A Missouri death row inmate who has received last-minute reprieves twice before over concerns about a rare medical condition is now scheduled to die in October.

The Missouri Supreme Court on Tuesday set an Oct. 1 execution date for Russell Bucklew, who was convicted in the 1996 shooting death of a man who was living with Bucklew’s former girlfriend.

Bucklew narrowly escaped execution in 2014 and again in 2018. Each time, the U.S. Supreme Court intervened moments before Bucklew was scheduled to be put to death.

His ailment, cavernous hemangioma, causes blood-filled tumors to grow in his head, neck and throat. Bucklew has argued that the throat tumor could burst during the execution, causing him to choke on his own blood.

The U.S. Supreme Court ruled 5-4 in April that the state could move ahead with the execution. The court’s five conservative justices rejected Bucklew’s argument that subjecting him to lethal injection would violate the Constitution’s ban on cruel and unusual punishment.

Justice Neil Gorsuch wrote that Bucklew’s claim “isn’t supported by either the law or the evidence.”

Justice Stephen Breyer wrote in a dissenting opinion that his colleagues acknowledged that the Constitution’s Eighth Amendment prohibits states from executing prisoners by “horrid modes of torture” such as burning at the stake.

“But the majority’s decision permits a state to execute a prisoner who suffers from a medical condition that would render his execution no less painful,” Breyer wrote.

Bucklew’s attorney, Cheryl Pilate, did not immediately respond to phone and email messages seeking comment. She has said previously that Bucklew’s condition, in addition to the tumors, causes weakened and malformed blood vessels and vein problems.

Missouri uses an injection of the drug pentobarbital for executions. Bucklew had proposed that the state execute him by having him breathe pure nitrogen gas through a mask. Missouri officials said no state has ever carried out an execution as Bucklew suggested.

Bucklew, now 51, was convicted of killing Michael Sanders. After entering a trailer where Sanders and Bucklew’s former girlfriend lived with their children, Bucklew fatally shot Sanders and later raped his former girlfriend. Bucklew was arrested after a car chase and shootout with police.

The execution would be the first in Missouri since Mark Christeson was put to death in January 2017. None of the 20 inmates executed since Missouri began using pentobarbital in 2013 have shown obvious signs of pain or suffering.

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