United States v. Simmons

• Court: Court of Appeals for the Tenth Circuit
• Decided: August 15, 2025
• Docket: 24-6077
• Status: Unpublished

Opinion

Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 1 FILED United States Court of Appeals UNITED STATES COURT OF APPEALS Tenth Circuit

FOR THE TENTH CIRCUIT August 15, 2025 _________________________________ Christopher M. Wolpert Clerk of Court UNITED STATES OF AMERICA,

Plaintiff - Appellee,

v. No. 24-6077 (D.C. No. 5:22-CR-00255-G-1) BOBBY DALE SIMMONS, (W.D. Okla.)

Defendant - Appellant. _________________________________

ORDER AND JUDGMENT* _________________________________

Before TYMKOVICH, PHILLIPS, and MORITZ, Circuit Judges. _________________________________

Bobby Dale Simmons pleaded guilty to unlawful firearm possession and was

sentenced in district court. In determining Simmons’ Sentencing Guidelines

imprisonment range, the district court applied a four-level enhancement to his offense

level pursuant to U.S.S.G. § 2K2.1(b)(6)(B) because it found Simmons possessed the

firearm in connection with another felony offense. On appeal, Simmons argues that

the enhancement was improperly applied because there was no coincident felony

offense.

* This order and judgment is not binding precedent, except under the doctrines of law of the case, res judicata, and collateral estoppel. It may be cited, however, for its persuasive value consistent with Fed. R. App. P. 32.1 and 10th Cir. R. 32.1. Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 2

We AFFIRM. Simmons fails to show the district court plainly erred in

applying the enhancement because his prior state drug convictions, listed in the

adopted Final Presentence Report, elevate his drug possession charge from a

misdemeanor to a felony pursuant to 21 U.S.C. § 844.

I. Background

A. Factual Background

Oklahoma City Police Department responded to a reported disturbance at a

hotel. They observed Simmons exit the hotel carrying a black case that they

suspected held a handgun. He placed the case in his vehicle as OCPD officers tried

to detain him. While taking Simmons into custody, the officers saw a revolver on the

driver’s side floorboard in plain sight. A search of the vehicle uncovered three

firearms, ammunition, and small quantities of various drugs. The drugs included:

(1) 4.41 grams total package weight of methamphetamine; (2) 2.40 grams total

package weight of marijuana; (3) approximately 14.32 grams total package weight of

a light brown powdery substance (not tested due to possibility of fentanyl); (4) five

fentanyl patches; and (5) 19 small blue pills marked “M30” identified on pill

identifier as Oxycodone and one unknown pink pill in the shape of an “X.” Also

found in the vehicle were numerous items consistent with drug distribution, including

scales, glass pipes, torches, and small plastic baggies. OCPD officers identified

Simmons as a convicted felon.

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Simmons was arrested and charged in the Western District of Oklahoma for

one count of unlawfully possessing firearms under 18 U.S.C. § 922(g). He pleaded

guilty to the single-count indictment without a plea agreement.

While on bond, however, Simmons was again arrested in relation to a

shoplifting investigation. During his arrest, officers found drugs in his pocket. The

drugs included: (1) two suboxone pills; (2) 0.8 grams of psilocybin; (3) 8.1 grams of

methamphetamine; (4) 2.7 grams of cocaine; and (5) 8.2 grams of marijuana. A

search of his car revealed a semi-automatic firearm and ammunition, as well as a

pipe, digital scales, and brass knuckles.

B. Simmons’ Final PSR and Sentencing Proceeding

Simmons’ Final PSR included a four-level enhancement under U.S.S.G.

§ 2K2.1(b)(6)(B) for possessing a firearm in connection with another felony offense.

Specifically, the relevant paragraph read: “As detailed in the offense conduct, the

defendant possessed a firearm in connection with the felony offense of possession of

controlled dangerous substance including methamphetamine and fentanyl; therefore,

pursuant to U.S.S.G. § 2K2.1(b)(6)(B), a four-level increase is warranted.” Vol. III,

35 (emphasis added) (Paragraph 24(a)). No objections were made to this sentencing

enhancement before or at the sentencing proceeding.

