6/27/25: Case on Guidelines commentary and a personal request

In United States v. Keller, --- F.4th ---, No. 23-656 (9th Cir. 2025), the Court affirmed Thomas Keller’s conviction and sentence on four counts of prescribing controlled substances outside the scope of professional practice.  

Keller raised four claims: (1) the district court erred in denying his motion to suppress a journal found at his residence that was seized pursuant to a search warrant justified by neither probable cause nor the “plain view” doctrine; (2) the district court erred in not holding an evidentiary hearing on his suppression motion; (3) the charges against him violated the nondelegation doctrine; and (4) the district court erred in calculating his sentencing range under U.S.S.G. § 2D1.1 by relying on a drug conversion ratio found in the Sentencing Guidelines commentary.

I'm going to focus on (2) and (4).  

As to the evidentiary hearing:  

A district court is “require[d] . . . to conduct an evidentiary hearing when the moving papers filed in connection with a pre-trial suppression motion show that there are contested issues of fact relating to the lawfulness of a search.”  But for moving papers to show that there are contested issues of fact warranting an evidentiary hearing, they must “allege facts with sufficient definiteness, clarity, and specificity to enable the trial court to conclude that contested issues of fact exist.”  A simple desire to cross-examine agents that a movant has accused of being untruthful does not itself create grounds for an evidentiary hearing.

The Court found that Keller did not meet his burden here. 

As to the sentencing issue, Keller's "challenge rests on the distinction between the Sentencing Guidelines and their accompanying commentary, and the reach of relatively recent case law addressing when courts may rely on Guidelines commentary."

Keller argues that the district court could not defer to the 6,700:1 ratio in Application Note 8 because the ratio is not a reasonable interpretation of an ambiguous Guideline under Kisor and Castillo. But we conclude that we need not and should not address whether the ratio is a permissible interpretation of the Guideline under Kisor because, in assessing the weight to be given to the commentary, the converted drug weight ratio for oxycodone is more properly regarded as part of the Guideline itself.

[T]he Guideline covers oxycodone, U.S.S.G. § 2D1.1(c), Note B, it provides base offense levels for “Converted Drug Weight”, id. § 2D1.1(c), and it expressly directs that “‘Converted Drug Weight,’ for purposes of this guideline, refers to a nominal reference designation that is used as a conversion factor in the Drug Conversion Tables set forth in the Commentary below,” id. § 2D1.1(c), Note K. As drafted, the ratios in the drug conversion tables are effectively part of § 2D1.1 itself because this section of the Guidelines expressly incorporates them. 

Furthermore, and critically, although the “commentary is not subject to mandatory congressional review,” Castillo, 69 F.4th at 655, the 6,700:1 oxycodone ratio underwent the same notice-and-comment and congressional-review process as the Guideline itself. The Sentencing Commission submitted this ratio to Congress for review on May 1, 2003, as part of Amendment 657.

There is also some helpful language on sentencing errors not being harmless:  “To establish harmlessness, the Government must show that ‘it is more probable than not’ that the error did not affect the sentence.”

 

6/26/25: SCOTUS decision on First Step Act retroactivity

In Hewitt v. United States, 606 U.S. ___, No. 23-1002 (2025), the Court addressed the First Step Act's retroactive application to section 924(c) convictions that previously would have been "stacked."  

Before the First Step Act was enacted in 2018, federal judges were required to sentence certain first-time offenders convicted of violating 18 U. S. C. §924(c)—a law that criminalizes the possession of a firearm while committing other crimes—to “stacked” 25-year periods of incarceration. The First Step Act, 132 Stat. 5194, eliminated this harsh mandatory minimum penalty. Congress also made the Act’s more lenient penalties partially retroactive. Section 403(b) specifies that the Act applies if a sentence “has not been imposed” upon an eligible §924(c) offender as of the date of the First Step Act’s enactment. Id., at 5222. 

The question presented here concerns an edge case: What penalties apply when a §924(c) offender had been sentenced as of the Act’s enactment, but that sentence was subsequently vacated, such that the offender must face a post-Act resentencing? We hold that, under that circumstance, a sentence “has not been imposed” for purposes of §403(b). Thus, the First Step Act’s more lenient penalties apply.

We granted certiorari to decide whether §403(b) of the First Step Act confers the benefit of the Act’s more lenient penalties to defendants facing post-Act resentencing following vacatur of their pre-Act sentence.

The Fifth Circuit held, and amicus and the dissent contend, that §403(b) excludes any defendant who was sentenced prior to the enactment date of the First Step Act— even if his sentence was later vacated. That is so, in their view, because the Act applies only “if a sentence for the offense has not been imposed as of ” the Act’s enactment date, and a sentence “has . . . been imposed” upon that defendant as a matter of historical fact. 132 Stat. 5222 (emphasis added). But based on the text of §403(b) and the nature of vacatur, we conclude that a sentence has been imposed for purposes of that provision if, and only if, the sentence is extant—i.e., has not been vacated.

6/20/25: Supreme Court decision on supervised release sentencing.

In Esteras v. United States, 606 U.S. ___ (2025), the Court vacated the Sixth Circuit's judgment affirming Esteras's supervised release sentence and remanded. 

