United States Court of Appeals

for the Fifth Circuit

No. 20-61073

United States of America, 

Plaintiff—Appellee,

versus

Jonathan Hilliam McDougal, 

Defendant—Appellant.

Appeal from the United States District Court

for the Southern District of Mississippi

USDC No. 3:15-CR-26-1

Before Jones, Southwick, and Engelhardt, Circuit Judges.

Per Curiam:*

Jonathan McDougal challenges a condition of supervised release 

imposed with his revocation sentence. Finding no error of fact or law, we 

AFFIRM.

* Pursuant to 5th Circuit Rule 47.5, the court has determined that this 

opinion should not be published and is not precedent except under the limited 

circumstances set forth in 5th Circuit Rule 47.5.4.

United States Court of Appeals

Fifth Circuit

FILED

August 11, 2021

Lyle W. Cayce

Clerk

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I. BACKGROUND

McDougal pled guilty in 2016 to one count of distribution of a 

detectable amount of cocaine base—“crack”—in violation of 18 U.S.C. § 2 

and 21 U.S.C. § 841(a)(1). The district court sentenced McDougal to 28 

months in prison and three years of supervised release. Additionally, 

McDougal was required to participate in a “program of testing and/or 

treatment for alcohol or drug abuse as directed by the probation officer.” 

Supervised release began on April 4, 2018.

In February 2020, McDougal’s probation officer petitioned the court 

for an arrest warrant. The petition alleged that McDougal violated a 

mandatory condition of his supervised release by committing a state felony. 

Specifically, it asserted that between May 1, 2018 and July 1, 2018, McDougal 

embezzled $7,924.91 belonging to the state of Mississippi. McDougal pled 

guilty in state court to the offense in November 2019 and was sentenced to 

ten years in prison and five years of supervised release.1

At the revocation hearing, McDougal admitted committing the 

offense. He explained that he used his state-issued fuel card to fuel other 

people’s cars in exchange for additional money.2 He claimed this was 

necessary to support eight children and pay outstanding debts. The money 

allegedly went towards food for his kids, child support, gas, and rent—

McDougal stated that after those expenditures, he often only had $30 to $50 

1 He was eligible for release after serving three years imprisonment. McDougal was 

subsequently released by the state on August 12, 2020 and was remanded to federal 

custody.

2 To do so, McDougal had to “cut deals” where he was only getting a portion of 

the value of the gas. For example, he would put $40 worth of fuel in another person’s 

vehicle in exchange for $20. McDougal admitted to converting the entire $7,924.91 (it was 

charged to the card) but only received $3000 to $4000 in actual cash.

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for each two-week period. McDougal’s counsel also noted that two of his 

children lived with him and that McDougal had not failed any drug tests while 

on supervised release, so “it [was] not an issue of whether or not this money 

was going towards drugs.” The district court noted that McDougal’s lack of 

proof for how he spent the money was “a negative,” and it was likely that he 

did “something else with the money.” The court recessed the hearing to 

allow the defense time to gather evidence of expenditures.

McDougal then presented two witnesses: his sister, Shama Harris, 

and one of his children, Jontaveyun Jones. Harris testified that McDougal 

had been living with her and paying for gas, food, and expenses for two of his 

children. She also saw him give money to the children’s mother and send 

money to his other children out of state. McDougal also helped pay for food 

and utilities at the house. Harris asserted that she did not know of any drug 

use by McDougal, had never heard of him using drugs, and that he had 

stopped drinking because he “didn’t like the taste of it.” Finally, Harris 

testified that McDougal had paid over $1000 in household expenses while 

living there, but she didn’t know what he did with all of the embezzled 

money. Jones testified that McDougal paid for food, clothes, and school 

sports equipment. He further stated that McDougal had given money 

directly to his mother and that he had lived with McDougal for nearly a year. 

But Jones conceded that he did not know how much McDougal had paid in 

child support or whether he was current on payments.

The district court then moved to sentencing. The court first noted 

that the embezzlement occurred less than a month after McDougal’s release 

from federal custody and that “one has to conclude that he hardly was 

rehabilitated since in less than a month’s time after being committed to 

supervised release . . . he committed a felony.” The court then explained 

that McDougal had failed to adduce evidence as to what became of the nearly 

$4000 that he received. Having received no testimony from the children’s 

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mothers, and no testimony that he attempted to satisfy his outstanding child 

support obligations, the court “heard nothing to persuade it that this 

defendant spent any significant money on his children, nor that he spent any 

significant money with his sister when he was staying there free with her and 

her husband.” The court concluded that it had no idea what McDougal did 

with the money since it found none of the testimony credible, and it was 

“troubled by the short interval between this defendant’s release from 

incarceration and his determination to reenter the realm of crime.” Finally, 

the court observed that McDougal had been “quite deep in the drug trade” 

and now “quite deep in embezzlement.” The court then sentenced 

McDougal to ten months imprisonment and 26 months supervised release.

