United States of America v. Christopher Michael Sledd

United States Court of Appeals
For the Eighth Circuit
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No. 24-2046
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United States of America
Plaintiff - Appellee
v.
Christopher Michael Sledd
Defendant - Appellant
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Appeal from United States District Court
for the Western District of Missouri - Jefferson City
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Submitted: January 15, 2025
Filed: August 21, 2025
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Before GRASZ, STRAS, and KOBES, Circuit Judges.
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STRAS, Circuit Judge.
Are drug conspiracies and possession always “committed on occasions
different from one another”? 18 U.S.C. § 924(e)(1). The answer could amount to a
decade-or-more difference in Christopher Sledd’s sentence. We conclude that there

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are no bright-line rules in this area, but that the one the district court1 adopted turned
out to be harmless on these facts.
I.
A reported “altercation” led to the discovery of a loaded pistol in a U-Haul
truck. Standing nearby was Sledd, who had a box of matching ammunition. He
pleaded guilty to illegally possessing the firearm. See id. § 922(g)(1) (prohibiting
possession by felons).
The default statutory-maximum sentence at the time was 10 years in prison.
See id. § 924(a)(2) (2018). It increased, however, for anyone with three or more
“previous convictions . . . for violent felon[ies] or . . . serious drug offense[s].” Id.
§ 924(e)(1). In those circumstances, the minimum jumped to 15 years, and the
maximum became life. See id.; Johnson v. United States, 576 U.S. 591, 593 (2015).
Sledd acknowledged having four prior convictions but reserved the right to
challenge whether they count.
The government conceded that one does not. As for two of the others, Sledd’s
position is that they combine into one because they were committed on the same
“occasion[].” 18 U.S.C. § 924(e)(1). Both were drug offenses: the first a conspiracy
to distribute cocaine base, see 21 U.S.C. §§ 841(a)(1), 846, and the other the
possession and distribution of it, see id. § 841(a)(1). Based on a prior case of ours
involving similar offenses, the district court disagreed. See United States v. Melbie,
751 F.3d 586, 589 (8th Cir. 2014). These two offenses, plus an uncontested third,
made three, so Sledd’s sentence was 20 years rather than 10 years or less. See 18
U.S.C. § 924(e)(1). Our review of whether each conviction counts separately is de
novo. See United States v. Stowell, 82 F.4th 607, 609 (8th Cir. 2023) (en banc).
1 The Honorable Brian C. Wimes, United States District Judge for the Western
District of Missouri.

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II.
To get to three, the government had to prove that Sledd’s two “serious drug
offense[s]” were committed “on occasions different from one another.” 18 U.S.C.
§ 924(e)(1). Whether they were is a “multi-factored,” Wooden v. United States, 595
U.S. 360, 369 (2022), “intensely factual . . . inquiry,” Erlinger v. United States, 602
U.S. 821, 828 (2024). The factors include whether they “were committed close in
time, whether they were committed near to or far from one another, and whether
[they] were similar or intertwined in purpose or character.” Id. (citation omitted).
The district court did not consider any of them. Rather, it compared “the facts
here” with Melbie and reasoned that if the conspiracy and possession offenses there
were committed on different occasions, then so were the ones here, regardless of the
specific circumstances. Unlike the element-by-element approach for determining if
an offense qualifies as a “violent felony” or “serious drug offense,” 18 U.S.C.
§ 924(e)(1); see United States v. Lung’aho, 72 F.4th 845, 848 (8th Cir. 2023)
(describing the categorical approach), the different-occasions determination looks at
the when, where, and why of the crimes, see Stowell, 82 F.4th at 609. The details
matter, in other words, so it follows that drug conspiracy and possession are not
always “committed on occasions different from one another.” 18 U.S.C.
§ 924(e)(1). Melbie itself recognizes as much.2
Two Melbie-like examples illustrate why a bright-line rule does not work. At
one extreme, suppose that two dealers meet on a street corner and discuss selling
drugs together. But before they do, they want to do a test run. Just minutes later,
and on the same street corner, they make the sale that seals the deal. Under Wooden,
2 The two drug offenses in Melbie counted separately because the “possession
offense was a punctuated event of limited duration” within the larger drug
conspiracy, 751 F.3d at 590, which is another way of saying they were not
“committed close [enough] in time,” Wooden, 595 U.S. at 369. The same underlying
facts without a “time lapse,” however, may have produced a different result. Melbie,
751 F.3d at 590.

