United States of America v. Aaron Loines

RECOMMENDED FOR PUBLICATION
Pursuant to Sixth Circuit I.O.P. 32.1(b)
File Name: 26a0018p.06
UNITED STATES COURT OF APPEALS
FOR THE SIXTH CIRCUIT
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
AARON LOINES,
Defendant-Appellant.
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No. 24-4056
Appeal from the United States District Court for the Northern District of Ohio at Cleveland.
No. 1:23-cr-00631-4—Benita Y. Pearson, District Judge.
Decided and Filed: January 21, 2026
Before: GILMAN, GRIFFIN, and MURPHY, Circuit Judges.
_________________
COUNSEL
ON BRIEF: Richard P. Kutuchief, THE KFARM, Coventry Township, Ohio, for Appellant.
Payum Doroodian, UNITED STATES ATTORNEY’S OFFICE, Cleveland, Ohio, for Appellee.
_________________
OPINION
_________________
MURPHY, Circuit Judge. The federal drug laws increase a defendant’s minimum
sentence for a new drug offense if the defendant had a prior “serious drug felony” conviction that
had “become final” before the defendant committed that new offense. 21 U.S.C. § 841(b)(1).
A previous crime can qualify as a “serious drug felony” only if the defendant “served” at least
“12 months” in prison and was released “within 15 years” of the current offense. Id. § 802(58).
In this case, the district court found as a fact that Aaron Loines’s prior federal drug
offense met these elements. It thus imposed the statutory enhancement when sentencing Loines
>

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for new drug crimes. Loines now challenges that decision on several grounds, claiming that the
Constitution required a jury to make the necessary findings, that the government acted arbitrarily
and vindictively by requesting the enhancement, and that his prior conviction was not “final”
when he committed his current crimes. But any error in failing to submit the issue to a jury was
harmless. His challenges to the government’s decision to ask for this enhancement also cannot
rebut our presumption that it properly exercised its prosecutorial discretion. And Loines
misunderstands what it takes to make a conviction “final.” Lastly, our precedent forecloses his
separate challenge to the district court’s use of a career-offender enhancement. We thus affirm.
I
In November 2022, officers began to investigate a drug-dealing ring centered on a certain
street in Cleveland, Ohio. Over the next year, they set up multiple controlled buys from the
conspirators. Wiretaps revealed that Loines sold fentanyl pills as part of the conspiracy. He
supplied over a thousand pills to an undercover agent in October 2023 and again in November
2023. After the second buy, officers found illegal narcotics in several homes. They also
uncovered drugs (including over 500 fentanyl pills) in Loines’s car when they arrested him on
November 13.
The next month, the government charged Loines and other conspirators with a single
count of conspiring to distribute controlled substances. It also alleged that Loines had committed
a prior “serious drug felony” within the meaning of 21 U.S.C. §§ 802(58) and 841(b)(1). This
allegation stemmed from a conviction back in April 2023—just months before Loines joined the
conspiracy. At that time, the district court convicted him of another federal drug offense and
sentenced him to time served. As the government later explained at Loines’s arraignment, this
previous offense increased his statutory minimum amount of imprisonment from 5 years to 10
years.
In early 2024, the government filed a superseding indictment that added dozens of counts
against the various conspirators. In addition to the overarching drug conspiracy, this indictment
charged Loines with two drug-distribution counts, three drug-possession counts, and one
facilitation count. It also mentioned Loines’s prior serious drug felony again.

