In the
United States Court of Appeals
For the Seventh Circuit
____________________
Nos. 12‐3738 & 12‐3739
UNITED STATES OF AMERICA,
Plaintiff‐Appellee,
v.
SCOTT ADKINS,
Defendant‐Appellant.
____________________
Appeals from the United States District Court for the
Northern District of Indiana, Hammond Division.
Nos. 2:09-CR-32-PPS & 2:10-CR-10-PPS — Philip P. Simon, Chief Judge.
____________________
ARGUED NOVEMBER 1, 2013 — DECIDED JANUARY 30, 2014
____________________
Before POSNER, FLAUM, and SYKES, Circuit Judges.
FLAUM, Circuit Judge. This is a consolidated appeal of two
separate, but related, cases against Scott Adkins. In one case,
a jury convicted Adkins of attempting to possess heroin with
intent to distribute, and of being a felon in possession of a
firearm. In the other, Adkins pled guilty to receipt of child
pornography. Adkins raises several arguments on appeal.
He first attacks his convictions on the heroin and firearm
charges, arguing that he is entitled to a new trial due to
Nos. 12‐3738 & 12‐3739 2
alleged errors regarding evidentiary decisions, jury
instructions, and improper statements by the government.
We reject these arguments and affirm Adkins’ heroin and
firearms convictions. Adkins next argues that we should
vacate his sentence on the heroin and firearm convictions
because of multiple alleged sentencing errors. We reject
these arguments and affirm his sentence as well. Finally,
with respect to his child pornography sentence, Adkins
contends that one special condition of his supervised release
is unconstitutionally vague and overbroad, and that we may
review this issue despite the appeal waiver in his guilty plea.
We agree. We therefore vacate and remand on this ground
alone.
I. Background
In January 2009, Adkins was living with Nathaniel
Jordan and Jordan’s two daughters in Gary, Indiana. On
January 27, United States customs agents at the UPS facility
in Louisville, Kentucky, inspected and opened a package
from Canada addressed to Jordan. The package allegedly
contained clothing and two heavy stuffed snowmen. Inside
the snowmen were pellets that field‐tested for narcotics; the
government says that the snowmen contained about 300
grams of heroin, a distribution quantity worth $30,000.
Agents then sent the pellets for further testing, and put fake
pellets in the snowmen as well as a transmitter that would
signal if the snowman was ripped open. Agents re‐wrapped
the package, which was delivered to Jordan’s house on
January 29 by a customs agent disguised as a UPS driver.1
1 A chemist later confirmed that the pellets contained heroin. The real
heroin was destroyed before trial due to a mistaken destruction order.
Nos. 12‐3738 & 12‐3739 3
Jordan signed for the package. One of Jordan’s daughters
testified that after the “UPS driver” left, Adkins went to
Jordan’s room, opened the package, said, “We’ve got some
goodies,” and took out a snowman. When the transmitter
alerted, agents entered Jordan’s home. Agents found an
open snowman on the upper shelf of Jordan’s bedroom
closet, and another snowman on the dresser. In that room,
agents also found plastic baggies and two digital scales, both
of which are often used in the drug trade. One scale tested
positive for heroin and cocaine, the other for heroin and
procaine (which is sometimes mixed with narcotics). A
search of Adkins’ person and of Adkins’ basement bedroom
revealed no drugs or drug paraphernalia, but did reveal two
handguns. In the living room, agents found three items that
were admitted at trial: Adkins’ passport; an itinerary for a
bus trip from Gary to Toronto (via Detroit), for which
Adkins was scheduled to depart on the morning of January
21, 2009; and a Western Union receipt from the afternoon of
January 21, showing that a Samuel John had wired $75 to
Adkins at the Detroit Greyhound bus station.
Agents then interviewed Adkins and Jordan.2 According
to the agents, Adkins admitted receiving and opening the
package, said he was surprised that the package got through
customs, and thought that it did “not feel like 300 grams.”
Adkins also allegedly told the agents that he had recently
tried to go to Canada to receive heroin from a man named
Sam but was denied entry, and that Sam then wired him
money through Western Union so he could return by bus to
2 Per department practice, these interviews were not recorded. The
agents took interview notes but were later unable to locate them. The
agents also prepared a report in the days following the interviews.
Nos. 12‐3738 & 12‐3739 4
Gary. Adkins allegedly knew how the proceeds from the
drugs would be split but did not admit that he would be
receiving any of them.3
Adkins also allegedly said that the guns in his room
belonged to an upstairs tenant. Adkins said that he had been
repairing them. He knew the guns worked because he test‐
fired them in the backyard. The government did not test the
guns for DNA or fingerprints.
While the agents were interviewing Adkins, he gave
written consent for a search of his computers. The search
revealed more than four hours of child pornography videos,
including videos depicting sexual conduct with girls who
appeared to be between five and seven years old.
In 2009, Adkins was indicted for his alleged drug and
gun conduct. In 2010, a separate two‐count indictment
charged Adkins with receipt of child pornography, and
possession of the same. After a jury trial on the heroin and
gun conduct, Adkins was convicted of attempting to possess
heroin with intent to distribute, and of being a felon in
possession of a firearm. Following his conviction, Adkins
pled guilty to receipt of child pornography and, in exchange,
the government dismissed the possession charge. The
district court sentenced Adkins to 210 months in prison for
the child pornography conviction, plus a fifteen‐year term of
supervised release. Adkins also received ninety months’
imprisonment for both the heroin and gun charges. Twelve
of those months ran consecutively to his child pornography
3 The agents’ report of the interview said that Adkins admitted going to
Canada to receive a “package,” but the report did not mention heroin
specifically.
Nos. 12‐3738 & 12‐3739 5
sentence, so Adkins’ total term of imprisonment is 222
months. The judge ordered four years of supervised release
on the heroin charge and three years on the gun charge, both
of which ran concurrently to the fifteen‐year term of
supervised release for the child pornography conviction.
