United States Court of Appeals For the First Circuit

No. 23-1685

UNITED STATES OF AMERICA,

Appellee,

v.

DOMINICK BAILEY,

Defendant, Appellant.

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

[Hon. Nathaniel M. Gorton, U.S. District Judge] [Hon. Douglas P. Woodlock, U.S. District Judge]

Before

Kayatta, Selya, and Aframe, Circuit Judges.

David J. Nathanson, with whom Wood & Nathanson, LLP was on brief, for appellant. Donald C. Lockhart, Assistant United States Attorney, with whom Joshua S. Levy, Acting United States Attorney, was on brief, for appellee.

November 20, 2024 AFRAME, Circuit Judge. This is an appeal from

defendant-appellant Dominick Bailey's guilty plea in the District

of Massachusetts to being a felon in possession of a firearm in

violation of

(g)(1). This is Bailey's third

felon-in-possession conviction. In 1997, Bailey pleaded guilty to

the same offense in the District of Vermont, resulting in a

thirty-seven-month sentence. And, in 2006, Bailey again pleaded

guilty to this offense in the District of New Hampshire, resulting

in a forty-one-month sentence. This time, the district court

sentenced Bailey to eighty-seven months of imprisonment. In

imposing this sentence, the court departed upward from the advisory

sentencing guideline range to account for Bailey's "horrific

record."

In the district court, Bailey objected only to the

sentencing departure. On appeal, he challenges all aspects of the

proceedings, alleging that (1) the indictment violated his rights

under the Second Amendment to the United States Constitution,

(2) his guilty plea was involuntary and unknowing, (3) the

sentencing proceeding was infected by procedural error, and

(4) the sentence imposed was substantively unreasonable. Bailey's

unpreserved claims are either waived or fail to meet the plain

error standard, and the court did not abuse its discretion by

imposing an upward sentencing departure.

- 2 - THE OFFENSE AND DISTRICT COURT PROCEEDINGS

We begin by describing the offense conduct, relying on

uncontested information in the presentence report and Bailey's

admissions at the change-of-plea hearing. See United States v.

Trahan,

(1st Cir. 2024) (citing United States

v. Spinks,

(1st Cir. 2023)).

In July 2019, Bailey and his co-conspirator, Glenn

Lacedra, contacted a methamphetamine dealer working as a

confidential informant to propose a guns-for-drugs transaction.

Lacedra introduced the informant to Bailey, who was to serve as

the source of the guns. Lacedra agreed to "middle" the deal

between Bailey and the informant. Months of start-and-stop

negotiations ensued, first with the informant and then with an

undercover agent posing as the informant over text message.

During these negotiations, Bailey was upfront in

admitting to the undercover agent that he could not purchase

firearms because of his felon status.1 Still, Bailey stated that

he had certain firearms in his possession to trade and that a

1 Bailey, in fact, was upfront about much with the agent. During one exchange, he boasted about a prior federal felon-in-possession conviction for trafficking "300 guns," remarking that he was a firearms "entrepreneur." He also cogently explained the difference between actual and constructive possession of a firearm under federal law, and why it is advantageous to plead incompetency when facing a state charge but better to "tak[e] it on the chin and not try[] the incompetent nonsense" in federal court.

- 3 - friend had an additional gun available for the transaction. Bailey

followed up by sending the agent a picture of two pistols and a

rifle with the comment that he had those firearms "right now" and

was "ready to do some business with [him]." Ultimately, Bailey

and the agent settled on Bailey bringing three pistols and a rifle

to Boston to exchange for drugs.

On November 14, 2019, Lacedra drove to Vermont to

retrieve Bailey and the guns. Bailey brought a .22 caliber firearm

and a duffle bag containing an AR-15 rifle and two pistols. When

Bailey and Lacedra arrived at the agreed-upon meeting place in

Boston, Massachusetts, they were confronted by various federal and

state law enforcement officials. The officials arrested Bailey

and Lacedra; they also seized the duffle bag containing the three

guns from the backseat and the .22 caliber firearm from the rear

pocket of the driver's seat.

In January 2020, a grand jury indicted Bailey on one

count of being a felon in possession of a firearm in violation of

(g)(1) and

, under principal and

aiding-and-abetting theories. Almost a year later, during the

COVID-19 pandemic, Bailey pleaded guilty without a plea agreement

during a virtual proceeding that he attended from his home in

Vermont. In August 2023, the district court sentenced Bailey to

eighty-seven months of imprisonment. Bailey appealed.

- 4 - THE INDICTMENT

On appeal, Bailey argues that the indictment was

unlawful because it violated his right under the Second Amendment

to "keep and bear Arms." U.S. Const. amend. II. Bailey claims

that the Second Amendment renders § 922(g)(1) unconstitutional,

both facially and as applied to him because none of his prior

convictions involved him "seriously physically harming another

human."

Bailey did not raise a Second Amendment challenge in the

district court. The government contends that he waived this

argument by not timely moving to dismiss on Second Amendment

grounds, as required by Federal Rule of Criminal

Procedure 12(b)(3). Rule 12 provides that, absent good cause

shown, Fed. R. Crim. P. 12(c)(3), a defendant must raise pretrial

any claim alleging "a defect in the indictment," including that it

"fail[s] to state an offense," where the claim was "reasonably

available" and could have been resolved "without a trial on the

merits," id. at 12(b)(3). The government contends that a Second

Amendment challenge to an indictment falls within the purview of

this Rule. Where the defendant fails to timely raise a claim

covered by Rule 12(b)(3) without demonstrating good cause, the

defendant "is not entitled to plain error review" on appeal.

