The Supreme Court appeared closely divided Wednesday over whether to order a new trial for Oklahoma death-row inmate Richard Glossip, whose case has attracted support from across the political spectrum after independent investigations revealed prosecutorial misconduct.

Glossip’s long-running appeal is highly unusual, in that Oklahoma’s top law enforcement official agrees with Glossip’s defense attorneys that he did not receive a fair trial for a 1997 killing. Both sides say prosecutors suppressed evidence and elicited false testimony from a key witness also implicated in the murder.

Oklahoma’s top criminal court nevertheless upheld the death sentence for Glossip, 61, leading to the Supreme Court case known as Glossip v. Oklahoma.

At oral argument on Wednesday, a majority of justices — conservatives as well as liberals — expressed concerns about the state court ruling and about whether Glossip received a fair trial. But it was unclear after nearly two hours of discussion whether at least five justices were open to giving Glossip a do-over. Some floated the possibility of ordering a hearing to resolve factual disputes such as the meaning of a prosecutor’s cryptic notes and what was known about the key witness’s mental health.

In one of the more animated moments of the morning, Justice Elena Kagan told the lawyer arguing to uphold Glossip’s conviction that the jury would probably have reached a different outcome had it known the star witness lied on the stand.

“Your one witness has been exposed as a liar,” Kagan said, adding: “False is false.”

Justice Brett M. Kavanaugh said he too was troubled by the possibility that the witness’s false testimony could have changed the verdict because “the whole case depended on his credibility.”

Glossip was convicted of murder in the death of Barry Van Treese at the Best Budget Inn in Oklahoma City, which Van Treese owned and Glossip managed. Glossip did not swing the bat that killed Van Treese. That was Justin Sneed, a drug-addled handyman whose testimony against Glossip was the only direct evidence connecting him to the killing.

Glossip was found guilty of commissioning Sneed to kill Van Treese, and was first sentenced to death in 1998. That sentence was overturned due to what a state court deemed ineffective legal counsel, but he was again sentenced to die in 2004.

Nearly 20 years later, independent investigations commissioned by Oklahoma lawmakers and the state’s attorney general reached the same conclusion — that Glossip’s prosecution was riddled with misconduct, errors and omissions, including a deficient police investigation, the destruction of critical physical evidence and the suppression of other evidence.

Prosecutors failed to disclose, according to the parties, that Sneed — a methamphetamine addict who testified against Glossip in exchange for a sentence of life in prison — also suffered from a serious psychiatric disorder and was prescribed lithium. And prosecutors, they say, allowed Sneed to falsely testify that he had never seen a psychiatrist, concealing information that could have cast doubt on his credibility and testimony against Glossip.

Last year, however, the Oklahoma Court of Criminal Appeals unanimously refused to accept the “confession of error” by Attorney General Gentner F. Drummond (R) and order a new trial for Glossip. The court said that the prosecutorial misconduct did not rise to the level of a constitutional violation of Glossip’s rights and that Glossip had not shown that a jury would have reached a different conclusion had prosecutors disclosed the evidence in advance of his trial.

“Glossip has exhausted every avenue and we have found no legal or factual ground which would require relief in this case,” the state court said.

Glossip has been scheduled for execution nine times. He was hours from being executed in 2015 when prison officials discovered they had received the wrong lethal drug, a mistake that led in part to a six-year moratorium on executions in the state.

The case before the Supreme Court was argued Wednesday by experienced lawyers well-known to the justices. Glossip’s lawyer is Seth Waxman, who served as solicitor general during Bill Clinton’s administration. Paul Clement, the former solicitor general appointed by George W. Bush, represented Drummond, who sat next to him at the front of the ornate courtroom on Wednesday.

Because Oklahoma’s attorney general now opposes putting Glossip to death, the Supreme Court appointed attorney Christopher Michel, a former law clerk to Chief Justice John G. Roberts Jr. and Kavanaugh, to argue in support of the ruling from the state court that would allow the execution to proceed.

Michel urged the justices to dismiss the case, saying the Supreme Court does not have jurisdiction to decide the state matter and the governor has the power to grant clemency. He and a lawyer for the victim’s family — retired federal judge Paul Cassell — questioned the attorney general’s interpretation of the recently disclosed handwritten notes that referred to lithium and the name of a doctor.

Cassell told the justices in a court filing that the notes do not reflect information withheld from the defense and that the prosecutor had not concealed any evidence. “This case presents a cautionary tale about the dangers of courts simply accepting an elected prosecutor’s confession of ‘error,’” Cassell wrote in a filing that includes photos of the scribbled notes.

Oklahoma’s pardon and parole board split 2-2 on Drummond’s request for intervention; a vote in Glossip’s favor would have been necessary to recommend that Gov. Kevin Stitt (R) commute his sentence to life without parole. One member of the board recused himself because his wife prosecuted the case. Michel told the justices Wednesday that the composition of the board has changed and that a new clemency hearing could be held.

The high court’s conservative majority has generally been skeptical of pleas for intervention from death row inmates and reluctant to review state Supreme Court decisions like the one from Oklahoma. The U.S. Supreme Court has said it will not undo lower-court rulings that are based on “adequate and independent state grounds,” and specifically asked the lawyers in Glossip’s case to address whether the justices can review the Oklahoma court’s ruling.

The U.S. Supreme Court has “become increasingly hostile to claims that there are flaws in death penalty cases — and any claims that argue state courts got it wrong,” said Christopher Slobogin, a Vanderbilt University law professor specializing in criminal justice.

Last year, however, the court granted an Arizona death row inmate a new sentencing hearing. In that case, Roberts and Kavanaugh joined with the court’s three liberals in reversing the state court.

An earlier death penalty case at the Supreme Court also carried Glossip’s name, though it was focused on the drugs used by Oklahoma and larger questions about how capital punishment is carried out in the United States.

In 2015, the justices ruled 5-4 against Glossip and other death-row inmates challenging Oklahoma’s method of execution. The inmates alleged that the use of a sedative called midazolam has resulted in troubling executions that violate the Constitution’s prohibition on cruel and unusual punishment.

The court’s composition has changed since then. Two justices who are no longer on the bench — Stephen G. Breyer and Ruth Bader Ginsburg — used their dissent in the 2015 case to say it was time for the court to take another look at whether the death penalty could ever be carried out in accordance with the Constitution.

This latest appeal is being reviewed at a time when the number of executions and death sentences has significantly declined compared to the late 1990s. But while some states have paused executions or abandoned capital punishment outright, it is still consistently used in other places — including Texas and Oklahoma, the two states that have carried out the most executions since 1976, according to the Death Penalty Information Center, a Washington-based group.

Last month, those two states — along with South Carolina, Missouri and Alabama — carried out a combined six executions over an 11-day period.

Mark Berman contributed to this report.

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