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A short time later, Loines decided to plead guilty to all the charged counts without a plea
agreement. Just before Loines’s change-of-plea hearing, the government formally notified
Loines under 21 U.S.C. § 851 that it would seek the enhanced 10-year statutory minimum based
on his previous serious drug felony. With notice of this increased punishment, Loines still chose
to plead guilty to all counts without a plea agreement.
Before sentencing, Loines objected to various enhancements that the presentence report
proposed. Of most note, he raised several challenges to the enhancement under 21 U.S.C.
§ 841(b)(1) for his prior federal drug offense. He claimed that § 851’s procedures for imposing
the enhancement violated the Constitution because they required a judge, not a jury, to identify
critical facts necessary for the enhancement. He also claimed that the enhancement should not
apply because his prior offense had yet to reach finality when he committed his current crimes.
And he claimed that the Department of Justice’s policies barred the enhancement.
These objections led the district court to hold an evidentiary hearing. See 21 U.S.C.
§ 851(c)(1). It later issued a written opinion overruling Loines’s objections and applying the
enhancement. See United States v. Loines, 2024 WL 4792083, at *6 (N.D. Ohio Nov. 13, 2024).
The court rejected Loines’s claim that the Constitution required a jury to find the facts required
for a prior conviction to trigger the serious-drug-felony enhancement. Id. at *4–5. It next held
that Loines’s prior conviction in April 2023 had become final before he committed the current
offenses. Id. at *5. And although the court criticized the government for failing to adequately
explain why it sought the enhancement under the Department of Justice’s policies, it held that it
could not control this prosecutorial discretion. See id. at *1–4. So Loines’s statutory minimum
sentence jumped to 10 years’ imprisonment. See 21 U.S.C. § 841(b)(1).
At sentencing, the district court rejected Loines’s other challenge to the career-offender
enhancement in U.S.S.G. § 4B1.1(a). He had claimed that a prior Ohio drug-trafficking
conviction did not qualify as a “controlled substance offense” for this enhancement. See id.
§ 4B1.2(b). And according to Loines, the statutory minimum (120 months) would become his
guidelines sentence if he were not a career offender. But the district court found that Sixth
Circuit precedent precluded this argument. The career-offender enhancement thus raised his
guidelines range to 262 to 327 months’ imprisonment. Still, the court chose to vary downward.

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It sentenced Loines to a total punishment of 160 months’ imprisonment for all counts. Loines
appealed.
II
Loines renews his challenge to the statutory and career-offender enhancements. But any
potential error in imposing the statutory enhancement was harmless, and the district court
properly applied the career-offender enhancement under our precedent.
A. Statutory Enhancement
The provision of the federal drug laws at issue here increases a defendant’s minimum
punishment from 5 years to 10 years if the defendant committed a drug offense “after a prior
conviction for a serious drug felony . . . has become final[.]” 21 U.S.C. § 841(b)(1)(B). Those
laws define the phrase “serious drug felony” to mean (among other things) a “serious drug
offense” under 18 U.S.C. § 924(e)(2) that meets certain conditions. 21 U.S.C. § 802(58); United
States v. Fields, 53 F.4th 1027, 1031 (6th Cir. 2022). The defendant must have “served a term of
imprisonment of more than 12 months” for this prior crime. 21 U.S.C. § 802(58)(A). And the
defendant’s “release from any term of imprisonment” for the offense must have been “within 15
years of the commencement of the” current crime. Id. § 802(58)(B).
In § 851, the federal drug laws identify the procedures for imposing this enhancement.
The government must file “an information” that seeks it. Id. § 851(a)(1). The defendant may
then deny that the enhancement applies in a response. Id. § 851(c)(1). If the defendant does so,
the court must “hold a hearing to determine any issues raised by the response which would
except the person from increased punishment.” Id. This hearing occurs “before the court
without a jury,” and the parties may introduce evidence on the relevant issues. Id. If the court
ultimately finds that the prior conviction triggers the enhancement, the court must impose it. Id.
§ 851(d)(1).
The district court in this case held the type of hearing that § 851 contemplated. It found
that Loines’s federal drug conviction from April 2023 met all the conditions to qualify as a
“serious drug felony” and to increase his minimum sentence from 5 years to 10 years. Loines