United States v. Lindsey,

(1st Cir. 2021).

- 5 - Here, despite having multiple opportunities to do so,

Bailey has offered no response to the government's argument that

his Second Amendment claim is within the scope of Rule 12(b)(3)'s

raise-or-waive provision. Nor has he attempted to demonstrate

good cause for failing to move to dismiss his indictment in the

district court. We will not rescue an appellant who "buries his

head in the sand and expects that [the] harm will pass him by."

United States v. Arroyo-Blas,

(1st Cir. 2015).

Because Bailey has entirely failed to address the government's

Rule 12 argument, he has waived his Second Amendment claims. See

THE CHANGE OF PLEA

Bailey argues that his Federal Rule of Criminal

Procedure 11 plea proceeding was defective in two respects. First,

Bailey contends that the district court failed to determine whether

he pleaded guilty voluntarily because it insufficiently inquired

into the potential effects of Bailey's mental health conditions

and medication use on his comprehension of the proceedings.

Second, Bailey claims that the court's confusing description of

the charge made it impossible for him to understand the elements

of the offense to which he admitted guilt.

Bailey did not present either argument to the district

court. We therefore review for plain error. See United States v.

Williams,

(1st Cir. 2022) (citing United States v.

- 6 - Vonn,

(2002)). Thus, to succeed, Bailey must

establish that there was a "clear or obvious" error which "affected

[his] substantial rights" and seriously impaired "the fairness,

integrity or public reputation of [the] judicial proceedings."

(alterations in original) (citing United States v. Kitts,

(1st Cir. 2022)). "In applying plain error analysis

in guilty plea cases, a defendant must, in order to demonstrate

that his substantial rights were affected, 'show a reasonable

probability that, but for the error, he would not have entered the

[guilty] plea.'" United States v. Caraballo-Rodriguez,

(1st Cir. 2007) (quoting United States v. Dominguez Benitez,

(2004)).

I. Voluntary Plea

We begin with Bailey's challenge to the adequacy of the

district court's inquiries into the effects of his mental health

conditions and medication use on the voluntariness of his plea.

See United States v. Kenney,

(1st Cir. 2014)

(explaining that Fed. R. Crim. P. 11(b) requires a district court

"to determine that the defendant's guilty plea is knowing and

voluntary").

The district court heard early in the Rule 11 colloquy

about Bailey's mental health history and medication use. Bailey

reported that he had been receiving disability benefits since

approximately 1995, when he sustained a skull fracture during an

- 7 - assault that resulted in a traumatic brain injury and posttraumatic

stress disorder. When asked if there was "[a]nything about [his]

experience with the disability" that would interfere with his

ability to understand his case and the change-of-plea proceeding,

Bailey replied, "No. I understand. Just some things I need

explaining. But other than that, no. I understand what's going

on." The court responded by advising Bailey that he could seek

clarification at any point during the plea colloquy.

The district court next asked Bailey about his substance

abuse history. Bailey explained that he "got into drugs" to avoid

"bad dreams and nightmares," which began after his head injury.

In response to further inquiry, Bailey identified cocaine as his

drug of choice but reported to be "doing great" after

rehabilitation and estimated that he had not used cocaine in ten

to fifteen years. Later in the hearing, Bailey's counsel advised

that Bailey had "passed every drug test" while on pretrial release.

Bailey also disclosed that he suffers from bipolar

disorder and volunteered that he had "come a long way" in managing

the condition through ongoing work with a therapist. The district

court responded with questions regarding Bailey's use of

medication to moderate his symptoms; he reported taking lithium

"as needed," explaining his therapeutic range is ".05 to 1," but

that he can sense "when [he is] getting [] manic" and will "go to

- 8 - counseling and take [his] meds . . . ." In response, the court

asked about Bailey's present ability to understand the proceeding:

THE COURT: So let's talk about right now.

THE DEFENDANT: Yeah, I'm fine. I'm taking my meds and everything. I'm fine. I'm doing good. And I go to therapy, every two weeks I go and stuff, yeah.

THE COURT: Okay. But for right now, for this occasion, are you in a position to make a clear-eyed judgment about a very important matter like this?

THE DEFENDANT: Yeah, yes, yes, I'm clear, yes.

THE COURT: Okay.

THE DEFENDANT: I understand, yes.

The district court confirmed that Bailey's mental health

center provided both counseling and psychiatric treatment

services. It also asked if Bailey's mental health condition could

be "broadly categorized as bipolar issues." He replied, "I think

so, yeah, bipolar and whatever. There's some other diagnosis I

was told, but yes." The court responded by inquiring further into

Bailey's medication use:

THE COURT: Let's turn to your current situation. You have [l]ithium that you're taking?

THE DEFENDANT: Yeah.

THE COURT: Any other prescription drugs?

THE DEFENDANT: I got a whole list. I have a hard time pronouncing it. I take Adderall. I take blood pressure meds. I take [l]ithium.

- 9 - I take stuff for side effects and anxiety, too. I take a bunch of different meds.

THE COURT: Without getting into the specifics of it, the reason I'm asking about the drugs is, are any of those interfering with your ability today --

THE DEFENDANT: No.

THE COURT: -- to tell me whether or not you're ready to plead guilty to this very serious felony?

THE DEFENDANT: No, no, they're not interfering with me understanding what you're saying, Your Honor.

The court ultimately accepted Bailey's guilty plea, concluding

that his "decision to plead guilty [was] knowing and voluntary."

