United States Court of Appeals

For the First Circuit

No. 22-1883

UNITED STATES,

Appellee,

v.

NATHAN REARDON,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF MAINE

[Hon. Lance E. Walker, U.S. District Judge]

Before

Kayatta, Thompson, and Rikelman,

Circuit Judges.

Hunter J. Tzovarras for appellant.

Benjamin M. Block, Assistant United States Attorney, with 

whom Darcie N. McElwee, United States Attorney, was on brief, for 

appellee.

May 23, 2024
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RIKELMAN, Circuit Judge. After pleading guilty to bank 

fraud, Nathan Reardon was sentenced to twenty months of 

imprisonment followed by three years of supervised release. As 

part of its sentence, the district court imposed a special 

condition that prohibits Reardon from all forms of self-employment 

during his supervised release term. Reardon -- concerned about

how he would support his family given that he was self-employed 

for the twenty-four years prior to sentencing -- challenges this

special condition on appeal. Because the district court imposed 

this ban without an explanation for why it was the minimum

restriction necessary to protect the public, as required by the 

U.S. Sentencing Guidelines, and we cannot infer from the record 

that the court engaged in this analysis, we vacate the ban and 

remand for reconsideration of the scope of that restriction.

I. BACKGROUND

A. The Paycheck Protection Program

We begin with the critical facts that led to Reardon's 

guilty plea. In March 2020, Congress enacted emergency financial 

assistance programs to ameliorate the economic fallout of the 

COVID-19 pandemic. See Coronavirus Aid, Relief, and Economic 

Security Act, Pub. L. No. 116-136, 134 Stat. 281 (2020) (codified 

as amended at 15 U.S.C. § 636(a)(36)). One such program, the 

Paycheck Protection Program (the "PPP"), facilitated loans to 

small businesses so that the businesses could continue to operate 
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and pay their workers during the economic downturn. See 15 U.S.C. 

§ 636(a)(36)(F)(i). PPP loans could be used only for certain 

expenses, such as payroll costs, mortgage or rent payments, and 

utility payments. See id. The maximum permitted loan amount could 

not exceed 2.5 times a business's average monthly payroll costs. 

See id. § 636(a)(36)(E). Although the loans were issued by private 

lenders, they were guaranteed by the federal government and could 

be forgiven if a business used the funds to cover its payroll costs 

and other specified expenses. See id. §§ 636(a)(36)(B), 636m(b). 

To obtain a PPP loan, a business was required to make 

several good-faith certifications, including that: it "ha[d]

employees for whom [it] paid salaries and payroll taxes"; it would 

use the funds "to retain workers and maintain payroll or other 

covered expenses," including rent, utility, and mortgage interest

payments; and the information provided in the loan application and 

supporting documents was "true and accurate." 

B. Reardon's Fraudulent PPP Loan Applications1

Between April and May of 2020, Reardon submitted to TD 

Bank four fraudulent PPP loan applications, each seeking $59,145,

on behalf of several of his businesses. Two of the applications 

sought loans for Global Disruptive Technologies, Inc. ("GDT"), and 

1 Because Reardon pleaded guilty, we draw these facts from 

the transcript of the sentencing hearing and undisputed portions 

of the revised presentence investigation report. See United States

v. Benoit, 975 F.3d 20, 21 (1st Cir. 2020).
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the other two concerned Choice Auto Sales Group, LLC and Membership 

Holdings, Inc. In each company's application, Reardon reported 

inflated payroll amounts,2 submitted documentation that 

misrepresented the true amounts, and certified that any PPP funds 

would be used to retain workers, maintain payroll costs, or cover 

other eligible expenses. TD Bank approved the first of the two 

GDT applications and denied the remaining applications. 

Reardon then spent the GDT loan funds on expenses that 

were not permissible under the PPP. In March 2021, he applied for 

forgiveness of the GDT loan, falsely certifying that he had used 

the funds for permissible purposes and that his initial loan 

application was true and accurate. TD Bank denied Reardon's

request for forgiveness of the GDT loan.

C. Procedural History

In May 2021, Reardon was indicted on five counts of bank 

fraud, three counts of attempted wire fraud, two counts of making 

false statements to a bank, and one count of perjury. He was 

released pending trial on certain conditions, one of which 

prohibited him from "apply[ing] for any pandemic-related financial 

2 Reardon certified $23,658 as each company's average monthly 

payroll costs during the first quarter of 2020. (The total he 

sought in each loan application, $59,145, is 2.5 times that 

amount.) However, GDT employees were actually paid only $1,353.18 

over the first three months of 2020, and Choice Auto Sales Group 

and Membership Holdings had no payroll costs at all, as they had 

no employees at the time.
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assistance without prior approval of the supervising [probation] 

officer." In April 2022, the district court revoked Reardon's 

pretrial release after it learned that he submitted eleven

unauthorized applications for pandemic-related financial 

assistance on behalf of one of his companies. The probation 

officer noted that the company in question, Ultimate Property 

Holdings, had no authority to do business in Maine at the time but 

did not suggest that any other aspect of these applications was 

misleading.3 In July 2022, pursuant to a plea agreement, Reardon 

pleaded guilty to the five counts of bank fraud.4 

Before sentencing, the probation officer prepared a 

revised presentence investigation report ("PSR") in which she

detailed Reardon's employment history. The probation officer

noted that Reardon had "been self-employed for 24 years"; had owned 

and operated various businesses; and, in 2020, "entered 

lease-to-own agreements for three apartment buildings" in Maine

(which, according to Reardon, were his only business ventures

operating at the time).