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mounts several challenges to this finding. He contests the constitutionality of § 851’s
procedures, argues that the government arbitrarily sought the enhancement, raises a claim of
vindictive prosecution, and disputes the finality of his prior drug offense. We will consider each
claim in turn.
1. Section 851’s Constitutionality. Loines first argues that § 851’s procedures violate the
Constitution because the statute tells district judges to decide—“without a jury”—whether a prior
offense meets all the serious-drug-felony requirements. Id. § 851(c)(1). He might have a valid
point. But we need not resolve this constitutional issue in this case because any error in failing
to submit factual questions to a jury did not harm him.
The Supreme Court has interpreted the Fifth and Sixth Amendments to establish a
general rule: juries (not judges) must find any fact that increases a defendant’s punishment
(including the defendant’s mandatory minimum sentence) using the beyond-a-reasonable-doubt
standard. See Erlinger v. United States, 602 U.S. 821, 837 (2024); Alleyne v. United States, 570
U.S. 99, 103 (2013). Does this rule cover the question whether a defendant has committed a
prior “serious drug felony” within the meaning of the drug laws? It is debatable. See Fields, 53
F.4th at 1036–38.
On the one hand, the Supreme Court has long recognized a narrow “exception” to its
general rule requiring jury findings of fact. Erlinger, 602 U.S. at 837. Under that exception, a
judge may find “the fact” that a defendant has “a prior conviction” even when that finding will
increase the defendant’s punishment. Id. (citing Almendarez-Torres v. United States, 523 U.S.
224, 246–47 (1998)). In other words, a judge may find as a fact the statutory offense (including
the offense’s elements) that a court previously convicted the defendant of. Id. at 838 (citation
omitted). And the enhancement in Loines’s case does depend on the fact of a prior conviction.
Cf. United States v. Williams, 2024 WL 712470, at *4 (6th Cir. Feb. 21, 2024); United States v.
Brown, 2023 WL 1861318, at *8–9 (6th Cir. Feb. 9, 2023); United States v. Rodriguez, 851 F.3d
931, 945 (9th Cir. 2017); United States v. Smith, 451 F.3d 209, 224 (4th Cir. 2006).
On the other hand, the Supreme Court has repeatedly made clear that this prior-
conviction exception has a narrow scope. See Erlinger, 602 U.S. at 838 & n.2; Jones v. United

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States, 526 U.S. 227, 248–49 & n.10 (1999). Most recently, it held that a jury must decide
whether a defendant committed three prior felonies “on separate occasions” from each other—a
fact critical to triggering the Armed Career Criminal Act’s enhancement. See Erlinger, 602 U.S.
at 825, 835. The Court reasoned that this separate-occasions inquiry goes beyond determining
the prior “crime” of conviction or the “elements” of that crime. Id. at 838–39. And in the
current context, a judge cannot determine whether a prior conviction qualifies as a “serious drug
felony” unless the judge resolves other post-conviction facts—such as the amount of time that a
defendant “served” in prison and whether the government released the defendant “within 15
years” of the current offense. 21 U.S.C. § 802(58); cf. United States v. Guyton, 144 F.4th 449,
466–67 (3d Cir. 2025).
Ultimately, we need not decide whether the Fifth and Sixth Amendments require a jury to
find these facts. See Fields, 53 F.4th at 1037–38. Even if a constitutional violation occurred, it
would have been harmless. As we have explained for the “separate occasions” question under
the Armed Career Criminal Act, a district court’s unconstitutional refusal to send “a sentencing
factor to the jury” does not require automatic reversal. United States v. Campbell, 122 F.4th 624,
630 (6th Cir. 2024) (quoting Washington v. Recuenco, 548 U.S. 212, 218, 222 (2006)). Rather, a
court may uphold a conviction despite this defect if the government proves “beyond a reasonable
doubt that” this error would not have changed the “outcome” of the case. Id. (citation omitted).
And for harmless-error purposes, we see no difference between the facts necessary to enhance a
sentence under the Armed Career Criminal Act and those necessary to enhance it under the
federal drug laws. See United States v. Lee, 100 F.4th 484, 489–90 (4th Cir. 2024).
The conclusion that harmless-error review can apply leads to two other questions.
Question One: What test should govern this harmless-error inquiry? The inquiry might change
depending on whether the defendant stood trial or pleaded guilty. See Greer v. United States,
593 U.S. 503, 508 (2021); United States v. Bradley, 2025 WL 2658388, at *2 (6th Cir. Apr. 17,
2025); see also United States v. Brown, 136 F.4th 87, 96–97 (4th Cir. 2025). Should we ask
whether the government showed beyond a reasonable doubt that a defendant still would have
pleaded guilty if the district court had “correctly” explained that the defendant had a jury-trial
right for the facts that triggered the statutory enhancement? Greer, 593 U.S. at 508. Or should