II. Discussion
A. Evidentiary challenges
Adkins first challenges his heroin and firearms
convictions on the ground that the district court should have
excluded the evidence relating to his alleged trip to Canada
to pick up heroin from “Sam” or “Sonny.” This evidence
consisted of Adkins’ passport; an itinerary for a bus trip
from Gary to Toronto (via Detroit), for which Adkins was
scheduled to depart on the morning of January 21, 2009; and
a Western Union receipt from the afternoon of January 21,
showing that Samuel John had wired $75 to Adkins at the
Detroit Greyhound bus station.
i. Legal standards and proceedings below
We review a district court’s evidentiary rulings for abuse
of discretion. United States v. Taylor, 604 F.3d 1011, 1014 (7th
Cir. 2010). Adkins’ challenges implicate two rules. First,
Federal Rule of Evidence 404(b) prohibits evidence of a
defendant’s prior bad acts to show his propensity for bad
behavior, but permits such evidence when offered to show
“motive, opportunity, intent, preparation, plan, knowledge,
identity, absence of mistake, or lack of accident.” Second,
Rule 403 generally prohibits unduly prejudicial evidence.
Before trial, the government moved in limine for the
admissibility of the trip‐related evidence, and the district
court agreed with the government. First, it found that the
Nos. 12‐3738 & 12‐3739 6
evidence was not evidence of prior bad acts, but instead was
direct evidence of the crime, because it tended to show
Adkins’ knowledge, preparation, and intent, “all of which
are elements of the crime charged.” The judge also found the
trip‐related evidence “to be extremely probative, and not
unfairly prejudicial. So any [Rule] 403 balance in here, in my
view, militates in favor of admitting the evidence.” Second,
and in the alternative, the district court found the trip
evidence admissible under our test for Rule 404(b) evidence.
ii. Analysis
In this case, the government needed to prove, among
other things, that Adkins “attempted to knowingly or
intentionally possess heroin” on or about January 29, 2009.
Attempt requires the government to prove specific intent.
United States v. Coté, 504 F.3d 682, 687 (7th Cir. 2007). Adkins
contends that his alleged conduct a week earlier could not
constitute evidence of his state of mind a week later when he
received the snowmen; instead, he argues, the evidence of
that trip was merely Rule 404(b) “bad acts” evidence.
Adkins’ argument is unpersuasive. The evidence of Adkins’
trip to Canada—his passport, his bus ticket to Canada, his
itinerary, and the Western Union receipt—served several
legitimate purposes in the government’s case. First, it tended
to show Adkins’ knowledge that the material he and Jordan
received on January 29, 2009, was indeed heroin, because it
was allegedly the same heroin he had tried to procure eight
days earlier from the same supplier. Second, and for the
same reasons, the evidence of Adkins’ trip to Canada
demonstrated his intent to procure heroin. Third, Adkins’
failed trip to Canada explains why the heroin‐filled package
was shipped in a snowman—i.e., the failed trip provides a
Nos. 12‐3738 & 12‐3739 7
motive for the package’s shipment. Thus, the trip evidence is
not evidence of a prior bad act, but of a determined
individual to obtain this specific heroin from this supplier at
this general time. Thus, Rule 404(b) does not apply here.
Adkins next argues that the district court’s Rule 403
analysis was “perfunctory.” It is true that the judge’s
reasoning could have been more extensive. In some cases, a
“bare bones” recitation of Rule 403 has led to a reversal. See,
e.g., United States v. Ciesiolka, 614 F.3d 347, 357 (7th Cir. 2010).
But in this case, the district court provided a sufficiently
thorough analysis because it appears, in context, that the
district court was relying upon the reasons articulated in its
404(b) analysis. In other words, the district court found the
Canada‐trip evidence more probative than prejudicial for the
same reasons that it found the evidence to be direct evidence
of criminality: the evidence went to Adkins’ knowledge,
preparation, and intent. Moreover, the trip‐related evidence
was prejudicial to Adkins only because it helped prove his
alleged crime. See United States v. Thompson, 359 F.3d 470, 479
(7th Cir. 2004) (“[A]ll probative evidence is prejudicial to the
party against whom it is offered.”).
Nonetheless, Adkins contends that the evidence was
unfairly prejudicial because some jurors might have been
unpersuaded that Adkins thought the snowmen contained
heroin, but convicted him anyway for trying to travel to
Canada a week earlier seeking the heroin. While this is
theoretically possible, the much more likely inference is that
the jurors convicted Adkins because he took the package,
opened it, took out a snowman, said “We’ve got some
goodies,” ripped open a snowman, tried to hide it when
agents arrived, and then told the agents afterward that he
Nos. 12‐3738 & 12‐3739 8
was surprised that the package made it through customs
and it “did not feel like 300 grams.”
Adkins makes three final arguments about the Canada‐
trip evidence, all of which we reject. First, he contends that
the district court erred by waiting until the end of trial to
give a limiting instruction that the trip evidence should be
considered only as to intent and knowledge. We have
expressly rejected this argument before, and do so again. See
United States v. Akinrinade, 61 F.3d 1279, 1284 (7th Cir. 1995).
Second, Adkins argues that the district court erred by giving
a generic limiting instruction about the trip‐related evidence,
rather than customizing that instruction to this case’s facts.
However, while we “encourage” district courts to give case‐
specific limiting instructions, we do not require them to do
so. United States v. Miller, 673 F.3d 688, 702 n.1 (7th Cir.
2012). Third, Adkins contends that it was erroneous not to
limit consideration of the Canada‐trip evidence to the heroin
charge. But there is no indication that this evidence affected
the jury’s consideration of the firearms charge. The only
plausible inference is that the jury convicted Adkins of the
firearms charge because two guns were found in his room
and he admitted to test‐firing them. We therefore reject all of
Adkins’ evidentiary arguments.
B. Jury instructions
Adkins contends that the jury instructions constructively
amended the indictment. Instruction No. 21 set forth the
elements of attempted heroin possession, but did not contain
a date on which the charged offense occurred. Instruction
No. 28 said: “The Superseding Indictment charges that the
offenses were committed ‘on or about’ January 29, 2009. The
government must prove that the offenses happened
Nos. 12‐3738 & 12‐3739 9
reasonably close to that date but is not required to prove that
the alleged offenses happened on that exact date.” Neither
party objected to either instruction.
