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. 

5/29/25: Case on statements in made in plea agreements under Fed. R. Evid. 410.

In United States v. Puig Valdes, --- F.4th ---, No. 23-3214 (9th Cir. 2025), on interlocutory appeal by the Government, the Court affirmed the district court’s ruling that the factual basis of a pre-indictment plea agreement signed by Yasiel Puig Valdes would be excluded at trial.

In July 2022, Defendant Yasiel Puig Valdes (“Puig”) signed a pre-indictment plea agreement with the Government, under which he would plead guilty to one count of making false statements to federal officers in violation of 18 U.S.C. § 1001, and in exchange, the Government would recommend a reduced sentence and decline to bring an additional charge of obstruction of justice under 18 U.S.C. § 1503. When Puig later declined to plead guilty, the Government declared that Puig was in breach of his plea agreement, and as a remedy it sought to enforce a provision of the agreement waiving all evidentiary objections to the admission of the plea agreement’s factual basis at trial. This waiver expressly included any objections based on Rule 410 of the Federal Rules of Evidence, which generally bars the admission, against a defendant, of any statements made during plea negotiations. The district court ultimately held that Rule 410 remained applicable here, and it therefore ruled that the factual basis of Puig’s plea agreement would be excluded at trial. Pursuant to 18 U.S.C. § 3731, the Government brought this interlocutory appeal challenging that pretrial ruling. Although our reasoning differs somewhat from the district court’s, we agree that Rule 410 remains applicable here, and we therefore affirm.

On appeal, the Government contends that, even though the district court had not yet accepted either Puig’s plea agreement or any guilty plea from him, that agreement remained binding and enforceable, including its waiver of the rule of exclusion contained in Federal Rule of Evidence 410.

[T]his written statement attributed to Puig plainly constitutes a “statement made during plea discussions with an attorney for the prosecuting authority,” and it is therefore “not admissible against the defendant who . . . participated in the plea discussions” where, as here, “the discussions did not result in a guilty plea.” 

However, because Evidence Rule 410 and Criminal Rule 11(f) were “enacted against a background presumption that legal rights generally, and evidentiary provisions specifically, are subject to waiver by voluntary agreement of the parties,” the Supreme Court has held that, “absent some affirmative indication that the agreement was entered into unknowingly or involuntarily, an agreement to waive the exclusionary provisions of [these] Rules is valid and enforceable.”

Here, of course, the plea agreement was never accepted or approved by the district court before Puig disavowed it, and under this line of authority, the agreement would generally be deemed not to be enforceable by the court. 

Viewing the language of Puig’s plea agreement against the backdrop of this case law, we conclude that Puig’s Rule 410 waiver was not triggered here. As we have explained, Puig’s waiver of the protections of Rule 410 (and Rule 11(f)) was expressly contingent on the district “[c]ourt’s finding” that there was a “breach of this agreement.” The terms of that waiver are most naturally understood as requiring that there be an “agreement” that, under our case law, was enforceable by the “[c]ourt[]” and as to which the court could therefore make the requisite “finding” of a “breach.” And because the plea agreement was a Type A agreement requiring the district court’s approval, and because that approval never occurred, the agreement was not enforceable by the court under our precedent. The waiver, by its own terms, therefore did not apply. Consequently, Rule 410 remains applicable with full force here, and the factual basis of Puig’s plea agreement is “not admissible against” Puig. FED. R. EVID. 410(a).

Also in FN 3, the Court explains that the factual basis is not admissible even for impeachment: "Although the Government argued in its opening brief that the factual basis of Puig’s plea agreement should at least be admissible at trial for impeachment purposes, the Government clarified in its reply brief that it was not contending that, even if Rule 410 applies, the Government is nonetheless entitled to a carve-out from that rule’s prohibitions if the evidence is used only for impeachment. Rather, the Government has clarified that its only argument on this score is that, if this court concludes “that public policy prohibits the admission of the factual basis in the government’s case-in-chief, [the court] should at least permit admission of the [factual basis] for impeachment and rebuttal.” Because we do not rely on “public policy,” but on the plain text of Rule 410, we have no authority to create exceptions to that rule’s terms. And because the Government concedes that Rule 410’s terms bar admission of covered statements for any purpose, including impeachment, no impeachment exception is applicable here."

5/23/25: Two Ninth Circuit decisions today

In United States v. Greene, --- F.4th ---, No. 23-4097 (9th Cir. 2025), the Court reversed the district court’s use of a “pseudo-count” of carjacking to calculate Namir Malik Ali Greene’s offense level at sentencing in a case in which Greene pleaded guilty to one count of Hobbs Act robbery.  Here are some key points from the opinion. 

Namir Malik Ali Greene challenges his 120-month sentence for interference with commerce by robbery (Hobbs Act robbery). 18 U.S.C. § 1951(a). He argues that the district court erred by basing his Sentencing Guidelines range on a “pseudo-count” of carjacking, 18 U.S.C. § 2119, because the elements of federal carjacking were not specifically established by his plea agreement. U.S. Sent’g Guidelines Manual (USSG) § 1B1.2(c) (U.S. Sent’g Comm’n 2023). We agree. Applying plain error review, we reverse and remand for resentencing on an open record.

Greene argues on appeal that the district court erred when it used the carjacking pseudo-count to calculate his offense level because the plea agreement did not establish all elements of federal carjacking.

