Harris v. United States
| Decision Date | 10 September 2021 |
| Docket Number | 19-3363 |
| Parties | Christopher Harris, Petitioner-Appellant, v. United States of America, Respondent-Appellee. |
| Court | U.S. Court of Appeals — Seventh Circuit |
ARGUED JUNE 3, 2021
Appeal from the United States District Court for the Southern District of Indiana, Indianapolis Division. No 1:18-cv-03105-JMS-DML - Jane Magnus-Stinson, Judge.
Before MANION, WOOD, and BRENNAN, Circuit Judges.
Christopher Harris faced federal drug charges. Counsel advised him that his two prior Indiana cocaine convictions were predicate "felony drug offenses" and could result in a mandatory life sentence. So, Harris entered into a plea agreement and received an agreed-upon 20-year sentence.
Harris now seeks federal habeas corpus relief under 28 U.S.C. § 2255. He argues his counsel was ineffective by not challenging whether those prior drug convictions were predicates, as Indiana law defined cocaine isomers more broadly than federal law. Such an argument, novel then, would succeed today.
Although Harris forfeited this theory of ineffectiveness in the district court, we conclude that it is subject to plain-error review. But because it was objectively reasonable for Harris's counsel not to advise risking a mandatory life sentence to pursue the isomer argument, the district court did not plainly err in ruling that counsel's performance was constitutionally adequate.
Harris was charged in 2016 with possessing with intent to distribute 50 grams or more of methamphetamine. See 21 U.S.C § 841(a)(1) (2010). Because of his prior drug convictions, Harris faced significant sentencing exposure. At the time, the statutory minimum sentence for this crime was 10 years. Id. § 841(b)(1)(A)(viii) (2010). But under that statute, the government could enhance the potential sentence by arguing that two of Harris's prior convictions were felony drug offenses: an Indiana conviction in 2006 for dealing cocaine, see IND. CODE § 35-48-4-1(a) (2006), and an Indiana conviction in 2001 for possessing cocaine, see id. § 35-48-4-6(a) (2001). At that time, one prior "felony drug offense" increased the mandatory minimum sentence to 20 years, while two required a life sentence. See 21 U.S.C. § 841(b)(1)(A)(viii) (2010).
To avoid a life sentence, Harris reached an agreement under Federal Rule of Criminal Procedure 11(c)(1)(C) with the government to plead guilty and accept a sentence of 20 years' imprisonment. Pursuant to that deal, the government filed a notice under 21 U.S.C. § 851 listing only one predicate offense, the 2006 Indiana conviction for dealing cocaine. At a joint change-of-plea and sentencing hearing in October 2017, the district court confirmed that "the basis" for Harris's plea was his (and his counsel's) understanding that he was avoiding a mandatory life sentence due to the government's agreement not to introduce his 2001 Indiana cocaine possession conviction. The court also confirmed that Harris knew he was waiving his right to challenge his conviction and sentence, except as to ineffective assistance of counsel.
Harris did not appeal. Instead, acting pro se, he timely moved to vacate his sentence pursuant to § 2255. Harris asserted his counsel had been ineffective "during plea bargaining for the failure to challenge the § 851 enhancement towards the prior dealing in cocaine case." In his petition, Harris attempted to explain:
Thomas Brodnick represented me during plea negotiations. My prior 2006 conviction for dealing in cocaine or narcotic was used to enhance my sentence under the statute from 10-years to 20-years minimum. This conviction was from when I was set up to bring someone some drugs when in fact, I was set up to be robbed. I had to fight for my life were [sic] I could have died if I did not defend myself. The State Statute 35-484-1 was used under Indiana state laws and the case was converted to have me plead guilty to dealing in cocaine or narcotic and the possession cocaine of [sic] narcotic and dealing in cocaine or narcotic was dismissed by the State for my plea of guilty.
The government read this submission as an argument that Harris's counsel should have challenged the sufficiency of the evidence supporting the 2006 conviction. In reply Harris reiterated his initial statements and asserted that his 2006 conviction "is not permissible to be used because of its unconstitutional nature in light of Descamps v. United States, 570 U.S. 254 (2013)."
