Oral Arguments - The Supreme Court of the United States

Case Summary:
On March 4, 2026, the Supreme Court heard oral arguments in Montgomery v. Caribe Transport II, LLC, a high-stakes case for the logistics industry that examines whether federal law protects freight brokers from state-law negligence lawsuits.
The case arose after Shawn Montgomery was severely injured when a tractor-trailer struck his vehicle on the shoulder of an Illinois highway. Montgomery sued the broker, C.H. Robinson, alleging it was "negligent" for hiring a motor carrier with a known history of safety issues. The lower courts dismissed the claim, ruling that the Federal Aviation Administration Authorization Act (FAAAA)—a 1994 law designed to deregulate the trucking industry—preempts such state-law claims.
Core Legal Issues
The justices are tasked with resolving a "circuit split" regarding two specific provisions of the FAAAA:
The Preemption Rule: Does a state-law "negligent hiring" claim "relate to a service" of a broker in a way that Congress intended to prohibit to ensure a uniform national market?
The Safety Exception: Even if the claim is generally prohibited, does it fall under the "safety regulatory authority of a State with respect to motor vehicles," which Congress explicitly carved out and preserved for the states?
Highlights from Oral Argument
Defining "Safety Regulation": Paul Clement, representing Montgomery, argued that personal injury lawsuits have historically been the primary way states regulate safety. However, several conservative justices, including Justice Clarence Thomas, questioned whether a lawsuit against a middleman who never touches a truck truly counts as regulation "with respect to motor vehicles."
The "Patchwork" Concern: Counsel for the broker, Theodore Boutrous, argued that allowing these suits would create a "patchwork" of 50 different state standards for how brokers must screen carriers, "bollixing up" interstate commerce and driving up insurance costs for the entire supply chain.
Practicality and Common Sense: Justice Brett Kavanaugh focused on the practical burden on small brokers, asking how they are supposed to verify complex safety data or driver English proficiency without being forced to only hire large, expensive carriers, potentially crushing small business competition.
The Intrastate Anomaly: Justices Samuel Alito and Brett Kavanaugh pointed out a potential "logical flip" in the statute: the law clearly bars these suits for intrastate (in-state) travel. They questioned why Congress would prohibit states from regulating safety within their own borders but allow them to do so for interstate (cross-border) trips.
The Solicitor General's View: The Department of Justice participated in the argument, siding largely with the brokers. The government argued that while states can regulate trucks and drivers directly, extending that authority to the "matchmaking" service of a broker stretches the safety exception too far.

Case Summary:
On March 3, 2026, the Supreme Court heard oral arguments in Hunter v. United States, a case that examines the limits of plea agreements and whether a defendant can truly waive their right to appeal a sentence that may be unconstitutional.
The case involves Munson P. Hunter III, who pleaded guilty to wire fraud. As part of his plea, he signed a standard "appellate waiver," giving up his right to challenge his sentence. However, at sentencing, the judge imposed a condition requiring Hunter to take any mental health medications prescribed by his doctors—a requirement Hunter argues violates his Fifth Amendment liberty interests. Crucially, after imposing the sentence, the judge explicitly told Hunter, "You have a right to appeal," and the government prosecutor did not object to that statement.
Core Legal Issues
The justices are deciding two major points that affect nearly 95% of federal criminal cases settled by pleas:
The Scope of Waivers: Are the only exceptions to an appeal waiver claims of "ineffective assistance of counsel" or a "sentence exceeding the statutory maximum," or are there broader exceptions for "miscarriages of justice" or unconstitutional sentencing conditions?
The "Waiver of the Waiver": Does a judge’s oral statement at sentencing—telling a defendant they have a right to appeal—override a previously signed written waiver, especially if the government remains silent?
Highlights from Oral Argument
Skepticism Toward the Government: Several justices, including Justice Elena Kagan and Justice Ketanji Brown Jackson, appeared troubled by the government’s "hard line" position. They questioned whether a waiver should really block a defendant from appealing a sentence if, for example, a judge was explicitly racist or imposed a "shocking" and unconstitutional condition.
The Contract Law Debate: Hunter’s counsel, Lisa Blatt, argued that plea deals are essentially contracts and should be subject to traditional contract defenses like "unconscionability" or "public policy." However, Justice Samuel Alito and others expressed concern that importing complex contract doctrines into criminal law might make plea deals too unpredictable.
Coercion and Power Imbalance: Justice Jackson highlighted the inherent power imbalance in plea negotiations, questioning whether a defendant can "voluntarily" waive a right to challenge a sentence that hasn't even been determined yet.
The "Silent Prosecutor" Problem: Much of the bench focused on the fact that the prosecutor did not correct the judge when Hunter was told he could appeal. Chief Justice John Roberts and Justice Brett Kavanaugh explored whether the government "forfeited" its right to enforce the waiver by failing to speak up in the courtroom.