3 The probation officer did state, however, that Reardon had 

used $125 of the fraudulently acquired PPP funds to create Ultimate 

Property Holdings in April 2020.

4 At the sentencing hearing and consistent with the plea 

agreement, the government dismissed the remaining charges for 

attempted wire fraud, making false statements, and perjury.
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As part of Reardon's term of supervised release, the 

probation officer recommended that the district court impose 

several special conditions, including the following (special 

condition six): 

Defendant shall not be self-employed and shall 

be continuously employed for compensation by 

a disinterested third party. Defendant shall 

not open any businesses, sole proprietorships, 

partnerships, limited partnerships, or 

corporations. Defendant shall dissolve any 

corporations and businesses that exist on the 

date of sentencing.5 

The probation officer offered the following rationale for the selfemployment ban: "[It] is based on the defendant's reported 21-

years of self-employment, during which he accrued extreme debt,

resulting in three separate applications for bankruptcy with a

combined debt of over $1,500,000, and likely led to his committing 

the instant offense. Indeed, he used his businesses to commit the 

instant offenses."

Reardon filed a written objection to the self-employment 

ban, arguing that it was "overly restrictive and unnecessary for 

the purposes of sentencing and supervised release." In response, 

the probation officer explained that the self-employment ban was 

appropriate because: 

[Reardon] reported only ever being 

self-employed which has resulted in three 

applications for bankruptcy associated with 

5 Following the parties' lead, we refer to special condition 

six as the "self-employment ban."
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businesses established by [him] as detailed in 

paragraph 65 [of the PSR] [and] the business 

involvement in the instant offense . . . . 

[Reardon] owes a significant amount in 

restitution. Prohibiting self-employment 

reduces the risk of [Reardon] engaging [in] 

criminal business practices and increases the 

likelihood of the restitution being paid in a 

timely fashion. 

In November 2022, Reardon appeared before the district 

court for sentencing and explained his objection to the proposed 

self-employment ban. His counsel argued that it was "overly 

restrictive," as "other conditions . . . could be imposed . . . 

[to] assure that he is not committing crimes and that he receives 

any services or supervision for rehabilitation appropriately." 

Defense counsel also noted: 

Mr. Reardon's been self-employed almost his 

entire career, 24 years . . . . He has a minor 

conviction, a misdemeanor . . . back in 2011 

for unpaid taxes and other than that and this 

current offense that we're here for in court, 

that occurred over approximately one month, 

Mr. Reardon has no criminal history related to 

his self-employment. He has gone years and 

years without incurring criminal conduct 

because of his self-employment, that's how he 

supported himself, that's how he supported his 

family6 really since he started working. 

And . . . over the last few months, Mr. 

Reardon has attempted to run his businesses, 

particularly the apartments that he rents in 

Dexter and Howland the best he can from jail 

6 Reardon has a wife (a homemaker) and five children (four of 

which -- according to his counsel at sentencing -- have special 

needs).
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and he's done that and [been] able to make and 

generate enough income to pay $9,000 towards 

restitution . . . .

The fact that Mr. Reardon's been able to use 

his business, the apartments, that he's rented 

over the last several months to start making 

the victim whole in this case, I think is 

significant and shows that he should be able 

to continue to run these apartments and be 

self-employed so he can continue to pay back 

the restitution that he's already started to 

pay. So for those reasons, Your Honor, we 

don't think you should restrict him from being 

self-employed during the course of supervised 

release.

The government, for its part, acknowledged that there 

could be a "middle ground," explaining that "the self-employment 

condition at least could be caveated appropriately to make sure 

that it's not a writ large prohibition against self-employment, 

but that there would be mandatory consultation with the supervising 

probation officer." The government also noted that, although the 

self-employment restriction was "a very well-founded proposed 

condition," it recognized that "an individual should be within 

certain . . . boundaries [] entitled to try to make a living." 

Finally, the government added that it was in its "best interest 

and restitution payee's best interest for Mr. Reardon to make a 

living after he serves the term of his sentence so he can pay 

restitution." 

The district court overruled Reardon's objection to the 

self-employment ban, providing the following reasoning:
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I take [the government]'s point [about a 

middle ground] . . . but under the 

circumstances, both in terms of the underlying 

conduct that brings us here today and in terms 

of the travel of this case, particularly as it 

related to Mr. Reardon's bail being revoked, 

I think the more cautious approach would 

simply be for me to adopt the proposed 

condition as it relates to self-employment and 

leave it at that. And to the extent that Mr. 