At sentencing, the district court began by resolving the remaining objections to

the Final PSR. Again, none pertained to the four-level enhancement. The court then

calculated Simmons’ Guidelines imprisonment range. But it did not make additional,

explicit findings as to the enhancement apart from its general adoption of the Final

3 Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 4

PSR. See Vol. III, 142–43. In fact, the court did not specify the exact felony

offense, nor did it cite any state or federal statute in applying the enhancement.

Simmons’ Guidelines imprisonment range was calculated to be 120 to 150 months

based on his total offense level of 27 and his criminal history score of 12 (criminal

history category of V).1 A statutory maximum of 10 years applied, however, and thus

Simmons’ Guidelines imprisonment recommendation was capped at 120 months.

Relying on the 18 U.S.C. § 3553(a) factors, the court subsequently presented

an individualized assessment of Simmons’ history and characteristics and the instant

offense to impose an appropriate sentence. Ultimately, the district court varied

downward and sentenced Simmons to 96 months of imprisonment and two years of

supervised release. The court expressed concern about Simmons’ criminal history

and drug possession, but recognized his education, military service, completion of a

mental intervention program, and the fact that he had no criminal convictions in the

five years leading up to the instant offense.

II. Discussion

Simmons appeals his sentence. He argues the felony offense requirement was

not satisfied for the sentencing enhancement because: (1) the Final PSR referred to

Oklahoma’s simple possession statute, a misdemeanor, in its reasoning for the

enhancement; and (2) his drug possession offense could not have been elevated from

1 Without the four-level enhancement, Simmons’ offense level would have been 23. The Guidelines range for an offense level of 23 and a criminal history category of V is imprisonment of 84 to 105 months. 4 Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 5

a misdemeanor to a felony under 21 U.S.C. § 844 because the categorical approach

plainly applies to the statute.

A. Standard of Review

Simmons concedes that the four-level enhancement was not challenged below

and thus plain error review applies. We find plain error only when there is:

“(1) error, (2) that is plain, (3) which affects substantial rights, and (4) which

seriously affects the fairness, integrity, or public reputation of judicial proceedings.”

United States v. Romero, 491 F.3d 1173, 1178 (10th Cir. 2007) (citation omitted).

Failure to satisfy even one of the requirements is fatal to Simmons’ claim.

B. No Plain Error: 21 U.S.C. § 844

We see no error in the district court’s application of the sentencing

enhancement, much less a plain one. The adopted Final PSR included Simmons’

prior drug-related misdemeanors, which enhance his instant drug possession from a

misdemeanor to a felony under 21 U.S.C. § 844. We do not agree with Simmons that

the categorical approach plainly applies to the federal statute.

Under federal law, simple possession of drugs—though generally a

misdemeanor under Oklahoma and federal statute—becomes a felony offense when

committed after a prior drug conviction that is final under state law. See 21 U.S.C.

§ 844(a). The statute provides:

It shall be unlawful for any person knowingly or intentionally to possess a controlled substance . . . . Any person who violates this subsection may be sentenced to a term of imprisonment of not more than 1 year, and shall be fined a minimum of $1,000, or both, except that if he

5 Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 6

commits such offense after a prior conviction under this subchapter or subchapter II, or a prior conviction for any drug, narcotic, or chemical offense chargeable under the law of any State, has become final, he shall be sentenced to a term of imprisonment for not less than 15 days but not more than 2 years . . . .

Id. (emphases added).

