Circuit Split Deepens Over Whether Inchoate Drug Crimes Trigger Career Offender Enhancement

By: John J. Dowling III

When a defendant qualifies for the career offender enhancement under the U.S. Sentencing Guidelines, it often dominates plea negotiations due to the outsized sentencing exposure it entails. For example, without the enhancement, a defendant could be subject to a guideline range with a maximum of three years in prison, whereas if the enhancement applies, he could be subject to a fifteen-year max. As the Second Circuit recently highlighted, the enhancement “often dwarfs all other Guidelines calculations and recommends the imposition of severe, even Draconian, penalties.”1 This article lays out a recent but deepening circuit split over the types of prior drug convictions that trigger the enhancement and explains how the split is likely to be resolved by re-examining the proper type and level of deference sentencing courts are to afford the Sentencing Commission’s interpretation of its sentencing guidelines.

I. The Law

A. Federal Sentencing and “Stinson Deference”

Federal sentencing in the United States is governed by statute, regulation, and a set of guidelines promulgated by the U.S. Sentencing Commission (the “Guidelines”). Congress created the Commission in the 1980s to promote uniformity in federal sentencing. While the Guidelines are only advisory,2 the U.S. Supreme Court has made clear that “district courts must begin their analysis with the Guidelines and remain cognizant of them throughout the sentencing process.”3 As such, while statutory mandatory minimums remain central in the sentencing process, the “Guidelines and their Commentary remain the lodestone of federal sentencing.”4

Given the centrality of the Guidelines in modern sentencing, the question has arisen: what role do the commentary and application notes play in interpreting the Guidelines? In 1993, the U.S. Supreme Court in Stinson v. United States answered that question and cited to Bowles v. Seminole Rock & Sand Co.5 (the predecessor to Auer deference6) in holding that “commentary… that interprets or explains a guideline is authoritative unless it violates the Constitution or a federal statute, or is inconsistent with, or a plainly erroneous reading of, that guideline.”7 Stinson departed from traditional Auer principles,8 creating a stripped down, super-deferential version of Auer unique to criminal cases—a version that did not, unlike virtually all other Auer deference cases, impose ambiguity as a prerequisite to deference to the Sentencing Commission’s commentary interpreting the guidelines. I call this version of administrative deference, unique to federal sentencing, “Stinson deference.”

B. The Career Offender Enhancement

Federal sentencing guidelines increase an offender’s punishment if he has previously been convicted of two or more “controlled substance offense[s].”9 The phrase “controlled substance offense” is broadly defined to include most state and federal felonies that criminalize the manufacture, distribution, or possession of a controlled substance.10 The text of this definition is, however, silent on inchoate offenses.11 Enter the Commission’s commentary accompanying the guideline, which provides that a “‘controlled substance offense’ include[s] the offenses of aiding and abetting, conspiring, and attempting to commit such offenses” (herein “Application Note 1”). 12 The Second Circuit recently handed down an opinion deepening a circuit split over whether Application Note 1 improperly adds offenses not listed in the text of the career offender guideline.13

II. The Circuit Split

Recently, a number of circuit courts have been asked to decide whether Application Note 1 improperly adds crimes to the text of the definition of a “controlled substance offense.” So far, at least two circuit courts have held that Application Note 1 improperly expands the list of crimes included in the guideline, while three have held that it does not. As explained below, the split has created two schools: one addressing the substance of the text and its meaning, and the other relying on Stinson deference. In a time of heightened attention to the importance of separation of powers in the context of judicial deference to administrative agencies—particularly in light of the U.S. Supreme Court’s recent decision in Kisor v. Wilkie14—, this circuit split implicates a slew of fundamental legal principles and practices including separation of powers; administrative procedure; due process; statutory interpretation; the rule of lenity; and the role of the Guidelines in sentencing.

