United States v. Boudreau ( 2023 )

United States Court of Appeals
For the First Circuit
No. 21–1973
UNITED STATES OF AMERICA,
Appellee,
v.
JASON D. BOUDREAU,
Defendant, Appellant.
APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF RHODE ISLAND
[Hon. John J. McConnell, Jr., U.S. District Judge]
Before
Barron, Chief Judge,
Lynch, Circuit Judge,
and Kelley, District Judge.*
Jeremy A. Pratt, with whom Jason D. Boudreau, pro se, was on
supplemental brief, for appellant.
Lauren S. Zurier, Assistant United States Attorney, with whom
Zachary A. Cunha, United States Attorney, was on brief, for
appellee.
January 24, 2023
* Of the District of Massachusetts, sitting by designation.
KELLEY, District Judge. Jason D. Boudreau (“Boudreau”)
was indicted on 34 child pornography possession charges in the
District of Rhode Island. Boudreau and the government reached a
plea agreement under which he pled guilty to Counts 19 and 34 of
the indictment, and the government dismissed the remaining 32
charges. In entering this plea agreement, Boudreau agreed to
waive his rights to appeal his conviction and sentence. Despite
executing this waiver, Boudreau now appeals various aspects of the
proceedings below, including the calculation of the Sentencing
Guidelines and the conditions of his life term of supervised
release. Because Boudreau's waiver of appeal is valid and
enforceable, we dismiss his appeal.
I. FACTUAL & PROCEDURAL BACKGROUND
We begin with a review of Boudreau's criminal history.
In 2009, Boudreau pleaded nolo contendere to a charge of simple
assault of an 11-year-old girl in Rhode Island state court.
Although the charge was “simple assault,” the facts underlying
this conviction indicate that the crime was sexual in nature:
Boudreau placed the child on his lap, unbuckled her belt, kissed
her lips, and tried to place his tongue in her mouth. This
conviction was originally “filed,” with no punishment imposed, but
was converted to a term of probation in 2010 after Boudreau failed
to appear in court.
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In 2012, Boudreau pleaded nolo contendere to a charge of
second-degree child molestation of a seven-year-old family member
in Rhode Island state court. This offense involved kissing and
feeling the child's intimate parts over her underwear. The court
sentenced Boudreau to eight years, two to be served in prison and
six to be served on probation as a suspended sentence.
In 2014, Boudreau pleaded nolo contendere to a charge of
possession of child pornography in Rhode Island state court. The
court sentenced him to a five-year suspended sentence with five
years of probation.
We now turn to the facts of this case. In March 2015, a
person using an IP address associated with Boudreau's residence
uploaded a video of child pornography to a website called
SendVid.com. The National Center for Missing and Exploited
Children alerted Rhode Island authorities to the upload of this
video in April 2015. Rhode Island authorities received
information from Verizon connecting Boudreau's residential address
to the video in September 2015. In November 2015, authorities
executed a search warrant at Boudreau's residence and seized
electronic devices, including cell phones. Boudreau acknowledged
ownership of these devices at the time of the search.
Analysis of Boudreau's cell phone indicated that between
August and November 2015, the phone had accessed 617 images of
child pornography. The phone's cache contained 677 images of
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child pornography. The analysis indicated that on September 20,
2015 (the date which formed the basis for “Count 19,” one of the
two instant charges here), the phone had accessed 76 images of
child pornography.
The District of Rhode Island issued an arrest warrant
for Boudreau in December 2015. When Boudreau was arrested in
Connecticut, authorities seized an additional cell phone from his
person. The SD card of this phone contained over 100 additional
images of child pornography as well as images of young girls in
Boudreau's family.
A federal grand jury indicted Boudreau in February 2016
on 33 counts of access with intent to view child pornography, for
images found on his devices at his residence. In June 2016, the
grand jury returned a superseding indictment adding one count of
possession of child pornography ("Count 34") to the original 33
counts, for the images found on his phone during his arrest.
In May 2018, Boudreau entered into a plea agreement under
which he was to plead guilty to Counts 19 and 34 and the government
would dismiss the remaining 32 counts. The parties agreed that
the government would recommend a sentence within the Guidelines
range and the parties further agreed to four sentencing
enhancements that would apply to the calculation of the offense
level. The plea agreement expressly contemplated the possibility
that additional enhancements could apply, and the parties reserved
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their rights to argue at sentencing as to the proper calculation
of the guidelines.
