Update, October 21, 11:45 am ET: The Supreme Court released a brief order on October 21, which ruled against the Trump administration’s request to deny gender-affirming care to transgender prisoners. The order is two sentences long. It is temporary. And it does not explain the Court’s reasoning. So it is not clear why the Court ruled against Trump or even whether Trump will lose if this case reaches the Court again after it has be fully litigated in lower courts. Justices Clarence Thomas and Samuel Alito dissented. The article below was originally published on October 13.

On the first day of his second term, President Donald Trump issued an executive order requiring the Bureau of Prisons to “ensure that no Federal funds are expended for any medical procedure, treatment, or drug for the purpose of conforming an inmate’s appearance to that of the opposite sex.” Issued alongside a record 26 other orders that day, it was an unsurprising development, because Trump had made this issue one of the centerpieces of his 2024 campaign.

The fate of that executive order, as well as the US Bureau of Prisons’ (“BOP”) memoranda implementing the order, is now before the Supreme Court in a case called Trump v. Kingdom. And, while this case obviously has high stakes for incarcerated transgender people specifically, the Court’s resolution of this case could potentially have far greater reach — cutting off many cis and transgender people’s access to healthcare while they are incarcerated.

That’s because one of the central questions in Kingdom — though this issue is not yet before the justices — is when the Constitution requires prisons to provide medical care to incarcerated people. In Estelle v. Gamble (1976), the Supreme Court held that the Eighth Amendment’s ban on “cruel and unusual punishments” imposes on the government an “obligation to provide medical care for those whom it is punishing by incarceration.” People in prison, after all, cannot simply drive themselves to the hospital if they get sick. If the prison does not give them adequate medical care, they will suffer untreated and potentially die.

For procedural reasons, the Court is unlikely to opine on whether Estelle requires prisons to provide gender-affirming care to trans people right away. But the question of when the Eighth Amendment requires prisons to provide medical care to incarcerated people is front and center in the Kingdom case, which means the Court could potentially use Kingdom to limit all imprisoned people’s access to healthcare — or even to undercut the Constitution’s protections against cruel and unusual punishments more broadly.

Ironically, this case also arises out of a famous political blunder by pro-trans advocates. In 2019, when then-Sen. Kamala Harris was seeking her party’s 2020 presidential nomination, the ACLU circulated a questionnaire to candidates that asked if they would use presidential authority “to ensure that transgender and nonbinary people who rely on the state for medical care — including those in prison and immigration detention — will have access to comprehensive treatment associated with gender transition, including all necessary surgical care?” 

Harris responded that she would, and also said that she “pushed the California Department of Corrections and Rehabilitation to provide gender transition surgery to state inmates” while she was state attorney general. 

Years later, during his 2024 debate with Harris, Trump claimed that the then-vice president “wants to do transgender operations on illegal aliens that are in prison.” And not long after, his opposition to gender-affirming care for trans people in prison became a key part of his campaign.

It’s unclear why the ACLU thought it was a good idea to shine a light on this issue in 2019 because, at the time, the BOP provided gender-affirming care to people in federal prison. The ACLU — which represents the pro-trans side in the Kingdom case — now argues that transgender people in federal prison have had access to at least some forms of gender-affirming care “since at least 1992.”

Indeed, Trump’s own administration concluded in a 2018 memo that the Bureau of Prisons’ “statutory mandate to provide basic medical and mental health care” to incarcerated people obligated it to provide “pharmaceutical interventions (e.g., cross-gender hormone therapy), hair removal and surgery (if individualized assessment indicates surgical intervention is applicable)” to transgender people in prison if their doctors determined that these interventions are “medically necessary care.”

In any event, regardless of why Trump fixated on cutting off trans healthcare for people in federal prison, Kingdom is now before the Court. That means that the fate of trans people in prison — and, if the Eighth Amendment issue eventually reaches the Court, all incarcerated people — is now in the hands of a Republican Court that is often hostile to trans litigants, and that has, at times, signaled that it wants to drastically roll back the scope of the Eighth Amendment.