Case Summary:
On March 2, 2026, the Supreme Court heard oral arguments in United States v. Hemani, a pivotal Second Amendment case determining whether the government can permanently disarm "unlawful users" of controlled substances, specifically marijuana.
The case involves Ali Danial Hemani, a Texas man who was indicted under 18 U.S.C. § 922(g)(3) after FBI agents found a Glock pistol and marijuana in his home. Hemani, who admitted to using marijuana roughly every other day but was not intoxicated at the time of the search, challenged the law as an unconstitutional violation of his right to bear arms.
Core Legal Issues
The justices are grappling with whether a categorical ban on gun ownership for drug users is consistent with the "history and tradition" of American firearm regulation. Under the standard set in Bruen, the government must prove that this modern restriction is analogous to historical laws from the founding era.
The United States argues that the ban is similar to historical "habitual drunkard" laws, which allowed for the disarmament of individuals deemed a danger to themselves or others. Hemani’s defense, however, contends that those historical laws only regulated the use or carry of firearms while actually intoxicated, rather than stripping away the fundamental right to possess a weapon in the home for self-defense based on occasional or regular drug use.
Highlights from Oral Argument
Justice Gorsuch’s Breakfast Hypo: Justice Neil Gorsuch expressed skepticism toward the government’s "habitual user" standard, pointing out that many of the Founding Fathers, including John Adams, consumed alcohol daily (such as hard cider with breakfast) without being considered "dangerous" or subject to disarmament.
The Ambien Problem: Justice Amy Coney Barrett pressed the government on the breadth of the statute, noting that under the current law, someone who takes a spouse’s Ambien or a single unprescribed Adderall could technically be labeled an "unlawful user" and face a 15-year felony sentence for owning a gun.
Vagueness Concerns: Several justices questioned the lack of a clear definition for "unlawful user." They noted that the statute does not specify how frequently one must use a substance or how recently the use must have occurred to trigger the loss of a constitutional right.
Individualized Dangerousness: Justice Sonia Sotomayor and Justice Brett Kavanaugh explored whether the Second Amendment requires an "individualized determination" of danger—similar to the domestic violence restrictions upheld in Rahimi—rather than a blanket ban based on the mere status of being a drug user.