A district court should inquire into a defendant's

mental health status to establish that a guilty plea is knowing

and voluntary because "impaired mental or emotional capacity can

interfere with [a defendant's] ability to understand what he is

being told and to exercise rational choice." United States v.

Pattee,

(2d Cir. 2016). So too should a court

inquire about the effects on comprehension caused by a defendant's

medication use. See United States v. Savinon-Acosta,

(1st Cir. 2000) ("[M]edication can in some circumstances

affect a defendant's mental state to a degree that undermines the

defendant's ability to enter a voluntary plea.").

The sufficiency of these inquiries depends on whether

there is an adequate record to support the district court's finding

- 10 - that a defendant pleaded guilty voluntarily. See Savinon-Acosta,

(emphasizing that "[t]he critical question" is

whether the defendant suffers from any impairment during a

change-of-plea hearing that presently affects his ability to

comprehend). Several factors are relevant, including "the

defendant's own assurance (and assurances from counsel) that the

defendant's mind is clear," the court's observations of the

defendant, and the defendant's performance throughout the

proceeding.

; see also United States v. Morrisette,

(1st Cir. 2005).

Here, the district court inquired into both Bailey's

mental health and medication use. Regarding mental health, the

court asked Bailey about the injury that caused certain of his

mental health conditions and the nature of those conditions. The

court also inquired into the consequences of his conditions,

including his difficulty in maintaining employment and issues with

substance abuse. The court sought and received Bailey's assurances

that he was receiving appropriate mental health services and was

no longer using non-prescribed drugs. As to his prescribed drugs,

the court asked Bailey about the medications that he was presently

taking. Bailey provided the court with a partial list, and the

court asked him about the effects that the drugs had on his

comprehension.

- 11 - The record contains multiple assurances from Bailey that

he understood the proceeding and the significance of pleading

guilty. When asked about the effect of his mental health

conditions on his ability to comprehend, Bailey stated that he

"underst[ood] what[] [was] going on." Similarly, after telling

the district court that he was taking lithium, Bailey was asked

whether he was "in a position to make a clear-eyed judgment about

a very important matter," and he replied in the affirmative. And,

after Bailey disclosed that he was taking medication in addition

to lithium, he told the court that none of those drugs were

"interfering with [his] understanding what [the court] [was]

saying."

Bailey's assurances were consistent with his conduct

during the remainder of the proceeding. The record shows that

Bailey paid close attention to the district court's description of

the potential penalties and offense elements and the government's

recitation of the evidence. For example, when the subject of

forfeiture came up, Bailey interjected with an attempt to suggest

that he did not own the guns at issue. Bailey's efforts to contest

ownership of the guns at that juncture demonstrated an

understanding that the government could only seek forfeiture of

property which he owned and underscores that he was following along

closely.

- 12 - Further, after he attempted to minimize his offense

conduct by denying ownership of the firearms at issue, Bailey spoke

with his counsel privately before admitting the essential facts of

the offense. See Fed. R. Crim. P. 11(b)(3). The district court

then asked Bailey's counsel if there was "any reason [the court]

shouldn't accept [the] plea." Counsel responded that there was no

such reason. Defense counsel's agreement that the court could

accept the plea immediately after talking to Bailey about the case

also supports that Bailey understood the proceeding and the nature

of his decision to plead. See, e.g., Miranda-Gonzalez v. United

States,

(affirming validity of plea where

defendant consulted with counsel and counsel did not "voice[] an

objection" when later asked by the court "whether [he] had any

doubts as to [the defendant's] competence to enter the guilty

plea"). Given the court's inquiries, Bailey's assurances,

counsel's comments, and Bailey's behavior during the Rule 11

proceeding, we conclude that the district court did not plainly

err in determining that Bailey voluntarily pleaded guilty.

Bailey argues otherwise. He focuses on the district

court's failure to obtain a full list of his medications and to

follow-up sufficiently when he provided a response that suggested

that he might not have been taking lithium as prescribed. But

there is "no settled rule that a hearing cannot proceed unless

precise names and quantities of drugs have been identified."

- 13 - Savinon-Acosta,

.2 Thus, we have held that a plea

colloquy was adequate where, after learning that a defendant took

lithium for a mental health condition, the district court asked

the "[m]ost important[]" question of whether the medication

affected the defendant's "ability to make reasoned decisions," and

received an assurance from the defendant that the medication had

no such effect. United States v. Cody,

(1st Cir.

2001).

The district court followed the same approach here.

After learning that Bailey was medicated, the court "[m]ost

importantly" ascertained that Bailey did not believe the drugs

were affecting his ability to comprehend the proceedings. Cody,

. Bailey's conduct during the remainder of the

proceeding aligned with that assurance. See Savinon-Acosta,

. While the court could have asked more questions about

the details of Bailey's medication regimen, see

we conclude

that it did not clearly or obviously err by declining to do so.

Bailey's reliance on United States v. Parra-Ibanez,

(1st Cir. 1991), to support his contrary argument

is unavailing. There, we remanded after the district court learned

that the defendant was taking tranquilizers and "failed to follow

2 Even though a district court is not required to ascertain specific information about the medication a defendant is taking, we have stated before and reiterate here that the best practice is for a court to do so. See id. at 269.

- 14 - up with any question whatsoever about whether the defendant's

medication affected his competence to plead." Cody,

(describing the error committed by the district court in

Parra-Ibanez); see also Miranda-Gonzalez,

("The

absolute failure to investigate further once apprised of the recent

ingestion of drugs doomed the plea entered by the defendant[] in

Parra-Ibanez . . . ."). Here, in contrast, the district court did

not ignore the effect of Bailey's prescriptions on his ability to

plead, instead asking Bailey about how his drug regimen affected

his comprehension and waiting until he confirmed that he was

clear-minded before proceeding.

