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Ineffective Assistance of Counsel–When the Sentencing Guidelines’ Language Controls the Commentary: United States v. Winstead, _ F.3d _ (D.C. Circuit, No. 12-3036 (May 25, 2018)

Ineffective Assistance of Counsel–When the Sentencing Guidelines’ Language Controls the Commentary: United States v. Winstead, _ F.3d _ (D.C. Circuit, No. 12-3036 (May 25, 2018) 2018).

Winning an ineffective assistance of counsel claim on direct appeal is not an occurrence that happens frequently, much less through a decision that issued just seven weeks after oral argument. Aumbrey Winstead, a man with a (to be gentle) checkered past, was convicted of possession of a firearm (by a person convicted of a crime punishable by imprisonment of more than one year), possession with intent to distribute cocaine, and possession of a firearm during a drug trafficking offense. The evidence against him was, in the appellate panel’s word, “overwhelming.” (slip op. at 2). Thanks to nimble footwork by the Federal Defender’s Office, on direct appeal his thirty-year sentence as an Armed Career Criminal was found improper and his case remanded for resentencing.

First, a digression for a merits-based issue that crops up with sufficient frequency that defense counsel should place this case in their trial toolbox. Based on the Circuit’s decision in United States v. Sheffield, 832 F.3d 296, 307-08 (D.C. Cir. 2016), Mr. Winstead protested that pointed out that district judge’s decision to admit prior crimes as evidence of knowledge under Federal Rules 403 and 404(b) was error because the offenses were more than a decade old. The government, invoking out-of-circuit authority, responded that the staleness of old crimes is lessened if part of the time between the defendant’s old crime and a new case was spent in prison. The panel (Garland, C.J., Edwards and Silberman JJ), found that distinction intellectually troubling but concluded that the error – if any – of admitting this evidence was harmless given the overwhelming evidence of Winstead’s guilt. (Slip Op. at 7-9).

The court then turned to Mr. Winstead’s claims of ineffective assistance of counsel, which contended that his past convictions for various attempt offenses should not have rendered him a Career Offender under U.S.S.G. §§ 4B1.1(a), (c)(3).

Speaking for the panel, Judge Silberman first noted, and brushed aside, the Government’s reference to other had acts known about Winstead – indeed it appears that over the past several he had avoided prosecution and possible incarceration only by luck. (Slip Op. at 10). But once Winstead was adjudged a career criminal, the guideline range for his sentence jumped from 211-248 months to 360 months-life. The district judge, describing Winstead as a career offender, sentenced him to 360 months. (Id.) Winstead’s trial counsel put up little by way of opposition to the proposed sentencing, a failure which appellate counsel seized upon, for there was in fact, a powerful legal argument available: “[A]ttempted drug offenses, which caused his career criminal status, are not included in the guidelines. Instead, attempts are only added in the commentary to the guidelines.” (Slip Op. at 11).

The threshold problem with that argument, according to the panel, is that this otherwise promising avenue of relief was foreclosed under a plain error standard in this Circuit and others. (Id.) (citing United States v. (Norman) Williams, 350 F.3d 128, 130 (D.C. Cir. 2003)). There was, however, a way out for Winstead, which his appellate counsel adroitly put forth: ineffective assistance of counsel below.

First, Winstead asserted that his former counsel had mishandled the plea negotiations. Given the “quite sketchy [record] regarding plea discussions,” and in accordance with the D.C. Circuit’s normal practice when it cannot definitely reject an ineffective assistance of counsel claim, it remanded that part of the case. (Slip Op. at 12-13) (citing United States v. Rashad, 331 F.3d 908, 912 (D.C. Cir. 2003)). In so doing, the panel noted that “Even with no plea offer, acceptance of responsibility alone would have reduced Appellant’s sentence significantly.” (Slip Op. at 13 n.10).

Second, Winstead contended that “by far the most damaging error the counsel made . . . was not to raise the textual argument referred to above: that his previous crimes which were counted to make him a career criminal – ‘attempted’ distribution of, and ‘attempted’ possession with intent to distribute, drugs – are listed in the commentary to the guidelines but not in the guidelines themselves.” (Slip Op. at 13)). This theory resonated with the panel, which explained: “As is apparent, neither the crime of attempting to distribute drugs nor attempted possession with intent to distribute drugs is included in the guideline list. The commentary to § 4B1.2, however, states that “‘controlled substance offense’ include[s] the offenses of aiding and abetting, conspiring, and attempting to commit such offenses.” Id., Application Note 1 (emphasis added [by panel]). Winstead argues that this commentary cannot be squared with the guideline – and that neither of his two previous drug crimes falls within the definition of “controlled substance offense,” because each conviction was for mere attempt.”(emphasis original). (Slip Op. at 15).