What are the legal issues in the Kingdom case?

At least since Estelle, the Court has held that people who are incarcerated are not also sentenced to live and die without medical care. As the Court said in Brown v. Plata (2011), “a prison that deprives prisoners of basic sustenance, including adequate medical care, is incompatible with the concept of human dignity and has no place in civilized society.”

Under Estelle and Brown, transgender people often have a right to gender-affirming care during their incarceration. As the US Court of Appeals for the Ninth Circuit held in Edmo v. Corizon (2019), such a person must show that they have a “serious medical need” for such care — typically by demonstrating that the care was prescribed to them by their health provider. But the Constitution does not permit prisons to deny medically necessary care to incarcerated people.

In Kingdom, the ACLU raised this Eighth Amendment argument in the lower courts, but those lower courts ruled in favor of transgender people in prison on different, much more technical legal grounds.

For over three decades, from at least 1992 to 2025, according to the ACLU’s brief to the justices, the BOP provided at least some gender-affirming care, including hormone therapy, to transgender people. This matters because, when a federal agency changes its policies, a federal law typically requires it to “examine the relevant data and articulate a satisfactory explanation for its action, including a rational connection between the facts found and the choice made.” This explanation often must explain the agency’s justification for “disregarding facts and circumstances” that justified the previous policy.

Both the ACLU and the lower courts that heard Kingdom argue that the Trump administration did not comply with this obligation when it cut off care for trans people in prison. 

Among other things, the district court that heard this case determined that the administration cited “zero evidence from its own medical or mental health care professionals to support its conclusions” against providing transgender healthcare. While the Trump administration argues that providing gender-affirming care makes prisons less safe, the district court also noted that “the government has not cited a single instance of gender-affirming care giving rise to safety concerns despite having provided such care for many years.”

Is this a persuasive legal argument against the Trump administration’s new policy? I think it is. And so did three federal judges that previously heard the Kingdom case. But the fate of trans people in prison is now in the hands of a Supreme Court that rarely rules in favor of transgender litigants, and that has a history of handing down legally incoherent opinions that are inconsistent with the Court’s own precedents, and that also deny legal rights to trans people.

The current Court’s uncertain commitment to the Eighth Amendment

Because the lower courts that heard Kingdom did not rule on the Eighth Amendment question, Kingdom should not currently give the justices an opportunity to roll back Estelle. But, in the likely event that this Court rejects the ACLU’s argument that the Trump administration did not adequately explain its new policy, the case will return to the lower courts and the Eighth Amendment issue will be fully litigated — teeing up the Eighth Amendment question for the justices to decide in the near future.

This issue could arise, moreover, at the exact moment that some justices are pushing for sweeping changes to how their Court understands the term “cruel and unusual punishments.” Indeed, at least some of the Supreme Court’s recent Eighth Amendment precedents suggest that the Republican justices want a wholesale rewrite of the Court’s previous precedents laying out what constitutes cruel and unusual punishment.

Since the mid-to-late twentieth century, the Court has held that, in Chief Justice Earl Warren’s words, the Eighth Amendment “must draw its meaning from the evolving standards of decency that mark the progress of a maturing society.” Thus, as certain forms of punishment grow more uncommon, they become more constitutionally dubious.

This “evolving standards of decency” framework is front and center in nearly every major Supreme Court decision interpreting the Eighth Amendment for the last five or six decades, including Estelle.

In Bucklew v. Precythe (2019), however, the Court’s Republican majority seemed to abandon this framework. Although decades worth of pre-Bucklew decisions established that a punishment is unconstitutional if it is considered cruel and unusual today, Bucklew suggested that a method of punishment is unconstitutional only if it “had fallen out of use” at “the time of the founding.” 

Bucklew did list some methods of punishment that fail this test, but they are things like “disemboweling” or “burning alive.”  