Reardon wishes to present to the Court, at a 

later date, a modification of his conditions 

of supervised release, whether it relates to 

the condition that he not be self-employed or 

any other conditions based on his success 

while on supervised release, . . . he can 

bring that to the Court in a more ordinar[y]

fashion.

Before imposing Reardon's sentence, the court stated that it was 

"adopt[ing] the revised presentence investigation report in its 

entirety as constituting [the court's] findings." The court then

sentenced Reardon to twenty months of imprisonment and three years 

of supervised release and ordered him to pay $60,316.39 in 

restitution.

For the supervised release term, the court imposed each 

of the special conditions recommended by the probation officer and 

explained that such conditions were "based on [its] findings, which 

[were] co-extensive with the four corners of the revised . . . 

PSR." The seven special conditions included, along with the 

self-employment ban, requirements that Reardon "provide the 

supervising [probation] officer any requested financial 

information" and "participate and comply with the requirements of 
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the Computer and Internet Monitoring Program (which may include 

partial or full restriction of computer(s), internet/intranet, 

and/or internet-capable devices), and . . . submit to periodic or 

random announced searches of his . . . computer(s) . . . and/or 

other electronic or internet-capable devices(s)."

Reardon timely appealed.

II. DISCUSSION

Reardon challenges the self-employment ban as an 

unnecessary and overbroad special condition of supervised release. 

Because Reardon preserved his challenge below, we review the 

district court's imposition of the ban for abuse of discretion. 

See United States v. Windle, 35 F.4th 62, 67 (1st Cir. 2022). 

Under this flexible standard, we evaluate "fact findings for clear 

error, legal issues de novo . . ., and judgment calls with some 

deference." United States v. McCullock, 991 F.3d 313, 317 (1st 

Cir. 2021). 

A. Special Conditions of Supervised Release

We have not previously analyzed when a court can restrict

self-employment during supervised release. Because there are 

specific statutory requirements for imposing occupational 

restrictions, we begin with a review of those requirements. 

All special conditions of supervised release must meet 

a threshold standard. They must be "based on the circumstances of 

the offense and the defendant's history" and "'involve[] no greater 
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deprivation of liberty than is reasonably necessary' to achieve 

the goals of sentencing, such as" protection of the public,

deterrence, and rehabilitation. United States v. Benoit, 975 F.3d 

20, 26 (1st Cir. 2020) (quoting 18 U.S.C. § 3583(d)); see U.S. 

Sent'g Guidelines Manual ("U.S.S.G.") § 5D1.3(b) (providing that 

district court may impose discretionary conditions of supervised

release); 18 U.S.C. § 3553(a)(2) (listing the goals of 

sentencing). 

Occupational restrictions, however, require even more. 

In recognition of the impact such restrictions can have on 

individuals' ability to re-enter society after imprisonment, 

occupational restrictions are subject to a heightened standard. 

See United States v. Vélez-Luciano, 814 F.3d 553, 562 (1st Cir. 

2016) (noting that courts must apply "the more-stringent U.S.S.G. 

§ 5F1.5 standard" when imposing occupational restrictions); United 

States v. Prochner, 417 F.3d 54, 65 (1st Cir. 2005) ("[A]n 

occupational restriction [is] subject to the specific limitations 

of 18 U.S.C. § 3563(b)(5) and U.S.S.G. § 5F1.5."). Thus, a court 

may impose such a restriction "only if" it determines that: "(1) 

a reasonably direct relationship existed between the defendant's 

occupation, business, or profession and the conduct relevant to 

the offense of conviction"; and "(2) . . . such a restriction is 

reasonably necessary to protect the public because there is reason 

to believe that, absent such restriction, the defendant will 
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continue to engage in" similar unlawful conduct. U.S.S.G. 

§ 5F1.5(a); see also 18 U.S.C. § 3563(b)(5) (permitting

occupational restrictions to the extent they are reasonably 

related to the § 3553(a)(1) and (a)(2) factors and "involve only 

such deprivations of liberty or property as are reasonably 

necessary for the purposes indicated in section 3553(a)(2)").

Further, if all the requirements for an occupational 

restriction are met and the district court decides to impose such 

a restriction, the Sentencing Guidelines limit its scope: the court

"shall impose the [restriction] for the minimum time and to the 

minimum extent necessary to protect the public." U.S.S.G.

§ 5F1.5(b) (emphases added); see, e.g., United States v. Mills, 

959 F.2d 516, 519–20 (5th Cir. 1992) (upholding portion of 

condition that prohibited defendant, who was convicted of 

manipulating odometers, from participating in sale of cars but 

rejecting other portion that required him to sell car dealership 

as "not the minimum condition reasonably necessary to protect the 

public"). This standard aims to "preclude the [defendant's] 

continuation or repetition of illegal activities while avoiding a 

bar from employment that exceeds [the scope] needed to achieve 

that result." U.S.S.G. § 5F1.5 cmt. background (quoting S. Rep. 