Finally, Bailey says that there were certain "red flags"

which should have prevented the district court from accepting his

assurances about his ability to voluntarily plead guilty. In this

regard, Bailey points first to the fact that he suffers from

multiple mental health conditions. But, as addressed above, the

district court inquired about these conditions and had the

opportunity to observe Bailey's answers in deciding whether his

assurances about being clear-minded were worthy of belief. See

United States v. Rodríguez-Leon,

, 25 n.8 (1st Cir.

2005) (declining to second-guess district court's assessment of

defendant's assurances because "the district judge had the benefit

- 15 - of directly perceiving [the defendant's] demeanor" as he answered

the court's questions).3

Bailey also identifies a moment in the hearing when he

expressed confusion about whether the district court was asking

him about his prior illegal drug use or his present prescription

regimen. But the record demonstrates that Bailey's confusion was

due to a lack of clarity in the question. Bailey's willingness to

seek clarification when he was unsure about an unclear question

reinforces that he was lucid during the sentencing hearing.

Lastly, Bailey argues that the district court should

have been concerned because he required time to speak with his

attorney about the offense conduct after he tried to disavow

ownership of the firearms at issue. But an attempt to minimize

culpability without jeopardizing the acceptance of the plea does

not typically suggest a lack of understanding of the proceedings.

Rather, it shows a defendant who has a nuanced appreciation of the

relevant legal issues and is trying to present himself in the best

light possible while still pleading guilty.4 In short, rather than

3 Bailey argues that the court could not gain a fair reading of his comprehension of the proceeding because it was conducted by video teleconference. But, during COVID-19, criminal proceedings by video were common, and the district court did not suggest it was having difficulty observing Bailey's demeanor because of the remote nature of the proceeding. See Gould Elecs. Inc. v. Livingston Cnty. Rd. Comm., Nos. 20-2257/2267,

, at *4 (6th Cir. May 10, 2022) (observing the ubiquitous use of videoconferencing technology during the COVID-19 pandemic). 4 This conclusion is consistent with Bailey's

- 16 - presenting red flags about his ability to comprehend, Bailey's

behavior during the proceeding "bore out [his] claim of

clearheadedness." Savinon-Acosta,

.5 While there

may be cases in which a defendant's erratic conduct during a

Rule 11 proceeding would mandate a district court inquiring

further before accepting a guilty plea, this was not one of them.

II. Understanding the Charge

Bailey's second argument is that he did not understand

the nature of the charge to which he was pleading. Rule 11 requires

that a district court "inform the defendant of, and determine that

the defendant understands, . . . the nature of each charge to which

the defendant is pleading." Fed. R. Crim. P. 11(b)(1)(G).

However, "[t]he manner in which the charge is explained and the

method for determining the defendant's understanding of the charge

will vary from case to case depending upon the complexity of the

charges, the capacity of the defendant, and the attendant

circumstances." United States v. Cotal-Crespo,

(1st

Cir. 1995). "[I]t is not necessary that the explanation of the

charges come directly from the court. . . if it can be discerned

conversations with the undercover agent in which he demonstrated a nuanced understanding of federal firearms law. 5 Bailey also points to the presence of his dog in the room during the proceeding as a distraction. Bailey, however, did not indicate that he was distracted by the dog, and cogently explained to the court that he lived in a small apartment such that there was nowhere else the dog could easily go.

- 17 - from a review of the proceeding that the defendant nevertheless

understood the charges."

at 5 (citing United States v. Allard,

(1st Cir. 1991)).

Here, the district court began by confirming that Bailey

had discussed the elements of the felon-in-possession charge with

his counsel. The court then summarized each element and explained

that possession can be either "direct" or "constructive." It also

stated that "the government could prove [the charge] as they allege

by saying [Bailey] [is] an aider and abett[o]r," and recited the

elements of aiding and abetting. After concluding its recitation

of the elements, the court asked Bailey whether he had "any

questions [] about what the government has to prove[,]" to which

he responded, "No, I don't, Your Honor."

The government then provided its recitation of the

offense conduct. The government described Lacedra as the

individual who facilitated the contemplated guns-for-drugs

transaction and Bailey as "the source of the guns." At the

conclusion of the government's presentation, the court asked

Bailey if he "disagree[d] with anything [the government] said."

Bailey responded by seeking clarification regarding the

government's statement that he had firearms "available to deliver

to the undercover agent," which the government clarified by

explaining that "[Bailey] traveled from Vermont to Massachusetts

with Mr. Lacedra in the driver['s] seat and himself in the

- 18 - passenger seat, and they transported firearms in Mr. Lacedra's

vehicle from Vermont to Massachusetts." Bailey offered the

following in response:

THE DEFENDANT: Okay, okay. . . . I got a question, Your Honor. Mr. Lacedra came to Vermont and purchased them guns and stuff from somebody else. I didn't understand. Okay.

After further discussion about Bailey's role in the

offense, the district court asked Bailey to confer with his

counsel. The court re-engaged Bailey after the break:

THE COURT: All right. So Mr. Bailey, you've had a chance to talk to your attorney. Let me pose the question in this fashion. [The government] has told us that there were guns in the vehicle that you traveled in from Vermont to Massachusetts with Mr. Lacedra. You've told me that you weren't the source of those guns, you didn't sell those guns. Is that right?

THE DEFENDANT: I -- I didn't understand the question. I was the source of the guns, but they weren't mine personally. That's all.