Thus, if taken seriously, Bucklew’s new approach to Eighth Amendment cases would dramatically expand the government’s power to impose harsh punishments. The late Justice Antonin Scalia, for example, argued that a Bucklew-like approach to the Eighth Amendment does not prohibit the government from executing most intellectually disabled offenders, and that it does not limit the government’s ability to impose excessive punishments for minor crimes.

In fairness, some of the Court’s post-Bucklew decisions are inconsistent with the framework the Court laid out in that case. So at least some of the justices who joined Bucklew may have since decided that it’s a bad idea to toss out the Court’s entire framework for Eighth Amendment cases. But Bucklew was one hell of a warning shot over the bow of the Eighth Amendment. And the mere fact that the Bucklew decision exists means that advocates for humane punishments must hold their breath any time this Court is asked whether a particular punishment is cruel and unusual.

In the worst-case scenario for people in prison, a case like Kingdom could inspire the Republican justices to overrule — or, at least, drastically limit — decisions like Estelle and Brown. That would mean that all incarcerated people, regardless of their gender identity, could lose access to medically necessary care unless the government decides to give it to them as an act of grace.

Late last month, the state of Tennessee attempted to execute Christa Pike, a woman who has been on death row for decades after killing a classmate as a teenager. 

The execution failed: Pike survived two doses of the lethal injection drug pentobarbital, making her the first person ever to do so.

The botched execution comes at a strange moment for capital punishment in America. Support for the death penalty has been declining for decades. And for a long time, the number of executions was falling, too. But since 2021, executions have been increasing again. The recent surge has been driven largely by one state: Florida.

According to Pamela Colloff, who covers the criminal justice system for ProPublica and wrote about Florida’s use of the death penalty for New York Times Magazine this summer, 40 percent of the executions conducted in the US last year were in Florida.

“There are so many things that make the administration of the death penalty interesting and unique in Florida,” Colloff explained on a recent episode of Vox’s The Gray Area podcast. “Among active death penalty states right now, Florida is unique in that one person determines, from the hundreds of men on death row, who will receive an execution date, and what that execution date is.”

I spoke with Colloff earlier this month following Pike’s failed execution about what happened in Tennessee, what’s driving Florida’s recent zeal for executions, and why victims’ families are often unsatisfied by the death penalty process. 

Below is an excerpt of our conversation, edited for length and clarity. There’s much more in the full podcast, so listen to The Gray Area wherever you get podcasts, including Apple Podcasts, Pandora, and Spotify. (This interview also appeared more recently on Vox’s Today, Explained podcast.)

We’re taping shortly after news came out that a woman in Tennessee who was on death row, authorities attempted to put her to death. They gave her two doses of lethal injection medication, and she survived. 

How much of the decline in the use of the death penalty has to do with, in your estimation, people feeling like there’s no way to do it that’s humane? 

This is the second botched execution in Tennessee this year, just to give you a sense of things. This is more common there than in other states. They’ve changed their drug protocols and we don’t know a lot about what went wrong with Christa Pike. In May, it was an issue with accessing veins, which can be an issue with lethal injection. 

I think it’s also important for people to remember that we had the electric chair as the method of execution through the ’80s and into the ’90s in some places. While [lethal injection] is considered a far more humane, quote-unquote, way to do this, we can see that nothing is perfect. 

I will say that while the issues of botched executions are very important, and I think there are some other ones coming up to be concerned about, I am more interested in how it is that other errors are made, that other people end up with the ultimate punishment when that perhaps was not the right punishment for what occurred.

You’ve also written that death penalty convictions are just expensive, right? And on top of that, DNA evidence has made it clear that many of the people who were being convicted were not guilty, or there wasn’t strong enough evidence to convict them. How do you think about that mix of factors?

Florida, which I’ve spent a lot of time writing about, is the leading place in America by a mile in terms of the number of executions, and has a very large death row. Florida’s also the leader in wrongful death row convictions. Just to give you a sense of things, Florida holds the distinction of 30 death row exonerations.

What that means is in the modern era — the past roughly 50 years — there have been 30 men who were given dates of execution who now walk free. And for anyone who pays any attention to how the criminal justice system works and how incredibly difficult it is to overturn a wrongful conviction, if we have 30 people in Florida who have that distinction, we know that there are many more.

