Drawing the Line Between “Misrepresentation” and “Marketing” Under §2D1.1(b)(13): The Sixth Circuit’s Textual Blueprint in United States v. Matthews & Livingston

Introduction

This consolidated appeal arises from a Lexington, Kentucky drug-trafficking enterprise distributing fentanyl and methamphetamine. Daniel Matthews, a supplier, pleaded guilty to drug and firearm offenses; Markel Levail Livingston, a downstream seller, pleaded guilty to a drug conspiracy. The district court sentenced Matthews to 228 months and Livingston to 74 months. Both challenged the procedural reasonableness of their sentences, focusing on the district court’s application of U.S.S.G. § 2D1.1(b)(13), a four-level enhancement for defendants who “knowingly misrepresented or knowingly marketed” fentanyl as another substance. Livingston additionally asserted ineffective assistance of counsel at sentencing, claimed error in the denial of a downward departure for diminished capacity, and challenged a special condition of supervised release requiring searches of electronic devices.

In a comprehensive textual analysis, the Sixth Circuit clarifies the ordinary meaning of “knowingly,” “misrepresent,” and “market” for purposes of § 2D1.1(b)(13). The court draws a bright-line distinction: “misrepresentation” requires a false assertion communicated through words, while “marketing” encompasses the act of selling or offering fentanyl as another drug, including when the product is designed to look like a different pharmaceutical. The court further holds that buyer knowledge does not defeat the “marketing” enhancement where the volume and circumstances indicate foreseeable resale to unsuspecting downstream purchasers—a rationale aligned with the Sentencing Commission’s stated purpose in adopting the enhancement.

Summary of the Opinion

• Guidelines enhancement under § 2D1.1(b)(13) upheld for both defendants.
  • Matthews: The court affirmed the “knowingly misrepresented” prong based on reliable hearsay from an identified cooperating witness that Matthews represented fentanyl pills as “Percocet 30 mg.” Because misrepresentation requires a false assertion via words, and Matthews knew the pills were fentanyl, the enhancement applied.
  • Livingston: The court affirmed the “knowingly marketed” prong. Livingston admitted he knew the pills contained fentanyl and that they were designed to look like oxycodone 30s; his sales in substantial quantities supported that the pills were marketed (sold) as something else. The court emphasized that initial buyer awareness does not negate the enhancement where resale to unsuspecting downstream buyers is foreseeable.
• Hearsay at sentencing: The district court did not plainly err by relying on an identified cooperator’s statement; sentencing hearsay is admissible if minimally reliable, and corroboration is only required for unidentified informants.
• Ineffective assistance of counsel (IAC): Declined on direct appeal due to an undeveloped record; the appropriate vehicle is a § 2255 motion.
• Downward departure (§ 5K2.13) for diminished capacity: Unreviewable absent a misunderstanding of authority; the district court recognized its discretion and declined to depart.
• Special condition of supervised release (electronic-device searches): No plain error. The court’s § 3553(a) rationale for incapacitating fentanyl trafficking supports the condition; only a slight inference is required to justify special conditions procedurally.
• Result: The Sixth Circuit affirmed both sentences in full.