* * *

THE COURT: Okay. But let me understand what you're saying. You got the guns from someone else. You didn't sponsor the transaction by which the guns were originally acquired. Is that right?

THE DEFENDANT: Yes.

THE COURT: Okay. And did you then pass them on to Mr. Lacedra?

THE DEFENDANT: Yes.

- 19 - THE COURT: And you assisted Mr. Lacedra by driving down to Massachusetts. . . with those guns?

THE DEFENDANT: Yes.

THE COURT: And that's because you were the person who was passing them on to Mr. Lacedra; is that right?

THE DEFENDANT: Yes.

THE COURT: Any question about that in your mind?

THE DEFENDANT: No. I didn't hear -- I didn't hear right when he first asked it. . . .

On appeal, Bailey emphasizes that he initially denied

being the source of the guns and stated that Lacedra had purchased

the guns from someone else. After offering this denial, Bailey

asserts that the district court guided him towards pleading guilty

to an aiding-and-abetting theory without explaining that such a

theory required proof that he knew that Lacedra had previously

been convicted of a crime punishable by more than one year in

prison. Bailey thus contends that the plea colloquy was "too

confusing" to meet Rule 11's requirements.

We do not discern any clear or obvious error in the

district court's explanation. While Bailey may have exhibited

some initial confusion about the government's characterization of

his role in the offense, he conceded, after conferring with his

counsel, that he was the "source" of the guns, that he "pass[ed]

[the guns] on" to Lacedra, and that he "assisted" Lacedra by

- 20 - "driving down to Massachusetts. . . with [the] guns." These

admissions demonstrate that he had at least a "basic understanding

of the conduct which the government alleged was criminal." United

States v. Ferguson,

(1st Cir. 1995).

Though the district court did not specifically explain

that an aiding-and-abetting theory required proof that Bailey knew

Lacedra was a felon, the government stated during its description

of the offense conduct that Bailey "knew that Mr. Lacedra was

prohibited from possessing a firearm. . . because [Mr. Lacedra] is

also a convicted felon. The defendant knew this because he and

Mr. Lacedra had served portions of their prior federal sentences

together at a federal prison in Devens, Massachusetts." Bailey

offered no objection to that aspect of the government's recitation

of facts even though he objected to other portions. It is thus

far from obvious that Bailey misunderstood the nature of the charge

to which he pleaded guilty.

Moreover, Bailey has failed to make a sufficient showing

that he would have opted to go to trial had the district court

provided a more robust explanation of the aiding-and-abetting

theory. See United States v. Santiago,

(1st

Cir. 2014). In examining the whole record, see

, the

evidence that Bailey unlawfully possessed the weapons as a

principal was strong, and there is no apparent defense that would

- 21 - have motivated him to elect a trial had he been told more about

aiding and abetting. See Dominguez Benitez,

.

Based on the undisputed facts as described in the

presentence report, Lacedra was the facilitator of the transaction

and expected to receive only a small quantity of drugs as a

commission for his services. The communications between Bailey

and the undercover agent demonstrate that Bailey was orchestrating

the gun transaction. He specifically communicated to the agent

that he had "the 9 and 22" and that his "friend ha[d] the other

9," adding, "I have all of them on me." Bailey then sent the agent

a photograph of two pistols and a rifle, writing: "I have all these

right now and I'm ready to do some business with you. So let me

know when [Lacedra] can come get me." Bailey was subsequently

arrested after he traveled with Lacedra to the proposed transaction

location in a car containing firearms of the types he claimed to

possess when communicating with the agent. This was overwhelming

evidence of Bailey's constructive possession of the firearms in

Lacedra's car when he was arrested.

The only point at which Bailey suggested that the guns

were not in his possession was when he tried to minimize his

culpability at the change-of-plea hearing by shifting primary

blame to Lacedra. Given the overwhelming amount of evidence

showing that he was the principal for the felon-in-possession

count, there is no basis to conclude that Bailey would have elected

- 22 - to go to trial had the district court only provided a more fulsome

aiding-and-abetting explanation. See Dominguez Benitez,

(identifying the "overall strength" of the government's case

and absence of "possible defenses" as factors undermining the

probability that a defendant would have gone to trial absent a

Rule 11 error).

THE SENTENCING

Following Bailey's guilty plea, the probation officer

filed a presentence report that calculated the advisory guideline

sentencing range as 51 to 63 months based on a total offense level

of 23 and a criminal history category of II. The presentence

report, which dedicated over thirty-five pages to detailing

Bailey's criminal history, concluded that an upward departure

could be warranted because the assigned criminal history score

"underrepresent[ed] the seriousness of [his] criminal history and

[the] likelihood of recidivism." See U.S.S.G. § 4A1.3. Bailey

objected to "the potential departure identified," but probation

did not change the report.

In its sentencing memorandum, the government

characterized Bailey as a "lifetime criminal" and requested a

sentence of ninety-six months "to specifically deter [him] from

continued criminal behavior." The government argued that Bailey's

criminal history score "grossly underestimate[d] his criminal

history" because many of his prior sentences, including one of his

- 23 - prior federal convictions, were excluded from the guideline

calculation due to their age. The government inventoried Bailey's

prior convictions for more than fifteen different offenses

spanning a broad range of conduct, including assault, lewd and

lascivious conduct, falsifying physical evidence, possession and

receipt of stolen property, forgery, stalking, unauthorized

removal of human remains, and multiple violations of abuse

prevention orders. The government also detailed evidence

suggesting that Bailey engaged in criminal conduct while on

pretrial release in the pending case.

