United States Court of Appeals

For the Eighth Circuit 

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No. 22-2148

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United States of America

 Plaintiff - Appellee

v.

Kyle Anthony Doolin

 Defendant - Appellant

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Appeal from United States District Court 

for the Northern District of Iowa

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Submitted: March 17, 2023

Filed: July 11, 2023

[Unpublished]

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Before SHEPHERD, ERICKSON, and GRASZ, Circuit Judges. 

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PER CURIAM.

Kyle Doolin pled guilty to one count of possession with intent to distribute a 

controlled substance (methamphetamine) near a protected location (Coe College) 

after having been previously convicted of a felony drug offense. See 21 U.S.C. 

§§ 841(a)(1) and (b)(1)(B), 851, and 860(a). Relying on two 1998 convictions 
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related to the possession and distribution of cocaine, the district court1 determined 

Doolin was a career offender under United States Sentencing Guidelines Manual 

(“Guidelines”) § 4B1.1(b)(1), increased Doolin’s total offense level by nine levels, 

and sentenced him to 157 months of imprisonment. Doolin challenges application 

of the career offender enhancement and the reasonableness of his sentence.

The district court determined Doolin’s Guidelines range was 157 to 196

months of imprisonment based on his total offense level and a category VI criminal 

history. Doolin argues his total offense level would be lower, resulting in a 

significantly lower sentence, absent the § 4B1.1(b)(1) enhancement. Doolin 

contends the two 1998 convictions should be considered a single conviction because

the earlier state offense is merely relevant conduct for the federal conviction and the 

state conviction is outside the 15-year lookback period. Additionally, Doolin argues 

his sentence was greater than necessary when considering his struggles with 

substance abuse and poor health. 

 The district court sentenced Doolin to the bottom of the sentencing range. 

Nevertheless, it noted, “The defendant’s criminal history is extremely troubling . . . . 

[H]e has 59 adult convictions. 9 of those were violent.” The district court stated,

It is one of the worst criminal histories I’ve seen as a judge. The 

defendant has earned the label of career offender in the commonsense 

term—or meaning of that term. In that vein, I would just note that if I 

was in error in my calculation of the defendant being a career offender 

under the guidelines, I would vary upward to the same level, finding 

that he should be at the same level as a career offender based on the

extreme criminal history he has, even if I was wrong in the 

technicalities of the guideline calculation of whether he meets the 

definition of a career offender.

1

The Honorable C.J. Williams, United States District Judge for the Northern 

District of Iowa.
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The district court applied the career offender enhancement after determining 

the two convictions were separate based on an intervening arrest between the 

charges, which were filed separately in state and federal courts, resulting in separate 

sentencing dates. The district court also considered Doolin’s argument about the 

age of the convictions, determining that although the records were “muddled,” the 

government met its burden to show it was more likely true than not “the defendant 

had his parole revoked and he was sentenced for a period of time within the 15-year

window applicable to the career offender status.” 

We discern no error in the district court’s determinations. Nevertheless, we 

hold that even assuming the career offender enhancement was improper, it was 

harmless error. See Fed. R. Crim. P. 52(a). The enhancement increased Doolin’s 

offense level under the Guidelines. However, even if the district court miscalculated 

Doolin’s Guidelines sentence, we have said this is harmless error “when the district 

court indicates it would have alternatively imposed the same sentence even if a lower 

guideline range applied.” United States v. Richardson, 40 F.4th 858, 868 (8th Cir. 

2022) (quoting United States v. Martinez, 821 F.3d 984, 988–89 (8th Cir. 2016)). 

Here the district court said that, based on Doolin’s “extreme criminal history” and 

the sentencing factors of 18 U.S.C. § 3553(a), it would have imposed the 157-month 

sentence because “if I was in error in my calculation of the defendant being a career 

offender under the guidelines, I would vary upward to the same level.” Accordingly, 

we find it “clear that the judge based the sentence . . . on factors independent of the 

Guidelines” and thus any miscalculation of Doolin’s Guidelines sentence was 

harmless. See Molina-Martinez v. United States, 578 U.S. 189, 200 (2016); see also

United States v. Williams, 968 F.3d 907, 912 (8th Cir. 2020). Therefore, Doolin’s 

challenge to the district court’s application of a career offender enhancement fails. 

Doolin also contends his sentence was unreasonable because the district court 

failed to grant him a downward variance based on his substance abuse issues and 

poor health. We review the substantive reasonableness of a sentence for abuse of 

discretion. United States v. Scanlan, 65 F.4th 406, 409 (8th Cir. 2023); but see

United States v. Dailey, 958 F.3d 742, 746 (8th Cir. 2020) (“Typically, we will not 
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review a district court’s refusal to grant a downward departure.”). Relevant here, a

sentencing court does abuse its discretion by “failing to consider a relevant factor 

that should have received significant weight” or “considering only the appropriate 

factors but in weighing them, committing a clear error of judgment.” Scanlan, 65 

F.4th at 409 (quoting United States v. Stoner, 795 F.3d 883, 884 (8th Cir. 2015)). 

Yet, a within-Guidelines-range sentence is presumed reasonable. Id. And the 

“district court has ‘wide latitude’ in weighing the § 3553(a) sentencing factors.” 

United States v. Hamilton, 46 F.4th 864, 871 (8th Cir. 2022) (quoting United States 

v. Nguyen, 829 F.3d 907, 925–26 (8th Cir. 2016)). 

Doolin has not rebutted the presumption that his within-Guidelines sentence 

was reasonable. The district court took into consideration the mitigating factors 

presented by Doolin, including his substance abuse issues and poor health. The 

district court discussed the factors set forth in 18 U.S.C. § 3553(a), including its 

observations that Doolin’s situation was not significantly mitigating to warrant a 

downward departure but would warrant adjusting the sentence to the bottom of the 

Guidelines range. “But ‘simply because the district court weighed relevant factors 

. . . more heavily than [Doolin] would prefer does not mean the district court abused 

its discretion.’” United States v. Sisk, 999 F.3d 631, 636 (8th Cir. 2021) (ellipses in 

original) (quoting United States v. Campbell, 986 F.3d 782, 808 (8th Cir. 2021)). 

Under these circumstances, the sentence was not unreasonable, and we affirm the 

district court’s within-Guidelines-range sentence. 

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