United States v. Boudreau

58 F.4th 26

UNITED STATES of America, Appellee,

v.Jason D. BOUDREAU, Defendant, Appellant.

No. 21-1973

United States Court of Appeals, First Circuit.

January 24, 2023

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.

Before Barron, Chief Judge, Lynch, Circuit Judge, and Kelley, District Judge.^*

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.

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 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 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 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 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 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...