The district court denied Harris's § 2255 motion. To that court, Harris had raised two theories of ineffective assistance: that his counsel should have (1) challenged the sufficiency of the evidence underlying his prior state conviction, and (2) argued that conviction did not qualify as a predicate offense after Descamps. The first theory failed because a defendant cannot collaterally attack a state conviction during federal sentencing unless it was obtained in a proceeding where the defendant was denied his right to counsel, which Harris did not allege. See Custis v United States, 511 U.S. 485, 496-97 (1994). On the second theory, the district court decided that a Descamps-based argument would have failed at sentencing because Harris's 2006 Indiana conviction for dealing cocaine fell within the definition of a "felony drug offense." That conviction was based "on conduct relating to narcotic drugs" and was punishable by a minimum of six years in prison.
Soon after judgment, two legal developments clarified whether Harris's prior convictions fit the definition of a "felony drug offense." First, in United States v. De La Torre, 940 F.3d 938, 952 (7th Cir. 2019), this court held that a different Indiana drug crime was not a "felony drug offense" because the state's definition of the controlled substance involved- including, among other terms, its definition of an "isomer"- applied more broadly than federal law. Less than a year later, this court decided in United States v. Ruth, 966 F.3d 642, 647, 650 (7th Cir. 2020), that an Illinois conviction for possession with intent to deliver cocaine was not a "felony drug offense" because Illinois's definition of cocaine-like Indiana's-in-cluded optical, positional, and geometric isomers, and therefore was broader than federal law.
Harris requested a certificate of appealability, which this court granted, as to whether his counsel was ineffective for failing to argue that his prior conviction did not qualify as a predicate "felony drug offense" because IND. CODE §§ 35-481-7 and 35-48-2-8(b) (2006) defined cocaine more broadly than the federal code, 21 U.S.C. §§ 802(17)(C)(D). The parties were also asked to address whether Harris waived this theory of ineffectiveness by insufficiently developing it in the district court.
Section 2255 provides relief for a federal prisoner if their sentence "was imposed in violation of the Constitution or laws of the United States, or [if] the court was without jurisdiction to impose such sentence, or [if] the sentence was in excess of the maximum authorized by law." 28 U.S.C. § 2255(a). "Relief under § 2255 is available 'only in extraordinary situations, such as an error of constitutional or jurisdictional magnitude or where a fundamental defect has occurred which results in a complete miscarriage of justice.'" United States v Coleman, 763 F.3d 706, 708 (7th Cir. 2014) (quoting Blake v. United States, 723 F.3d 870, 878-79 (7th Cir. 2013)).
When considering the denial of a federal prisoner's § 2255 motion, we typically review the district court's legal conclusions de novo. Reyes v. United States, 998 F.3d 753, 757 (7th Cir. 2021). But in the district court, Harris did not properly present the theory of ineffective assistance that he pursues before us. His opening motion was barely comprehensible; at most, it asserted that counsel was ineffective because he should have challenged his 2006 conviction, but it provided no clear basis for a challenge.
Harris did raise the Descamps-based argument in his reply brief, however. He says his citation to Descamps-which requires that a state predicate offense fall within the federal def-inition-simply "clarified" the claim he raised initially in his § 2255 motion. But that did not preserve the issue for appeal. A movant must present his specific theory of ineffectiveness in the district court, see Rittenhouse v. Battles, 263 F.3d 689, 694-95 (7th Cir. 2001), with enough detail to allow the government to respond to it, see Wright v. United States, 139 F.3d 551, 553 (7th Cir. 1998). Harris's opening motion did not alert the government that he wished his counsel had raised a categorical challenge to his 2006 conviction's predicate-offense status. So, unsurprisingly, the government did not respond as to whether Harris's prior conviction fit the federal definition of a "felony drug offense."
Just so, the government is incorrect to argue that Harris did not raise this issue in reply. Construing Harris's pro se briefing liberally as we must, see McNeil v. United States, 508 U.S. 106, 113 (1993), the citation to Descamps sufficiently raised the claim that counsel should have made a categorical challenge. And a categorical challenge requires comparing not just the elements of a statute but also "the provisions it cross-referenc[es]." Brock-Miller v. United States, 887 F.3d 298, 310 (7th Cir. 2018). Here, that includes the drug definition.
Harris urges that any failure by him to preserve this issue is a forfeiture, not waiver. "Forfeiture results from 'inadvertence, neglect, or oversight.'" Bourgeois v. Watson, 977 F.3d 620, 631 (7th Cir. 2020) (quoting Henry v. Hulett, 969 F.3d 769, 786 (7th Cir. 2020) (en banc)). Harris contends his failure in the district court was inadvertent because there he proceeded pro se. The government...
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