Last month, Jeffery Lee sat in the death watch cell in Alabama's William C. Holman Correctional Facility. After more than a quarter-century on death row, the 49-year-old was just days away from execution by nitrogen hypoxia. As the hours ticked away, Lee's lawyers tried desperately to prevent him from becoming the eighth person in the state to be executed via suffocation with nitrogen gas.

Judging by history, the odds were not in Lee's favor. Many men had been in Lee's position on Alabama's death watch, praying as they waited for a court to halt their execution or the governor to issue clemency. They almost always end up strapped to a gurney.

But on June 9, Lee was granted a rare reprieve when a federal district judge permanently enjoined the state from executing him by its nitrogen hypoxia protocol, in which a mask is strapped to a prisoner's face and the person breathes nitrogen, loses consciousness and suffocates to death. Partly at the prodding of the U.S. Court of Appeals for the Eleventh Circuit, the judge found the procedure violated the U.S. Constitution's Eighth Amendment.

The ruling was unprecedented, but the legal battle was not over. The following day, the Eleventh Circuit denied the state's emergency stay of that decision.

Lee's lawyers from Arnold & Porter Kaye Scholer LLP called him with the news.

"He was quiet for a long moment, and then gave thanks to God," Anna K. Thompson and Paige H. Sharpe told Law360 via email.

The U.S. Supreme Court later rebuffed Alabama's emergency petition to stay the lower court's ruling.

"It's really hard to overstate the significance of a federal court finding Alabama's nitrogen gas protocol unconstitutional," Robin Maher, executive director of the Death Penalty Information Center, said.

"This is the first time a federal court has ever declared a method of execution unconstitutional under this current [...] Glossip legal standard the Supreme Court established," Maher added, referencing the Supreme Court ruling Glossip v. Gross.

What happens now is unclear, as the typical playbook for capital punishment litigation has been torn up. After criticizing the Supreme Court's decision as "a miscarriage of justice," the state of Alabama has now made a series of arguments in an effort to resume executions by lethal injection. Just hours after the nation's top court declined to intervene, the state moved to execute Lee in that fashion — in spite of Lee's prior legal challenge against the method, which he agreed to drop after electing for death by nitrogen under an undeveloped protocol.

On Wednesday, the Alabama Supreme Court granted the state's request to authorize a new death warrant for Lee, meaning the governor can set another execution date.

"It's remarkable enough that Mr. Lee won this injunction at all, given that the Supreme Court has never once found a state's execution method unconstitutional," Lee's attorneys said via email. "What's happened since may be even more unusual: The state now wants to switch him to a method he legally rejected years ago, and there's no roadmap for how that resolves."

The state has also indicated that it may move to execute other prisoners by nitrogen hypoxia, despite the constitutional challenge to Alabama's protocol and a trial judge's ruling that the state's protocol does in fact violate the Eighth Amendment.

In 2018, over 40 men elected to be executed via nitrogen hypoxia at a time when the state's protocol for such executions had not been developed. More than 30 currently remain on death row. Like Lee, their fates now hang in the balance.

"We're in uncharted territory," Maher said.

To close watchers of death penalty litigation, Lee's legal victory was a long shot.

In its 2015 Glossip opinion, the U.S. Supreme Court established a two-pronged test necessary for prisoners to succeed in challenges against execution protocols under the Eighth Amendment, which bars cruel and unusual punishment. In order to win, prisoners must both demonstrate that an execution method presents a substantial risk of serious pain and identify another method that is "feasible, readily implemented" and significantly reduces the risk of harm.

"The Supreme Court has intentionally created a standard that's almost impossible to meet, and you need an extraordinary set of occurrences in order to meet it," Robert Dunham, the director of the Death Penalty Policy Project, said.

In February, Lee sought to clear that high bar, proposing an execution by firing squad instead of by nitrogen hypoxia. A week later, Alabama moved to execute him, and on April 15, Gov. Kay Ivey set Lee's execution date for June.

Against this backdrop, U.S. District Judge Emily Marks granted the country's first full evidentiary hearing on nitrogen hypoxia. Over three days, the Alabama district court heard testimony from 11 witnesses. During the trial, a doctor retained by Lee's legal team said that four people executed under Alabama's nitrogen protocol suffered from flash pulmonary edema, a condition that Judge Marks wrote is "triggered by extreme distress" and in which "the lungs 'almost instantaneously' fill with fluid."

Judge Marks determined that prisoners executed by nitrogen suffer one to three minutes of "air hunger," which she described as "the most severe form of breathing discomfort." Nonetheless, she ruled that the nitrogen executions could continue.