The plea agreement also contained the following waiver
of appeal clause:
Defendant hereby waives Defendant's right to
appeal the convictions and sentences imposed
by the Court, if the sentences imposed by the
Court are within or below the sentencing
guideline[s] range determined by the Court.
This agreement does not affect the rights or
obligations of the United States as set forth
in 18 U.S.C. § 3742(b), and the government
retains its right to appeal any of the Court's
sentencing determinations.
The district court conducted a change of plea hearing at
which Boudreau was questioned about his understanding of the plea
agreement and waiver of appeal. Under oath, Boudreau testified
that he understood the terms of the agreement, including the waiver
of appeal, that he had discussed the agreement with his attorney,
and that he was fully satisfied with his attorney's performance.
The district court did not, however, state as a part of the
colloquy that Boudreau could not withdraw his plea of guilty if he
was dissatisfied with the sentence he received, as required by
Federal Rules of Criminal Procedure Rule 11(c)(3)(B).
The Probation Department prepared a Presentence
Investigation Report ("PSR") that contained a detailed statement
of facts supporting each application of a sentencing enhancement.
The PSR further recommended that the four sentencing enhancements
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that the parties had agreed to in the plea agreement should apply.
The PSR also recommended the application of a five-point
enhancement for a "pattern of activity involving the sexual abuse
or exploitation of a minor" should apply to Boudreau's offense
level, pursuant to U.S.S.G. § 2G2.2(b)(5).
At sentencing, the district judge calculated the
Sentencing Guidelines as the PSR had recommended. The district
judge determined that the base offense level was 18 and added each
of the four enhancements the parties had agreed upon in the plea
agreement: two-level increase for material depicting prepubescent
minors; four-level increase for depiction of sadistic or
masochistic conduct; two-level increase for use of a computer; and
five-level increase for access to 600 or more images. The district
court also applied the PSR's suggested five-level increase for a
"pattern of activity involving the sexual abuse or exploitation of
a minor" and a three-level decrease for Boudreau's acceptance of
responsibility. This brought the offense level to 33. Neither
party objected to the calculation of the offense level, including
the application of the enhancements. The district court further
determined that the criminal history score was 9 and the criminal
history category was IV, resulting in a Sentencing Guidelines range
of 188 to 235 months.
When imposing the sentence, the district court again
asked Boudreau if he had assented to the appeal waiver in his plea
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agreement, and Boudreau again indicated that he had. The district
court imposed a sentence at the top of the Guidelines range of 235
months. Because this sentence fell within the Guidelines range,
the appeal waiver Boudreau agreed to in his plea agreement applied.
In explaining its sentence, the district court expressed concern
that Boudreau's risk of recidivism was nearly 100 percent and cited
his past instances of child abuse and child pornography possession
in reaching this conclusion. The district court indicated that
it would have imposed a harsher sentence if the Sentencing
Guidelines range had been higher and stated that it needed to keep
Boudreau "locked up as long as [it] can in order to protect the
public from [Boudreau] based on [his] history."
The district court further imposed a sentence of a
lifetime term of supervised release with several special
conditions including a "suspicionless search" provision that would
permit the Probation Officer to search Boudreau's property,
including electronic devices, at any time, without a requirement
of reasonable suspicion of a violation. Additionally, the court
imposed a special condition restricting Boudreau's abilities to
access devices capable of connecting to the internet and to
interact with persons under the age of 18.
II. DISCUSSION
Boudreau appeals his sentence on various procedural and
substantive grounds. However, because Boudreau executed a waiver
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of appeal in his plea agreement, we first assess whether Boudreau's
waiver is valid and enforceable. If an appeal is subject to a
waiver that is valid and enforceable, we will dismiss the appeal.
See United States v. Morales-Arroyo, 854 F.3d 118, 121–22 (1st
Cir. 2017).