No. 225, at 96-97 (1983), as reprinted in 1984 U.S.C.C.A.N. 3182, 

3279-80). 
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As with any special condition of supervised release, a 

sentencing court should provide a "reasoned and case-specific 

explanation" for an occupational restriction and its scope. United 

States v. Pabon, 819 F.3d 26, 30 (1st Cir. 2016) (citation 

omitted); see 18 U.S.C. § 3553(c) ("The court, at the time of 

sentencing, shall state in open court the reasons for its 

imposition of the particular sentence . . . ."). When a court 

does not provide such an explanation, we may infer its reasoning 

"by comparing what was argued . . . [or what was] in the 

pre-sentence report with what the judge did." United States v. 

Colón-Cordero, 91 F.4th 41, 53 (1st Cir. 2024) (quoting United 

States v. Carrasquillo-Sánchez, 9 F.4th 56, 62 (1st Cir. 2021)).

Still, "'there are limits' to our willingness to supply our own 

justification for a particular [condition]." United States v. 

Perazza-Mercado, 553 F.3d 65, 75 (1st Cir. 2009) (quoting United 

States v. Gilman, 478 F.3d 440, 446 (1st Cir. 2007)); cf.

Colón-Cordero, 91 F.4th at 54 (acknowledging "different ways a 

ghost gun being in the factual mix . . . could affect" sentencing 

court's decision to impose a variance but declining to speculate 

"which reasons -- if any -- were actually what the sentencing court 

had in mind when pronouncing sentence" because "the court didn't 

say"). 

When we cannot readily discern from the record the 

district court's reasoning, "'it is incumbent upon us to vacate, 
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though not necessarily to reverse' the decision below to provide 

the district court an opportunity to explain its reasoning at 

resentencing." Gilman, 478 F.3d at 446–47 (citation omitted) 

(quoting United States v. Feliz, 453 F.3d 33, 36 (1st Cir. 2006)); 

see, e.g., Perazza-Mercado, 553 F.3d at 76, 79 (vacating special 

condition and remanding where district court did not adequately 

explain, and record did not support, the condition). We are 

especially inclined to vacate and remand when a district court 

does not engage with one of the defendant's primary, nonfrivolous 

arguments at sentencing. See Colón-Cordero, 91 F.4th at 55-56; 

cf. Rita v. United States, 551 U.S. 338, 357 (2007) ("Where the 

defendant or prosecutor presents nonfrivolous reasons for imposing 

a . . . sentence [that departs from the Sentencing 

Guidelines], . . . the judge will normally go further and explain 

why he has rejected those arguments."). 

And, depending on the sentencing decision, a court may 

need to provide a more robust explanation. See Rita, 551 U.S. at

356 ("The appropriateness of brevity or length, conciseness or 

detail, when to write, what to say, depends upon circumstances."). 

For example, a sentence that falls outside the range recommended 

by the Sentencing Guidelines requires more explanation than a 

sentence within the range, and the greater the deviation from that 

range, the greater the justification required. See Colón-Cordero, 

91 F.4th at 51. Similarly, the more restrictive a special 
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condition of supervised release, the greater the justification 

required. See, e.g., United States v. Del Valle-Cruz, 785 F.3d 

48, 62 (1st Cir. 2015) (explaining that condition impairing 

defendant's relationship with his child "require[d] a greater 

justification" because it "involve[d] a very significant 

deprivation of liberty"); see also United States v. Boyd, 5 F.4th 

550, 557 (4th Cir. 2021) ("[A]s a general matter, the more onerous 

the term of supervised release -- whether due to its duration or 

to the rigor of its conditions -- 'the greater the justification 

required.'" (citation omitted)). Given the heightened standard 

for occupational restrictions, it is especially important for 

district courts to provide sufficient explanation for the scope of 

such restrictions.

With this framework in mind, we turn to Reardon's 

challenge to the self-employment ban. We address the validity of 

such a ban only in the narrow set of circumstances before us.

B. The District Court's Imposition of a Self-Employment Ban

Reardon contends that the self-employment ban is not

reasonably related to his offense conduct because it broadly 

prohibits any type of self-employment rather than targeting a 

particular occupation, is more restrictive than necessary to 

achieve the purposes of supervised release, and is unnecessary to 
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protect the public.7 He also argues that the district court 

"offered no explanation" suggesting otherwise. The government 

disagrees and emphasizes that, even if "the district court's

commentary was deficient," the court's reasoning for the 

self-employment ban is evident from the record. Additionally, the 

government highlights the possibility that the self-employment ban 

could be modified at some point during Reardon's supervised 

release, as the district court alluded to at sentencing.

As we noted above, we have not previously considered

when a district court may impose a self-employment ban during 

supervised release. And there are few published decisions on point 

from our sister circuits. See, e.g., United States v. Ferguson, 

537 F. App'x 713, 716 (9th Cir. 2013) (unpublished) (finding no 

abuse of discretion where sentencing court imposed self-employment 

ban based on "concern that defendant is an economic danger to the 

community" and could repeat his fraud scheme if his business 

conduct was not supervised); United States v. Heaser, 298 F. App'x 

7 Reardon argues in his opening brief that the self-employment 

ban is "unnecessary for the purposes of sentencing" but presents 

a narrower argument in his reply brief that the ban is "unnecessary 

to protect the public." Because he has not developed his argument 

as to how the self-employment ban is unnecessary to achieve the 

goals of sentencing other than protection of the public, such as 

deterrence and rehabilitation, we do not consider here whether the 

ban "involves [a] greater deprivation of liberty than is reasonably 

necessary" to achieve those other goals. 18 U.S.C. § 3583(d)(2). 