Analysis

Precedents Cited and Their Influence

• Gall v. United States, 552 U.S. 38 (2007): Sets the abuse-of-discretion framework for reviewing procedural reasonableness—proper Guidelines calculation, advisory treatment, § 3553(a) consideration, fact-finding free of clear error, and adequate explanation.
• Holguin-Hernandez v. United States, 589 U.S. 169 (2020): Preservation principles; used here to frame plain-error review for unpreserved procedural challenges.
• Greer v. United States, 593 U.S. 503 (2021): Plain-error elements; the court requires an error that is plain, affects substantial rights, and seriously affects the fairness, integrity, or public reputation of judicial proceedings.
• United States v. Jones, 81 F.4th 591 (6th Cir. 2023): Guides the interpretive mode for the Guidelines—text first; de novo review of legal interpretation and clear-error review of facts.
• United States v. Ashrafkhan, 129 F.4th 980 (6th Cir. 2025): Reinforces textualism for Guidelines interpretation, focusing on ordinary meaning and the design of the guideline as a whole.
• United States v. Nicolescu, 17 F.4th 706 (6th Cir. 2021), and United States v. Sands, 948 F.3d 709 (6th Cir. 2020): Endorse reliance on ordinary meaning and dictionaries to define undefined Guidelines terms.
• Model Penal Code § 2.02(2)(b)(i): Applied to define “knowingly” in prior Sixth Circuit practice; used here to anchor the mens rea requirement.
• Asgrow Seed Co. v. Winterboer, 513 U.S. 179 (1995): Supplies the ordinary meaning of “marketing” as holding forth for sale and preparatory activities; dictionary sources and Black’s Law Dictionary corroborate this meaning.
• Restatement (Second) of Contracts § 159 (1981): “Misrepresentation” as an assertion not in accord with the facts; importantly, it commonly takes the form of spoken or written words—central to the court’s demarcation of the “misrepresentation” prong.
• United States v. Armstrong, 920 F.3d 395 (6th Cir. 2019): Sets the sentencing hearsay standard—admissible if minimally reliable; corroboration required only for hearsay from unidentified informants.
• United States v. Wiley, 122 F.4th 725 (8th Cir. 2024): Persuasive authority upholding the “marketing” prong where a defendant advertised pills as Percocet despite knowing they contained fentanyl.
• U.S.S.G. Supp. to App. C, amend. 807 (2018): Explains the policy basis for § 2D1.1(b)(13): fentanyl disguised as other substances creates heightened risks for unsuspecting purchasers; the Sixth Circuit uses this contextual rationale to confirm its reading of “marketing.”
• United States v. Madden, 515 F.3d 601 (6th Cir. 2008): Denials of downward departures are unreviewable absent a mistaken belief about authority to depart.
• United States v. Muchow, 924 F.3d 272 (6th Cir. 2019): Within-Guidelines sentences are presumptively reasonable.
• United States v. Zobel, 696 F.3d 558 (6th Cir. 2012): A district court must state reasons for special conditions of supervised release; consideration of § 3553(a) in the sentencing explanation can suffice.
• IAC on direct appeal line of cases: United States v. Hynes, 467 F.3d 951 (6th Cir. 2006); United States v. Martinez, 430 F.3d 317 (6th Cir. 2005); Massaro v. United States, 538 U.S. 500 (2003) — together counseling against deciding IAC on direct appeal absent a fully developed record.
• Waiver/invited error: United States v. Olano, 507 U.S. 725 (1993); United States v. Wells, 519 U.S. 482 (1997); United States v. Akridge, 62 F.4th 258 (6th Cir. 2023) — framing why Livingston’s concession at sentencing foreclosed his challenge to knowledge, and, alternatively, failed on plain error given the unobjected PSR.

Legal Reasoning

The court starts with the text of § 2D1.1(b)(13)(A), which enhances the offense level if the defendant “knowingly misrepresented or knowingly marketed” fentanyl as another substance. Because the Guideline does not define these terms, the panel employs ordinary-meaning tools—dictionary definitions, the Restatement for “misrepresentation,” Supreme Court usage for “marketing,” and the MPC for the mens rea “knowingly.” From these sources it derives a two-pronged framework:

• Knowingly misrepresented: Requires that the defendant, knowing the substance contains fentanyl, makes a false or misleading assertion about the substance’s identity. The court emphasizes that “without a false or misleading assertion—through written or spoken words—about the contents of the substance, there can be no misrepresentation.” In other words, misrepresentation is communicative conduct; disguising a pill’s appearance alone will not satisfy this prong.
• Knowingly marketed: Encompasses the act of selling or advertising fentanyl as another substance while aware of its true content. This includes sales of fentanyl pressed to mimic legitimate pharmaceuticals (e.g., blue, imprinted “oxycodone 30” pills). The court adopts Asgrow’s common-sense notion that “marketing” means “holding forth for sale,” thus not requiring separate “advertising” if the sales themselves present the product as something else.

