United States Court of Appeals

For the Eighth Circuit 

___________________________

No. 21-2791

___________________________ 

Derrick Anthony Stewart

 Petitioner - Appellant

v.

United States of America

 Respondent - Appellee

____________

Appeal from United States District Court 

for the Southern District of Iowa - Central 

____________ 

Submitted: April 13, 2022

Filed: August 5, 2022

[Unpublished]

____________ 

Before SHEPHERD, ERICKSON, and STRAS, Circuit Judges. 

____________

PER CURIAM. 

Derrick Stewart appeals following the district court’s1 denial of his motion to 

vacate or set aside his sentence under 28 U.S.C § 2255. Because Stewart cannot 

show counsel performed deficiently at the time of his sentencing, we affirm. 

1

The Honorable Stephanie M. Rose, Chief Judge, United States District Court

for the Southern District of Iowa.
-2- 

On November 13, 2017, Stewart pled guilty to conspiracy to distribute a 

substance containing a detectable amount of heroin, in violation of 21 U.S.C. §§ 

841(a)(1), (b)(1)(A), 846 and 851; and possession of a firearm in furtherance of a 

drug trafficking crime, in violation of 18 U.S.C. § 924(c). Stewart had a prior Illinois 

felony drug conviction, which the government gave notice of under 21 U.S.C. § 851. 

In March 2018, the court sentenced Stewart to a mandatory minimum sentence of 

240 months’ imprisonment on the drug count and 60 months on the firearms count, 

to run consecutively. Without the § 851 enhancement, Stewart’s guidelines range 

would have been 168 to 210 months, plus 60 months on the § 924(c) count to run 

consecutively. Stewart unsuccessfully appealed the denial of his suppression 

motion. United States v. Stewart, 761 F. App’x 659 (8th Cir. 2019) (unpublished). 

On December 5, 2019, Stewart filed a motion to set aside or vacate his 

sentence under § 2255 claiming for the first time that the § 851 enhancement was 

improper, because under the categorical approach the Illinois statute of conviction 

was broader than the federal definition of a felony drug offense. Stewart also 

claimed ineffective assistance of counsel. The district court denied the motion but 

granted a certificate of appealability. 

We review de novo the district court’s denial of a § 2255 motion to vacate or 

set aside a sentence. Jackson v. United States, 956 F.3d 1001, 1006 (8th Cir. 2020). 

“[A] petitioner may not raise an issue before the district court for the first time in a 

§ 2255 motion if the issue was not presented on direct appeal from the conviction.” 

Jennings v. United States, 696 F.3d 759, 762-63 (8th Cir. 2012). To prevail on a 

claim that has been procedurally defaulted, a defendant must demonstrate either: (1) 

cause that excuses the default and actual prejudice, or (2) that he is actually innocent. 

Bousley v. United States, 523 U.S. 614, 622 (1998). As the district court concluded, 

actual prejudice can be shown here because Stewart likely would have received a 

much lower sentence without the § 851 enhancement and resulting mandatory 

minimum. To obtain relief, Stewart must prevail on his ineffective assistance of 

counsel claim that would operate to excuse the default.
-3- 

In 2008, we held that a conviction under Illinois 570/402(c), the same statute 

under which Stewart was convicted, was a predicate conviction to support a 

sentencing enhancement under § 851. United States v. Hawkins, 548 F.3d 1143, 

1150 (8th Cir. 2008); see also 720 Ill. Comp. Stat. 570/402(c) (2000). Although the 

decision did not mention the categorical approach, it did look broadly at the 

definition of “felony drug offense” in § 802(44) to determine that the Illinois statute 

“fits within th[at] definition.” Id. When Stewart was sentenced on March 19, 2018, 

Hawkins was the governing law in our circuit. 

More than one year after Stewart’s sentencing, we held that the categorical 

approach should be used to determine whether a statute qualifies as a predicate 

conviction under certain federal sentencing enhancement schemes, including the 

Controlled Substances Act (“CSA”). United States v. Boleyn, 929 F.3d 932, 936 

(8th Cir. 2019). We evaluate counsel’s performance from counsel’s perspective at 

the time and ignore the “distorting effects of hindsight.” Love v. United States, 949 

F.3d 406, 410 (quoting Davis v. United States, 858 F.3d 529, 534 (8th Cir. 2017)); 

see Brown v. United States, 311 F.3d 875, 878 (8th Cir. 2002) (“[C]ounsel’s decision 

not to raise an issue unsupported by then-existing precedent did not constitute 

ineffective assistance.”). Because under the law of our circuit at the time of 

Stewart’s sentencing his prior conviction under § 570/402(c) was a predicate 

conviction under § 851, Stewart’s counsel did not perform deficiently. 

The judgment of the district court is affirmed.

______________________________