Jury instructions may not amend the indictment. United
States v. Trennell, 290 F.3d 881, 888 (7th Cir. 2002). The Fifth
Amendment requires that the allegations in the indictment
and the proof at trial “match in order ‘to insure that the
defendant is not subject to a second prosecution, and to give
the defendant reasonable notice so that he may prepare a
defense.’” Id. (quoting United States v. Folks, 236 F.3d 384, 390
(7th Cir. 2001)). To prove that a constructive amendment has
occurred, “the crime charged in the indictment must be
materially different or substantially altered at trial, [so that]
it is impossible to know whether the grand jury would have
indicted for the crime actually proved.” Id. (citation and
internal quotation marks omitted). Because Adkins did not
object below to the jury instructions, we review for plain
error. See United States. v. Olano, 507 U.S. 725, 731 (1993).4
Adkins argues that Instruction No. 21 “permitted the jury
to find—as the Government argued in its initial closing
argument—that Mr. Adkins took his substantial step by
leaving Indiana for Canada” eight days earlier. Adkins is
referring to the fact that, during closing arguments, the
prosecutor mentioned several acts when discussing the
“substantial step” necessary to prove attempt: “Going to
4 An error is plain if it was (1) clear at the time of the appeal and (2)
affected the outcome in the district court. See United States v. Wheeler, 540
F.3d 683, 689 (7th Cir. 2008). If these criteria are satisfied, we must then
“decide whether the error is so fundamental in nature that upholding
[the decision below] results in an intolerable miscarriage of justice.”
United States v. Kirklin, 727 F.3d 711, 718 (7th Cir. 2013).
Nos. 12‐3738 & 12‐3739 10
Canada. Receiving a package that’s supposed to have
$30,000 worth of heroin. Open[ing] the package. Cutting
open the snowmen. Those are all substantial steps towards
putting that heroin in your possession.” Adkins contends
that the instructions allowed the jury to convict him for his
trip to Canada because “the jury could have found that prior
trip ‘reasonably close’ to the date” in the indictment.
We reject Adkins’ argument for several reasons. First, the
indictment charged Adkins with committing both the heroin
and firearms offenses “on or about January 29, 2009.” The
district court’s instructions were therefore perfectly
consistent with the indictment. Second, although the
prosecutor should not have said that a trip to Canada eight
days earlier sufficed as a substantial step, the government
was otherwise clear that the primary focus of the case was
January 29, 2009. That was the day on which the package
arrived, Adkins eagerly opened it, and he allegedly made
inculpating statements to federal agents. Third, there was
ample permissible evidence that the jury could have relied
upon in convicting him (e.g., Adkins received the package,
opened it, took out a snowman, said “We’ve got some
goodies,” ripped open a snowman, and then tried to hide it
when agents arrived). See United States v. Natour, 700 F.3d
962, 969 (7th Cir. 2012) (“[E]ven where we have found a
constructive amendment, we have not reversed if … the
defendant was unable to show that the outcome of his trial
would have been different … .”).
C. Striking inadmissible evidence instead of declaring
a mistrial sua sponte
Adkins next argues that the district court plainly erred
when it struck inadmissible Rule 404(b) evidence rather than
Nos. 12‐3738 & 12‐3739 11
declaring a mistrial sua sponte. Adkins is referring to the fact
that, during the government’s cross‐examination of co‐
defendant Jordan, the prosecutor asked, “Well, you knew
when you sent Adkins to Canada to go visit—Sonny—to go
visit Sam—Sonny, that Sonny had previously given Adkins
drugs to smuggle?” Adkins immediately objected. The
district court sustained the objection, and instructed the jury:
“Ladies and gentlemen, that last line of inquiry, I am striking
from the record, the last question and answer, and I’m going
to admonish you to disregard it.” Additionally, the district
judge later reiterated during jury instructions that the jury
“must not” consider anything that the judge had stricken
from the record.
It was improper for the government to try to solicit
testimony from Jordan that Adkins had allegedly smuggled
drugs for Sam in the past. This was beyond the scope of both
the government’s notice and the court’s ruling on the motion
in limine. It should not have occurred.
Adkins faces several hurdles, however. First, our review
is again for plain error because Adkins did not object to the
instruction or request a mistrial. Second, we have repeatedly
emphasized that district courts are “in the best position to
evaluate the effect that an error may have on the overall
course of the proceedings, as well as whether a limiting
instruction can cure any potential prejudice.” United States v.
Curry, 538 F.3d 718, 728 (7th Cir. 2008). As a result, district
judges have “broad discretion in deciding to give a
cautionary instruction rather than to declare a mistrial.” Id.
Third, we presume that jurors “follow limiting and curative
instructions unless the matter improperly before them is so
powerfully incriminating that they cannot reasonably be
Nos. 12‐3738 & 12‐3739 12
expected to put it out of their minds.” Id. (quoting United
States v. Danford, 435 F.3d 682, 687 (7th Cir. 2006)).
Fourth, Adkins’ argument does not persuade us because
the improprieties in his trial are quite similar to those in
United States v. Harris, 325 F.3d 865 (7th Cir. 2003), where we
affirmed a conviction. In that case, the government charged
both Barbara Harris and Terry Riley with, inter alia,
possession of crack cocaine with intent to distribute. Harris’s
defense was that she did not know Riley had drugs in their
shared residence. A police detective testified at trial that he
arrested Harris based on the physical evidence in her home
and the fact that he had received information “in the past
that Barbara Harris was delivering cocaine for Terry Riley.”
Id. at 871. The district court struck the testimony and gave a
limiting instruction; after her conviction, Harris argued on
appeal that the district court should have ordered a mistrial
sua sponte. Id. We affirmed, explaining that although the
testimony was improper, the district judge’s “corrective
action … overc[a]me the prejudicial effect of the witness’
statement.” Id. In Harris, the potentially prejudicial statement
was a witness’s answer; in Adkins’ case, the potentially
prejudicial statement was a prosecutor’s question. If
anything, an answer seems more potentially prejudicial than
a question. Given Harris and our general deference to district
courts in taking curative actions, we reject the argument that
the judge plainly erred in not ordering a mistrial sua sponte.
D. Improper vouching during closing argument
During closing arguments, both defendants attacked the
government’s case, noting that the agents had lost their
interview notes, that they chose not to record the
defendants’ statements even though recording equipment
Nos. 12‐3738 & 12‐3739 13
was available, that the agents’ report was not prepared
immediately and was not verbatim, that the agents had
inconsistencies in their testimony, that their report had
factual mistakes, and that the heroin was accidentally
destroyed before trial. In rebuttal, the government
responded to these attacks. Specifically, the prosecutor said
that it was agency practice not to record statements, that the
agents took careful notes, and that they consulted those
notes to write reports two days later. Then, the prosecutor
said: “Ladies and gentlemen, you can—we can—the
Government can state with confidence that the agents relied
on their memory and those notes and gave you a complete
record of those Defendants’ statements and what they said.”
