Legal Docket: Lines that hold

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MARY REICHARD, HOST: It’s The World and Everything in It for this 23rd day of March, 2026. We’re so glad you’ve joined us today. 

Good morning! I’m Mary Reichard.

NICK EICHER, HOST: And I’m Nick Eicher. 

Time now for Legal Docket, and we begin with one unanimous opinion, it came down on Friday, it’s a 9-0 decision in favor of a street preacher from Mississippi.

The court ruled that being convicted under a law one time does not mean you lose the right to challenge that law in the future.

REICHARD: Here’s the background: Gabriel Olivier had been fined under a city rule requiring protesters and demonstrators to stay in a designated area near a local amphitheater. But Olivier said that space was too remote to reach people effectively, so he went back to the sidewalk in front of the venue—and got himself arrested. 

The city said a prior Supreme Court precedent barred him from challenging that ordinance at all.

EICHER: But the high court said Olivier is not trying to undo his old conviction. What he's trying to do is stop future enforcement of the ordinance, so that he can return to the amphitheater and preach without fear of another prosecution.

And during arguments in December, Justice Samuel Alito spelled out the practical problem in plain English:

ALITO: And doesn’t it seem a stretch of the underlying reasoning to say, "no, you can’t ever do that, you’re forever barred from engaging in what you think is protected First Amendment activity because you were previously convicted under this statue." 

REICHARD: So now Olivier may go forward with a federal lawsuit aimed at the one thing he seeks: the right to return to the amphitheater to preach without the threat of another prosecution.

EICHER: Alright, on now to argument in Hunter v United States, this is the first of two cases today.

Munson Hunter pleaded guilty in federal court to aiding and abetting wire fraud. As part of that plea deal, he gave up his right to appeal even before he knew the sentence he would receive.

Later, after sentencing, Hunter objected to one of the conditions of his supervised release: that he take mental health medications as prescribed by a doctor.

REICHARD: Hunter says that violates his constitutional right to refuse unwanted medical treatment.

The trial judge said Hunter could appeal. But the Fifth Circuit later said that waiver in his plea deal had already given that right away.

EICHER: So the question for the justices is simple: When a defendant signs away his right to appeal, does that also block him from challenging a sentence condition he says is unconstitutional?

Hunter’s lawyer Lisa Blatt framed the case around principles of contract law:

BLATT: All contracts are subject to defenses. So appeal waivers are also subject to defenses and can be excused in more circumstances than the two recognized below.

Her point is that, yes, plea agreements are contracts—but contracts have limits, defenses, and exceptions.

Blatt said the Fifth Circuit’s rule is so rigid it would leave defendants stuck even with plainly unlawful sentence conditions:

BLATT: No appeal for sentences above the statutory maximum based on race, religion, national origin, tribal status, or pure vindictiveness. No appeal for pregnancy bans, castration, or compelled church attendance either. These scenarios are all real cases.

Then she tied it back to her client’s situation:

BLATT: Only the most paramount government interest overcomes the fundamental right to refuse medical treatment.

REICHARD: She reiterated that her client was ordered to comply with medical treatment even though he had no demonstrated mental health condition tied to his crime.

Justice Clarence Thomas questioned her on a key premise:

THOMAS: Ms. Blatt, if you can waive constitutional rights or statutory rights, why can't you waive these contractual rights that are statutory here?

BLATT: You absolutely can waive…the right to appeal and there's an appeal agreement, but the issue here is, absent this plea agreement, which is a contract, the defendant could just walk away.

Blatt’s answer: Yes, defendants can waive appeal rights—but not in a way that wipes out every contract defense when the government wants strict enforcement.

She put this bluntly:

BLATT: That's absurd when everyone from Elon Musk to billionaires to corporations to…mom-and-pops can assert contract defenses. The government doesn't even tell you why this contract, unlike any other contract in the entire universe, can't have a defense.

Justice Amy Coney Barrett acknowledged the appeal of the contract analogy for plea deals. But she also noted that the lower courts have not been consistent in treating them as ordinary contracts.

EICHER: On the other side, though, the government argues that a deal is a deal.

Zoe Jacoby represented the United States and she argued that waiving appeal just means the trial court is the final decision maker.

Then she added a colorful hypothetical:

JACOBY: To be clear: an appeal waiver is not an agreement to receive an unlawful sentence. You couldn't agree to receive “trial by 12 orangutans.” That would be an unlawful bargain.

REICHARD: Justice Neil Gorsuch was not buying that: what if the district court itself behaves unlawfully?