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we ask whether the government showed beyond a reasonable doubt that no jury could have
“rationally” made a “contrary finding” over the critical fact used to impose the enhancement?
United States v. Thomas, 142 F.4th 412, 418 (6th Cir. 2025). Because Loines pleaded guilty, the
government may well have to prove the former test. But the parties did not brief this issue, and
the government can prove either test here. So we need not choose between them. See Bradley,
2025 WL 2658388, at *2.
Question Two: What materials may we use to undertake this harmlessness analysis? Our
caselaw on the harmlessness inquiry in the separate-occasions context answers this question.
There, we explained that courts may consider “all ‘relevant and reliable information’ in the
‘entire record,’” including the sentencing materials on which the district court relied to find the
key facts. Campbell, 122 F.4th at 633 (quoting Greer, 593 U.S. at 510–11). Courts thus may
examine the facts in the defendant’s presentence report, especially when the defendant does not
object to those facts. See Thomas, 142 F.4th at 419; Campbell, 122 F.4th at 633. And they may
examine the facts that a defendant concedes in “colloquies between a judge and the defendant.”
Erlinger, 602 U.S. at 839; see Campbell, 122 F.4th at 632–33.
These materials leave no doubt that the alleged error was harmless. According to Loines,
the Constitution required a jury (not a judge) to resolve two factual questions for a conviction to
qualify as a “serious drug felony”: Did he “serve[] a term of imprisonment of more than
12 months” on his prior drug conviction from April 2023? 21 U.S.C. § 802(58)(A). And was his
“release from [that] term of imprisonment . . . within 15 years of the commencement of” his
current drug offenses? Id. § 802(58)(B).
But he never contested the answers to these questions. Cf. Thomas, 142 F.4th at 419;
Lee, 100 F.4th at 489. Loines’s presentence report and prison records indicated that the district
court sentenced him to “time served” on this prior conviction, which ended up spanning about
three years (well above 12 months). Rep., R.174, PageID 1816; Inmate Data, R.130-2, PageID
1074. And those documents showed that the federal government released Loines in April
2023—well within the required 15-year window. Inmate Data, R.130-2, PageID 1073. Loines
admitted as much. At the § 851 hearing, he conceded that he served about “36 months” for his
prior offense. Tr., R.133, PageID 1130. And at sentencing, he said he had been “recently

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released” from that term of imprisonment. Sent. Tr., R.195, PageID 1999. Even his appellate
brief says that he served 36 months on his prior offense and that he was still serving his two-year
term of supervised release when he committed the current drug offenses. Appellant’s Br. 16, 37.
He also pleaded guilty after the prosecutor informed him that he would face the “enhanced
penalties” that these facts would trigger. Plea Tr., R.78, PageID 574–76.
As a result, this alleged error (again, assuming it was error) was harmless beyond a
reasonable doubt. We have no doubt that Loines would have still pleaded guilty if he had known
that a jury (rather than a judge) must decide these facts. See Greer, 593 U.S. at 508. And we
have no doubt that every rational juror would have answered these factual questions in a way that
triggered the statutory enhancement. See Thomas, 142 F.4th at 418. So the “outcome” would
have remained the same under any harmless-error test. Campbell, 122 F.4th at 630 (citation
omitted).
2. Prosecutorial Discretion. Loines next argues that—as a matter of “what is fair and
proper”—the government arbitrarily applied the statutory enhancement to him. Appellant’s Br.
17. But this claim fails because prosecutors, not judges, control charging decisions, and Loines
has not shown that the decision in his case violated any constitutional or statutory command.
The Supreme Court has long recognized that federal prosecutors have “broad discretion”
in deciding what charges to bring once they have probable cause to believe that a defendant has
committed a federal offense. Wayte v. United States, 470 U.S. 598, 607 (1985) (quoting United
States v. Goodwin, 457 U.S. 368, 380 n.11 (1982)). In the federal drug laws, Congress has also
extended this discretion to the decision whether to seek a statutory enhancement for past criminal
offenses. See 21 U.S.C. § 851(a)(1); Carachuri-Rosendo v. Holder, 560 U.S. 563, 579 (2010);
United States v. LaBonte, 520 U.S. 751, 761–62 (1997). And out of respect for the separation of
powers, the judicial branch should generally presume that prosecutors have properly exercised
this discretion, which falls within the executive branch’s authority to faithfully execute the
criminal laws. United States v. Armstrong, 517 U.S. 456, 464 (1996).
But this discretion has both constitutional and statutory limits. As a constitutional matter,
the equal-protection guarantee that the Supreme Court has read into the Fifth Amendment’s Due