In ruling for Winstead, the panel looked to the familiar standards governing ineffective assistance claims. There was an “enormous difference in Appellant’s potential term of imprisonment if sentenced as a career criminal (over ten years).” Hence “under Strickland v. Washington, 466 U.S. 668 (1984), an appellant must show both that the errors were serious – which should be obvious in this case – and that there is, at least, a reasonable probability that the result of the proceeding would have been different. Id. at 687; see also U.S. v. Abney, 812 F.3d 1079, 1086-95 (D.C. Cir.2016).” (Slip Op. at 15). And while “the Guidelines are only discretionary[,] the Supreme Court ‘has made clear that the Guidelines are to be the sentencing court’s “starting point and . . . initial benchmark.’” Molina-Martinez v. United States, 136 S.Ct. 1338, 1345 (2016) (quoting Gall v. United States, 552 U.S. 38, 49 (2007)).” Thus understood, “‘The Guidelines inform and instruct the district court’s determination of an appropriate sentence. In the usual case, then, the systemic function of the selected Guidelines range will affect the sentence.’ Id. at 1346.” (Slip Op. at 15).

Luckily for Winstead, whose facially appealing (no pun intended) claim would have been foreclosed under a plain error standard and consigned to the district court on a remand, there was an available option for direct review. Predecessor counsel had muffed an “obvious legal argument” and that error in overlooking the textual conflict between the Guidelines and the Commentary was cognizable on direct appeal under a de novo standard of review. (Slip Op. at 16).

Finding merit in Mr. Winstead’s ineffectiveness claim, Judge Silberman accepted three key points advanced in Winstead’s brief. For one thing, the Circuit’s decision in United States v. Price, 990 F.2d 1367 (D.C. Cir.1993), “had reversed a career offender sentence in similar circumstances because the commentary impermissibly purported to expand the scope of a penalty to include conspiracy to violate substantive drug provisions.” Then, too, “United States v. Alexander, 331 F.3d 116 (D.C. Cir. 2003) – which held that the term ‘serious drug offense’ in the Armed Criminal Career Act includes attempts – relied heavily on the presence of the word ‘involving’ in the statutory definition, which has ‘expansive connotations’” whereas “Section 4B1.2, by contrast, includes no such broad language.” Finally, in James v. United States, 550 U.S. 192 (2007), the Supreme Court “held that the Armed Criminal Career Act’s definition of ‘violent felony’ did not encompass attempted burglary simply by including the completed offense of burglary.” (Slip Op, at 17). Quoting from Winstead’s brief, the panel recognized that, in effect “‘Attempted distribution’ is not‘distribution’ any more than ‘attempted burglary’ is ‘burglary.’” (Slip Op. at 18).

In response, the Government referred to decisions from five other circuit courts of appeals, including one en banc opinion. This contention the panel ruled, missed the mark. “Section 4B1.2(b) presents a very detailed ’definition’ of controlled substance offense that clearly excludes inchoate offenses. Expressio unius est exclusion alterius.” (Slip Op. at 18). Indeed, the panel went a step farther, declaring that “the government’s failure to even address Winstead’s textual arguments, and its near-exclusive reliance on cases from outside this circuit which generally do the same, is reminiscent of United States v. Glover, 736 F.3d 509 (D.C. Cir. 2013), cited with approval in Dahda v. United States, 584 U.S. ___ (2018). There, we found plain error where sister circuit decisions ran ‘contrary to the plain text of the statute,’ id. at 513, and considered ‘the government’s reluctance to come to grips with the language . . . quite revealing.’ Id. at 516.” (Slip Op. at 19).

Assistant Federal Defender Lisa Wright once more played “Ann Bonny “in the starring role, advancing cogent legal arguments before as demanding a panel as one could face in this Circuit. She was aided by her fellow buccaneers, A.J. Kramer and Tony Axam.

  • Steve Leckar, of counsel to Kalbian Hagerty LLP, enjoys following and occasionally arguing in the D.C. Circuit.







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