For much of the hour, Justice Brett M. Kavanaugh had been quietly shifting in his seat, resting cheek against palm and looking down at the lawyers as they argued. Finally, he spoke, asking D. John Sauer, the state solicitor of Missouri, “Are you saying that even if the method creates gruesome and brutal pain, you can still do it because there’s no alternative?”

The question sat there for a second. In the press area, located at the side of the courtroom gallery, twenty-some pairs of eyes ping-ponged between the justice and the solicitor. Mr. Sauer said, “Any petitioner who is claiming that it would create gruesome and brutal pain must…offer an alternative method that significantly reduces the pain.”

“So,” repeated Justice Kavanaugh, “you’re saying that even if the method imposes gruesome, brutal pain, you can still go forward?”

“Well, I would say again that that petitioner has to, if they want to—”

“Is that a yes?”

“Yes, it is, your honor.”

Justices Clarence Thomas and Samuel Alito rocked to and fro in their high-backed chairs.

Bucklew v. Precythe, argued before the Supreme Court on Nov. 6, is about pain and cruelty. Russell E. Bucklew has been on death row since 1997, when a Missouri court convicted him of murder, kidnapping, burglary, forcible rape and armed criminal conduct. At issue two decades later is whether an injection of pentobarbital, the chemical agent used to execute prisoners in the state of Missouri, would result in an unduly painful death for Mr. Bucklew, who suffers from a rare medical condition called cavernous hemangioma. He says the lethal injection protocol would cause him to choke on his own blood and has proposed an alternative, nitrogen hypoxia (a lethal gas).

Justice Kavanaugh: “You’re saying that even if the method imposes gruesome, brutal pain, you can still go forward?”

But Mr. Sauer argued there was no indication that nitrogen hypoxia would bring about a less painful death. And anyway, he said, “to eliminate the risk of pain completely is impossible.”

This is one of the first death penalty cases to come before the Supreme Court since Anthony Kennedy retired, and since Pope Francis revised the Catechism of the Catholic Church in August to say that capital punishment is “inadmissible” under all circumstances. The case parallels a number of recent challenges to the death penalty, like Madison v. Alabama, argued in October before the Supreme Court, which asks if a man with dementia—who cannot remember the murder for which he was convicted—should be executed.

Bucklew v. Precythe is an “as applied” challenge (the decision, to be handed down by next June, will apply only to this “individual with a unique circumstance,” as Justice Sonia Sotomayor remarked), and it carries a strange poignancy. Mr. Bucklew is resigned to his fate, said his attorney, Robert Hochman. He just wants a say in how he goes out.

The cruel and unusual standard

In 1958, Chief Justice Earl Warren wrote of the Eighth Amendment, which prohibits “cruel and unusual punishment,” that it “must draw its meaning from the evolving standards of decency that mark the progress of a maturing society.” Other past justices, like Antonin Scalia, have vociferously disagreed. In their view, alterations to, or abolition of, the death penalty should depend “on persuading our fellow citizens and not five justices of the Supreme Court,” as Richard Garnett, a professor of law at the University of Notre Dame, wrote in America in 2015.

As it exists now, the death penalty is informed by decades of winding precedent and bound up with contested interpretations of “cruelty”—a slippery term. Since the 1780s, and particularly since the turn of the present century, “evolving standards” have eliminated capital punishment for juveniles, people with intellectual disabilities and crimes other than murder, even the rape of minors. In 2015, Justices Stephen Breyer and Ruth Bader Ginsburg suggested in a dissenting opinion that capital punishment itself is unconstitutional.

Certain methods of execution have fallen out of favor. In the late 19th century, the Supreme Court affirmed the constitutionality of the electric chair. Throughout the 20th century, a number of high-profile cases ended in electrocution, including those of Julius and Ethel Rosenberg (convicted of conspiracy to commit espionage) and Bruno Richard Hauptmann (convicted of kidnapping and murdering Charles Lindbergh Jr.). But several failed electrocutions turned public opinion against the method.

Throughout the 20th century, a number of high-profile cases ended in electrocution, including those of Julius and Ethel Rosenberg.

Until this decade, lethal injection had been widely regarded within the justice system as a “humane” way to end a life, though some, like Deborah Denno, a professor of law at Fordham University in New York, have always been skeptical of that characterization.

“The first lethal-injection execution was in 1982, and that was botched,” says Ms. Denno, who adds, “we’re just looking at this with much more criticism and scrutiny than we did before.”

Ms. Denno says that problems with executions are simply better known these days. Not only do some executions fail, others take hours to carry out. Where these instances were once covered only by local newspapers, their details are now shared by millions online.

The search for a humane method

Back at the Supreme Court, Justice Breyer tried out some hypotheticals with Mr. Sauer.

“X has a rare medical condition that makes the method of execution to him feel exactly like being burned at the stake. O.K.? The Constitution would rule that out, wouldn’t it?”

“The Constitution would rule out burning at the stake,” said Mr. Sauer, “absolutely, Your Honor.”