We thus begin with Boudreau's challenge to the validity
of his waiver of appeal. We identified a three-factor standard
for validity in United States v. Teeter, 257 F.3d 14, 24–25 (1st
Cir. 2001). First, the waiver must "comprise 'a clear statement'
describing the waiver and specifying its scope." United States
v. Morillo, 910 F.3d 1, 2 (1st Cir. 2018) (quoting Teeter, 257
F.3d at 24). Second, the "record must show that the judge’s
interrogation 'suffice[d] to ensure that the defendant freely and
intelligently agreed to waive [his or] her right to appeal [his
or] her forthcoming sentence.'" Id. (alterations in original)
(quoting Teeter, 257 F.3d at 24). And third, denying a right to
appeal must not "work a miscarriage of justice." Id. (quoting
Teeter, 257 F.3d at 25).
Here, there is no argument on the first Teeter factor,
as Boudreau does not dispute that the plea agreement plainly states
the terms and scope of the waiver. On the second factor -- the
sufficiency of the district court's plea colloquy -- Boudreau
contends that the court should not give effect to the appeal waiver
based on this factor in part because the district court failed to
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inform him that he did not have a right to withdraw his plea, in
violation of Rule 11(c)(3)(B), and failed to inform him about the
nature of each charge to which he was pleading, in violation of
Rule 11(b)(1)(G). Regarding the district court's failure to
inform Boudreau about his right to withdraw his plea, we do not
see how this error, even if true, has any bearing on whether
Boudreau was adequately informed about his right to appeal his
conviction and sentence, and we therefore do not see how this error
is relevant to the second Teeter factor.
As to Boudreau's claim that the district court failed to
inform him about the nature of each charge to which he was
pleading, a court's failure in this regard could affect a
defendant's ability to "intelligently" waive his right to appeal
his conviction and sentence on those charges and is thus relevant
to the Teeter analysis. See Morillo, 910 F.3d at 2. However,
Boudreau does not sufficiently develop his argument regarding this
error; although he argues that the prosecutor "provided the court
with an incorrect explanation" regarding the charges against him,
Boudreau does not provide any argument for how exactly the
prosecutor erred and how that error affected Boudreau's
intelligent waiver of his right to appeal. We therefore treat
this argument as insufficiently developed and, thus, waived. See
United States v. Zannino, 895 F.2d 1, 17 (1st Cir. 1990). Thus,
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the two errors Boudreau asserts, which he casts as Rule 11 errors,1
provide no support for the argument that the district court's
interrogation was insufficient to show that Boudreau waived his
right to appeal "freely and intelligently." See Morillo, 910 F.3d
at 2.
Having dispensed with Boudreau's Rule 11-based
challenges to the validity of his appeal waiver, we turn to the
other arguments he makes regarding the second Teeter factor. We
do not find them persuasive. Boudreau's principal argument is
that the plea agreement's language is complex, and his answers at
the plea colloquy were brief and thus insufficient to establish
full understanding of the plea. These concerns, which we have
never identified as factors that can support relief on this claim,
are minimal, given that Boudreau was represented by counsel --
whose duties included explaining any complexities in the plea
agreement to Boudreau -- throughout plea negotiations and at his
change of plea hearing. Further, Boudreau stated at his plea
hearing that he was fully satisfied with the performance of his
1 Insofar as Boudreau argues that Rule 11 errors not only
affected his ability to intelligently waive his right to appeal
but invalidated the plea agreement itself, with the effect of
freeing him not only from the appeal waiver but from all other
aspects of the agreement reached as part of his plea, this
challenge fails under plain error review, as Boudreau has not shown
"a reasonable probability that, but for the error, he would not
have entered the plea." United States v. Dominguez-Benitez, 542
U.S. 74, 83 (2004); see United States v. Rivera-Clemente, 813 F.3d
43, 47 (1st Cir. 2016) (same).