What’s going on in Florida? When did you realize that something was different there?

It really ramped up last year. Last year, Florida executed 40 percent of the people who were executed in the US in the last calendar year. In this year, there have been 16 men who’ve been executed in Florida so far. 

Just to give you a comparison, Texas is the next state with the highest number of executions, and they’ve executed six men in that time. We already have outlier states, primarily southern states, and then we have Florida being the ultimate outlier.

There are so many things that make the administration of the death penalty interesting and unique in Florida. The thing that fascinated me the most is, among active death penalty states right now, Florida is unique in that one person determines, from the hundreds of men on death row, who will receive an execution date, and what that execution date is.

Who is it?

Gov. Ron DeSantis. I went back and looked at what were the patterns here, what were the things guiding Gov. DeSantis’s thinking in setting these dates, and was fascinated to see and very troubled to see that there are a number of men who’ve been there so long.

They’ve been there since the 1970s. These are men who were convicted when Gerald Ford was president, just to make this real to people. But the dates are not being set among the men who are what are called death-eligible, meaning that they’ve gone through all their appeals. They aren’t being done chronologically.

There’s no rhyme or reason to the process. And so there’s this speculation game among victims’ families, prisoners, their advocates about who will be next. And men can sit there on death row for decades with that hanging over them, and that is a Florida phenomenon.

You wrote about Florida’s death row turning from something like a purgatory where people stay for a long time into something closer to an assembly line, right?

I was so struck by the fact that in Florida, in order to have this pace of executions, there were people who were receiving their dates 30 days, sometimes fewer, from their execution dates. 

Just to give people a sense of why that is unusual, there are so many things that kick into gear when a death warrant is written. There are numerous legal maneuvers and next steps that happen in the courts. To give you a quick example, there was one defendant in Florida this spring who, five days before he was scheduled to be executed, was finally granted the ability to test DNA evidence in his case that had gone untested.

He had great lawyers who didn’t sleep to make that happen, but that it came as close as five days to his execution date. I think that should give us all pause about how fast this is moving. 

You have multiple people in the queue at the same time. There’s a place — a different unit than Florida’s death row — that you’re taken to once you get your date, called death watch.

Tell me about death watch. What does it look like and what does it feel like?

Death watch is roughly 30 feet from the execution chamber. There are three cells. When you receive your date, you are taken from death row to death watch where you’re put — I don’t want to say solitary because if there are one or two other men who are held there — but you’re in a far different situation than you would be on death row where there are guards and other people you know.

From that point forward, there are roughly 30 days where you are held within steps of where this will take place. To me, it was chilling that when I was doing my reporting in the spring on the story that I published this summer, all three cells were filled, and as soon as one person was executed, the pattern was that often the next day a new death warrant would be signed, and there would be a new person in place.

Why do they do that? Why do they put these people next to the place where they’ll die?

That’s one of the many questions I had about that. We talk about not wanting to have cruel and unusual punishment. Our Constitution does not uphold that. But it’s such a unique kind of mental torture, I think, to be 30 feet from where you’ll be put to death.

The other thing I was struck by was the waiting aspect. If you’re on death row, again, you always have this hanging over you. I talked about the way in which, when you’re in that kind of sensory deprivation, you become highly attuned to sounds and smells and things like that.

I interviewed someone who’s not on death row anymore, whose sentence was commuted, who talked to me about recognizing that jangle of keys and the steps that this group of people who come to deliver the death warrant take, and knowing that someone is about to be served with a death warrant, but not knowing, “Is it me? Is it the guy next to me? Is it someone down the hall?”

I just want to say, I understand that there’s a counterargument to all of this, which is that these are people who most often committed terrible crimes. Their victims did not know when they were going to be killed.

I do think, however, as a state that administers this thing, there has to be a rhyme or reason to this. Otherwise, you have total chaos, including for victims’ families, who never know. Are they going to wait one month? Are they going to wait 15 years? They don’t know.