Image:Kibble Facts
May 2026 was not a quiet month at the Supreme Court.
Across eleven decisions, the Court moved through some of the legal system’s most consequential pressure points: prison sentences, racial discrimination in jury selection, arbitration, trucking safety, federal employee speech, pension liability, Cuban confiscated property, and the death penalty.
The pattern was revealing. The Court repeatedly protected formal legal channels. Prisoners challenging convictions must use habeas, not compassionate release. Federal employees must generally use civil-service review systems. Arbitration awards stay tethered to the federal courts that sent cases there. Removal deadlines stay strict. Pension calculations follow statutory text, not employer-friendly assumptions.
But May was not simply a month of institutional closure. The Court also opened doors for plaintiffs injured by unsafe trucking brokers, workers seeking to avoid forced arbitration, and a death-row prisoner whose Batson claim had been mishandled by state courts.
May’s deeper story is about legal pathways. The Court asked, again and again, which door the law allows people to use — and which doors are now closed.
1) Rutherford v. United States
No. 24-820 — May 28, 2026
Decision:
The Supreme Court held that a nonretroactive change to federal sentencing law cannot, by itself or in combination with other factors, qualify as an “extraordinary and compelling” reason for compassionate release.
Opinion:
The case involved prisoners sentenced under the old §924(c) “stacking” regime before the First Step Act reduced penalties for future defendants. The Court held that Congress’s decision not to make that change fully retroactive must be respected. The resulting sentencing disparity cannot be converted into compassionate-release eligibility.
Vote Breakdown:
6–3 decision.
Who voted yes:
Roberts, Thomas, Alito, Gorsuch, Kavanaugh, Barrett.
Who dissented:
Sotomayor, joined by Kagan and Jackson.
What it means for the public:
Federal prisoners serving older, harsher sentences cannot rely on later sentencing reforms to seek compassionate release unless Congress made those reforms retroactive.
Who benefits:
The federal government, prosecutors, and finality interests in criminal sentencing.
Who gets harmed:
Prisoners serving long sentences that would likely be shorter if imposed today.
Who stays central:
Congress, because the Court made clear that retroactivity choices belong to lawmakers, not sentencing judges.
Official Slip Opinion:
Rutherford v. United States
2) Fernandez v. United States
No. 24-556 — May 28, 2026
Decision:
The Supreme Court held that prisoners cannot use compassionate release to collaterally attack the validity of their convictions.
Opinion:
A prisoner who claims his conviction is invalid must proceed through §2255, the federal habeas-like postconviction statute. The Court rejected the idea that alleged innocence or doubts about the verdict can be repackaged as an “extraordinary and compelling” reason for compassionate release under §3582.
Vote Breakdown:
6–3 alignment on the main judgment.
Who voted yes:
Roberts, Thomas, Alito, Gorsuch, Kavanaugh, Barrett.
Who concurred in judgment:
Sotomayor, joined by Kagan.
Who dissented:
Jackson.
What it means for the public:
Compassionate release remains a sentence-reduction tool, not a second route to overturn a conviction.
Who benefits:
The federal government and courts seeking to preserve habeas procedures.
Who gets harmed:
Prisoners trying to raise innocence or trial-error claims outside the strict §2255 framework.
Who stays central:
Federal postconviction procedure, especially the divide between sentence modification and conviction review.
Official Slip Opinion:
Fernandez v. United States
3) Pitchford v. Cain
No. 24-7351 — May 28, 2026
Decision:
The Supreme Court ruled for Mississippi death-row prisoner Terry Pitchford, holding that the state court unreasonably applied Batson precedents and unreasonably found that Pitchford had waived his jury-discrimination claim.
Opinion:
The Court said the trial judge failed to complete Batson’s third step. Pitchford’s counsel was not given a sufficient opportunity to rebut the prosecutor’s explanations for striking four Black prospective jurors, and the state court’s waiver finding was unreasonable.
Vote Breakdown:
5–4 decision.
Who voted yes:
Roberts, Sotomayor, Kagan, Kavanaugh, Jackson.
Who dissented:
Gorsuch, joined by Thomas, Alito, and Barrett.
What it means for the public:
Trial courts cannot short-circuit Batson review and then blame defendants for failing to preserve arguments they were not allowed to fully make.