“He has a medical condition of some kind. It makes it exactly the same…. It feels exactly the same.”

“I would have to know more about the hypothetical.”

“Well, that’s it. I’m making it up as I go along.”

The courtroom thrummed with laughter.

“Of course, these hypotheticals about being burned at the stake aren’t really implemented in the real world,” Mr. Sauer said. “What’s implemented in the real world is a situation where capital petitioners have every incentive to engage in interminable litigation, interminable litigation, multiple challenges.”

To which Justice Sotomayor replied, “That may well be, but the reality is that there are alternatives. Many of them have not been implemented because people don’t want to see them: the firing squad, electrocution. There’s a whole lot of things that people don’t want to accept the reality of, but they’re there.”

Justice Sotomayor: “There’s a whole lot of things that people don’t want to accept the reality of, but they’re there.”

A shortage of lethal-injection drugs (many pharmaceutical companies refuse to sell drugs to correctional systems for use in executions), combined with those high-visibility execution failures, has prodded some states, and death row inmates themselves, to seek older methods. “We already have seen in Tennessee now that there have been two requests for electrocution from inmates,” says Ms. Denno. “An inmate was electrocuted just about a week ago, and another inmate has requested electrocution over lethal injection.”

Also in Tennessee, there is a movement to bring back firing squads. Utah reintroduced death by firing squad in 2015, after an 11-year suspension. Justice Sotomayor has indicated that she believes it is a less painful alternative to lethal injection.

But like cruelty, pain is a slippery term, subject to interpretation and disagreement. In the plurality opinion for the 2008 case Baze v. Rees, Chief Justice John G. Roberts wrote that “an execution method may result in pain, either by accident or as an inescapable consequence of death, [but that] does not establish the sort of ‘objectively intolerable risk of harm’ that qualifies as cruel and unusual.”

He also wrote that “capital punishment is constitutional. It necessarily follows that there must be a means of carrying it out.” (He said much the same thing last month: “If the death penalty is constitutional, as it now is, there must be a way to administer it.”) He added that throughout its history, the court has rejected challenges to the constitutionality of methods of execution. “Our society has nonetheless steadily moved to more humane methods of carrying out capital punishment,” he wrote.

This year, public support for the death penalty crept back up to 54 percent, according to the Pew Research Center, after hitting a four-decade low of 49 percent in 2016. In the mid-’90s, that number hovered near 80 percent.

The public tends to be “pretty horrified by a botched execution,” says Ms. Denno. “Not everybody, of course—some people love them, and they think they’re a good deterrent and all that.”

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As long as there is a death penalty, there will be public officials yearning to wield it. In April 1997, when Mr. Bucklew was on trial in Missouri, Morley Swingle, the Cape Girardeau County prosecutor, extolled the death penalty in his closing argument: “It’s the old idea of an eye for an eye and a tooth for a tooth. And as you use your collective experience and knowledge and wisdom, you might think back to American history class in high school. And the Hatfields and McCoys from 1882, where a Hatfield killed a McCoy and McCoy killed a Hatfield and this went on…until finally the government stepped in and successfully prosecuted people and stopped it from happening.”

He said the government had a duty to seek justice for the victim’s family. “And that’s why retribution in this case calls for the death penalty for this premeditated, deliberated, cold-blooded killing.”

At the end of the hour on Nov. 6, Mr. Bucklew’s attorney emphasized again that he was familiar with the court’s prior rulings and knew that the death penalty was constitutional. “And so there has to be a way to carry it out. This claim about this individual person doesn’t call that into question at all.”

“Thank you, counsel,” said Chief Justice Roberts, indicating the end of the time allotted for argument. “The case is submitted.”

Update (April 5): In a 5-to-4 ruling handed down on April 1, the Supreme Court held that Russell E. Bucklew may be executed by lethal injection, and that “the Eighth Amendment does not guarantee a prisoner a painless death—something that, of course, isn’t guaranteed to many people, including most victims of capital crimes.” The majority ruled that Mr. Bucklew did not establish lethal gas as a viable, less painful alternative to the lethal injection protocol. Justice Anthony Kennedy’s successor, Brett M. Kavanaugh, voted with the majority.   

The dissenting opinion, written by Justice Stephen Breyer, asserted that “Bucklew has provided evidence of a serious risk that his execution will be excruciating and grotesque. The majority holds that the State may execute him anyway.”

Months after the oral arguments before the court, many key facts remain contested, including the nature of the lethal injection protocol, its potential effects on Mr. Bucklew and the effects of lethal gas. During those arguments, Missouri state solicitor D. John Sauer said there was no indication that nitrogen hypoxia would reduce the risk of pain, as it “has never been tried by any state.” In his dissent, Justice Breyer cited scientific literature claiming that nitrogen hypoxia would bring about a “simple and painless” death.
 

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Brandon Sanchez is an audience voices reporter at The Wall Street Journal. Previously, he was an O’Hare fellow at America.