Our inquiry instead focuses on whether the imposition of the selfemployment ban satisfies the heightened requirements of U.S.S.G. 

§ 5F1.5. 
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502, 504-05 (7th Cir. 2008) (unpublished) (upholding on plain error 

review "conditions prohibiting [the defendant] from working for 

himself or an immediate relative" because he "used his 'self 

employment' to conceal from the probation officer purchases with 

funds that should have gone to [the] victims [of his mail fraud] 

and could easily use a business under the name of his wife or a 

close family member to do the same"). Thus, we focus on the plain 

text of section 5F1.5 in evaluating the ban. 

To review, to impose a restriction on self-employment,

the district court was required to find that: (1) "a reasonably 

direct relationship existed between" Reardon's self-employment and 

his offense conduct (i.e., his bank fraud); (2) "there [was] reason 

to believe that, absent such restriction, [Reardon would] continue 

to engage in" similar unlawful conduct, and, therefore, the 

"restriction [was] reasonably necessary to protect the public"; 

and (3) the scope of the restriction was "the minimum extent

necessary to protect the public." U.S.S.G. § 5F1.5(a)-(b). We 

consider whether the record allows us to evaluate the district 

court's analysis for all three requirements, and, if so, whether 

the total ban satisfies all three requirements. 

As we explain in greater detail below, the district court 

did not discuss section 5F1.5(b) or the "minimum extent necessary"

standard, and there is no mention of section 5F1.5(b) or its 

substantive requirements in the PSR. Thus, although we can well 
- 18 -

understand why the district court exercised its discretion to 

impose an occupational restriction here, we cannot be sure on this 

record that an analysis of whether a complete self-employment ban 

was the minimum restriction necessary was ever undertaken. 

Instead, the record suggests that the focus below was on crafting 

a broad restriction as a precautionary measure. We therefore 

vacate and remand for resentencing on this special condition.

1. Whether a "Reasonably Direct Relationship"

Existed Between Reardon's Self-Employment and 

Offense Conduct and a Self-Employment Ban 

Would Be Reasonably Necessary to Protect the Public

Before imposing the self-employment ban, the district 

court was required to evaluate if there was "a reasonably direct 

relationship" between Reardon's self-employment and his offense

conduct and, if so, whether the ban was necessary to protect the 

public against future unlawful conduct. See id.

§ 5F1.5(a)(1)-(2). We do not dwell on these requirements because 

we remand for re-evaluation of the scope of the restriction here. 

But we observe that the record certainly would support a finding 

that an occupational restriction was warranted. The PSR detailed 

how Reardon leveraged three of his businesses to submit four

fraudulent PPP loan applications and, after one application was 

approved, misused the loan funds and fraudulently sought 

forgiveness on the loan. These facts demonstrate, as the probation 

officer concluded in the PSR, that Reardon "used his businesses to 
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commit the instant offenses." Because Reardon's fraudulent 

conduct was inextricably tied to his ownership of several 

businesses, the district court could find that "a reasonably direct 

relationship existed between" Reardon's offense conduct and his

occupation as an owner of these businesses. U.S.S.G. 

§ 5F1.5(a)(1); see also United States v. Turner, 88 F. App'x 307,

314 (10th Cir. 2004) (unpublished) (finding reasonably direct 

relationship between defendant's bank fraud and restricting his 

self-employment as a roofer because he used his roofing business 

to facilitate the fraud and, after initial sentence, failed to 

provide information about his business activities to probation 

officer).

Reardon's reliance on United States v. Farmer, 755 F.3d 

849 (7th Cir. 2014), where the connection between the occupational

restriction and the offense conduct was far more tenuous, is

therefore misplaced. In Farmer, the district court imposed a 

self-employment ban on a defendant who attempted to extort a casino 

employee with "information from a golfing and gambling companion."

755 F.3d at 850-51. The U.S. Court of Appeals for the Seventh 

Circuit vacated the condition because "[t]he district court did 

not determine that [the defendant]'s activities as a self-employed 

entrepreneur caused him to attempt to extort [the victim]" and 

"focused instead on its belief that [the defendant]'s lack of 

success as an entrepreneur was causing him to turn to con 
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activities to fund himself." Id. at 855. Here, as we have just 

explained, Reardon's status as a business owner was central to and 

inseparable from his bank fraud. Thus, the district court could 

have found there was "reason to believe" that Reardon would engage 

in similar unlawful conduct if he were not subject to some

restriction on his occupation during supervised release. See

U.S.S.G. § 5F1.5(a)(2).