Adkins alleges that, with this last statement, the prosecutor
improperly vouched for the agents’ credibility.
Because Adkins did not object at trial, we review for
plain error, so Adkins must demonstrate that the outcome of
his trial would have differed but for these remarks. United
States v. Wolfe, 701 F.3d 1206, 1211 (7th Cir. 2012). He faces an
uphill battle, as “improper statements during closing
argument rarely constitute reversible error.” Id.
We engage in a two‐part inquiry in reviewing a
prosecutor’s comments. First, we ask whether the challenged
statement was improper. Id. There are two types of
impermissible vouching: “a prosecutor may not express her
personal belief in the truthfulness of a witness, and a
prosecutor may not imply that facts not before the jury lend
a witness credibility.” Id. at 1212 (citation omitted).
However, a prosecutor may comment on a witness’s
credibility so long as “the comment reflects reasonable
inferences from the evidence adduced at trial rather than
Nos. 12‐3738 & 12‐3739 14
personal opinion.” Id. (citation omitted). For instance, we
found it permissible for a prosecutor during closing to
comment on a witness’s veracity where the comment was
“immediately preceded by the prosecutor’s argument that
corroborating evidence showed the witness to be truthful.”
United States v. Johnson, 437 F.3d 665, 673 (7th Cir. 2006)
(citation omitted). Second, if the prosecutor’s remark was
improper, we consider whether that comment deprived the
defendant of a fair trial. Wolfe, 701 F.3d at 1211. We look to
five factors to make this determination: “(1) the nature and
seriousness of the misconduct; (2) the extent to which the
comments were invited by the defense; (3) the extent to
which any prejudice was ameliorated by the court’s
instruction to the jury; (4) the defense’s opportunity to
counter any prejudice; and (5) the weight of the evidence
supporting the conviction.” Id. (citation omitted).
With respect to the first step of the inquiry, the
government contends that, in context, these remarks were
tied to evidence and therefore permissible. We disagree. We
are troubled by the statement, “the Government can state
with confidence” that the agents provided a complete and
accurate report. That statement is quite different from
saying, as did the prosecutor in Johnson, that “all of the
evidence” supports a witness’s veracity. 437 F.3d at 673
(emphasis added). Rather than making reasonable inferences
from the evidence, the prosecutor explicitly vouched for the
accuracy of the agents’ memories. Such a statement is
impermissible. It expresses “personal belief in the
truthfulness of a witness” and also might “imply that facts
not before the jury lend a witness credibility.” Wolfe, 701
F.3d at 1212. This statement is even more disconcerting here,
Nos. 12‐3738 & 12‐3739 15
because the defense’s major theme was that the government
conducted a sloppy investigation.
We therefore proceed to the second step of the analysis,
the five‐factor test. One factor—the fourth—supports
Adkins, because defense counsel had no opportunity to
respond to the statement made in the rebuttal portion of
closing arguments. However, other factors support the
government: the remark was “a solitary statement,” United
States v. Griffin, 194 F.3d 808, 824 (7th Cir. 1999); the district
judge instructed the jurors that closing arguments were not
evidence; and finally, the weight of the evidence was clearly
against Adkins, for the reasons discussed above. We are
therefore satisfied that Adkins was not deprived of a fair
trial, despite the prosecutor’s improper vouching.
E. Sentencing
Adkins argues that we should vacate his sentence and
remand for resentencing (on the heroin/firearms conviction)
because the district court erred in calculating the proper
guidelines range. Addressing this contention requires
summarizing, in some detail, what happened at sentencing.
i. The sentencing proceedings
The district court sentenced Adkins separately in these
two cases, sentencing him first on the child pornography
conviction. The presentence investigation report (PSR)
recommended an offense level of 35, after a three‐level
reduction for Adkins’ acceptance of responsibility. The PSR
attributed four criminal history points to Adkins: three from
his 1995 conviction for possession of a stolen vehicle and
unlawful use of a weapon, and a fourth for his
heroin/firearms conviction in the other case before us on
Nos. 12‐3738 & 12‐3739 16
appeal. (Although Adkins had not yet been sentenced on
those charges, the guidelines state that a defendant should
receive one point for most offenses for which he has been
convicted but not yet sentenced. See U.S.S.G. § 4A1.2(a)(4).)
This fourth point bumped his criminal history category up
from II to III, increasing his guidelines imprisonment range
from 188–235 months to 210–262 months. The district court
accepted these calculations, and sentenced Adkins to 210
months’ imprisonment and fifteen years of supervised
release.
After a recess, the district court sentenced Adkins on the
heroin and firearms charges. The PSR recommended a base
offense level of 26 for Adkins’ alleged possession of about
299 grams of heroin. The PSR assigned Adkins four criminal
history points, again yielding a criminal history category of
III. The PSR also computed “an alternate guideline
calculation” that it claimed would have applied if Adkins’
two cases had been charged together. In this scenario, the
PSR reported that Adkins would have faced a total offense
level of 38, matching his initial total offense level on the
child pornography guideline, effectively subsuming the
heroin and firearms offenses. The PSR said that Adkins
would have been entitled to a two‐level acceptance of
responsibility reduction under U.S.S.G. § 3E1.1(a). The PSR
did not award a three‐level reduction under U.S.S.G.
§ 3E1.1(b). These “alternative” calculations yielded a total
offense level of 36 (one level higher than that used at
Adkins’ child pornography sentencing), but also a criminal
history category of II (which was one notch lower than that
actually used). That discrepancy did not matter, however,
because a base offense level of 35 and criminal history
category of III and a base offense level of 36 and criminal
Nos. 12‐3738 & 12‐3739 17
history category of II result in the same advisory range: 210–
262 months. See U.S.S.G. § 5A (Table).