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Process Clause forbids federal prosecutors from charging defendants for an “unjustifiable”
reason like “race, religion, or other arbitrary classification.” Id. (citation omitted); see Wayte,
470 U.S. at 608–09. And the process guarantee in that clause likewise requires federal
prosecutors to give defendants sufficient notice that they intend to seek the statutory
enhancement and an opportunity to object over whether it applies. See United States v. King,
127 F.3d 483, 488–89 (6th Cir. 1997); see also Mullane v. Cent. Hanover Bank & Tr. Co., 339
U.S. 306, 313 (1950). As a statutory matter, federal prosecutors must comply with the
procedures listed in 21 U.S.C. § 851 to seek an enhancement. See King, 127 F.3d at 487.
Among other things, the government must file the required “information” that alerts the
defendant it will seek the enhancement either “before trial” or “before entry of a plea of
guilty[.]” 21 U.S.C. § 851(a)(1). The notice must also state the previous conviction that
supports the enhancement. Id.
Here, Loines argues that prosecutors “arbitrarily” sought this statutory enhancement, but
he does not raise any traditional constitutional or statutory challenge. Appellant’s Br. 19. To
start, Loines asserts no viable equal-protection theory. For example, he does not allege that
prosecutors sought the enhancement for an improper reason, such as his race or other personal
trait. Armstrong, 517 U.S. at 464 (citation omitted). To be sure, he does highlight statistics
allegedly showing that prosecutors seek the enhancement less often for “youthful offender[s],”
and he points to his young age as a reason why he should not have received it. Appellant’s Br.
22. To the extent he argues that prosecutors discriminated against him based on his age, he
points to no evidence that they sought this enhancement “‘because of,’ not merely ‘in spite of,’”
his youth. Wayte, 470 U.S. at 610 (quoting Personnel Adm’r of Mass. v. Feeney, 442 U.S. 256,
279 (1979)). To the extent he alleges that prosecutors violated equal protection because they
sought this enhancement against him and not similarly aged defendants, his conclusory statistics
fall well short of rebutting “the presumption that a prosecutor has not violated equal protection”
when charging a defendant. Armstrong, 517 U.S. at 465. He does not even explain what the
governing equal-protection standards should be for this type of claim. Nor does he try to show
that his circumstances make him “similarly situated” to the youthful defendants who avoided the
enhancement—as compared to those who received it. Engquist v. Ore. Dep’t of Agric., 553 U.S.
591, 602 (2008).

