Circuit Split Deepens On Career Offender Enhancement

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.

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.”

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

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.

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

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

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. 

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.