The district court ultimately found that the advisory
range for Adkins’ heroin and firearms convictions was
seventy‐eight to ninety‐seven months’ imprisonment, and
four to five years of supervised release. The parties then
debated whether any portion of Adkins’ term of
imprisonment should run consecutively to his child
pornography sentence. The government emphasized that
Adkins had committed a serious drug offense that merited
some extra punishment. The court said that this case
presented a “complex situation” under the guidelines,
stating that “the guidelines would suggest, had I sentenced
these cases together, to essentially disregard the heroin
case.” (Because of the large differential between his offenses,
the child pornography offense would have “swallowed up”
the heroin and firearms offenses.)
The court decided that ninety months’ imprisonment was
appropriate, and chose, under U.S.S.G. § 5G1.3, to run
twelve of those months consecutively to the child
pornography prison term in light of the seriousness of the
drug conviction and Adkins’ lengthy criminal history.5 The
court also imposed four years of supervised release on the
heroin charge, and three years on the firearms charge, both
of which ran concurrently to the fifteen years of supervised
release on the child pornography charge.
5 Although these convictions did not count for purposes of calculating
Adkins’ guidelines range, Adkins also had pre‐1995 convictions for
unlawful use of a weapon, possession of a stolen vehicle, and retail theft,
as well as a conviction in 2006 for importing cocaine in Great Britain.
Nos. 12‐3738 & 12‐3739 18
The court filed a post‐sentencing memorandum further
explaining its reasoning. The memorandum included
consideration of the “alternate” world that the PSR had
considered, stating: “In determining whether to run the drug
sentence consecutive, concurrent or partially concurrent to
the child pornography sentence, it was important to know
what Adkins’ guidelines range would have been had he
been sentenced in one proceeding on all the charges.” The
court adopted the PSR’s calculations: in this alternate world,
after a two‐level reduction for accepting responsibility,
Adkins would have had an offense level of 36 and a criminal
history category of II, yielding the same guidelines range as
in the child pornography sentencing (210–262 months).
ii. Analysis
At sentencing, a district court must engage in a two‐part
analysis. First, it must determine the defendant’s sentencing
range under the guidelines. United States v. Dale, 498 F.3d
604, 611 (7th Cir. 2007). Second, it must “hear the arguments
of the parties and conclude by making an individualized
assessment of the appropriate sentence based on the
§ 3553(a) factors.” United States v. Boroczk, 705 F.3d 616, 622
(7th Cir. 2013) (citation omitted). We review the district
court’s interpretation and application of the guidelines de
novo, and its findings of fact for clear error. United States v.
Sutton, 582 F.3d 781, 783–84 (7th Cir. 2009).
Adkins argues that the district court engaged in two
guidelines calculations—the actual offenses, and the
alternate‐world hypothetical—but erred in its hypothetical
calculation. Specifically, in conducting the hypothetical
calculation, the district court awarded Adkins a two‐point
reduction for his acceptance of responsibility, but Adkins
Nos. 12‐3738 & 12‐3739 19
argues that it should have awarded him the full three‐point
reduction. This would have produced a guidelines range of
188–235 months, instead of a range of 210–262 months.
Because of this difference, Adkins argues, the error was not
harmless and we should remand for resentencing. The
government responds that there was an error in calculating
the hypothetical guidelines range, but the error worked to
Adkins’ benefit, as he should not have received any
reduction in the hypothetical calculation because he pleaded
guilty to only one of the two charges.
The plain text of the guidelines cuts against Adkins’
argument. It suggests that a third point reduction is only
merited where, among other things, a plea “permitt[ed] the
government to avoid preparing for trial.” U.S.S.G. § 3E1.1(b).
But if Adkins had been charged and sentenced together, and
if he had pled guilty to only the child pornography charge,
the government would still have needed to prepare for and
conduct a trial on the heroin and firearms charges. The
government would therefore have not avoided preparing for
trial. Indeed, where a defendant is indicted on multiple
counts but pleads guilty to only some of the charged
conduct, our sister circuits have held that a defendant is not
entitled to a three‐point reduction. See United States v.
McDowell, 888 F.2d 285, 292–93 (3d Cir. 1989); United States v.
Kleinebreil, 966 F.2d 945, 952–54 (5th Cir. 1992); United States
v. Chambers, 195 F.3d 274, 277–79 (6th Cir. 1999); United States
v. Ginn, 87 F.3d 367, 370–71 (9th Cir. 1996); United States v.
Thomas, 242 F.3d 1028, 1033–34 (11th Cir. 2001); see also
United States v. Kellum, 372 F.3d 1141, 1145–46 (9th Cir. 2004)
(noting that a different situation might arise in some cases
where all conduct is not charged in the same indictment, and
Nos. 12‐3738 & 12‐3739 20
affirming a two‐level reduction).6 Accordingly, we reject
Adkins’ argument that the district court erred in calculating
the guidelines range.
F. Lack of a jury finding on the quantity of heroin
The jury instructions and verdict forms did not ask the
jury to make a drug quantity finding. This was error; as the
government candidly acknowledged, “the drug quantity
question should have been submitted to the jury.” Apprendi
v. United States, 530 U.S. 446 (2000), requires that the jury
find any fact, other than a previous conviction, that increases
a defendant’s statutory maximum sentence, and this extends
to mandatory minimum sentences. Alleyne v. United States,
133 S. Ct. 2151, 2155 (2013). The question is whether, in this
case, the failure to submit the drug quantity to the jury is
reversible error.
The government contends that plain error review applies
to this challenge, whereas Adkins argues for de novo review.
Adkins alleges that the district court misapplied the
guidelines because it sentenced him to a punishment that
exceeded the crime the jury found he committed. During the
proceedings below, the government specifically asked the
court to include a drug quantity finding on the verdict form.
Adkins’ attorney did not object, but he responded that “it
seems like it confuses the issues a little bit for the jury.”
6 Several of these cases go further and state that a defendant is not
entitled to any reduction for acceptance of responsibility where he does
not plead guilty to all conduct charged in the same indictment. See, e.g.,
Chambers, 195 F.3d at 278. However, we need not reach that issue on the
facts of this case, where all conduct was not charged in the same
indictment and the district court only considered that possibility in the
midst of a hypothetical.
Nos. 12‐3738 & 12‐3739 21
When the court raised the issue again after a recess, the
government withdrew its request and Adkins did not object.