To begin, Simmons argues we cannot rely on 21 U.S.C. § 844 because the

district court considered only Oklahoma’s simple possession statute in applying the

enhancement. Specifically, Simmons underscores that Paragraph 24(a) of the Final

PSR used the term controlled dangerous substance, a term that he claims can only

refer to the state statute.2 Aplt. Br. 8–9 (citing OKLA. STAT. ANN. tit. 63, § 2-101 to

§ 2-1101). But the Final PSR did not cite or limit its analysis of the enhancement to

only Oklahoma’s simple possession statute in justifying the enhancement, nor did it

use the term, “simple.” In other words, the text of the Final PSR does not require nor

restrict us from relying on only one, or even a specific, authority. Rather, we read

Paragraph 24(a) to explain that Simmons’ possession of controlled dangerous

substances under Oklahoma law is to be heightened from a misdemeanor to a felony

under § 844 due to Simmons’ prior drug-related criminal history. To assume the

Final PSR was only referring to the Oklahoma statute, and that it is mutually

2 OKLA. STAT. ANN. tit. 63, § 2-101 (“‘Controlled dangerous substance’ means a drug, substance or immediate precursor in Schedules I through V of the Uniform Controlled Dangerous Substances Act or any drug, substance or immediate precursor listed either temporarily or permanently as a federally controlled substance.”). 21 U.S.C. § 844 similarly uses the term, controlled substance. 21 U.S.C. § 802(6) (“The term ‘controlled substance’ means a drug or other substance, or immediate precursor, included in schedule I, II, III, IV, or V of part B of this subchapter.”). 6 Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 7

exclusive with any reliance or application of the federal statute, is too rigid of an

interpretation that is unsupported by the record.3

We find 21 U.S.C. § 844 supports Simmons’ enhancement. While it is true

that Simmons was found possessing allegedly small quantities of drugs that amount

only to misdemeanor quantities, Simmons’ prior, final state drug convictions convert

his misdemeanor offense to a felony. Simmons’ long rap sheet includes numerous

state drug-related offenses, which were explicitly listed in the Final PSR, unobjected

to, and adopted by the court. See FED. R. CRIM. P. 32(i)(3) (a sentencing court “may

accept any undisputed portion of the presentence report as a finding of fact[.]”);

United States v. Hooks, 551 F.3d 1205, 1217 (10th Cir. 2009) (“If a defendant fails to

specifically object to a fact in the PSR, the fact is deemed admitted by the defendant

and the government need not produce additional evidence in support of the admitted

fact.” (citation omitted)). The Final PSR stated, for example:

• In 2014, Simmons pleaded guilty and was sentenced to 12 years,

suspended, with supervised probation for possession of a controlled

dangerous substance with intent to distribute (1.65 grams of meth) in

Oklahoma state court.

3 Simmons argues that the government “implicitly asks for affirmance on alternative grounds” by relying on § 844. Aplt. Reply 10. He maintains that the government waived this argument because it did not “brief the appropriate standard of review.” Id. at 5–6, 10. But for the reasons explained, we disagree that reliance on the federal statute is an alternative argument. 7 Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 8

• In 2016, Simmons pleaded guilty and was admitted to mental health court

for possession of a controlled dangerous substance (6.4 grams of meth) in

Vol. III, 9–16.

Simmons counters that it was plainly erroneous to not apply the categorical

approach in determining whether a prior drug conviction constitutes a “drug,

narcotic, or chemical offense” under 21 U.S.C. § 844.4 Aplt. Br. 13. He argues that

the state statutes under which he was previously convicted are plainly overbroad and

do not categorically match the federal definition to elevate his misdemeanor to a

§ 844 felony.

“An error is plain ‘when it is contrary to well-settled law.’” United States v.

Thornton, 846 F.3d 1110, 1118 (10th Cir. 2017) (quoting United States v. Ruiz-Gea,

340 F.3d 1181, 1187 (10th Cir. 2003)). And “[f]or that inquiry[,] we look to whether

the Supreme Court or the Tenth Circuit has addressed the issue.” Id. (quoting

Ruiz-Gea, 340 F.3d at 1187).

