Defining “Import” Under the Career Offender Guideline: Intrastate “Bringing In” Constitutes a Controlled Substance Offense – Stegemann v. United States

Introduction

This commentary examines the Second Circuit’s decision in Stegemann v. United States (23-7712), decided March 20, 2025. Petitioner-Appellant Joshua G. Stegemann sought to amend his sixth § 2255 motion to challenge the use of his 1999 Massachusetts conviction under Mass. Gen. Laws ch. 94C, § 32E(b) as a career offender predicate. He argued that the state statute’s “bringing in” language criminalized conduct broader than the federal guideline’s concept of “import,” and that his counsel had been ineffective for not raising this point at sentencing. The district court denied leave to amend as futile under the law-of-the-case doctrine. The Second Circuit affirmed, holding (1) no change in controlling law or intervening authority justified departure from its prior panel mandate, and (2) under U.S.S.G. § 4B1.2(b)(1), “import” plainly includes bringing a substance in from out of state.

Summary of the Judgment

The appellate court affirmed the district court’s denial of Stegemann’s motion for leave to amend his § 2255 petition. It held:

The proposed amendment simply repeated an argument the Second Circuit had already considered and rejected on direct appeal—namely, that Massachusetts’s “bringing in” provision did not qualify as “import” under the career offender guideline.
The law-of-the-case (mandate rule) bound the district court to follow the earlier panel’s decision unless a “cogent and compelling” reason justified departure—such as an intervening change in law, new evidence, or clear error causing manifest injustice.
No intervening change in controlling law: the First Circuit’s interpretation in Montoya, the Ninth Circuit’s decision in Martinez, and the Massachusetts district court’s grant of relief in Bain did not alter the legal landscape applicable at sentencing.
No clear error or manifest injustice: the plain meaning of “import” encompasses intrastate “bringing in,” and the Jerome presumption against reliance on state definitions did not defeat that meaning.
Accordingly, amendment would have been futile, and the denial of leave to amend was not an abuse of discretion.

Analysis

Precedents Cited

United States v. Montoya (1st Cir. 2016): Held that Mass. Gen. Laws ch. 94C, § 32E(b) is “unarguably a conviction for a controlled substance offense” under the career offender guideline. The Second Circuit relied on Montoya to show that no authority at sentencing supported Stegemann’s novel “bringing in” theory.
United States v. Stegemann (2d Cir. 2022): The prior panel affirmed denial of Stegemann’s initial § 2255 claims, concluding counsel’s failure to raise the “bringing in” argument did not fall below professional norms and could not have changed the outcome.
Burrell v. United States and United States v. Aquart: Articulated the mandate rule and law-of-the-case doctrine that bar relitigation of issues “explicitly or implicitly decided on appeal.”
Littlejohn v. Artuz and Jones v. New York State Division of Military & Naval Affairs: Established that leave to amend under Rule 15(a) must be freely given unless amendment is dilatory, prejudicial, abusive, or futile.
United States v. Bain (D. Mass. 2022): Held that the ACCA’s “serious drug offense” definition did not cover § 32E(b)’s “bringing in” language. The Second Circuit distinguished ACCA’s narrower scope from the Sentencing Guidelines’ broader definition of “import.”
Townsend v. United States and the Jerome presumption: Addressed the interpretive rule that undefined terms in federal law should not be made to depend on heterogeneous state definitions, particularly for “controlled substance.” The court distinguished that context from the ordinary meaning of “import.”
Asgrow Seed Co. v. Winterboer and related Supreme Court authorities on giving undefined statutory words their ordinary meaning.

Legal Reasoning

The Second Circuit’s opinion proceeds in two stages:

Futility and Law-of-the-Case Doctrine: Under the mandate rule, the district court was bound by the prior panel’s decision rejecting the “bringing in” argument unless a recognized exception applied. The exceptions—intervening change in law, new evidence, or clear error/manifest injustice—were not met. Montoya, Bain, and other authority post-dating sentencing were not controlling changes in law at the critical time. The First Circuit’s Montoya ruling, correctly understood, supported qualification of § 32E(b) as a “controlled substance offense” under the guidelines. The letter from the Massachusetts Supreme Judicial Court misidentifying a parallel state subsection did not undermine Montoya’s analysis of § 32E(b).
Interpretation of “Import” in U.S.S.G. § 4B1.2(b)(1): The guideline defines a “controlled substance offense” to include any state or federal law prohibiting “manufacture, import, export, distribution, or dispensing.” The court applied ordinary-meaning principles: “import” means “to bring from a foreign or external source,” which includes out-of-state movement of goods. Unlike ACCA’s “serious drug offense” which focuses on manufacturing and distribution, the guideline’s enumerated terms plainly cover intrastate importation. The Jerome presumption did not override that plain meaning, because “import” here is a general descriptive term, not a technical concept tied exclusively to federal law.

Impact

The decision has two principal effects:

Habeas Practice and § 2255 Amendments: Reinforces that successive or repetitive claims already decided on appeal will be denied as futile absent compelling new circumstances. Practitioners must identify genuine changes in law or fact before seeking leave to amend at late stages.
Career Offender and Controlled Substance Offenses: Clarifies that under U.S.S.G. § 4B1.2(b)(1), the concept of “import” is not limited to international border crossings but encompasses bringing drugs into a jurisdiction from any external source. This interpretation may streamline career offender analyses and reduce challenges to state statutes with “bringing in” provisions.

Complex Concepts Simplified

Law-of-the-Case Doctrine: A principle that once an appellate court decides an issue, trial courts and subsequent panels should not reexamine that same issue unless there is a strong reason (new law, new evidence, clear error).
Mandate Rule: A variant of law-of-the-case that “rigidly binds” lower courts to follow an appellate court’s explicit or implicit directions.
Futility of Amendment: Under Rule 15(a) and habeas practice, a proposed amendment is “futile” if it cannot survive a motion to dismiss—e.g., because it raises a point already rejected as a matter of law.
Career Offender Guideline (§ 4B1.2): Provides an enhanced sentencing guideline range for offenders with two or more prior convictions for controlled substance offenses or crimes of violence.
Jerome Presumption: The interpretive rule that when a statute uses a term found in another federal law, it is presumed to carry the same technical meaning, unless Congress indicates otherwise.
ACCA vs. Guidelines Definitions: The Armed Career Criminal Act’s “serious drug offense” requires manufacturing, distributing, or possession with intent—narrower than the guidelines’ broader list (including import/export).

Conclusion

The Second Circuit’s decision in Stegemann v. United States reiterates two bedrock principles: first, that the law-of-the-case and mandate rule prevent relitigation of issues already decided, absent a compelling ground to revisit them; and second, that the Sentencing Guidelines’ definition of a controlled substance offense includes intrastate importation. As a result, state statutes criminalizing the “bringing in” of drugs from outside the state qualify as predicate offenses under § 4B1.2(b)(1). Moving forward, § 2255 practitioners must carefully assess whether new authority truly alters the legal landscape before seeking amendment, and sentencing courts can apply a uniform, ordinary-meaning interpretation of “import” in career offender cases.