A. The Text School

The circuit courts having held that Application Note 1 improperly expands the ambit of a controlled substance offense have directly addressed the substance of the definition’s text. For example, in United States v. Winstead, the D.C. Circuit held that “there is no question that . . . the commentary adds a crime, ‘attempted distribution,’ that is not included in the guideline.”15 The Winstead court reasoned that “a definition which declares what a term ‘means’ . . . excludes any meaning that is not stated. . . [And] [s]ection 4B1.2(b) presents a very detailed ‘definition’ of controlled substance offense that clearly excludes inchoate offenses.”16 Similarly, in United States v. Havis, the Sixth Circuit reasoned that “[t]o make attempt crimes a part of § 4B1.2(b), the Commission did not interpret a term in the guideline itself—no term in § 4B1.2(b) would bear that construction. Rather, the Commission used Application Note 1 to add an offense not listed in the guideline.”17

B. The Deference School

The First, Second, Fourth, Seventh, and Eleventh Circuits form the other side of the split, relying on Stinson deference to hold that Application Note 1 is valid. For example, in United States v. Nieves-Borrero, the First Circuit cited Stinson in holding that Application Note 1 is not “arbitrary, unreasonable, [or] inconsistent with” the text of the definition of a “controlled substance offense.”18 The First Circuit’s reasoning stopped there. Similarly, the Eleventh Circuit in United States v. Smith cited Stinson in simply holding that attempt offenses are included within the career offender enhancement.19 Decisions of the Fourth and Seventh Circuits have come out the same way.20

Another case relying on Stinson deference is the Ninth Circuit’s decision in United States v. Crum, in which the court acknowledged, albeit in dicta, that “[i]f we were free to do so, we would follow the Sixth and D.C. Circuits’ lead. In our view, the commentary improperly expands the definition of ‘controlled substance offense’ to include other offenses not listed in the text of the guideline.”21 The Ninth Circuit went on to explain that it was bound to reject Winstead and Havis because of binding circuit precedent.22

The most recent decision on this side of the split is the Second Circuit’s February 2020 decision in United States v. Tabb.23 The Tabb court relied on circuit precedent24 to hold that § 4B1.2 includes inchoate offenses.25 The precedent the Tabb court relied on had itself simply clung to Stinson for the proposition that deference to the commentary is required.26 Like the Ninth Circuit in Crum, however, the three-judge panel in Tabb noted that it was bound by circuit precedent absent an intervening supreme court case or an en banc decision of its own court.27

III. Who’s Right?

Courts in the text school have squarely addressed the substantive questions of whether the text of the definition of a “controlled substance offense” is ambiguous and whether it can fairly be read to encompass the offenses listed in Application Note 1. Courts in the deference school, however, have all predicated their decisions on a faithful adherence to Stinson deference. Indeed, at least one of these courts has agreed (in dicta) that Application Note 1 improperly adds offenses not listed in the guideline,28 and two have noted that they were bound by circuit precedent to reject the argument that Application Note 1 is invalid.29 In light of this, two points seem clear.

First, based on the reasoning of the courts in Winstead, Havis, and Crum, the text of the definition does not include inchoate offenses. Indeed, none of the courts in the deference school have held that the text of the definition is ambiguous; they have simply relied on Stinson deference to find that Application Note 1 is not “inconsistent” with the text of the definition. Even the Second Circuit, in its 1995 decision holding that Application Note 1 is valid, explicitly acknowledged that Application Note 1 “expand[s]” the definition of “controlled substance offense.”30 And even the Ninth Circuit in Crum noted in dicta that the reasoning of Winstead and Havis is more persuasive.31

Second (and in light of the first point), the resolution of this issue will likely turn on the proper scope and operation of Stinson deference. Indeed, judicial deference to administrative agencies has enjoyed its own wave of recent litigation in light of the U.S. Supreme Court’s 2019 decision in Kisor v. Wilkie,32 in which the court declined to overrule Auer but did hold that courts cannot defer to administrative agencies’ interpretation of their own regulations unless the regulation is “genuinely ambiguous.”33

The question of whether Application Note 1 improperly adds crimes not listed in the career offender guideline is an important one because whether the enhancement applies can increase a defendant’s sentencing exposure by at least 400%. If and when the U.S. Supreme Court takes up the issue, we can expect to see a renewed version of the decades-old debate regarding the awkward position the Sentencing Commission occupies in tripartite government.