Who benefits:
Defendants challenging racial discrimination in jury selection.
Who gets harmed:
State convictions built on incomplete Batson proceedings.
Who stays central:
Trial judges, because Batson enforcement begins with how they handle jury-selection objections in real time.
Official Slip Opinion:
Pitchford v. Cain
4) Flowers Foods, Inc. v. Brock
No. 24-935 — May 28, 2026
Decision:
The Supreme Court held that a worker can fall within the Federal Arbitration Act’s transportation-worker exemption even if he does not cross state lines or interact with vehicles that do.
Opinion:
The case involved a Flowers Foods distributor who delivered products locally in Colorado. The Court rejected Flowers’s bright-line rule that workers must personally cross state lines, or touch vehicles that cross state lines, to qualify as workers engaged in interstate commerce.
Vote Breakdown:
Unanimous decision.
Who voted yes:
All Justices.
Opinion author:
Justice Gorsuch.
What it means for the public:
Companies cannot force arbitration simply because a transportation worker handles only the in-state leg of an interstate supply chain.
Who benefits:
Certain delivery workers, distributors, and transportation workers resisting forced arbitration.
Who gets harmed:
Companies seeking narrow readings of the FAA’s transportation-worker exemption.
Who stays central:
Lower courts deciding whether a worker plays a direct and necessary role in moving goods across state lines.
Official Slip Opinion:
Flowers Foods, Inc. v. Brock
5) Margolin v. National Association of Immigration Judges
No. 25-767 — May 26, 2026
Decision:
The Supreme Court reversed the Fourth Circuit in a dispute over speech restrictions on immigration judges.
Opinion:
The Court ruled that the Fourth Circuit violated the party-presentation principle by deciding the case on an issue the parties had not raised. The underlying dispute involved a policy requiring immigration judges to obtain supervisory approval before certain public speeches related to official duties.
Vote Breakdown:
Per curiam decision.
Separate opinion:
Justice Thomas concurred, joined by Justice Barrett, arguing that the challenge belonged in the Civil Service Reform Act’s administrative review system rather than federal district court.
What it means for the public:
Federal courts cannot rewrite a case around issues the parties did not present, even in politically sensitive disputes.
Who benefits:
Federal agencies defending workplace policies through administrative channels.
Who gets harmed:
Federal employee groups trying to keep constitutional workplace challenges in district court.
Who stays central:
The Civil Service Reform Act, the Merit Systems Protection Board, and the limits of federal employee litigation.
Official Slip Opinion:
Margolin v. National Association of Immigration Judges
6) Hamm v. Smith
No. 24-872 — May 21, 2026
Decision:
The Supreme Court dismissed the writ of certiorari as improvidently granted, leaving the lower-court ruling in place.
Opinion:
The case involved Joseph Smith, an Alabama death-row prisoner whose intellectual-disability claim under Atkins had been litigated through multiple IQ scores and adaptive-functioning evidence. The Court declined to use the case to provide a broader rule for how courts must evaluate multiple IQ scores in Atkins claims.
Vote Breakdown:
Dismissed as improvidently granted.
Separate opinions:
Justice Sotomayor concurred, joined by Justice Jackson. Justice Thomas dissented. Justice Alito also dissented, joined by Thomas, and joined in part by Roberts and Gorsuch.
What it means for the public:
The Court avoided issuing a broad death-penalty rule on multiple IQ scores, leaving lower courts with limited additional guidance.
Who benefits:
Smith, because the lower-court ruling blocking his execution remains intact.
Who gets harmed:
States seeking clearer, stricter rules for litigating Atkins intellectual-disability claims.
Who stays central:
Lower courts handling capital cases involving intellectual disability and competing expert testimony.
Official Slip Opinion:
Hamm v. Smith
7) M & K Employee Solutions, LLC v. Trustees of the IAM National Pension Fund
No. 23-1209 — May 21, 2026
Decision:
The Supreme Court held that ERISA does not require actuarial assumptions for withdrawal-liability calculations to be selected on or before the measurement date.
Opinion:
The Court ruled that the statute fixes the date for plan data, not the deadline for selecting actuarial assumptions. Actuaries may select assumptions after the measurement date, so long as they satisfy ERISA’s reasonableness and best-estimate requirements.