Here, even if there was an error, it does not surpass the “plain” prong because

it is not clearly established that the categorical approach applies to § 844. First,

Simmons notes there is no caselaw directly on point and instead leans on cases in

4 “[W]hen the language of the enhancement confines the court’s inquiry to the terms of the statute of conviction, courts employ the categorical approach, looking not to the particular facts of the prior conviction but to the terms of the underlying statute.” United States v. Martinez-Hernandez, 422 F.3d 1084, 1086 (10th Cir. 2005) (cleaned up). 8 Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 9

which the categorical approach was applied to allegedly analogous statutes.5 But

those cases did not address the federal statute before us. Second, an unpublished

decision in this Circuit declined to hold that the district court should have applied the

categorical approach to determine whether a defendant’s Missouri drug offense was a

“prior [drug] conviction” under 21 U.S.C. § 844(a). United States v. Shaw,

No. 22-3251, 2023 WL 3335596, at *2 (10th Cir. May 10, 2023).6 We clarified in

Shaw that Ҥ 844(a) does not require the prior offense to be a violation of [the

Federal Controlled Substance] Act. It simply refers to ‘any drug, narcotic, or

chemical offense chargeable under the law of any State.’” Id. at *4. And tellingly,

we found that “[a]lthough the categorical approach applies to serious drug offenses

under the ACCA, it does not pertain to § 844(a).” Id. Simmons’ arguments

analogizing § 844 to seemingly parallel statutes is thus unconvincing and, even if the

district court erred, it was not plain error given a persuasive circuit case on the

matter.

5 See, e.g., United States v. Cantu, 964 F.3d 924, 926 (10th Cir. 2020) (applying the categorical approach to “determine whether a state [Oklahoma] conviction was for a serious drug offense” under the Armed Career Criminal Act); United States v. Herrera-Roldan, 414 F.3d 1238, 1241 (10th Cir. 2005) (applying a categorical approach to a Texas statute based on Guidelines text). 6 Unpublished cases are not binding precedent, but we consider them for their persuasive value. See FED. R. APP. P. 32.1; 10th Cir. R. 32.1.

9 Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 10

Accordingly, we find the district court did not plainly err in applying the

four-level sentencing enhancement to Simmons.7

III. Conclusion

It is a party’s responsibility to timely seek clarification of a defendant’s

sentence, and to timely object or challenge sentencing adjustments or related facts in

the Final PSR. Even though we agree that the district court could have more

thoroughly explained its reasoning, application of the sentencing enhancement did

not amount to plain error.

7 Based on the district court’s findings, it is doubtful Simmons could demonstrate the alleged errors prejudiced him. United States v. Gonzalez-Huerta, 403 F.3d 727, 733 (10th Cir. 2005) (“To meet this burden, the appellant must show ‘a reasonable probability that, but for the error claimed, the result of the proceeding would have been different.’” (citation omitted)); United States v. Mendoza, 543 F.3d 1186, 1194 (10th Cir. 2008) (“The party that failed to raise the issue below bears the burden of establishing this probability.” (citation omitted)). In sentencing Simmons, the court recognized that he possessed, on two occasions, “paraphernalia used in the consumption and the sale of illegal drugs[,]” including pipes, scales, torches, small plastic baggies. Vol. III, 31–32; Vol. II, 5–7 (Final PSR). Relatedly, the Guidelines provide that “the enhancement applies ‘in the case of a drug trafficking offense in which a firearm is found in close proximity to drugs, drug-manufacturing materials, or drug paraphernalia . . . .’”, United States v. Tobanche, 643 F. App’x 781, 783 (10th Cir. 2016) (emphasis added) (unpublished), because “the presence of the firearm has the potential of facilitating another felony offense.” U.S.S.G. § 2K2.1(b)(6)(B) cmt. 14(B)(ii). Ultimately, we do not reach the question of whether there is a reasonable probability the sentencing enhancement would have been applied to Simmons regardless of the alleged errors based on the adopted facts suggesting he intended to distribute drugs—even so, Simmons cannot satisfy the second prong of the plain error standard. 10 Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 11

Thus, for the foregoing reasons, we affirm.8

Entered for the Court

Timothy M. Tymkovich Circuit Judge

8 Simmons argued in his appellate brief, for preservation purposes only, that his conviction must be vacated because 18 U.S.C. § 922(g)(1) is plainly unconstitutional, both on its face and as applied to him. While his appeal was pending, we clarified in Vincent v. Bondi that § 922(g)(1) is constitutional under the Second Amendment “without drawing constitutional distinctions based on the type of felony involved.” 127 F.4th 1263, 1266 (10th Cir. 2025) (citations omitted). Simmons therefore cannot demonstrate plain error as to his preserved argument. 11 Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 12

24-6077, United States v. Simmons

MORITZ, Circuit Judge, dissenting.