On these facts, plain error review—at most—applies. See
United States v. Kirklin, 727 F.3d 711, 717 (7th Cir. 2013). Like
the defendant in Kirklin, Adkins did not object at trial to the
judge’s finding a fact that increased the mandatory
minimum. See id. Moreover, as in Kirklin, the Supreme Court
handed down Alleyne after Adkins was sentenced but before
we considered the appeal. And as in Kirklin, the government
conceded error in this case. See id. at 718. We can also
assume arguendo, like the court in Kirklin, that the error
affected Adkins’ substantial rights, leaving us the remaining
discretionary inquiry: “whether the error seriously affected
the ‘fairness, integrity, or public reputation of judicial
proceedings.’” Id. (quoting Olano, 507 U.S. at 732). As in
Kirklin, we conclude that the error did not have such an
effect. See Kirklin, 727 F.3d at 719.
In Adkins’ case, the major question was whether to
convict, not the quantity of drugs. According to the agents,
Adkins said he was surprised that the package got through
customs, and thought it did “not feel like 300 grams.” The
snowmen were initially heavy because they contained
pellets, which field‐tested for narcotics and which a chemist
later confirmed were heroin—299.7 grams, specifically. The
heroin was accidentally destroyed before trial due to a
mistaken destruction order, but there was extensive
paperwork and chain of custody evidence, which
consistently pointed to 299.7 grams of heroin. See Knox v.
United States, 400 F.3d 519, 523 (7th Cir. 2005) (affirming,
despite Apprendi error, due to “the strength of the
evidence”). As the district court noted at sentencing, “to the
Nos. 12‐3738 & 12‐3739 22
extent there was a quantity of drugs in that house, that …
quantity was in fact 299 net grams of heroin.” Thus, a jury
that convicted Adkins of attempting to possess heroin with
intent to distribute convicted him of trying to obtain 299 or
so grams.7 See United States v. Nance, 236 F.3d 820, 826 (7th
Cir. 2000) (“If this jury was going to convict [the defendant]
at all—which it plainly did—there is simply no way on this
record that it could have failed to find that he was
conspiring to distribute” a particular quantity of drugs).
Because we will not “find a miscarriage of justice on plain
error review” when we are “convinced that … a properly
instructed jury would have found the defendants guilty of
distributing the requisite threshold quantities of narcotics,”
we affirm Adkins’ sentence. Kirklin, 727 F.3d at 718–19
(citation and internal quotation marks omitted).
G. Special Condition Five
Adkins pled guilty to receipt of child pornography in an
agreement that contained an appeal waiver: Adkins
“expressly waive[d]” the right to appeal his child
pornography conviction, sentence, or the restitution
imposed to “any Court on any ground,” except a limited
exception for ineffective assistance of counsel. The district
court imposed several special conditions as part of Adkins’
fifteen‐year term of supervised release, but Adkins now
7 The crucial number in the statutory scheme is actually only 100 grams
of heroin—a number Adkins seems to have far surpassed. See 21 U.S.C.
§§ 841(b)(1)(B)–(C) (if the crime involves less than 100 grams, a
defendant will be imprisoned for 0–20 years, with supervised release
ranging from 3 years to life; for 100 grams or more, a defendant will be
imprisoned for 5–40 years, with supervised release ranging from 4 years
to life).
Nos. 12‐3738 & 12‐3739 23
challenges only one—Special Condition Five. It states that
Adkins “shall not view or listen to any pornography or
sexually stimulating material or sexually oriented material
or patronize locations where such material is available.”
Neither party objected to the condition at the time. Two
issues are presented here. The first is whether the appeal
waiver bars review in this court. If it does not, the second
issue is whether this special condition is unconstitutionally
vague and overbroad. For the following reasons, we hold
that there is a vagueness exception to appellate waivers, and
that this special condition is unconstitutionally vague and
overbroad.
i. Appeal waiver
Adkins makes two arguments for why the appeal waiver
does not bar our review. He first contends that this appeal
falls outside the scope of his waiver. We disagree. He next
argues that an appeal waiver does not preclude this court
from reviewing a condition of supervised release to
determine if it is unconstitutionally vague. We agree.
1. Scope of waiver argument
Appeal waivers in plea agreements are typically
enforceable. United States v. Chapa, 602 F.3d 865, 868 (7th Cir.
2010). However, for an appeal waiver to bar review, the
issue appealed “must fall within its scope.” Id. Contract
principles generally apply to plea agreements. Id. Adkins’
plea agreement states that he will not appeal his conviction,
sentence, or restitution order to any court on any ground. He
contends that the inclusion of “restitution” suggests that
“sentence” refers only to the period of incarceration. (If
“sentence” included “restitution,” then the plea might
Nos. 12‐3738 & 12‐3739 24
include superfluous terms—a result we disfavor. See United
States v. Rourke, 74 F.3d 802, 807 (7th Cir. 1996)). Thus, he
argues, the conditions of supervised release are not part of
his “sentence” as that term is used in his plea agreement. Cf.
id. at 806 (significant ambiguities in a plea agreement should
be construed in favor of the defendant). However, Adkins’
argument conflicts with our precedent, which suggests that
terms of supervised release are part of the sentence. See
United States v. Sines, 303 F.3d 793, 798–99 (7th Cir. 2002)
(holding that the defendant “waived the right to appeal his
sentence, including the terms and conditions of his supervised
release,” when he agreed to a plea agreement that said he
“expressly waives his right to appeal the conviction and
sentence imposed on any ground.” (emphasis added)); see
also id. at 799 n.3 (“[W]e find that Mr. Sines waived his right
to appeal the terms of his supervised release when he signed
the plea agreement.”).
2. Due process argument
Adkins next argues that, notwithstanding the appeal
waiver, we can decide whether Special Condition Five is
unconstitutional because a waiver cannot preclude review of
an obvious due process violation on account of vagueness.
Our cases establish that there are at least some due
process exceptions to a waiver of appellate review. See
United States v. Bownes, 405 F.3d 634, 637 (7th Cir. 2005)
(noting that there are “limitations on waiver of the right of
appeal in a criminal case that are imposed by judicial
interpretations of the due process clause”) (citing, inter alia,
United States v. Schilling, 142 F.3d 388, 394–95 (7th Cir. 1998)).