Vote Breakdown:
Unanimous decision.
Who voted yes:
All Justices.
Opinion author:
Justice Jackson.
What it means for the public:
Multiemployer pension plans retain flexibility in calculating withdrawal liability when employers leave underfunded plans.
Who benefits:
Pension funds and plan actuaries.
Who gets harmed:
Withdrawing employers seeking to lock in earlier, potentially more favorable actuarial assumptions.
Who stays central:
ERISA’s statutory text and the actuaries responsible for calculating pension obligations.
Official Slip Opinion:
M & K Employee Solutions, LLC v. Trustees of the IAM National Pension Fund
8) Havana Docks Corp. v. Royal Caribbean Cruises, Ltd.
No. 24-983 — May 21, 2026
Decision:
The Supreme Court held that cruise lines’ use of docks confiscated by the Cuban government could trigger liability under Title III of the Cuban Liberty and Democratic Solidarity Act.
Opinion:
The Court rejected the Eleventh Circuit’s narrow view that Havana Docks had to show the cruise lines trafficked in its specific property interest. It was enough that the cruise lines used physical property confiscated by the Cuban government and tied to Havana Docks’s certified claim.
Vote Breakdown:
8–1 decision.
Who voted yes:
Roberts, Thomas, Alito, Sotomayor, Gorsuch, Kavanaugh, Barrett, Jackson.
Who dissented:
Kagan.
Separate opinion:
Sotomayor concurred, joined by Kavanaugh.
What it means for the public:
Companies that use property confiscated by the Cuban government may face liability even when the original property interest would have expired before the challenged use.
Who benefits:
U.S. claimants seeking compensation for confiscated Cuban property.
Who gets harmed:
Companies doing business with assets connected to Cuban expropriations.
Who stays central:
Congress’s Title III remedy and courts interpreting what counts as trafficking in confiscated property.
Official Slip Opinion:
Havana Docks Corp. v. Royal Caribbean Cruises, Ltd.
9) Montgomery v. Caribe Transport II, LLC
No. 24-1238 — May 14, 2026
Decision:
The Supreme Court held that negligent-hiring claims against freight brokers are not preempted by the FAAAA when they fall within the statute’s motor-vehicle safety exception.
Opinion:
The case involved a severely injured truck driver who sued C.H. Robinson, alleging that the broker negligently hired an unsafe motor carrier. The Court held that such claims concern motor-vehicle safety and are saved from preemption by the FAAAA’s safety exception.
Vote Breakdown:
Unanimous decision.
Who voted yes:
All Justices.
Separate opinion:
Justice Kavanaugh concurred, joined by Justice Alito.
What it means for the public:
Injury victims may sue brokers for negligent hiring when unsafe carrier selection leads to motor-vehicle crashes.
Who benefits:
Crash victims and plaintiffs bringing state-law safety claims.
Who gets harmed:
Transportation brokers relying on federal preemption to avoid negligent-hiring suits.
Who stays central:
State tort law and the safety exception Congress preserved inside federal trucking law.
Official Slip Opinion:
Montgomery v. Caribe Transport II, LLC
10) Jules v. Andre Balazs Properties
No. 25-83 — May 14, 2026
Decision:
The Supreme Court held that a federal court that stayed a case for arbitration keeps jurisdiction to confirm or vacate the resulting arbitral award.
Opinion:
The Court distinguished this situation from freestanding FAA confirmation or vacatur actions. When a case began in federal court and was stayed under §3 of the FAA, the same court may supervise the arbitration result under §§9 and 10.
Vote Breakdown:
Unanimous decision.
Who voted yes:
All Justices.
Opinion author:
Justice Sotomayor.
What it means for the public:
Parties sent to arbitration from federal court do not necessarily need to start a brand-new state-court fight to confirm or challenge the award.
Who benefits:
Parties seeking efficient court supervision after arbitration.
Who gets harmed:
Litigants arguing that federal courts lose power once arbitration is complete unless a new jurisdictional basis exists.
Who stays central:
Federal courts managing cases stayed under the FAA.
Official Slip Opinion:
Jules v. Andre Balazs Properties