Applying that framework:

• Matthews: A cooperating witness—identified to the court—stated that “Matthews always represented” the pills as “Percocet 30s” and never told the buyer they contained fentanyl. Because Matthews knew the pills were fentanyl and made a false assertion about their identity, the misrepresentation prong was satisfied. On evidentiary objections, the court (reviewing for plain error due to no objection below) held the statement met the “minimal indicium of reliability” threshold for sentencing hearsay and did not require corroboration because the informant was identified.
• Livingston: Livingston admitted he knew the pills contained fentanyl and that they looked identical to oxycodone 30s. He sold substantial quantities (50, 100, and 1,000 pills within eight days). The court found this was knowing “marketing” of fentanyl as another substance. Crucially, it rejected the contention that the enhancement fails if the immediate buyer knew the pills contained fentanyl, emphasizing the high-volume, resale-oriented context where downstream buyers would likely be unaware—a key concern motivating Amendment 807. The Sixth Circuit’s approach aligns with the Eighth Circuit’s in Wiley and its own recent unpublished decision in Radovic.

On Livingston’s additional issues:

• Ineffective assistance: The court declined to consider the claim on direct appeal (defense counsel conceded knowledge at sentencing) because the record did not reveal counsel’s strategy or permit a prejudice analysis. The appropriate vehicle is a § 2255 motion, consistent with Hynes, Martinez, and Massaro.
• Downward departure (§ 5K2.13): Unreviewable absent a mistaken belief about authority to depart. The district court acknowledged Livingston’s mental-health issues and knew it could vary or depart but chose not to; alternatively, the within-Guidelines sentence is presumptively reasonable and the presumption was not rebutted.
• Supervised release condition (electronic-device searches): On plain-error review, the court held that the district court’s overall § 3553(a) explanation—particularly its concern with public safety and fentanyl trafficking—was sufficient to support the condition under Zobel. The “slight inference” threshold for tying conditions to sentencing goals was satisfied.

Impact

This opinion establishes important Sixth Circuit guidance on § 2D1.1(b)(13) with practical and doctrinal consequences:

• Definitional clarity and division of labor between prongs:
  • “Misrepresentation” is narrower and requires words—false assertions made knowingly about the substance. Visual deception alone will not do.
  • “Marketing” is broader and includes selling fentanyl in a form designed to be perceived as another substance, capturing conduct where defendants refrain from explicit false statements but intentionally trade in lookalike pills.
• Buyer awareness is not a silver bullet: The court signals that when volume and context indicate foreseeable resale, the enhancement may apply even if the immediate purchaser knows the pills contain fentanyl. This focuses the inquiry on the risk to downstream, unsuspecting buyers—the central policy concern underlying Amendment 807.
• Textualism over commentary: The court builds primarily from text and ordinary meaning, using the Commission’s amendment history for confirmation rather than as the starting point. Post-Kisor caution about deference to commentary makes this textual approach especially salient, and lower courts now have a clear vocabulary to apply—minimizing inconsistent applications.
• Sentencing evidence practice: The opinion underscores the low threshold for admitting sentencing hearsay, especially when the informant is identified and the defendant does not object. Defense counsel must object contemporaneously to preserve reliability challenges and should contest pertinent PSR facts; otherwise, the PSR will be adopted and can independently sustain findings (as with Livingston’s knowledge).
• Supervised release conditions and digital-era enforcement: The court’s acceptance of device-search conditions on plain-error review, based on general public-safety rationales in fentanyl cases, will embolden probation offices and district courts to incorporate similar conditions. Defense counsel seeking to limit such conditions must object and build a record tailored to the defendant’s circumstances and narrower means.
• Downward departures and reasonableness review: The opinion reiterates familiar but critical constraints: denials of departures are rarely reviewable, and within-Guidelines sentences enjoy a presumption of reasonableness—reinforcing the need to frame mitigation arguments as § 3553(a) variances and to preserve them clearly.