That segued into a sharp comment from Justice Sonia Sotomayor:

SOTOMAYOR: That's exactly what you're saying, which is, if the judge uses impermissible race factors, impermissible sex factors, religious factors, that can be waived…that’s saying, you're entering a contract that says, if your judge is biased, if he doesn't follow the Constitution,...if he makes plain error judgments that are clear and undisputed, there's no remedy for you.

EICHER: Lawyer Blatt reinforced that idea with another hypothetical dealing with judges:

BLATT: It's—I'm going to get this example out—if there was a law that was passed that said all judges must take antidepressants recommended by their physician, I think you would find it stupidly unconstitutional and offensive.

JUDGE: Well, I think we already have [laughs]

The practical question is whether appeal waivers are nearly absolute—or whether courts must leave room to correct sentence conditions that cross a constitutional line.

REICHARD: Alright, on to our last case:

ROBERTS: We will hear argument this morning in case 24-1238, Montgomery v Caribe Transport.

This one arises from a terrible accident. Shawn Montgomery was parked in a tractor-trailer on the side of the highway when another tractor-trailer slammed into his vehicle. He suffered many injuries, including the loss of a leg.

Montgomery sued the driver, the trucking company, and also the freight broker who had arranged the shipment—C.H. Robinson.

EICHER: Robinson is a freight broker who doesn’t own trucks or employ drivers. It matches shippers with motor carriers.

Montgomery says the broker was negligent in choosing an unsafe carrier.

But the broker says Congress already shielded companies like his from that kind of lawsuit. He cited a federal deregulation law with the unwieldy name Federal Aviation Administration Authorization Act.

REICHARD: In plain English, Congress told states: stay out of the trucking business when it comes to prices, routes, and services. But Congress also said states may still protect public safety. 

So the question is whether this lawsuit is really about highway safety—or whether it is an end run around federal deregulation.

EICHER: Montgomery’s lawyer is former Solicitor General Paul Clement. He argued for state law to prevail. And he put it this way: if this lawsuit cannot go forward, then a broker may help put a dangerous truck on the road and still avoid responsibility.

CLEMENT: While Congress favored economic deregulation, the last thing it wanted was safety deregulation. …Thus, the question in this case boils down to whether the negligent hiring claim here is with respect to motor vehicles. Of course, it is. The whole point of the tort is to keep dangerous motor vehicles off of the road.

But the federal government is on the side of the broker. It says the safety exception should be read more narrowly. Here is Assistant to the Solicitor General Sopan Joshi:

JOSHI: Put it this way. Suppose there were a rule that applied with respect to coffee, cream, and sugar, and then an exception that applied only with respect to coffee. You would naturally think that the exception does not apply with respect to cream and sugar, even though that phrase in isolation might cause you to adopt the opposite view. 

I think that’s kind of what’s going on here, and that’s why I think the respondent’s (the companies) reading of the statute is the better one.

REICHARD: In other words, the government says this lawsuit is one step too far removed from the truck itself.

But Clement, for the injured man, had a counter to that:

CLEMENT: But the thing is if you have one of these McDonalds torts where the problem is the piping-hot coffee spilled in your lap, I would say that's a tort with respect to coffee. And for the same reasons, this is a tort with respect to motor vehicles.

The broker’s own lawyer pushed that point even harder: brokers arrange shipments, he says. They do not drive trucks:

BOUTROUS: Congress assigned freight brokers a defined role to arrange for transportation of property by connecting shippers with motor carriers. …Brokers lack sufficient connection to motor vehicles. Brokers don't own, operate, or control motor vehicles...

EICHER: And therefore, a broker’s connection to the motor vehicles is just too far removed to fall within the safety exception.

Justice Brett Kavanaugh had a practical concern:

KAVANAUGH: If tort liability extends to them, how are they going to assess and evaluate the safety of drivers in a particular trucking company? How are they going to figure out do they have an alcohol/drug issue? How are they going to figure out English proficiency which of course is a critical issue at the current moment...in the real world of how brokers operate, it's very difficult.

…later… CLEMENT: So I think it's going to be pretty easy for them to protect themselves by hiring quality carriers.

Justice Alito brought a moment of levity in search of a clean legal theory, with Clement happy to join in:

ALITO: I came to the argument hoping you were going to give us some brilliant way of reconciling these two provisions other than just live with it, but I guess there's no -- there is no such theory.

CLEMENT: If there is, it has escaped me.

REICHARD: At bottom, the justices have to decide how far federal deregulation goes: does it protect brokers from negligent-hiring suits, or does state safety law still reach them when bad choices put dangerous trucks on the road?

We’ll know who prevails sometime before the end of June. 

And that’s this week’s Legal Docket.

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