Although we construe “plea agreements as contracts,” we
regard plea agreements as “unique contracts ‘in which
Nos. 12‐3738 & 12‐3739 25
special due process concerns for fairness and the adequacy
of procedural safeguards obtain.’” Carnine v. United States,
974 F.2d 924, 928 (7th Cir. 1992) (quoting United States v.
Ataya, 864 F.2d 1324, 1329 (7th Cir. 1988)). Thus, an appeal
waiver will not prevent a defendant from challenging (1) a
sentence based on “constitutionally impermissible criteria,
such as race”; (2) a sentence that exceeds the statutory
maximum for the defendant’s particular crime;
(3) deprivation of “some minimum of civilized procedure”
(such as if the parties stipulated to trial by twelve
orangutans); and (4) ineffective assistance of counsel in
negotiating the plea agreement. Bownes, 405 F.3d at 637
(citations omitted).
There are multiple rationales for these exceptions, such as
fundamental fairness to the particular defendant and the
fundamental legitimacy of the judicial process generally.
These rationales apply to obviously vague special conditions
as well. If the defendant cannot reasonably know what he is
and is not allowed to do, he should be able to obtain judicial
review. He is entitled to special conditions that generally
apprise him of what conduct is lawful and what could land
him back in prison for violating his supervised release
conditions. See Grayned v. City of Rockford, 408 U.S. 104, 108–
09 (1972) (“[W]e insist that laws give the person of ordinary
intelligence a reasonable opportunity to know what is
prohibited, so that he may act accordingly.”). Nor can we
accept the government’s invitation to address this problem
after Adkins has served his sentence, for that risks
sanctioning an unconstitutional special condition that
should not be used in the meantime in other cases.
Nos. 12‐3738 & 12‐3739 26
We pause to emphasize the narrowness of our holding. It
remains the case that plea agreements are typically
enforceable and that contractual principles generally apply.
Nor is there a “general ‘constitutional‐argument exception’
to waivers in plea agreements.” See United States v. Behrman,
235 F.3d 1049, 1051 (7th Cir. 2000). Thus, it remains generally
unproblematic to knowingly waive a constitutional right or
to lose a constitutional right (in a clearly demarcated way
and in accord with 18 U.S.C. § 3583(d)) via special conditions
of supervised release.
The crucial distinction in this case, as we explain below,
is that no reasonable person could know what conduct is or
is not proscribed by Special Condition Five. This lack of
notice is troubling in part because of the inefficiency it
causes, as a defendant must avoid a wide range of conduct,
some permissible and some not. See Laura A. Napoli,
Demystifying “Pornography”: Tailoring Special Release
Conditions Concerning Pornography and Sexually Oriented
Expression, 11 U.N.H. L. Rev. 69, 74 (2013). The possibility for
inconsistent enforcement also concerns us, as different
minds may interpret the same broad phrases differently. Cf.
Hill v. Colorado, 530 U.S. 703, 732 (2000). In sum, we hold that
despite a waiver of appellate review, the Due Process Clause
permits review when a special condition is so vague that no
reasonable person could know what conduct is permitted
and what is prohibited.
ii. Special Condition Five is unconstitutional
The parties agree that plain error review applies. District
courts have “wide discretion” in determining conditions of
supervised release. Sines, 303 F.3d at 800. That discretion has
Nos. 12‐3738 & 12‐3739 27
limits, however. “A condition of supervised release is
unconstitutionally vague if it would not afford a person of
reasonable intelligence with sufficient notice as to the
conduct prohibited.” United States v. Schave, 186 F.3d 839, 843
(7th Cir. 1999); see also United States v. Guagliardo, 278 F.3d
868, 872 (9th Cir. 2002) (“A probationer, however, has a
separate due process right to conditions of supervised
release that are sufficiently clear to inform him of what
conduct will result in his being returned to prison.”); Birzon
v. King, 469 F.2d 1241, 1243 (2d Cir. 1972). Moreover, unlike
obscenity and child pornography, pornographic materials
enjoy First Amendment protection, which means that we
must be sensitive to the possible overbreadth of the
condition as well. See United States v. Williams, 553 U.S. 285,
288 (2008); United States v. Loy, 237 F.3d 251, 259 n.2 (3d Cir.
2001) (“When a statute is vague and arguably involves
protected conduct, vagueness analysis will necessarily
intertwine with overbreadth analysis.” (citing Hoffman
Estates v. Flipside, Hoffman Estates, Inc., 455 U.S. 489, 494 n.6
(1982))); see also 18 U.S.C. § 3583 (noting that conditions of
supervised release must, inter alia, be “reasonably related”
to the § 3553(a) sentencing factors and must “involve[] no
greater deprivation of liberty than is reasonably necessary”).
Special Condition Five states: “The defendant shall not
view or listen to any pornography or sexually stimulating
material or sexually oriented material or patronize locations
where such material is available.” Read literally, this
provision might preclude Adkins from using a computer or
entering a library—irrespective of what he views in either
place—because both are “locations” where “sexually
stimulating material … is available.” Indeed, he might not be
able to ride the bus, enter a grocery store, watch television,
Nos. 12‐3738 & 12‐3739 28
open a magazine or newspaper, read a classic like Romeo and
Juliet, or even go out in public (given the ubiquity of
advertisements that use potentially sexually oriented or
sexually stimulating images to pique consumer interest).
More practically, how can we tell which images or voices are
sexually stimulating for Adkins? Cf. United States v. Smith,
972 F.2d 960, 962 (8th Cir. 1992) (striking down a supervised
release condition and criticizing it as “unworkable” in
practice). It is hard to see how the potential breadth of
Special Condition Five would satisfy the narrow tailoring
requirement of 18 U.S.C. § 3583(d).
Last year, in United States v. Goodwin, 717 F.3d 511 (7th
Cir. 2013), we struck down a condition of supervised release
that said: “You shall neither possess nor have under your
control any material, legal or illegal, that contains nudity or
that depicts or alludes to sexual activity or depicts sexually
arousing material.” We explained, in part:
The inclusion of material that “alludes to”
sexual activity within Condition 6’s purview is
particularly problematic. This dictate goes
beyond a ban on the possession of
pornography. If read literally, the inclusion of
this term could block Goodwin from
possessing much of the Western literary
canon—or arguably even from possessing a
slip copy of this opinion. Such a deprivation of
liberty certainly would be greater than is
reasonably necessary to achieve the goals of
supervised release.