In addition, the court ordered that “based on [his] history of drug 

abuse, [McDougal] must participate in an alcohol/drug abuse treatment 

program and follow the rules and regulations of the program.” The court 

explained that it “didn’t see very much about [McDougal’s] potential use of 

drugs, but certainly [his] possession and sale of drugs is evident.”3

 

Accordingly, the court ordered that McDougal be evaluated and observed—

this was to be supervised by the probation officer. But if there was no drug 

problem then the probation officer was not to execute this portion of the 

order. The court later reiterated that it was “ordering treatment if the 

probation officer deems it necessary . . . [b]ut that decision will lie with the 

probation officer.”

McDougal objected that “[t]here’s nothing before the Court to say 

that he has a potential for drug use. Maybe ten years ago. There’s nothing 

certainly since he’s been on supervised release for drug use. There’s been 

nothing while he was on pretrial release prior to his sentence in 2016.” 

3 The court recognized that McDougal had not tested positive for drugs.

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According to the defense, there was “no evidence here before the Court to 

require such a treatment requirement, and so we’d object to the sentence as 

a whole but that one as well specifically.”

The court denied the objection, stating “your protest is a frivolous 

protest if he doesn’t have a problem, because I’ve already said the probation 

officer does not have to impose those conditions if it does not have a 

problem.” The court also added that it has to look out for public safety, and 

it was not aware of what McDougal had done with the money: “The Court 

doesn’t know whether he invested in some drug trade. The Court doesn’t 

know whether he picked up with his prior partners and purchased some 

drugs. The Court doesn’t know any of that.” The prosecution then 

attempted to clarify that the court was only ordering that McDougal be 

evaluated, and that the court and probation officer could take further steps 

based on that. The court agreed “[b]ased on the evaluation and what the 

probation officer knows based on that.” McDougal timely appealed the 

sentence.

II. DISCUSSION

McDougal raises two issues on appeal. First, he challenges the district 

court’s imposition of required participation in an alcohol and drug abuse 

treatment program as a special condition of his supervised release. Second, 

McDougal asserts that the district court impermissibly delegated the decision 

of whether to require treatment to the probation officer. Neither argument 

prevails.

A. Substance Abuse Treatment Condition

This court reviews a preserved challenge to a special condition of 

supervised release for abuse of discretion. United States v. Caravayo, 

809 F.3d 269, 272 (5th Cir. 2015). “District courts have ‘wide discretion in 

imposing terms and conditions of supervised release.’” United States v. 

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Dean, 940 F.3d 888, 891 (5th Cir. 2019) (quoting United States v. Paul, 

274 F.3d 155, 164 (5th Cir. 2001)). The sentencing court “may impose any 

condition it deems appropriate” subject to two limitations. Id. First, the 

condition must reasonably relate to at least one of the four statutory factors 

enumerated in 18 U.S.C. § 3553(a): 

(1) the nature and characteristics of the offense and the history 

and characteristics of the defendant; (2) the need for the 

sentence imposed to afford adequate deterrence to criminal 

conduct; (3) the need for the sentence imposed to protect the 

public from further crimes of the defendant; and (4) the need 

for the sentence imposed to provide the defendant with needed 

educational or vocational training, medical care, or other 

correctional treatment in the most effective manner.

United States v. Bree, 927 F.3d 856, 859–60 (5th Cir. 2019). Second, “‘the 

condition must be narrowly tailored such that it does not involve a greater 

deprivation of liberty than is reasonably necessary to fulfill the purposes set 

forth in’ § 3553(a).” Dean, 940 F.3d at 891 (quoting United States v. Scott, 

821 F.3d 562, 570 (5th Cir. 2016)).

Further, the district court must make factual findings in terms of the 

§ 3553(a) factors to justify the special condition. United States v. Salazar, 

743 F.3d 445, 451 (5th Cir. 2014). But “[i]n the absence of a factual finding, 

a court of appeals may nevertheless affirm a special condition ‘where the 

[district] court’s reasoning can be inferred after an examination of the 

record.’” Caravayo, 809 F.3d at 275 (quoting Salazar, 743 F.3d at 451).

McDougal principally argues that the special condition here fails at 

step one. It is not reasonably related to any of the factors because there is no 

evidence that he is using drugs or that any of the embezzled funds went 

toward drugs. Without this evidence, the condition does not relate to 

deterrence, public protection, or medical care. Last, he claims, the district 

court failed to provide factual support for the condition.

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In rebuttal, the government argues that the condition is properly 

related to McDougal’s past history of alcohol and marijuana abuse, and his 

prior conviction for possessing and selling drugs. The government keys in on 

the district court’s concern that the embezzled money was used for drug 

purchases and argues that the court was in the best position to judge 

credibility.