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Next, Loines asserts no viable due-process theory. He had notice that the government
would pursue this enhancement from the start. See King, 127 F.3d at 488. The government
indicated that his prior federal drug conviction qualified as a “serious drug felony” in its original
and superseding indictments. It also explained that the enhancement would apply at his original
arraignment. And it did so again at his change-of-plea hearing. Next, Loines had an
“opportunity to be heard” over the propriety of the enhancement. Id. (citation omitted). He
argued against it at the evidentiary hearing that the court held to decide whether it should apply.
Lastly, Loines asserts no viable statutory theory. He suggests that the government
delayed filing the required notice under § 851 until the morning that he pleaded guilty. But it
still acted timely. Under the statute’s plain text, the government must file the notice only “before
entry of a plea of guilty”—a time limit that all agree it met here. 21 U.S.C. § 851(a)(1).
In response, Loines asks us to determine whether the statutory enhancement should apply
by balancing the sentencing factors in 18 U.S.C. § 3553(a). But this subsection’s language
indicates that these factors regulate a district court when choosing a defendant’s sentence after a
conviction. Id. They do not regulate a prosecutor when choosing a defendant’s charges before
the conviction. So the section’s restrictions on a district court’s sentencing discretion are
irrelevant to Loines’s challenge to the prosecutor’s charging discretion. See United States v.
Branham, 97 F.3d 835, 847–48 (6th Cir. 1996).
Loines next suggests that the government’s decision to seek the enhancement
contradicted the Department of Justice’s internal guidance. That guidance suggests that
prosecutors should decline to file the enhancement when (among other things) the defendant’s
crime involved no violence or firearms, the defendant did not have a managerial role, and the
defendant’s criminal history did not include personal involvement in distributing large amounts
of drugs. Even if this guidance applies despite Loines’s two prior drug convictions, it does not
grant him any enforceable rights. See United States v. Strong, 844 F.3d 133, 136 (2d Cir. 2016)
(per curiam); United States v. Johnson, 628 F. App’x 124, 131 (3d Cir. 2015); see also United
States v. Santos, 612 F. App’x 376, 377 (6th Cir. 2015) (per curiam); United States v. Nagy, 760
F.3d 485, 490 (6th Cir. 2014). The guidance merely channels prosecutorial discretion in the

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executive branch; it does not provide a basis for a challenge in the judicial branch. See Strong,
844 F.3d at 136.
At bottom, Loines makes a full-scale attack on the traditional discretion that prosecutors
have exercised when deciding whether to seek a statutory enhancement. Appellant’s Br. 17. But
constitutional structure and judicial precedent alike require us to reject this attack.
3. Vindictive Prosecution. Relatedly, Loines argues that the prosecutors acted
vindictively because they sought the statutory enhancement to punish him for exercising his
rights in a prior criminal case. He did not assert this claim below, so we review it under the
plain-error standard. See United States v. Young, 847 F.3d 328, 361 (6th Cir. 2017). And he has
failed to establish any “error, let alone a plain one.” United States v. Lear, 90 F.4th 519, 531
(6th Cir. 2024).
The Due Process Clause bars federal prosecutors from “depriv[ing]” criminal defendants
of their “liberty” without providing them “due process of law[.]” U.S. Const. amend. V. The
Supreme Court has interpreted this text to bar prosecutors from vindictively punishing criminal
defendants for exercising their legal rights. See Goodwin, 457 U.S. at 372; Bordenkircher v.
Hayes, 434 U.S. 357, 363 (1978). So if the prosecution seeks a longer prison sentence on a
retrial because of the defendant’s successful appeal after the first trial, it would violate due
process. See North Carolina v. Pearce, 395 U.S. 711, 723–24 (1969).
But defendants often will have trouble proving that prosecutors harbored such a
retaliatory motive. After all, prosecutors routinely seek to impose punishment for a “legitimate”
reason: because the defendant committed a crime. Goodwin, 457 U.S. at 372–73. The Court has
thus sometimes relieved defendants of the burden to prove actual vindictiveness. See id. at 373.
In some situations, it will “presume” that prosecutors acted with an “improper motive” when
imposing more punishment after a defendant exercised a legal right. Id.; see Alabama v. Smith,
490 U.S. 794, 798–99 (1989). The Court applies this presumption if a “realistic likelihood of
‘vindictiveness’” exists. Blackledge v. Perry, 417 U.S. 21, 27 (1974). It has found such a
likelihood, for example, when prosecutors sought more serious charges after a defendant
exercised his right to appeal a conviction for less serious ones. See id. at 27–28. And we have