"While Lee establishes that death by nitrogen hypoxia involves some suffering, he fails to show that the protocol is cruel and unusual in violation of the Eighth Amendment," she wrote in her ruling at the end of May.

In June, the Eleventh Circuit overturned this determination.

Finding that the first prong of the Glossip test had been met, the circuit panel wrote that Lee has shown that the protocol "presents a 'substantial risk of serious harm' — severe pain over and above death itself."

It sent the case back down to Judge Marks to evaluate whether the second prong of the Glossip test had been met. Judge Marks found that it had, determining that firing squad was a feasible and readily implemented method that reduces the risk of substantial harm.

"The district court was looking for a way not to rule in favor of the defense," Dunham said. "The district court didn't want to grant relief, but you had an honest judge, so the judge wasn't looking to contort the facts."

The full evidentiary hearing was key to reaching that decision, experts told Law360.

Last year, as Louisiana prepared to become just the second state to conduct a nitrogen hypoxia execution, a different district court ordered a shorter evidentiary hearing.

U.S. District Judge Shelly Dick blocked the execution of Jessie Hoffman Jr., finding that Hoffman is "substantially likely to prove that nitrogen hypoxia poses a substantial risk of conscious terror and psychological pain." After an appeal, the Fifth Circuit let the execution proceed.

At the Alabama hearing, Lee's attorneys focused heavily on presenting scientific testimony, calling three doctors and presenting a wealth of evidence that people killed by nitrogen were suffering.

"What we really should learn from Jeffrey Lee's case is that having a full and fair evidentiary hearing on these methods is absolutely critical," Maria DeLiberato, senior counsel on the American Civil Liberties Union's Capital Punishment Project, told Law360, "If the courts are diligent in making sure that the evidence that comes in is from qualified experts who are qualified in that field, then the science is supportive of what the litigants are saying that these execution methods are cruel and unusual."

Lee's legal victory reflects the nation's broader struggle to carry out capital punishment amidst declining public support for the death penalty and a constantly evolving list of methods that are promised to be more humane yet generate new ethical concerns.

Last year, 47 people were executed in the U.S. — a figure that is far lower than the number killed by capital punishment in 2000. That year, Lee was convicted of two murders during a robbery of a pawn shop. A jury voted to sentence Lee to life in prison without the possibility of parole, but the judge presiding over his trial overrode that recommendation and sentenced Lee to death. Alabama became the last state to abolish judicial override in 2017, but did not clear the death sentences of people like Lee.

"Everything that the United States Supreme Court justices wrote about in Furman v. Georgia as reasons why the death penalty was unconstitutionally arbitrary and capricious, everything they wrote about is true today and worse," Dunham said, referring to the case that halted executions for a four-year period in the 1970s.

Throughout the 2010s, states struggled to carry out capital punishment via lethal injection, stymied by both an inability to obtain the medications needed amidst greater pharmaceutical controls and a series of executions that did not go as planned.

During a 2014 execution in Oklahoma, Clayton Lockett rose from a gurney after a doctor declared him unconscious. He died from a heart attack during an execution that lasted 43 minutes and was deemed by the prison's warden to have been a "bloody mess." That same year, Dennis McGuire appeared to gasp for air repeatedly during a lethal injection in Ohio that took 25 minutes. In the last execution of 2016, conducted in Alabama, Ronald Bert Smith Jr. heaved and coughed for around 13 minutes.

Set against this backdrop, states began tinkering with their execution protocols by devising new drug combinations and seeking alternate ways of killing people on death row. In March 2018, Alabama legislators approved nitrogen hypoxia.

The prior month, the state was forced to call off the execution of Doyle Hamm, a 61-year-old with lymphatic cancer, after spending 2.5 hours unsuccessfully attempting to insert an IV by which to administer lethal injection drugs.

Hamm's failed execution kicked off a string of issues with the state's lethal injection protocol that drew intense national scrutiny, including repeated issues setting IV lines and an execution that lasted over three hours.

After the state authorized nitrogen hypoxia as a method of capital punishment, Alabama offered a brief period in which prisoners on death row could choose to be executed via the still-unproven method. The state had not yet outlined its proposed protocol for nitrogen executions.

Lee, like multiple other prisoners, was engaged in litigation over the constitutionality of Alabama's lethal injection protocol. After electing for nitrogen hypoxia executions, Lee and others agreed to dismiss their existing complaints over lethal injection.

Alabama promised that the method would go smoothly, with the attorney general's office telling appeals court judges that nitrogen hypoxia is "the most painless and humane method of execution known to man." The state argued in legal briefings that people executed with the method would be unconscious "within seconds."