The starting point here is determining what condition the court 

actually imposed. The written judgment states that McDougal “must 

participate in an alcohol/drug abuse treatment program and . . . [t]he 

probation officer will supervise [] participation in the program.” At 

sentencing, the court reiterated that McDougal “must participate” in a 

treatment program. Yet the court further stated that it wanted McDougal 

“evaluated and observed to see if [he] ha[s] a drug problem . . . . [I]f [he] 

do[esn’t] have a drug problem, the probation officer will not execute this 

portion of the order.”4 The written judgment makes participation 

mandatory, but the verbal judgment appears to make initial participation (the 

evaluation and observation) mandatory and continued participation only 

required upon a determination that McDougal has a “drug problem.” In a 

sense, the probation officer will either terminate treatment or escalate the 

intensity after the threshold determination.

“If the in-court pronouncement differs from the judgment that later 

issues, what the judge said at sentencing controls.” United States v. Diggles, 

4 To be sure, though the district court states that “the probation officer will not 

execute” the treatment condition, evaluation and observation are necessary 

prerequisites—meaning that the condition will be initially executed. The probation officer 

will then cease to execute the treatment condition if McDougal does not have a drug 

problem. That the district court used the words “evaluated and observed” makes no 

difference. Evaluation and observation are as much a component of a treatment program 

as any subsequent therapy.

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957 F.3d 551, 557 (5th Cir. 2020) (en banc). A conflict exists where “the 

written judgment broadens the restrictions or requirements of supervised 

release from an oral pronouncement,” United States v. Mireles, 471 F.3d 551, 

558 (5th Cir. 2006), or “impos[es] a more burdensome requirement,” United 

States v. Bigelow, 462 F.3d 378, 383 (5th Cir. 2006). Here they conflict,5 so 

the oral pronouncement trumps and continued participation in the treatment 

program is contingent on whether McDougal actually has a “drug problem.”

That condition reasonably relates to the § 3553(a) factors. First, 

McDougal has a past conviction for a drug offense, and the original 

Presentence Report indicated that he had previously been addicted to alcohol 

and marijuana. Second, the current offense involved the embezzlement of 

nearly $8000 (over $3000 of which McDougal received), and the district 

court rejected McDougal’s explanation of where that money went. The 

court drew a reasonable connection between the unaccounted-for funds and 

the possibility that McDougal may have a drug problem. If McDougal does 

have a drug problem, substance abuse treatment would reasonably constitute 

appropriate medical care. By requiring a threshold determination that 

McDougal actually has a drug problem before mandating continued

participation, the condition is narrowly tailored.

Here the district court made explicit, and the record supports, its 

concern that McDougal may have fallen into a drug problem. That is 

sufficient to trigger an inquiry. Whether McDougal is found to be clean or 

5 If the two judgments do not actually conflict, and instead “the written judgment 

simply clarifies an ambiguity in the oral pronouncement, [this court] look[s] to the 

sentencing court’s intent to determine the sentence.” United States v. Tang, 718 F.3d 476, 

487 (5th Cir. 2013) (per curiam). Intent is determined by examining the record as a whole. 

United States v. Tanner, 984 F.3d 454, 456 (5th Cir. 2021). This approach leads to the same 

result. The record clearly indicates that the district court intended to limit the extent of 

treatment depending on whether McDougal actually had a drug problem.

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not, the condition accounts for the result of the inquiry. Accordingly, the 

district court did not abuse its discretion in imposing this drug treatment 

condition.

B. Impermissible Judicial Delegation

“The imposition of a sentence, including the terms and conditions of 

supervised release, is a core judicial function that cannot be delegated.” 

Sealed Appellee v. Sealed Appellant, 937 F.3d 392, 400 (5th Cir. 2019) (quoting 

United States v. Franklin, 838 F.3d 564, 568 (5th Cir. 2016)). The district 

court must have “the final say” on whether to impose a condition. United 

States v. Huerta, 994 F.3d 711, 716–17 (5th Cir. 2021) (quoting United States 

v. Medel-Guadalupe, 987 F.3d 424, 431 (5th Cir. 2021)). Thus, it is not 

permissible for a district court to delegate the decision “whether a defendant 

will participate in a treatment program,” but “a district court may properly 

delegate to a probation officer decisions as to the details of a condition of 

supervised release.”6 Sealed Appellee, 937 F.3d at 400 (internal quotation 

marks and citations omitted).

Consistent with this distinction, a probation officer’s authority can 

permissibly extend to the “modality, intensity, and duration” of a treatment 

condition. Medel-Guadalupe, 987 F.3d at 431. Here, the district court plainly 

required treatment and left only the duration and intensity of that treatment 

to the probation officer. If McDougal is found not to have a condition 

warranting further treatment, then the probation officer is instructed not to 

require treatment. Since the district court exercised its “final say” over the

6 There are additional limitations on the delegation of the details of a condition 

when it involves a “significant deprivation of liberty.” United States v. Martinez, 987 F.3d 

432, 434–36 (5th Cir. 2021); see also Medel-Guadalupe, 987 F.3d at 430–31. This is not 

implicated here.

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initial treatment decision, delegating questions of duration and intensity was 

permissible. See Huerta, 994 F.3d at 716–17.

III. CONCLUSION

The judgment of the district court is AFFIRMED.

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