Bailey, in his sentencing memorandum, asked the district

court to not apply an "upward variance," asserting that a low-end

guideline sentence of thirty-three months would be sufficient

under the circumstances. He contended that his admittedly "lengthy

criminal history" was a reflection of "both his age and []

struggles" with mental illness and substance abuse, and

characterized "the vast majority" of his recent convictions as

driving-related offenses attributable to living "in a rural

community without public transportation." He concluded by

identifying "addiction" as "the catalyst" for the present offense

and argued that he would pose "little risk of reoffending" so long

as he maintained his sobriety.

At the sentencing hearing, the government again noted

Bailey's extensive criminal record. The government also

- 24 - referenced communications with the undercover agent in which

Bailey boasted that he was a firearms "entrepreneur." The

government noted that Bailey's criminal history had been a category

VI at his most recent federal sentencing but was now only a

category II because of the passage of time. Ultimately, the

government reiterated its request for a ninety-six-month sentence,

which would "bring [Bailey] into Criminal History Category V."

Bailey reiterated his request for a thirty-three-month

sentence. Bailey's sentencing argument emphasized his history of

substance abuse and offered explanations for the multiple

instances in which he violated the terms of his home incarceration,

including by allegedly participating in post-arrest criminal

conduct. Regarding his prior convictions, Bailey acknowledged

having "a lengthy criminal record" but argued that "a majority of

those criminal offenses" were for traffic-related offenses and

many others were non-violent or "the equivalent of criminal

harassment claims." He also noted in passing that the most recent

conviction listed in the government's sentencing memorandum was

from 2009. In sum, Bailey argued, the government's

characterization of his record as "terrible" and suggestion that

he "wouldn't be safe in society" were "a little misleading."

The district court ultimately imposed an upward

departure, explaining its rationale as follows:

- 25 - You are apologizing, which is appropriate, and you are acknowledging that you have a problem. Obviously, you do with substance abuse and that is something that you're going to have to work on the rest of your life. My duty is to impose a sentence that is appropriate for the crime that was committed by the defendant in front of me. I have to think not only about you but about the victims of your crime and about the necessity to deter anybody else from doing crimes of a similar nature.

You stand convicted of a serious crime of being a felon in possession of firearms, and not just any firearms. One of them was an assault rifle. And this is not the first time that you have been convicted of such a crime or the exchange of drugs for guns. In fact, it’s the third time that you’ve been convicted for the very same crime.

You are very experienced in the criminal behavior side of life. In fact, I think I have not seen in my many years a longer section of a criminal report. It’s 36 pages long. It records 38 convictions, two pending charges, one for a violation of a protective order, and the other for receiving stolen goods. And it reports 40 other arrests. By my calculation, that’s one conviction and one arrest for every year of your adult life. And it includes crimes such as simple assault, lewd and lascivious behavior, disorderly conduct, possession of stolen goods, unlawful trespass, receiving stolen property, issuing bad checks, disturbing the [peace], falsifying physical evidence, criminal mischief, uttering forged instruments, violation of abuse prevention orders, stalking, unauthorized removal of human remains, and multiple women have obtained restraining orders against you. That’s a horrific record, Mr. Bailey.

At least up to this point in your life, you have shown no intent or effort to abide by the law or to avoid committing crimes, so you do deserve a sentence that either upwardly

- 26 - departs or is applicable to the very highest end of the range that is applicable to you, not only to stop you from committing such crimes every time you get a chance, but also to deter anyone else who thinks he can do likewise and get away with it.

I am going to depart upward from the guideline range not as far as the government would have me, but it is intended to send a message to you. It is my opinion that Criminal History Category II underrepresents the seriousness of your criminal history and the likelihood of recidivism such that an upward departure pursuant to Guideline Section 4A1.3 is warranted and, therefore, I am going to apply one.

The court sentenced Bailey to eighty-seven months of imprisonment.

Bailey challenges both procedural and substantive

aspects of his sentence. Procedurally, he contends that the

district court misapplied U.S.S.G. § 4A1.3, failed to adequately

explain its chosen sentence or file a sufficient written statement

of reasons, and relied on erroneous facts and irrelevant

information. Substantively, he asserts that the sentence was too

harsh because the court did not adequately consider his mitigating

personal circumstances.

"[W]e first determine whether the sentence imposed is

procedurally reasonable and then determine whether it is

substantively reasonable." United States v. Ramirez-Ayala,

(1st Cir. 2024) (citing United States v. Reyes-Torres,

(1st Cir. 2020)). At both stages, we review

preserved claims for abuse of discretion. United States v. Leach,

- 27 -

(1st Cir. 2023). Under that rubric, "we review

the sentencing court's findings of fact for clear error and

questions of law . . . de novo." United States v.

Carrasquillo-Vilches,

(1st Cir. 2022) (citing

United States v. Rivera-Morales,

(1st Cir. 2020)).

Unpreserved claims are reviewed for plain error. United States v.

Contreras-Delgado,

(1st Cir. 2019). Virtually

none of Bailey's procedural claims are preserved. Thus, we apply

abuse of discretion review only to the preserved substantive

reasonableness claim and the claim that the district court failed

to file an adequate written statement of reasons. See United

States v. Fletcher,

(1st Cir. 2022).

I. Procedural Reasonableness

Bailey's first procedural contention is that the

district court improperly ordered an upward departure under

U.S.S.G. § 4A1.3 because it considered certain prior sentences

that the guideline commentary excludes from consideration.

Section 4A1.3 permits an upward departure where "the defendant's

criminal history category substantially under-represents the

seriousness of the defendant's criminal history or the likelihood

that the defendant will commit other crimes." Id. § 4A1.3(a)(1).