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there would be a strong argument that the conspiracy and sale happened on the same
“occasion.” 595 U.S. at 367 (discussing “the ordinary meaning” of the word and
noting that a single occasion may “include temporally discrete offenses”). The
offenses would have been “committed close in time, in an uninterrupted course of
conduct” and at the same “location,” as part of “a common scheme.” Id. at 369. The
when, where, and why all line up.
At the other extreme, suppose that the two of them sell drugs together months
later, perhaps on a different street corner, long after their conspiracy began. Melbie
would describe the sale as a “punctuated event within that conspiracy.” 751 F.3d at
589. A reasonable observer would think the conspiracy and the sale are different
“event[s], occurrence[s], happening[s], or episode[s]” because the when and where
no longer match. Wooden, 595 U.S. at 367; cf. Melbie, 751 F.3d at 590 (comparing
the relative length of the conspiracy to the “punctuated” nature of the possession
offense). Same people, same conspiracy, and same crimes, but one would involve
offenses committed on “occasions different from one another” and the other would
not. 18 U.S.C. § 924(e)(1); see Wooden, 595 U.S. at 369–70 (“In many cases, a
single factor—especially of time or place—can decisively differentiate occasions.”).
These examples show why bright-line rules are a poor fit for such a “fact-laden task.”
See Erlinger, 602 U.S. at 834.
A bright-line rule is also inconsistent with the Sixth Amendment jury-trial
right recognized in Erlinger. See id. at 835. If a district court could simply find a
case with similar facts and conclude as a matter of law that two crimes were
committed on different occasions, then there would be nothing left for the jury to
decide. See id. It would effectively take a jury question and put it right back in the
hands of the court, where the Supreme Court just decided it does not belong. See id.
at 834 (“Judges may not assume the jury’s factfinding function for
themselves . . . .”); United States v. Perry, 908 F.3d 1126, 1134 (8th Cir. 2018)
(Stras, J., concurring) (“A finding that [the defendant] committed his past crimes on
different occasions exposes him to a longer sentence, so the jury should make the
finding, not the court.”); see also United States v. U.S. Gypsum Co., 438 U.S. 422,

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447 (1978) (holding that a bright-line legal conclusion “invade[s] [the] factfinding
function”); Morissette v. United States, 342 U.S. 246, 275 (1952) (“A conclusive
presumption . . . would prejudge a conclusion which the [factfinder] should reach of
its own volition.”).
III.
The decisionmaker here was the district court, not a jury, but only because
Sledd pleaded guilty and agreed to have the court decide whether he had three
“previous . . . serious drug offense[s].” 18 U.S.C. § 924(e)(1). It did not do,
however, what the jury would have done, which was consider the three Wooden
factors before deciding whether the different-occasions requirement had been
satisfied. See Erlinger, 602 U.S. at 834. Nor did it make any findings.
Even so, we can still affirm if the error was harmless. See Stowell, 82 F.4th
at 610. Although the government does not urge us to go down that route, we can do
so if the record “warrants a harmless[-]error ruling that is beyond reasonable
argument.” United States v. Hansen, 944 F.3d 718, 724 n.3 (8th Cir. 2019) (citation
omitted); see United States v. Stoney End of Horn, 829 F.3d 681, 686 (8th Cir. 2016)
(explaining that “[a] non-constitutional error is harmless if we are confident that [it]
did not influence the [factfinder] or had only a slight influence on the verdict”).
Here, it does.
Sledd’s plea agreement provides all the facts we need. It says the drug
distribution occurred “on May 5, 1998, in Boone County, Missouri,” when Sledd
sold “at least 50 grams of . . . cocaine base.” It also discusses that he had first
conspired to sell drugs almost two years earlier, “beginning on June 1, 1996, . . . in
Boone, Cole, and Callaway Counties.” Even though these offenses “share a
common scheme or purpose” and possibly even a “[p]roximity of location,” they are
not part of “the same criminal event,” Wooden, 595 U.S. at 369, because the
conspiracy had been ongoing for nearly two years before the “discrete” sale
occurred, Melbie, 751 F.3d at 587; see Wooden, 595 U.S. at 370 (noting that courts

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“nearly always treat[] offenses as occurring on separate occasions if a person
committed them a day or more apart”); Stowell, 82 F.4th at 609 (holding that a
“multi-day gap separating [two] offenses strongly support[s]” a finding they
occurred on different occasions). As charged and confirmed through the facts in the
plea agreement, there is no “reasonable argument” that these two offenses were
committed on the same occasion. Hansen, 944 F.3d at 724 n.3.
IV.
We accordingly affirm the judgment of the district court.
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