Going forward, prosecutors can expect the “marketing” prong to reach a broad swath of fentanyl lookalike-pill cases even without explicit misstatements; defendants, in turn, may focus on undermining knowledge, disputing the “as another substance” characterization (e.g., proving buyers were fully apprised and no downstream resale was foreseeable), and drawing factual distinctions for smaller, user-quantity transactions. The Sixth Circuit leaves for another day whether buyer awareness could matter in a truly end-user, non-resale scenario; this opinion resolves only that it does not defeat the enhancement under resale circumstances like those present here.

Complex Concepts Simplified

• Procedural reasonableness: A sentence is procedurally reasonable if the court correctly calculates the Guidelines, treats them as advisory, considers § 3553(a) factors, relies on non-clearly-erroneous facts, and explains the sentence.
• Plain error: For unpreserved objections, the appellant must show an error that is obvious, affects substantial rights (usually outcome-affecting), and seriously undermines the fairness or integrity of the proceedings.
• “Knowingly” (mens rea): Acting with awareness that a circumstance exists—in this context, knowing the pills contain fentanyl.
• “Misrepresentation” under § 2D1.1(b)(13): A false assertion in words (spoken or written) about the identity of the substance. Visual mimicry alone is not enough.
• “Marketing” under § 2D1.1(b)(13): Offering for sale or selling fentanyl as something else. Selling pills deliberately made to look like oxycodone suffices if the seller knows the truth.
• Sentencing hearsay: The rules of evidence do not apply; statements may be considered if they have minimal indicia of reliability. If the informant is unidentified, corroboration is required; if identified, corroboration is not mandatory.
• Downward departure vs. variance: A departure is a Guidelines-authorized reduction based on specific policy statements (e.g., § 5K2.13 diminished capacity). A variance is a non-Guidelines sentence based on § 3553(a). Denials of departures are largely unreviewable; variances are reviewed for reasonableness.
• Within-Guidelines presumption: A sentence within the advisory range is presumed reasonable on appeal; the defendant bears the burden to rebut it.
• Invited error and waiver: A defendant who intentionally agrees to or proposes an approach cannot complain on appeal; even if reviewed to prevent manifest injustice, the standard is plain error and is rarely met.
• Special conditions of supervised release: Must be reasonably related to § 3553(a) goals and impose no greater deprivation of liberty than necessary. A sentencing court’s broader explanation can justify conditions if the connection is reasonably inferable.

Conclusion

The Sixth Circuit’s opinion in United States v. Matthews & Livingston provides the most precise circuit-level blueprint to date for applying U.S.S.G. § 2D1.1(b)(13). It establishes a crisp, text-driven division: “misrepresentation” requires knowing false assertions in words; “marketing” includes the sale of fentanyl disguised as other drugs when the seller knows the truth. The court’s treatment of buyer awareness is pragmatic and policy-sensitive: in resale contexts with substantial quantities, the risk to unsuspecting downstream buyers—recognized by the Sentencing Commission in Amendment 807—supports the enhancement even if the initial buyer knows.

The opinion also reinforces practical sentencing norms: the low bar for reliable hearsay at sentencing, the limited reviewability of downward-departure denials, the presumption of reasonableness for within-Guidelines sentences, and the permissibility of targeted supervised-release conditions—especially in fentanyl cases—when tied to public-safety concerns. Defense counsel seeking to avoid § 2D1.1(b)(13) should focus on contesting knowledge, the “as another substance” characterization, and the foreseeability of downstream resale; they must also preserve evidentiary and PSR objections. Prosecutors, conversely, will likely rely on pill design, sales practices, and volume to establish “marketing.”

In short, this precedential decision harmonizes textual interpretation with the Sentencing Commission’s policy objectives, providing clear guidance to district courts and litigants in the increasingly common prosecutions involving fentanyl-laced counterfeit pills.