2. Whether the Self-Employment Ban Was the

Minimum Restriction Necessary to Protect the Public

The record is silent, however, as to whether the district 

court determined that the ban was the minimum restriction necessary 

to protect the public, as section 5F1.5(b) requires. The 

government and the dissent suggest that we can infer the analysis 

occurred and affirm, but we disagree for three reasons. First, 

the district court never mentioned the substantive requirements of 

section 5F1.5(b). Second, we cannot infer the court's reasoning 

from the parties' arguments at sentencing or the PSR, as the 

government conceded that a narrower restriction would be 

reasonable and the PSR never cited section 5F1.5(b), discussed the 

heightened standard for occupational restrictions, or otherwise

grappled with whether a total self-employment ban was the "minimum" 

restriction necessary. To the contrary, the record suggests that 

the probation officer urged the broadest possible restriction as 

a precautionary measure. Finally, the government points to the 
- 21 -

possibility that the district court may in the future 

modify -- and, in doing so, more narrowly tailor -- the 

self-employment ban, but that fact has no bearing on the validity 

of the ban as it stands now. 

To begin, the district court did not discuss section 

5F1.5(b) or otherwise analyze why this broad ban was the "minimum" 

restriction necessary. Notably, although the court offered some 

reasoning for the ban, it did not explain its rationale for 

imposing a restriction that prohibited Reardon not only from owning 

any business but also from engaging in any form of self-employment.

For instance, Reardon specifically highlighted at the sentencing 

hearing his ability to earn rental income from apartments he 

managed under a lease-to-own arrangement and how he had used the 

income to begin his restitution payments.8 It appears that the 

ban would prohibit even this limited form of self-employment. The 

only explanation by the court for declining to narrow the ban was 

that it believed a complete ban would be "the more cautious 

approach," considering Reardon's offense conduct and pretrial 

release violation.

But the pretrial release condition that Reardon violated 

was not an occupational restriction. Instead, it was a limitation

8 The dissent briefly acknowledges this argument by Reardon 

in its discussion of the options proposed to the district court, 

see Dissent at 29, but, unlike us, equates this option with no 

self-employment restriction at all. 
- 22 -

on applying for pandemic-related aid without prior approval from 

the probation office. Although the district court was surely 

correct in taking into account Reardon's violation of the pretrial 

condition in setting his sentence, a sufficient gap exists between 

no occupational restriction and a complete ban on all forms of 

self-employment (the only type of work Reardon had engaged in for 

more than two decades) to give us pause. Given that the district 

court never mentioned the heightened requirements for occupational 

restrictions, its statement that this broad ban was the more 

"cautious approach" is not enough for us to conclude that it 

engaged in the analysis required by section 5F1.5(b) -- whether 

the total ban was the minimum restriction necessary.9

Next, having found no discussion by the district court

of section 5F1.5(b)'s requirements, we turn to whether the record 

permits us to infer the court's reasoning on this score. The 

government, notably, did not argue that the self-employment ban

was necessary and instead suggested a "middle ground" in which the 

9 The dissent suggests that, because Reardon used one of his 

businesses to skirt the restrictions of his pretrial release, it 

was reasonable for the district court to adopt a more cautious 

approach going forward. See Dissent at 30-31. We in no way 

question the district court's caution and agree that it was 

entirely reasonable. But a more cautious approach does not mandate 

an all-out ban. The court's well-supported decision to take into 

account Reardon's pretrial release violation in crafting his 

sentence does not change the fact that there is no consideration 

in the record of whether this complete ban was "the minimum

[restriction] necessary to protect the public," as section 

5F1.5(b) instructs. 
- 23 -

"condition at least could be caveated appropriately to . . . 

[avoid] a writ large prohibition against self-employment." Thus, 

the government's statements at the sentencing hearing offer no 

support for why the total ban was the minimum restriction 

necessary.10 Additionally, the PSR suggested that the restriction

was "appropriate" because "[p]rohibiting self-employment reduces 

the risk of [Reardon] engaging [in] criminal business practices 

and increases the likelihood of the restitution being paid in a 

timely fashion." But this rationale only goes to the point that 

the ban would protect the public; it does not support a finding 

that the total ban is the minimum restriction necessary to do so. 

Those are two entirely separate inquiries, and there is no evidence

the second inquiry was ever conducted here. Indeed, the PSR does 

not reference section 5F1.5(b), and there is no other indication 

that the probation officer considered its requirements.

The government maintains that the court's reasoning for 

the total self-employment ban is evident from the record, as "the 

10 The dissent maintains that the district court's decision 

to reject the government's alternative cannot be an abuse of 

discretion on this record. See Dissent at 30-31. Again, we agree 

that the district court was well within its discretion to conclude 

that a stricter approach was necessary. But section 5F1.5(b) 

requires, without exception or reservation, that the court 

restrict a defendant's occupation to the "minimum extent necessary 

to protect the public." U.S.S.G. § 5F1.5(b) (emphasis added). 

