In May, Last Mile Reigned Supreme in the News

Two unanimous Supreme Court decisions landed in the same month, both touching last-mile delivery. Here’s what happened, what changed, and what operators should be thinking about.

In May 2026, the Supreme Court issued two unanimous rulings directly affecting last-mile delivery. Montgomery v. Caribe Transport II (May 14) opened the door for negligence lawsuits against freight brokers who select unsafe carriers. Flowers Foods v. Brock (May 28) ruled that last-mile drivers delivering interstate goods can bypass mandatory arbitration, even if they never cross state lines. Together, they signal that the legal framework around last-mile is tightening, and fast.

What is Montgomery v. Caribe Transport?

Shawn Montgomery, a truck driver, had pulled his tractor-trailer onto the shoulder of an Illinois highway when another truck driver left the roadway and hit him. Montgomery lost his leg.

The driver worked for Caribe Transport II, a carrier C.H. Robinson had selected to move freight. Montgomery’s attorneys argued that C.H. Robinson should have known Caribe posed a safety risk. The driver had previously been cited for careless driving after another crash, and Caribe had been involved in multiple crashes within a short period of time.

Montgomery sued the driver and Caribe, then brought a negligent selection claim against C.H. Robinson. He argued that brokers should not be shielded from liability when they place freight with carriers that have known or knowable safety problems.

C.H. Robinson’s defense relied on the Federal Aviation Administration Authorization Act, a 1994 federal law that prohibits states from enforcing regulations “related to a price, route, or service” of a broker. For decades, the brokerage industry read that language broadly. Any state-law claim touching a broker’s operations was preempted, full stop. Federal courts were split on whether that interpretation held up, and brokers in many jurisdictions used it to avoid negligence lawsuits entirely.

The Supreme Court disagreed. Justice Barrett, writing for a unanimous bench, held that a general negligence claim about safety isn’t the kind of state regulation the FAAAA was designed to block. The statute preempts state laws that target broker business decisions (pricing, routes, service offerings). It does not give brokers blanket immunity from the same negligence standards that apply to every other business.

The result: brokers can now be sued in state court for the carriers they choose.

What is Flowers Foods v. Brock?

Angelo Brock delivers baked goods for Flowers Foods entirely within Colorado. He picks up product from a local warehouse and drives it to stores. He never crosses a state line.

When Brock tried to bring an employment dispute to court, Flowers Foods pointed to a mandatory arbitration clause in his contract. The Federal Arbitration Act generally makes those clauses enforceable, but it exempts transportation workers engaged in interstate commerce. For those workers, an employer cannot use the FAA to force the dispute into arbitration.

Flowers Foods argued that Brock did not qualify because his routes were local and the goods’ interstate journey ended at the Colorado warehouse. The Supreme Court disagreed. What mattered was not whether Brock personally crossed state lines, but whether the goods were still moving through a continuous interstate supply chain.

The baked goods originated out of state, and Brock delivered them on the final leg to stores. That made him part of interstate commerce, which means Flowers Foods could not use the FAA to enforce the arbitration clause and keep his case out of court.

The result: last-mile delivery drivers who handle goods that traveled interstate can take employment disputes to court, even if they personally never leave the state.

What do these rulings actually change?

Let’s start with what these rulings don’t do. Montgomery doesn’t create new safety regulations for brokers. There’s no federal checklist brokers are now required to follow when selecting a carrier. Flowers Foods doesn’t reclassify last-mile workers or rewrite employment law. Neither ruling tells any company to do something it wasn’t doing yesterday.

What they do is remove legal shields that companies have relied on for years.

• Montgomery removes the preemption defense that lets brokers avoid negligence lawsuits.
• Flowers Foods removes the ability to enforce arbitration clauses against last-mile drivers delivering interstate goods.

In both cases, the door to the courtroom is now open where it was previously closed. The rulings make clear that accountability standards long applied across the supply chain also apply to last-mile operations.

Last-mile delivery has scaled faster than the regulatory framework around it. But the framework is catching up. And when the Court resolves both questions unanimously in the same month, we can see where things are heading.

What should delivery operators be thinking about?

If you run a delivery network, these decisions are worth bringing to your team and your legal counsel. Not as emergencies, but as prompts to pressure-test assumptions that may have shifted underneath you.

Carrier selection and visibility

Montgomery means that carrier selection decisions may need to be defensible in court. If you work with third-party carriers, how much do you actually know about them, not just at the point of onboarding, but on an ongoing basis? Do you have visibility into safety records, incident history, and driver quality across your network? Is that data documented in a way you could point to if you needed to?

The brokers most exposed by this ruling are the ones who optimized purely for cost and speed without a paper trail on safety.

Arbitration and workforce agreements

If your driver contracts include mandatory arbitration clauses, Flowers Foods is worth a hard look. The ruling applies to workers who deliver goods that originated out of state, which describes a significant portion of last-mile delivery. If your agreements were drafted on the assumption that intrastate drivers aren’t “engaged in interstate commerce,” that assumption may no longer hold. This doesn’t mean your clauses are automatically unenforceable, but it means the question is open in a way it wasn’t before.

Operational model fit

Zoom out from the specifics for a moment. Both rulings point in the same direction: the legal environment around last-mile is changing. If your delivery operation was built for speed-to-market five years ago (stitched together from multiple carriers, gig platforms, and contractor agreements) it’s time to ask whether that model still holds up, both operationally, and in terms of the legal and compliance exposure it creates.

Where we sit

Nash works with enterprises orchestrating delivery across carriers, fleets, and third-party providers. The questions above aren’t new to us. Carrier visibility, driver quality, operational rigor: that’s what we build for every day. That’s what running last-mile well actually requires. These decisions reinforce what the best operators in the industry have already figured out.

What comes next for last-mile regulation?

Two unanimous decisions in one month is a signal that the Supreme Court sees last-mile delivery as a mature industry and expects it to operate like one. More clarity is coming, and likely more scrutiny with it.