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found that such a likelihood existed when prosecutors charged a more serious crime after the
defendant successfully moved to suppress key evidence. See United States v. LaDeau, 734 F.3d
561, 567–70 (6th Cir. 2013).
At the same time, the Court has made clear that this presumption of vindictiveness has a
“limited” scope and that a defendant must prove actual vindictiveness when it does not apply.
See Smith, 490 U.S. at 799. So it has refused to apply such a presumption when prosecutors
brought more serious charges after the defendant refused to plead guilty and exercised his right
to a jury trial. See Goodwin, 457 U.S. at 381–84. And we have held that the presumption does
not apply when the government filed a notice seeking a statutory enhancement after the parties’
plea negotiations collapsed and defendants chose to stand trial. See Young, 847 F.3d at 361–62;
United States v. Zolicoffer, 570 F. App’x 540, 543–44 (6th Cir. 2014) (per curiam).
Applying these principles here, Loines argues that prosecutors sought the statutory
enhancement on unconstitutional grounds: that he exercised his right to appeal in his earlier
federal case. In that case, the district court first sentenced Loines to 93 months’ imprisonment.
See United States v. Loines, 56 F.4th 1099, 1105 (6th Cir. 2023). On appeal, however, we
reversed the denial of his motion to suppress certain evidence. See id. at 1111. Loines pleaded
guilty on remand, and the district court sentenced him to time served (about 36 months) in April
2023. According to Loines, the prosecutors in the current case sought the statutory enhancement
because of his successful appeal in that earlier one. But he points to no proof that the
prosecutors harbored actual vindictiveness against him because of this earlier appeal. Rather, he
claims these facts trigger a presumption of vindictiveness.
He is mistaken. As a general matter, Loines cites no case in which a court has used a
defendant’s exercise of some legal right in an unrelated earlier case to presume that a prosecutor
acted vindictively in a second case involving new criminal conduct. At most, we have suggested
that a presumption might arise if prosecutors brought a perjury prosecution based on the
defendant’s testimony in an earlier case that ended in an acquittal. See United States v. Eddy,
737 F.2d 564, 571–72 (6th Cir. 1984). There, though, the second perjury prosecution grew out
of the earlier case. See id. When, by contrast, the second case involves unrelated conduct, we
see “good reason to be cautious before adopting an inflexible presumption of prosecutorial

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vindictiveness[.]” Goodwin, 457 U.S. at 381. The second case’s charges (and potential
punishments) more likely arise from the prosecutor’s analysis of the “nature and extent” of the
new criminal conduct than from whatever rights the defendant exercised in the earlier case.
Smith, 490 U.S. at 801.
As a specific matter, Loines has met neither of our requirements to trigger this
presumption: that the prosecutor had a “stake” in discouraging him from exercising his legal
rights and that the prosecutor acted in an “unreasonable” way. United States v. Howell, 17 F.4th
673, 687 (6th Cir. 2021) (quoting LaDeau, 734 F.3d at 566). For starters, what “stake” did the
prosecutors in this case have in deterring Loines from exercising a legal right in the earlier case?
United States v. Andrew, 633 F.2d 449, 454 (6th Cir. 1980) (en banc). When they filed the
current charges, the earlier case had been closed for months. And the prosecutors had no need to
deter any rights in the current case because they filed the § 851 notice after Loines had already
expressed his intent to plead guilty to all charges.
Next, the prosecutors did not “unreasonabl[y]” seek the statutory enhancement. Howell,
17 F.4th at 687 (quoting LaDeau, 734 F.3d at 566). To the contrary, they reasonably sought
greater punishment because Loines returned to drug trafficking only months after his release
from prison. A shorter sentence thus had not adequately deterred him. And the prosecution’s
decision to file the § 851 notice against Loines but not against other defendants “does not raise
an inference of misconduct” because discretion inheres in § 851. Zolicoffer, 570 F. App’x at
544.
Loines responds by citing LaDeau. There, the district court granted a defendant’s motion
to suppress. LaDeau, 734 F.3d at 564. The prosecution then filed a superseding indictment
charging a more serious crime based on evidence it had in its possession from the beginning. Id.
at 564–65. We found that it had a “stake” in the defendant’s exercise of his rights because the
suppression ruling had “inflicted a mortal blow” on its case. Id. at 568–69. And we found the
filing of the substitute charge unreasonable because it relied “on the same” conduct but carried
harsher penalties. Id. at 570–71. Here, by contrast, prosecutors brought charges against Loines
in a different case based on new conduct. The two cases look nothing alike.