The issue was whether district courts may consider the factors in §3553(a)(2)(A) when revoking supervised release.  In line with what is already the law in the Ninth Circuit, the Supreme Court held they may not.  Below are some  key parts of the majority opinion. 

A criminal sentence may include both time in prison and a term of supervised release. 18 U. S. C. §3583(a). Supervised release comes with conditions—for instance, the defendant must refrain from committing another crime. §3583(d). If the defendant violates one of these conditions, then the district court may revoke the term of supervised release and require reimprisonment. But a court may do so only “after considering” an enumerated list of sentencing factors: those “set forth in section 3553(a)(1), (a)(2)(B), (a)(2)(C), (a)(2)(D), (a)(4), (a)(5), (a)(6), and (a)(7).” §3583(e). Conspicuously missing from this list is §3553(a)(2)(A), which directs a district court to consider “the need for the sentence imposed” “to reflect the seriousness of the offense, to promote respect for the law, and to provide just punishment for the offense.” The Sixth Circuit held that a district court may consider that factor nonetheless.

We disagree. Congress’s decision to enumerate most of the sentencing factors while omitting §3553(a)(2)(A) raises a strong inference that courts may not consider that factor when deciding whether to revoke a term of supervised release. This inference is consistent with both the statutory structure and the role that supervised release plays in the sentencing process. Accordingly, we vacate the judgments of the Sixth Circuit and remand for further proceedings. 

At oral argument, the Government expressed concern that it would be difficult for appellate courts to determine whether a district court has impermissibly relied on §3553(a)(2)(A). See Tr. of Oral Arg. 49–50. So we conclude with a few observations about appellate review. 

Much will turn on whether the defendant objects. If the defendant does not make the district court aware that it may be impermissibly relying on §3553(a)(2)(A), then the defendant’s appeal will be governed by plain-error review. See Fed. Rule Crim. Proc. 52(b). In that event, the district court’s order revoking supervised release and requiring reimprisonment will be affirmed unless it is “‘clear’” or “‘obvious’” that the district court actually relied on §3553(a)(2)(A)—because it did so either expressly or by unmistakable implication. United States v. Olano, 507 U. S. 725, 734 (1993). 

If the defendant does object to the district court’s reliance on §3553(a)(2)(A), we anticipate that the district court will recognize its potential error and clarify its revocation decision to make clear that it is not taking account of §3553(a)(2)(A). For example, the district court could withdraw any impermissible justification or explain that a stray reference to a §3553(a)(2)(A) factor was intended to bear on another §3553(a) factor or merely prefatory. If the court nonetheless considers the need to exact retribution for the defendant’s original criminal offense, and if the error was not harmless, then the court of appeals should vacate the court’s order and remand for the court to apply the correct standard. See Fed. Rule Crim. Proc. 52(a). 

This does not mean, as the Government suggests, that our reading of §3583(e) amounts to a “substance-free reverse magic-words requirement.” Brief for United States 37. The Government conflates the proper interpretation of §3583(e) with an appellate court’s ability to enforce that interpretation. The “requirement” here is very much substantive: District courts may not consider the retributive purpose of §3553(a)(2)(A) before revoking supervised release. We trust that district courts will heed that instruction regardless of the practical likelihood of reversal.

District courts may revoke a term of supervised release after considering the factors enumerated in §3583(e). Because §3553(a)(2)(A) is excluded from that list, district courts may not consider it. The judgments of the Sixth Circuit are vacated, and the cases are remanded for further proceedings consistent with this opinion.

6/18/25: 1326(d) case

In United States v. Sanchez, --- F.4th ---, No. 22-50072 (9th Cir. 2025), the Court affirmed the district court’s denial of Eliel Nunez Sanchez’s motion to dismiss an indictment charging him with illegal reentry after removal in violation of 8 U.S.C. § 1326.

This decision illustrates how difficult it will be to prevail on a 1326(d) in the Ninth Circuit.  If you are litigating such a motion, this case is a must read. The opinion is long and detailed, but the conclusion sums it up:

Each element of § 1326(d)’s bar on collateral attacks to removal orders is mandatory. See Palomar-Santiago, 593 U.S. at 329. And Nunez satisfies none of them: he did not exhaust his administrative remedies pursuant to § 1326(d)(1); he was not deprived of the opportunity for judicial review under § 1326(d)(2); and entry of the Removal Order was not fundamentally unfair under § 1326(d)(3). Accordingly, Nunez’s collateral attack on the Removal Order cannot proceed. 

6/17/25: probation search case

In United States v. Barry, --- F.4th ---, No. 23-2101 (9th Cir. 2025), the Court affirmed the district court’s denial of Ryan Barry’s motion to suppress evidence found in a warrantless search of his apartment.  The case turned on whether police officers had probable cause to believe that Barry, a probationer who was subject to warrantless search conditions, resided at the apartment.  The Court held they did. 

Nothing about this decision breaks new ground.  But there are two concurrences discussing whether the Ninth Circuit's precedent on these types of cases -- requiring probable cause to believe the parolee / probationer resides at the residence -- should be reconsidered.