Yet from the first nitrogen execution in January 2024, witnesses found the state's promises of how nitrogen executions would proceed sharply contrasted with their observations. At the execution of Kenneth Eugene Smith, eyewitnesses noted that Smith writhed and shook for more than two minutes before taking a series of deep, gasping breaths.

Attorney General Steve Marshall told reporters after the execution that "what occurred last night was textbook."

The executions continued to deviate from the relatively quick process the state had described. In September 2024, Alan Eugene Miller struggled against the restraints holding him to a gurney while shaking and trembling.

"Despite misinformation campaigns by political activists, out-of-state lawyers, and biased media, the state proved once again that nitrogen hypoxia is both humane and effective. Miller's execution went as expected and without incident," Marshall said in a statement issued after Miller's execution.

Those declarations ended up hurting the state in court, Dunham said.

"I think that Alabama gets hoisted on its own petard because Steve Marshall, the attorney general, lies to the court about how long it's going to take. The prisoner is going to be unconscious in seconds, which is nonsense. And then he declares, despite the consistent statements of neutral observers to the contrary, that nothing unusual has happened, he declares it to be a textbook execution," Dunham said.

As the nitrogen executions proceeded, some of those who had previously elected to be executed via the method grew concerned.

One of them was Anthony Boyd. Boyd had sought to be executed by firing squad, hanging or drugs used for medical aid in dying. That request was denied, and in October 2025, the state executed him via nitrogen. The process took more than 40 minutes. Witnesses said that Boyd heaved and convulsed for 15 minutes.

The state has not carried out any capital punishment since Boyd's prolonged death, but in the aftermath of the Eleventh Circuit's ruling, has resumed efforts to conduct executions.

Earlier this month, Lee's lawyers also noted that the state does have a legal pathway to carry out lethal injection executions for prisoners who previously opted for death by nitrogen — but argued the state has squandered its opportunity to do so. State law permits lethal injection executions of such prisoners if nitrogen hypoxia, as a method of execution, is held to be unconstitutional by the U.S. Supreme Court. A finding by the Alabama Supreme Court or the Eleventh Circuit would also suffice, if the U.S. Supreme Court declines to review that decision.

Despite the Eleventh Circuit's rejection of the state's emergency request for a stay of the ruling barring Lee's execution by nitrogen, Alabama's merits appeal was still pending. But in a move that perplexed legal observers, the state voluntarily dismissed its appeal of the permanent injunction in Lee's case at the end of June.

Along with its efforts to pursue the execution of Lee, the state is also pushing ahead with an attempt to kill another man, Michael S. Taylor. Like Lee, Taylor was among the prisoners who opted into the nitrogen protocol in 2018.

The state is now seeking to execute him via lethal injection. In July, Taylor argued in the Alabama Supreme Court that the state has conducted an "about-face" that "offends the integrity of the courts" by trying to conduct the prisoner's execution via lethal injection.

The Alabama Department of Corrections did not respond to questions sent by Law360 for this article, including a query about why it dismissed its appeal in Lee's case. The ADOC said that Law360's questions for this article had been forwarded to the state attorney general's office. The attorney general's office declined to respond to questions sent by Law360 for this article, stating in an email that "it is longstanding policy of this office to not comment on pending litigation."

The same day that the Alabama Supreme Court authorized the issuance of a new death warrant for Lee, Judge Marks dealt a blow to his efforts to block his execution by lethal injection.

After Judge Marks found that the state's nitrogen protocol "facially violates the Eighth Amendment," Lee had argued that the federal court should prevent the state from executing him via lethal injection.

But Wednesday, Judge Marks denied that request, writing that "granting Lee the relief he seeks would, in substance, require this court to determine that the state's actions violate state law and to order the state to comply with state law, which the court lacks the authority to do."

Lee can now appeal the order or take it up in state court.

The men on Alabama's death row are watching these legal developments closely, tracking whether the state legislature will move to implement firing squad executions or whether the state will succeed in its arguments that it can force people who opted for nitrogen executions to accept capital punishment by lethal injection.

"We're kind of left to our imaginations in a lot of this stuff, right? Because we don't know what direction they're going to take next," a friend of Lee's and fellow death row prisoner told Law360. He was granted anonymity to speak without fear of retaliation.

Some on death row are concerned that the state will find a way to revive its nitrogen protocol.

"They could change mask manufacturers," Lee's friend on death row said. "They could change from a mask to something else ... I don't think it'll be any less horrific because you're still basically choking somebody out, and that's always going to look like that person is being choked to death."

--Editing by Alex Hubbard.

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