Id. at 524–25 (citing United States v. Monteiro, 270 F.3d 465,
473 (7th Cir. 2001) (vacating a “vague and overbroad”
Nos. 12‐3738 & 12‐3739 29
special condition to enable the district court “to craft more
precisely” the condition)). The terms of the Special
Condition in this case are not identical to those in Goodwin,
but if anything, the terms before us may be more all‐
encompassing because they prohibit viewing or listening to
sexually stimulating material, not merely “possess[ing]” it,
as in Goodwin. Goodwin found that the Special Condition in
that case could not survive irrespective of whether plain‐
error review or abuse‐of‐discretion review applied, and
compels the same result here.
Our conclusion is generally consistent with our sister
circuits’ approaches to this challenging area. See, e.g., United
States v. Antelope, 395 F.3d 1128, 1141–42 (9th Cir. 2005)
(striking down as unconstitutionally vague a supervised
release condition banning the possession of “any
pornographic, sexually oriented or sexually stimulating
materials”); United States v. Guagliardo, 278 F.3d 868, 872 (9th
Cir. 2002) (striking down as unconstitutionally vague a
supervised release condition banning the possession of “any
pornography,” including legal adult pornography, because
“a probationer cannot reasonably understand what is
encompassed by a blanket prohibition on ‘pornography’”);
United States v. Loy, 237 F.3d 251, 265 (3d Cir. 2001) (striking
down as unconstitutionally vague a supervised release
condition banning the possession of “all forms of
pornography, including legal adult pornography”); Farrell v.
Burke, 449 F.3d 470, 486 (2d Cir. 2006) (noting that the
Second Circuit has “strongly suggest[ed] that the term
‘pornography’ is inherently vague for defendants whose
statute of conviction does not define it.” (citing United States
v. Simmons, 343 F.3d 72 (2d Cir. 2003)); United States v. Cabot,
325 F.3d 384 (2d Cir. 2003)); see also United States v. Perazza‐
Nos. 12‐3738 & 12‐3739 30
Mercado, 553 F.3d 65, 74–76 (1st Cir. 2009) (vacating a
condition of supervised release that banned the “possession
of any kind of pornographic material” because the district
court did not provide an explanation for this condition, and
“no evidence in the record … justifies the ban”); cf. United
States v. Armel, 585 F.3d 182, 185–87 (4th Cir. 2009) (holding
that sentencing court abused its discretion by imposing an
unexplained three‐year prohibition on adult “pornography”
where defendant had been convicted of threatening federal
officials). But see United States v. Boston, 494 F.3d 660, 667–68
(8th Cir. 2007) (upholding the breadth of the supervised
release condition in part because the defendant was found
guilty of producing child pornography); United States v.
Phipps, 319 F.3d 177, 192–93 (5th Cir. 2003) (acknowledging
that the ban on “sexually oriented or sexually stimulating
materials” is “somewhat vague,” but narrowing it so that it
does not reach magazines and so that “the prohibition on
patronizing sexually oriented establishments refers … to
places such as strip clubs and adult theaters or bookstores”).
The government argues that instead of vacating and
remanding, we could avoid the condition’s constitutional
difficulties through a “commonsense” limiting construction.
Some of our sister circuits have taken this approach in
certain cases. For instance, when a supervised release
condition prevents a supervisee from patronizing locations
that offer sexually explicit materials, some courts have held
that supervisees may go to libraries and grocery stores but
not strip clubs and adult bookstores. See, e.g., United States v.
Ellis, 720 F.3d 220, 226–27 (5th Cir. 2013); United States v.
Accardi, 669 F.3d 340, 346–47 (D.C. Cir. 2012). In some cases,
a limiting construction is the appropriate course. For
example, in Schave, we found that constitutional difficulties
Nos. 12‐3738 & 12‐3739 31
could be “easily avoided through an appropriate limiting
instruction.” 186 F.3d at 843. In that case, the defendant was
a member of a white supremacist organization and sold
explosives (to an undercover agent) that were meant to be
used in violent acts that furthered the group’s aims. Id. at
840. A condition of supervised release provided that Schave
“shall not associate, either directly or indirectly, with any
member or organization which espouses violence or the
supremacy of the white race.” Id. at 843. We were troubled
by the absence of a scienter requirement, but found that
“[w]ithout much difficulty,” we could construe the provision
to “reach only those activities which would reasonably relate
to the danger of [the defendant’s] reassociating with white
supremacist groups … which pursue their aims through
violent means.” Id. at 843, 844.
However, this is not a case where we can tweak the
relevant condition “easily.” Id. at 843. In order to render this
special condition constitutional, we would need to define
multiple key terms or provide multiple limiting
constructions. In other cases where we found the special
condition vague or much broader than necessary, we have
vacated and remanded. See, e.g., Goodwin, 717 F.3d at 524–25;
Monteiro, 270 F.3d at 473. And because the district court will
retain jurisdiction over this case for many years, including
the power to amend the conditions of supervised release at
any time, see 18 U.S.C. § 3583(e)(2), it is in a superior position
to write a new condition, if it so chooses.
We recognize the difficulty of drafting special conditions
in this context. We therefore emphasize that various options
remain open, including (1) defining the crucial terms in the
existing special condition in a way that (a) provides clear
Nos. 12‐3738 & 12‐3739 32
notice to Adkins (preferably through objective rather than
subjective terms), (b) includes a mens rea requirement (such
as intentional conduct), and/or (c) is not broader than
reasonably necessary to achieve the goals of 18 U.S.C.
§ 3553(a)(2)(b), (a)(2)(C), and (a)(2)(D), see § 3583(d); and
(2) narrowing the scope of proscribed conduct, such as by
(a) focusing on child pornography, which federal statutes
objectively define, see, e.g., 18 U.S.C. § 2256(8), and/or
(b) focusing on particular establishments such as strip clubs,
adult bookstores, and adult theaters.
In sum, given the importance of notice and reasonably
narrow tailoring, see 18 U.S.C. § 3583(d)—which our
precedent, Goodwin, reinforces—we vacate Special Condition
Five and remand to the district court.
III. Conclusion
We AFFIRM Adkins’ heroin and firearms convictions and
sentences. We VACATE Special Condition Five of Adkins’
child pornography sentence and REMAND so that the district
court may revisit the condition in light of this opinion.