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counsel, and he has not contested the quality of his
representation. See United States v. Rivera-Clemente, 813 F.3d
43, 48–49 (1st Cir. 2016); United States v. Hernandez-Maldonado,
793 F.3d 223, 226 (1st Cir. 2015). Additionally, during the
colloquy, Boudreau was again afforded the opportunity to consult
with counsel and to ask the court to further explain anything that
he did not understand. Consequently, Boudreau has failed to carry
his burden to establish that his appeal waiver was not entered
"freely and intelligently." Morillo, 910 F.3d at 2.2
Our final task is to determine whether, per the third
Teeter factor, denying Boudreau his appeal would "work a
miscarriage of justice." 257 F.3d at 25. Whether a district
court's error constitutes a miscarriage of justice is "more a
concept than a constant," and the factors that we may weigh include
"the clarity of the error, its gravity, its character (e.g.,
whether it concerns a fact issue, a sentencing guideline, or a
statutory maximum), the impact of the error on the defendant, the
impact of correcting the error on the government, and the extent
2 Boudreau separately contends in his counseled brief to us
that he did not "freely and intelligently" waive his right to
appeal the suspicionless search condition imposed on him as part
of his supervised release because he could not have reasonably
foreseen that it would be imposed and that it was, in any event,
outside the scope of his appeal waiver. But, given the terms of
his plea agreement and colloquy, these contentions are meritless
under our precedent. See United States v. Santiago, 769 F.3d 1, 7-
8 (1st Cir. 2014).
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to which the defendant acquiesced in the result." Id. at 26. We
will reverse on this factor "only in 'egregious cases,'" not in
"garden-variety" sentencing disputes. Morillo, 910 F.3d at 4(quoting Teeter, 257 F.3d at 25–26). As we have explained, for
the imposition of a condition of supervised release to result in
a "miscarriage of justice," the condition must be "so lacking in
rationality or so wholly unrelated to legitimate sentencing
purposes as to necessitate invalidating [the] waiver of appeal."
United States v. Rivera-López, 736 F.3d 633, 636 (1st Cir. 2015).
Here, Boudreau has alleged no error sufficiently
egregious for us to consider piercing his waiver of appeal. We
will comment briefly on Boudreau's assertions that certain
conditions of supervised release amount to a miscarriage of
justice. Specifically, Boudreau challenges Special Condition 6,
which permits the Probation Officer to search his residence and
property without reasonable suspicion of a violation; Special
Condition 7, which restricts him from accessing devices that are
capable of connecting to the internet; and Special Condition 8,
which restricts his ability to contact children, either male or
female, under the age of 18.
Each of these challenges fails on plain error review, as
Boudreau does not identify precedent that would provide a basis
for concluding that it would be clear or obvious error to impose
any of these conditions. See Rivera-López, 736 F.3d at 63.
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Indeed, we have permitted the imposition of a suspicionless search
condition in another context as reasonably related to the goals of
supervised release, see United States v. Windle, 35 F.4th 62, 67-
68 (1st Cir. 2022), and three of our sister circuits have upheld
the imposition of similar conditions on child pornography
offenders, see United States v. Sulik, 807 F. App'x. 489, 492–93
(6th Cir. 2020); United States v. Rosenthal, 295 F. App'x 985, 986
(11th Cir. 2008); United States v. White, 244 F.3d 1199, 1208 (10th
Cir. 2001). In addition, we have upheld on plain error review
both a supervised release condition barring a child sex offender's
ability to have contact with minors, see United States v. Pabon,
819 F.3d 26, 29, 34–35 (1st Cir. 2016), and a restriction on a
child pornography offender's ability to access the internet, see
United States v. Velez-Luciano, 814 F.3d 553, 560 (1st Cir. 2016).
Thus, Boudreau has not met his burden to show that the imposition
of the conditions that he challenges resulted in a miscarriage of
justice in his case.
We need not go further.3 The district court's sentence
was supported by meticulous factfinding and a clear consideration
3Boudreau contests the validity of the plea agreement on a
number of additional grounds in his pro se supplemental brief. To
the extent these arguments were not waived, they are meritless.
The record does not suggest that the plea agreement was
procedurally invalid or lacked consideration, that any of the
prosecutor’s actions were taken in bad faith or in breach of the
agreement, or that any of the supervised release conditions imposed
on Boudreau were outside the scope of the appeal waiver. Because
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of the statutorily required factors, and falls squarely within the
scope of what courts within and outside this circuit have
permitted. There has been no miscarriage of justice. We find
that Boudreau's waiver of appeal is valid, enforceable, and bars
our further consideration of his arguments. We thus dismiss and,
as to the arguments addressed in Footnote 1, affirm as there was
no plain error.
counsel declined to make these arguments, we need not address their
deficiencies in any further detail.
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