The majority concludes that Simmons qualifies for a four-level enhancement

under United States Sentencing Guidelines § 2K2.1(b)(6)(B) because he possessed a

firearm in connection with a felony. Specifically, the majority concludes that Simmons

committed federal felony drug possession, violating 21 U.S.C. § 844. But there’s a

problem with that view: the district court never specified which felony justifies the

enhancement. The district court adopted the presentence investigation report (PSR) in full

without directly addressing the enhancement. And the PSR—the only place in the record

that discusses the enhancement—never mentions § 844.

The PSR recommended that Simmons receive a four-level enhancement for

possessing “a firearm in connection with the felony offense of possession of controlled

dangerous substance[s,] including methamphetamine and fentanyl.” R. vol. 2, 35. The

majority reads this sentence “to explain that Simmons’[s] possession of controlled

dangerous substances under Oklahoma law is to be heightened from a misdemeanor to a

felony under § 844 due to Simmons’[s] prior drug-related criminal history.” Maj. Op. 6

(cleaned up). That’s not a reading of the PSR—that’s conjuring a felony from thin air.

I would remand this case for the district court to explain which felony it used to

apply the enhancement. The majority’s use of § 844 makes a remand all the more

necessary because the one hint that the PSR does provide does not point to § 844. The

parties agree that the PSR’s use of the phrase “the felony offense of possession of

controlled dangerous substance[s]” references Oklahoma law. Indeed, Oklahoma’s drug Appellate Case: 24-6077 Document: 98-1 Date Filed: 08/15/2025 Page: 13

laws appear in its “Uniformed Controlled Dangerous Substances Act.” Okla. Stat. tit. 63,

ch. 2. And there’s a fatal flaw with invoking Oklahoma’s drug laws as the predicate

felony for the enhancement: drug possession is a misdemeanor under Oklahoma law, not

a felony. Okla. Stat. tit. 63 § 2-402(A)(1) (“It shall be unlawful for any person knowingly

or intentionally to possess a controlled dangerous substance.”); id. § 2-402(B)(1) (“Any

person who violates this section is guilty of a misdemeanor punishable by confinement

for not more than one . . . year.”).

So if the district court invoked Oklahoma’s drug-possession law to justify the

enhancement—and the signs suggest that it did—then the district court erred. Such an

error would be plain, too, given the plain language of the Oklahoma statute and the

Guidelines’ definition of a felony offense under § 2K2.1(b)(6)(B). See United States v.

Arellanes-Portillo, 34 F.4th 1132, 1140 (10th Cir. 2022) (“Error may be plain based on

the text of statutes or Guidelines.”). Erroneously applying § 2K2.1(b)(6) also satisfies the

third and fourth prongs of plain-error review because the four-level enhancement

increased Simmons’s Guidelines range from 84 to 105 months to 120 months, U.S.S.G.

ch. 5 pt. A (sentencing table), causing obvious prejudice that requires reversal, United

States v. Sabillon-Umana, 772 F.3d 1328, 1333 (10th Cir. 2014) (“[A]n obvious

misapplication of the sentencing guidelines will usually satisfy the third and fourth

elements of the plain[-]error test.”); id. (“[W]hat reasonable citizen wouldn’t bear a

rightly diminished view of the judicial process and its integrity if courts refused to correct

obvious errors of their own devise that threaten to require individuals to linger longer in

federal prison than the law demands?”).

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Perhaps the district court erred. Perhaps the district court meant to invoke § 844.

But rather than read the PSR to say something it doesn’t, I would remand this case. I

respectfully dissent.