The guidelines do not count certain prior sentences in figuring

criminal history because of their age. Id. § 4A1.2(e). The

guideline commentary states, however, that a court may consider a

- 28 - sentence too old to factor into the criminal history calculation

to fashion an upward departure under § 4A1.3 if the earlier

sentence "is evidence of similar, or serious dissimilar, criminal

conduct." Id. § 4A1.2, cmt. 8.

Bailey contends that, in applying § 4A1.3, the district

court did not comply with U.S.S.G. § 4A1.2, commentary note 8

because it relied on "outdated convictions for minor, dissimilar

misconduct." In particular, Bailey says that the court erroneously

relied on old sentences for "crimes such as trespass and disorderly

conduct" to impose the departure. He argues that these crimes are

neither serious nor like the charged offense.

While he objected generally to the district court's

imposition of an upward departure based on his prior convictions,

Bailey never asserted below that the court had to analyze his

criminal record on a sentence-by-sentence basis. United States v.

Reyes-Correa,

(1st Cir. 2023) (stating that to

preserve an argument for appeal, the argument presented below must

"be sufficiently specific to call the district court's attention

to the asserted error" (quoting United States v. Soto-Soto,

, 448 n.1 (1st Cir. 2017))). We thus apply plain error

review.

There was no plain error for several reasons. We have

held that there is no requirement that a district court, in

imposing an upward departure under § 4A1.3, make specific findings

- 29 - about which of the prior convictions represent "similar, or serious

dissimilar, criminal conduct" so long as the court relies on

"reliable information" in making those determinations. See United

States v. Footman,

(1st Cir. 2000). Here, the

district court did point to obvious similar conduct when it

referenced Bailey's first federal conviction for being a

felon-in-possession of a firearm. There was also nothing plainly

wrong with the court viewing many of Bailey's other prior sentences

as arising from serious, dissimilar conduct, including (1) an

assault in which Bailey broke the victim's nose; (2) lewd and

lascivious conduct in which Bailey exposed himself to a woman,

stating "[d]o you want it baby?"; (3) possession of stolen property

in which Bailey possessed over $100,000 in property obtained from

sixteen burglaries; and (4) stalking where Bailey violated an abuse

prevention order.

Finally, Bailey has not shown that he was likely to

receive a lower sentence if the district court had excluded from

consideration his sentences for offenses such as trespass and

disorderly conduct. See United States v. McCullock,

(1st Cir. 2021). Given the length of his record and the court's

stated objectives of public protection and deterrence, there is no

basis to think that removing from consideration a few of Bailey's

many prior convictions would have changed the court's bottom-line

- 30 - conclusion that an "upward departure" was warranted to reflect his

"horrific record."

Bailey's next procedural contention is that the district

court's departure explanation was inadequate in two respects.

First, he suggests that the impact of his mental health conditions

was the thrust of his argument minimizing the seriousness of his

record and, accordingly, it was incumbent on the district court to

address his mental health specifically in its departure

explanation. We disagree. Bailey did not contend at the

sentencing hearing that his mental health conditions explained his

prior criminal conduct; rather, he argued that the government had

overstated the seriousness of his record because of the allegedly

trivial nature of many of the offenses.6 Thus, Bailey criticizes

the court for failing to address an argument he did not develop.

Moreover, at the sentencing hearing, when Bailey

discussed his personal mitigating circumstances as they related to

the present offense, he focused mostly on his substance abuse

problem, not his mental health conditions. He described how the

pain medications he received for his head injuries had led him to

6 In his sentencing memorandum, Bailey asserted that "[h]is lengthy criminal history reflects both his age and [his] struggles [with mental illness and substance abuse]." He offered no explanation as to how his mental health conditions contextualized any specific prior conviction, his criminal history as a whole, or his risk of recidivism, nor, as discussed above, did he argue as much at the sentencing hearing.

- 31 - become a "raging drug abuser," which resulted in the pending case.

The district court addressed Bailey's drug abuse during its

sentencing explanation, acknowledging that it was something that

Bailey was "going to have to work on [for] the rest of [his] life,"

but was not an excuse for his poor record. The court did not err

in declining to give Bailey's drug use the weight he hoped in

evaluating his criminal history. See United States v. Colcord,

(1st Cir. 2024) ("While [the defendant] surely would

want the district court to give greater weight to his personal

mitigating circumstances, the district court was entirely within

its discretion to find that these mitigating factors were

outweighed by the seriousness of the offense, [the defendant's]

criminal history, and the need to protect the public." (citing

Gall v. United States,

(2007))).

Bailey also criticizes the district court for not

providing a sufficiently comprehensive explanation for the extent

of the upward departure. Specifically, he says that the court

failed to follow U.S.S.G. § 4A1.3(a)(4)(A), which requires the

court to identify the criminal history category that "most closely

resembles that of the defendant's."

The government sought a departure to criminal history

category V. The district court indicated that it was not going to

depart "as far as the government" requested and then imposed an

eighty-seven-month sentence, which is the high-end sentence for an

- 32 - offense level of 23 (Bailey's offense level) and a criminal history

category of IV. We think it is sufficiently clear for purposes of

plain error review that the court sentenced Bailey pursuant to a

criminal history category IV, since that category is one level

below the government's request and contains the precise sentence

imposed.