Case Summary:
On February 25, 2026, the Supreme Court heard oral arguments in Pung v. Isabella County, a case that examines the constitutional limits of "home equity theft" and could fundamentally change how local governments handle tax foreclosures.
The dispute began over a relatively minor tax bill of approximately $2,242 on a Michigan property. Despite a tax tribunal previously ruling that the owner was entitled to an exemption, Isabella County foreclosed on the home, sold it at auction for $76,000, and initially attempted to keep the entire amount. While lower courts ordered the county to return the "surplus" (the auction price minus the debt), the family argued they were still cheated because the home’s fair market value was roughly $194,400.
Core Legal Issues
The justices are considering two primary constitutional questions:
The Fifth Amendment (Takings Clause): Does "just compensation" mean the government only owes the former owner the surplus cash from a forced auction, or must it pay the full fair market value of the property?
The Eighth Amendment (Excessive Fines Clause): Is the loss of over $100,000 in home equity to satisfy a $2,200 debt—an amount 50 times the original bill—a "grossly disproportionate" fine that is unconstitutional?
Highlights from Oral Argument
Focus on Fairness: Several justices expressed significant discomfort with the facts of the case, with Justice Amy Coney Barrett likening the relentless tax assessor to Inspector Javert from Les Misérables, noting it was "even worse" because the family likely didn't even owe the tax.
The Auction vs. Market Value: Justice Sonia Sotomayor and Chief Justice John Roberts pushed back on the idea of a "fair market value" requirement. They questioned whether an auction, by its very nature as a forced sale, shouldn't be the standard measure of value, asking if a "fairly conducted" auction is all the Constitution requires.
The "Infinite Windfall" Problem: Counsel for the county warned that requiring fair market value would "effectively eliminate" foreclosure as a tool for debt collection, as governments would be forced to pay out hundreds of millions of dollars in equity they didn't actually collect at auction.
Property as a "Bundle of Sticks": Justice Neil Gorsuch emphasized that when the state takes a house, it takes the entire "bundle of property rights." He suggested that the state should be responsible for the full value of what it takes, not just what it manages to sell it for under pressure.
What Happens Next
A decision is expected by June 2026. This ruling will clarify whether the 2023 landmark case Tyler v. Hennepin County (which stopped states from keeping all auction profits) goes a step further to require that states ensure homeowners receive the full, un-depressed value of their life's savings.

Case Summary:
On February 24, 2026, the Supreme Court heard oral arguments in Enbridge Energy, LP v. Nessel, a case that could determine the fate of the controversial Line 5 pipeline through a technical dispute over court deadlines.
The litigation began in 2019 when Michigan Attorney General Dana Nessel sued in state court to shut down a segment of the Enbridge pipeline running beneath the Straits of Mackinac, citing environmental risks. Nearly 30 months into the state court proceedings, Enbridge attempted to "remove" the case to federal court—far beyond the standard 30-day statutory deadline for such moves.
Core Legal Issues
The central question before the Court is whether the 30-day deadline for removing a case from state to federal court (28 U.S.C. § 1446(b)) is a rigid, mandatory rule or if district courts have the "equitable" authority to extend it in exceptional circumstances.
Enbridge argues that the deadline functions like a statute of limitations and should be subject to "equitable tolling," allowing a judge to excuse a late filing if the federal interests are significant enough. Michigan contends that the deadline is a firm procedural requirement designed to prevent "forum shopping" and that allowing exceptions would cause unpredictable delays in state-level litigation.
Highlights from Oral Argument
The Forum Stakes: Several justices noted that the choice of court is pivotal; federal courts are generally viewed as more sympathetic to Enbridge’s arguments regarding federal safety preemption, while state courts are seen as more likely to favor Michigan's environmental protection claims.
Justice Sotomayor’s Skepticism: Justice Sonia Sotomayor pointed out that unlike a statute of limitations where a late filing might end a case entirely, a late removal just means the case stays in state court. She questioned if Enbridge was truly "losing" any rights, or simply losing its preferred venue.
International Implications: Justice Samuel Alito expressed concern over the potential for "severe" diplomatic fallout with Canada if a state court were to order the pipeline shut down, suggesting this broader context might justify federal court oversight.
The "Clear Command" Debate: The argument heavily featured the "clear statement rule." Michigan’s Solicitor General argued that Congress’s inclusion of specific, narrow exceptions in the statute proves that it did not intend for judges to create their own "equitable" loopholes.
What Happens Next
The Supreme Court is expected to rule by June 2026. If Enbridge wins, the case will likely move back to federal court, where the pipeline is more likely to remain operational. If Michigan wins, the case will proceed in state court, bringing the Attorney General one step closer to her goal of decommissioning the Line 5 segment.