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No. 24-4056 United States v. Loines Page 14
4. Finality of Prior Offense. Loines lastly argues that the conviction for his prior federal
drug offense had not become “final” when he committed his current offenses. This fact would
mean that the district court could not increase his statutory minimum sentence because the
serious-drug-felony enhancement applies only if he committed his current offenses “after [his]
prior conviction for a serious drug felony . . . [had] become final[.]” 21 U.S.C. § 841(b)(1)(B).
But our precedent dooms this claim. We have held that a conviction becomes “final”
when a defendant’s time to appeal the judgment of conviction “has expired.” United States v.
Miller, 434 F.3d 820, 823 (6th Cir. 2006); see also United States v. Corona, 493 F. App’x 645,
655 (6th Cir. 2012). Here, the district court in Loines’s prior federal case entered its judgment
on April 18, 2023. His time to file a direct appeal thus expired on May 2, 2023. See Fed. R.
App. P. 4(b). But he did not appeal. And when pleading guilty, Loines admitted that his current
offenses started “on or about August 25, 2023” (as alleged in the indictment). Plea Tr., R.78,
PageID 583–85. So Loines’s prior serious-drug-felony conviction became final before he began
his current drug crimes. Miller, 434 F.3d at 823.
In response, Loines does not dispute these facts. He instead disputes the law. He argues
that a prior conviction does not become final until a defendant has completed all the punishment
for that offense. And Loines remained on supervised release for this past offense when he
committed his current ones. But our precedent ties finality to the time to appeal, not the
completion of sanctions. See Miller, 434 F.3d at 823. This claim thus rests on a legal mistake.
One last point. Loines at times suggests that the Constitution requires a jury (not a judge)
to answer this finality question too. Even if he preserved this claim, we would find any
constitutional error harmless for the same reasons that we found the error harmless on the other
underlying factual questions. Under a proper view of the law, the facts are “uncontested”: his
prior conviction was final. Lee, 100 F.4th at 489 (citation omitted). So Loines would have still
pleaded guilty if he had known that a jury must resolve this finality question, and any rational
jury would have found the conviction final. See Greer, 593 U.S. at 508; Thomas, 142 F.4th at
418.

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No. 24-4056 United States v. Loines Page 15
B. Career-Offender Enhancement
Loines lastly contends that he was not a “career offender” subject to the increased
punishment in U.S.S.G. § 4B1.1(b). To qualify as a “career offender,” Loines must have had
two prior felony convictions for “either a crime of violence or a controlled substance offense.”
Id. § 4B1.1(a). All agree that his prior federal drug conviction fell within the definition of a
“controlled substance offense” in U.S.S.G. § 4B1.2(b). But Loines argues that his prior drug-
trafficking conviction under Ohio Revised Code § 2925.03(A)(2) does not qualify as a
controlled-substance offense. In his view, this Ohio statute covers more conduct than the
guidelines definition and so categorically falls outside that definition.
Our caselaw also dooms this claim. In United States v. Smith, 960 F.3d 883 (6th Cir.
2020), we held that Ohio Revised Code § 2925.03(A)(2) “falls safely within” § 4B1.2(b)’s
definition of a controlled-substance offense. Id. at 889. Since Smith, we have repeatedly
rejected efforts to distinguish that binding precedent. See United States v. Hoyle, 148 F.4th 396,
407 (6th Cir. 2025); United States v. Johnson, 2023 WL 8651268, at *3 (6th Cir. Dec. 14, 2023);
United States v. Sharp, 2023 WL 3966739, at *9–10 (6th Cir. June 13, 2023). Loines’s
conclusory arguments also do nothing to distinguish Smith, so we must follow it here too.
We affirm.

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