The record only indicates why something more than the pretrial 

release conditions was needed here; it does not explain why this 

total ban is the minimum restriction that would suffice, which is 

a separate inquiry.
- 24 -

court's sentencing comments as a whole suggest a substantial 

concern regarding Reardon's risk of recidivism and the need to 

protect the public from that possibility." For example, the 

government explains, when the court set forth its "key findings 

regarding the nature and circumstances of the offense," it 

characterized Reardon's offense as "a fundamental breach of the 

public trust at a time of a public emergency." It also expressed 

the need for the sentence "to deter [Reardon] from committing 

future crimes," suggesting that Reardon's violation of his 

pretrial release conditions called into question his ability to 

"maintain a law-abiding lifestyle." These statements support a

conclusion that Reardon might reoffend and, therefore, some

occupational restriction would be reasonably necessary to protect 

the public. But, again, they do not explain why such a broad ban 

was the minimum restriction that would do. 

Finally, we cannot conclude, as the government suggests,

that the district court's reminder that Reardon is free to file a 

motion to modify the conditions of supervised release after he 

finishes his prison term explains this broad ban. "[I]n light of 

[Reardon's] offenses," the government adds, "the requirement that 

he be subject to oversight in his employment while on supervised 

release is proportionate and reasonable." But the self-employment 

restriction as it stands now does not provide "oversight" of 

Reardon's employment. Unlike those conditions that "simply 
- 25 -

require preapproval from probation" or the court, the restriction 

here is "a flat ban." McCullock, 991 F.3d at 322. That the 

district court may ultimately modify the ban to permit selfemployment with such oversight has no bearing on whether the 

current ban satisfies the statutory requirements. As we have 

previously pointed out, "[t]o approve problematic conditions 

because a judge or a probation officer might, in her or his 

discretion, relax them in the future, undermines the command to 

sentencing courts to not deprive offenders of more liberty than is 

necessary to carry out the goals of supervised release." United 

States v. Ramos, 763 F.3d 45, 61 (1st Cir. 2014).

The government's comparison of this case to United 

States v. Carpenter, 280 F. App'x 866 (11th Cir. 2008) is therefore 

inapt. The condition in Carpenter permitted the defendant to enter 

into self-employment with "prior written permission of the court." 

280 F. App'x at 867. The condition did not, as is the case here, 

categorically prohibit the defendant from self-employment. See

id. at 870 (concluding that condition requiring defendant to obtain 

approval for future self-employment "involve[d] no great 

deprivation of liberty because [the defendant could] obtain court 

approval for legitimate self-employment"); see also United States

v. Mercado, 777 F.3d 532, 539 (1st Cir. 2015) (finding it 

"[i]mportant[]" that a condition was not "an outright ban" and 

instead "merely require[d] . . . pre-approv[al] by the probation 
- 26 -

officer"). Because the total self-employment ban is not "subject 

to supervision by the probation officer," there is no "safeguard" 

permitting Reardon to "petition the district court to modify the 

condition in the event that approval has been unreasonably 

withheld." Pabon, 819 F.3d at 32; see United States v. DaSilva, 

844 F.3d 8, 14 (1st Cir. 2016) ("[G]iving the probation officer 

some authority to make exceptions as warranted is generally seen 

as a benefit of such orders in that it allows for flexibility and 

permits personal circumstances to be dealt with as they arise."); 

see also United States v. Fey, 834 F.3d 1, 6 (1st Cir. 2016) 

(upholding condition imposed without "express explanation" that 

required defendant to "seek approval from probation before 

accepting a job or volunteer activity that would bring him into 

direct contact with minors").

To wrap up our discussion, we briefly address two other 

out-of-circuit decisions that the government highlights, one of 

which is also cited by the dissent. See United States v. Choate,

101 F.3d 562, 566-67 (8th Cir. 1996) (upholding self-employment 

ban); United States v. Turner, 88 F. App'x 307, 314-15 (10th Cir. 

2004) (unpublished) (same). Critically, although Choate and 

Turner involved analogous facts, neither addressed whether the 

self-employment ban imposed was the minimum restriction necessary 

to protect the public under section 5F1.5(b). We are therefore 

not persuaded that these two cases are instructive here.
- 27 -

"A district court's duty to specifically find that [an 

occupational] restriction is minimally restrictive is 

'mandatory.'" United States v. Butler, 694 F.3d 1177, 1184 (10th 

Cir. 2012) (citation omitted); see U.S.S.G. § 5F1.5(b) ("[T]he 

court shall impose the condition for the minimum time and to the 

minimum extent necessary to protect the public." (emphasis 

added)). Further, we are obligated to evaluate if the occupational 

restriction here satisfies the statutory requirements. See

Benoit, 975 F.3d at 26. Based on this record, we cannot be certain 

that the district court considered whether the total selfemployment ban was the minimum restriction necessary and thus 

cannot evaluate its analysis for imposing the ban.

We therefore vacate the self-employment ban and remand 

to the district court for resentencing limited to a reexamination

of the scope of that restriction. See Perazza-Mercado, 553 F.3d 

at 75 ("[W]here we are unable, through our own examination of the 

record, to discern the court's reasoning, 'it is incumbent upon us 

to vacate . . . .'" (citation omitted)). To be clear, nothing in 

our decision prohibits the re-imposition of an occupational 

restriction on remand that satisfies section 5F1.5's requirements.
- 28 -

III. CONCLUSION

For these reasons, we vacate the self-employment ban 

(special condition six) and remand for resentencing limited to a 

re-examination of that condition. 