John J. Dowling III. is third-year law student at Syracuse University College of Law and an intern at the Office of the Federal Public Defender for the Northern District of New York. His email address is johndowlingiii@hotmail.com

1 United States v. Tabb, 949 F.3d 81, 83 n.2 (2d Cir. 2020).

2 United States v. Booker, 543 U.S. 220 (2005).

3 Gall v. United States, 552 U.S. 38, 50 n.6 (2007).

4 United States v. Havis, 907 F.3d 439, 444 (6th Cir. 2018) (“Havis I”), rev’d en banc, 927 F.3d 382 (6th Cir. 2019) (“Havis II”).

5 325 U.S. 410, 414 (1945).

6 Auer v. Robbins, 519 U.S. 452, 461 (1997), and Seminole Rock, supra, hold that federal courts must defer to an agency’s reasonable interpretation of its own ambiguous regulation.

7 508 U.S. 36, 38 (1993).

8 Although Auer was decided four years after Stinson, it is more convenient to speak of Auer deference because most practitioners are familiar with Auer, whereas Seminole Rock is less known.

9 USSG § 4B1.1 (Nov. 1, 2018).

10 USSG § 4B1.2(b) (Nov. 1, 2018).

11 United States v. Crum, 934 F.3d 963, 966 (9th Cir. 2019) (stating in dicta that the text of § 4B1.2(b) does not include attempts), cert. denied, 2020 WL 1496759 (2020); Havis II, 927 F.3d 382 (holding that the text of § 4B1.2(b) does not include attempts); United States v. Winstead, 890 F.3d 1082, 1090 (D.C. Cir. 2018) (per curium) (same); United States v. Jackson, 60 F.3d 128, 133 (2d Cir. 1995) (same).

12 App. Note 1, USSG § 4B1.2 (Nov. 1, 2018) (emphasis added).

13 See Tabb, 949 F.3d 81.

14 139 S. Ct. 2400 (2019) (holding that federal courts cannot afford Auer deference to an administrative agency’s interpretation of its own regulation unless the regulation is “genuinely ambiguous.”).

15 890 F.3d at 1090 (D.C. Cir. 2018).

16 Id. at 1090-91 (quoting Burgess v. United States, 553 U.S. 124, 128 (2008)) (internal brackets omitted).

17 927 F.3d 382, 386 (6th Cir. 2019) (en banc).

18 856 F.3d 5, 9 (1st Cir. 2017).

19 54 F.3d 690, 693 (11th Cir. 1995).

20 See United States v. Dozier, 848 F.3d 180 (4th Cir. 2017) (holding, without directly addressing or discussing, that an “attempt” falls within ambit of “controlled substance offense.”); United States v. Rollins, 836 F.3d 737, 739 (7th Cir. 2016) (en banc) (per curium).

21 934 F.3d 963, 966 (9th Cir. 2019) (dicta), cert. denied, 2020 WL 1496759 (2020) (citations omitted).

22 934 F.3d at 966-67.

23 949 F.3d 81.

24 United States v. Jackson, 60 F.3d 128 (2d Cir. 1995).

25 Tabb, 949 F.3d at 87.

26 See Jackson, 60 F.3d at 131.

27 Tabb, 949 F.3d at 81.

28 See Crum, 934 F.3d at 966 (dicta).

29 See Tabb, 949 F.3d at 87; Crum, 934 F.3d at 966.

30 Jackson, 60 F.3d at 133.

31 934 F.3d at 966.

32 139 S. Ct. 2400 (2019).

33 Kisor, 139 S. Ct. at 2418.