Moreover, Bailey has not shown that the district court

would impose a lower sentence if the case were remanded. The court

explained that its eighty-seven-month sentence was based on the

need to protect the public and promote specific and general

deterrence, which would be sufficient reasons for imposing an

upward variance under

(a) (instead of an upward

departure under U.S.S.G. § 4A1.3) based on Bailey's poor criminal

history. See United States v. Aponte-Vellón,

(1st

Cir. 2014) ("[A]ny error in a departure is harmless where the

district court would have imposed the same sentence as a

variance. . . ."); see also United States v. Laboy-Nadal,

(1st Cir. 2021) (concluding that procedural error under

§ 4A1.3 was harmless where "court would have arrived at the same

sentence had it done so under the name of a variance").7

7 Bailey also alleges that the brief written statement of reasons for the departure provided by the district court after sentencing lacks the level of detail required by U.S.S.G. § 4A1.3(c)(1). The court, however, provided a thorough oral statement of reasons for the departure, and we think it clear that the court would have imposed the same sentence had it provided a

- 33 - Bailey further contends that the case should be remanded

for resentencing because the district court mentioned that the

presentence report identified forty other arrests in addition to

thirty-eight prior convictions. See U.S.S.G. § 4A1.3, ("A prior

arrest record itself shall not be considered for purposes of an

upward departure under this policy statement."). We disagree.

A district court errs when it "relies on an arrest

report, without some greater indicia of reliability that the

conduct underlying the arrest took place" and when it "equate[s]

arrest with guilt." United States v. Marrero-Pérez,

(1st Cir. 2019). However, while arrests cannot be considered

as aggravating sentencing factors, "sentencing courts are not

prohibited from simply recounting a defendant's arrest history

. . . ." United States v. Diaz-Serrano,

(1st Cir.

2023) (quoting United States v. Santa-Soler,

(1st

Cir. 2021)).

The government concedes that the district court should

have refrained from mentioning Bailey's arrest record when

discussing the U.S.S.G. § 4A1.3 departure. Nevertheless, unlike

in Marrero-Pérez, the court did not "equate [Bailey's] arrest[s]

with guilt."

. Furthermore, it is apparent that

more robust written statement. See Fletcher,

. Thus, any procedural error resulting from this claimed technical deficiency is harmless. See

- 34 - Bailey's convictions, not his arrest record, motivated the

decision to depart. The court's reference to Bailey's arrest

record was provided during a summary of the presentence report

section describing his criminal history. See United States v.

Miranda-Díaz,

(1st Cir. 2019) ("[N]othing in our

precedents forbids a sentencing court's mere mention of the

undisputed facts surrounding a dismissed charge as part of a

broader assessment of the defendant's troubling trajectory

regarding his serial encounters with the criminal justice

system."). The court relied primarily on a long list of

convictions to support its conclusion that Bailey had a "horrific

record." Because the court did not base its departure decision on

the defendant's arrest record, any error in mentioning his arrests

did not affect his substantial rights. See

.

Bailey's final procedural claims pertain to the district

court's alleged misapprehension of facts in fashioning Bailey's

sentence. He contends first that the court misunderstood the

number of women who had obtained restraining orders against him.

To support this argument, he points to the transcription of the

government's sentencing argument, which includes a line stating

that "from 2004 to 2021, about 20 multiple women have received a

restraining order against the defendant."8 Bailey, citing the

8 The government notes that this may have been a transcription error, as there are other similar errors in the

- 35 - presentence report, says that, in truth, only four women have

secured restraining orders against him. But the district court

never mentioned twenty women; it merely said that "multiple women

ha[d] obtained restraining orders against [him]," which is an

accurate statement. If Bailey believed that the court was under

a misimpression when it referred to "multiple women," it was

incumbent on him to say so.

Second, Bailey highlights the district court's statement

that its duty in sentencing him required thinking "not only about

[Bailey]" but also "the victims of [Bailey's] crime" and "the

necessity to deter anybody else from doing crimes of a similar

nature." Bailey argues this was a clear error because "[t]here

was no victim in this offense." But the court's statement was a

prefatory remark to the subsequent sentencing explanation that

focused on the "seriousness of [Bailey's] criminal history," "the

likelihood of recidivism," and the need for public protection and

deterrence. There is no reason to believe that this isolated

reference to "victims" affected the sentencing decision.

II. Substantive Reasonableness

Finally, we reach Bailey's substantive reasonableness

challenge, which we review for an abuse of discretion. A sentence

is substantively reasonable so long as there is "a plausible

sentencing hearing transcript. We take no view of this explanation, as our conclusion is based on other reasoning.

- 36 - sentencing rationale and a defensible result." United States v.

Morales-Veléz,

(1st Cir. 2024) (quoting United

States v. Rodríguez-Cruz,

(1st Cir. 2021)).

The district court thoroughly explained that Bailey's

criminal history score did not accurately capture the seriousness

of his criminal history and his likelihood of recidivism. Given

his persistent criminality and that the present case involved an

assault rifle, the court acted within reason when it determined

that the nature of the offense, public protection, and deterrence

warranted an above-guideline sentence of eighty-seven months. To

be sure, Bailey suffers from addiction and mental health

conditions, but those factors do not undermine the reasonableness

of the district court's assessment that he had a "horrific record"

worthy of additional punishment. Nor do they exclude the sentence

imposed from the "universe of reasonable sentencing outcomes."

United States v. Clogston,

(1st Cir. 2011)

(citing United States v. Martin,

(1st Cir. 2008)).

CONCLUSION

Bailey's appellate counsel ably scoured the record for

potential errors. But none of the alleged errors warrant relief.

Bailey is a repeat offender who was trafficking in dangerous

firearms. An eighty-seven-month sentence is a reasonable outcome

resulting from a fair proceeding. We affirm the judgment.

- 37 -