § 3583(d)(2), to
    achieve     the   goals     of     criminal          sentencing,      see   
    id. §§ 3583(a)(2)(B)-(D),
    compels us to vacate the first sentence--
    and no more--of Condition 4 of Hinkel's supervised release.
    For similar reasons, we also find that the last two
    sentences of Condition 7 in the excerpt above sweep too broadly
    and, in the case of the last sentence, too ambiguously.                     The
    penultimate sentence suffers from the same defect as we have
    identified in Condition 4, flatly prohibiting (other than in the
    course of outside employment or classwork) the use of what have
    now become standard forms of communicating and associating on
    essentially all subjects.         The last sentence, in turn, expands
    what would be a reasonable effort to preclude access to sites and
    - 29 -
    services related to sex with minors, or child pornography, into a
    ban covering access to all sites that are in any way "sex-related,"
    thereby covering, for example, a large swath of generally accepted
    modern entertainment, and even news.
    In        finding     the    first    sentence    of    Condition   4
    unreasonable, we simultaneously sustain as reasonable the first
    sentence of Condition 7.            Forbidding Hinkel from using devices "to
    access child pornography or to communicate with any individual or
    group for the purpose of promoting sexual relations with children"
    speaks closely to the conduct at the heart of the offense Hinkel
    committed and is reasonably limited to the particular forms of
    communication that enabled his crime.
    Finally, we may briefly dispense with Hinkel's challenge
    to Conditions 9 and 13.                  These Conditions essentially act as
    enforcement subsidies in the government's favor, supporting the
    Probation Office's efforts to ensure Hinkel's compliance with the
    conditions limiting his freedom in his first five post-carceral
    years.   While these provisions make it easier for the government
    to invade his privacy, they are reasonably related to either the
    Conditions we have approved or the ones Hinkel has not challenged.
    Without such tools to "mandate compliance," the district court's
    imposition        of     special     conditions     would     be    "ineffectual."
    
    Stergios, 659 F.3d at 134
    (quoting United States v. Sebastian, 
    612 F.3d 47
    , 52 (1st Cir. 2010)).
    - 30 -
    III. Conclusion
    Having carefully considered Hinkel's very well briefed
    and argued challenge, we affirm his conviction and affirm his
    sentence, with the exception of the first sentence of Condition 4
    and the last two sentences of Condition 7 governing the terms of
    his supervised release, each of which we vacate.
    - 31 -