The first two prongs of the plain error test are satisfied because the plea agreement did not specifically establish all elements of federal carjacking; in particular, the stipulated facts do not specifically establish that Greene acted with the “intent to cause death or serious bodily harm,” which is the mens rea required for federal carjacking. 18 U.S.C. § 2119; USSG § 1B1.2(c). This error was plain under Supreme Court precedent. Braxton v. United States, 500 U.S. 344, 350–51 (1991).

A sentencing court “must consider only conduct included in the plea agreement” when selecting a Guideline under § 1B1.2(a). That conduct must “specifically establish[]” all elements of the base offense. USSG § 1B1.2(c). To determine whether a plea agreement “specifically establishes” an offense, the Supreme Court has explained that we are to interpret a plea agreement the same way we would interpret a contract.

Braxton instructs that a plea agreement must evince a defendant’s stipulation to facts that unambiguously establish the required elements of a separate offense in order for the separate offense to be treated as “specifically established” for purposes of sentencing. As the Court explained, “a stipulation that at best supports two reasonable readings” does not specifically establish an additional offense.

Greene’s plea agreement stipulated only that “using the BB-gun to intimidate a vehicle owner, [he] stole a vehicle, namely, a 2010 Honda Accord.” This stipulation does not specifically establish the mens rea for § 2119 carjacking because it does not unambiguously support the conclusion that Greene had the specific “intent to cause death or serious bodily harm.”

Because the stipulated facts fell short of establishing all elements of a § 2119 carjacking, this offense should not have served as the base offense for the calculation of Greene’s Guidelines range.

Our case law does not permit district courts to infer a defendant’s mental state from ambiguous facts in a plea agreement, even if the inference is “reasonable,” as the government argues. And without facts specifically establishing the requisite mens rea, it was error to treat § 2119 carjacking as a pseudo-offense for the calculation of Greene’s offense level. After Braxton, this error was plain.

Turning to the third prong of the plain error test, we are persuaded that the error in the Guidelines calculation affected Greene’s substantial rights. By relying on a base offense of § 2119 carjacking, the court calculated Greene’s total offense level as 30, two levels higher than the total offense level would have been if based on the Hobbs Act robbery conviction. 

[T]he broad authority of the Commerce Clause does not permit the federal government to “convert congressional authority under the Commerce Clause to a general police power of the sort retained by the States.”

Turning to the fourth prong of plain error review, we exercise our discretion to correct the error because, on the facts of this case, the miscalculated base offense level “seriously affect[s] the fairness, integrity, or public reputation of judicial proceedings.”

Next, in United States v. Watson, --- F.4th ---, No. 24-1865 (9th Cir. 2025), the Court affirmed the district court’s denial of Tyler Jay Watson’s motion to suppress incriminating statements he made to police officers and the fruits thereof in a case in which Watson entered a conditional guilty plea to one count of possession with intent to distribute fentanyl.  Here are some key points from the opinion. 

Based on information received from a reliable confidential informant (“CI”), a police task force in Nampa, Idaho, began investigating Defendant-Appellant Tyler Jay Watson for drug distribution. When law enforcement learned that Watson was on parole, they coordinated with Probation and Parole (“P&P”) officers to conduct a compliance search of Watson’s vehicle and residence. The CI had advised officers that Watson transported drugs in magnetized containers under his vehicle. After officers found methamphetamine attached to the vehicle’s undercarriage, they drove to Watson’s residence and conducted a search. While the search was ongoing, Watson remained detained in Officer Scott’s patrol vehicle parked down the street. A police officer, Detective Coronado, approached Watson in the back of the patrol car and read Watson his Miranda rights. Watson acknowledged his rights and stated his willingness to cooperate. Watson then admitted he was holding more of “the product” at his grandmother’s home. Following Watson’s confession, officers drove to Watson’s grandmother’s house and obtained her consent to search her garage. Officers discovered and seized fentanyl, methamphetamine, and cash.

On appeal, Watson argues that his Agreement of Supervision’s (“Agreement”) condition requiring that he “cooperate with the requests of [his] probation/parole officer,” where “[c]ooperation includes being truthful,” created a “classic penalty situation” in which Watson was compelled—under threat of parole revocation—to make incriminating statements to law enforcement. We disagree. Watson’s statements were made to a police officer, not his P&P officer, after an adequate Miranda warning.

Because Watson’s Agreement required cooperation and truthfulness with his parole officer, but not all law enforcement officers, we cannot conclude that a Mirandized interrogation by police in the course of investigating a new, separate offense was involuntarily compelled. Accordingly, we affirm the district court’s denial of Watson’s motion to suppress and hold that Watson was not subject to a penalty situation under these circumstances.

The Fifth Amendment’s privilege against self-incrimination generally applies only to those who “claim it.” However, this general rule does not apply when an individual is “denied the free choice to admit, to deny, or to refuse to answer.” Id. This can occur when the government creates a situation where “an individual’s refusal to answer incriminating questions subjects him to a penalty.” Id. In a “penalty situation,” the Fifth Amendment becomes self-executing. In other words, “if the state, either expressly or by implication, asserts that invocation of the privilege would lead to revocation of probation . . . the failure to assert the privilege would be excused, and the probationer’s answer would be deemed compelled and inadmissible in a criminal prosecution.” 

Watson was not subject to a penalty situation because nothing in Watson’s Agreement required that he speak, cooperate, or be truthful with law enforcement; he was properly Mirandized immediately prior to his incriminating statements, stated he understood his rights, and agreed to cooperate; and he was never told that refusing to answer officers’ questions would result in the revocation of his parole or any other penalty. Because Watson’s statements were not involuntarily compelled under penalty of parole revocation, the district court properly denied Watson’s motion to suppress.