-Dissenting Opinion Follows-

 
- 29 -

KAYATTA, Circuit Judge, dissenting. I respectfully 

dissent. I would find that the district court did not abuse its 

ample discretion in adopting a supervised release condition that 

closely corresponded to the nature of Reardon's crime -- repeated 

fraud motivated by a history of failed business ventures.

The majority five-times stresses that the district court 

neither cited nor expressly applied U.S.S.G. § 5F1.5(b)'s 

requirement that an occupational restriction be minimally 

necessary to protect the public. But the majority concedes that 

we may infer the district court's reasoning "by comparing what was 

argued . . . [or what was] in the pre-sentence report with what 

the judge did." United States v. Colón-Cordero, 91 F.4th 41, 53 

(1st Cir. 2024). And on this record, we can easily infer that the 

district court concluded that the self-employment restriction was 

minimally necessary to protect the public.

The parties presented the district court with three 

alternatives: no occupational restriction at all (Reardon's 

proposal); a self-employment restriction that the Probation Office 

could modify on an ad hoc basis (the government's middle-ground 

suggestion); and a complete self-employment restriction (the 

Probation Office's proposal). As an example of potential 

self-employment in the absence of any restriction, Reardon pointed 

to managing apartment buildings that he owned. The court asked 

counsel to address these alternatives. After hearing out counsel, 
- 30 -

the court found that some form of occupational restriction was 

necessary, adopting the reasoning set forth in the pre-sentence 

report ("PSR"). Even the majority concedes that the record 

supported this conclusion. So, Reardon's proposed "no 

restriction" alternative was out.

The court also explained why a middle-ground 

alternative, such as the one proposed by the government, was also 

out. First, as the PSR noted, Reardon's self-employment risked 

the type of financial losses that had, in the past, motivated his 

fraud. A middle-ground approach that still allowed some 

self-employment would not alleviate this concern at all. Second, 

the district court noted that the "travel" of the case counseled 

against a middle-ground approach. After his first indictment, 

Reardon convinced the court to release him on bail, subject to a 

condition barring him from seeking further pandemic-related 

assistance without Probation Office approval. He then promptly 

violated that condition. He used the proceeds of his prior fraud 

to establish a Florida-based limited liability company -- which 

had no authority to conduct business in Maine -- to apply for 

pandemic-related rental assistance. Thus, the court reasonably 

concluded that giving Reardon similar leeway the second time around 

would likely endanger the public.

My colleagues appear bothered by the court's caution. 

But the district court's point was simple and obvious: Given 
- 31 -

Reardon's remarkable post-arraignment record of skirting court 

supervision and filing dubious applications for government 

assistance, a more cautious approach was necessary to protect the 

public during Reardon's supervised release. I cannot see how this 

approach was an abuse of discretion, especially when crafting a 

sentence that would have Reardon back on the street within two 

years.11

In short, the district court's reasoning justified 

rejecting the alternatives proposed by the government and by 

Reardon. That left only the self-employment ban proposed by the 

Probation Office. The district court had no obligation to consider 

additional alternatives that no one proposed. See United States

v. Choate, 101 F.3d 562, 566 (8th Cir. 1996) (affirming a broad 

ban on self-employment, while stating that "[t]he district court 

is not required to pit its imagination against [the defendant's] 

to anticipate what sort of business [the defendant] could put to 

fraudulent use"). Therefore, the Probation Office's alternative 

was -- among the options proposed -- the one that was minimally 

necessary to protect the public.

11 The majority's rejoinder that Reardon's pre-trial release 

condition was "not an occupational restriction" misses the point. 

What matters is that Reardon had a track record of flouting 

supervision while on release. Given this past behavior, the court 

reasonably found that the government's middle-ground alternative

-- which provided no standards for assessing Reardon's proposed 

exceptions to the self-employment ban -- would not sufficiently 

protect the public.
- 32 -

And even if further justification for the complete 

self-employment ban were required, the district court also 

defended the ban against Reardon's objections. For instance, 

Reardon noted that a complete self-employment ban would bar him 

from managing his apartment buildings and generating funds for 

restitution. But the PSR reasonably concluded that Reardon --

whose entrepreneurial track record was spotty at best -- was more 

likely to pay restitution in a "timely fashion" if he worked for 

a third party and earned a steady wage.

Reardon clearly had difficulties working for himself 

without a reliable wage. And he had difficulty avoiding the 

temptation to use his businesses to perpetuate fraud. So, on this 

record, the district court did not abuse its considerable 

discretion in deciding that Reardon's post-imprisonment transition 

to civil society should begin with a reliable and steady 

wage-paying job, which he would find harder to turn into an 

incentive or a vehicle for further fraud. Because the majority 

gives too little deference to the district court's reasoned 

justification for the self-employment ban, I respectfully dissent.