*This story has been updated to reflect the execution.

On Tuesday night, Rolando Ruiz sat in a holding cell outside of Texas’ execution chamber for the second time, waiting to see if he would have to enter it.

Last time, in 2007, a federal court halted his execution the night it was scheduled, and he walked out knowing he would live to see another day. This time, the U.S. Supreme Court denied his final appeals more than four hours after his execution was originally scheduled, with a dissent from Justice Stephen Breyer.

He was sent into the chamber, strapped to a gurney and injected with a lethal dose of pentobarbital at 10:37 p.m. Twenty-nine minutes later, Ruiz, 44, was pronounced dead. It was the third execution in Texas this year — and the fifth in the country.

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“Words cannot begin to express how sorry I am and the hurt that I have caused you and your family,” Ruiz said to his victim’s family in his final statement. “To my family, thank you for all your love and support. I am at peace. Jesus Christ is Lord. I love you all.”

In July 1992, Ruiz shot and killed 29-year-old Theresa Rodriguez in her San Antonio garage. He was a 20-year-old hitman, paid $2,000 by the woman's husband and brother-in-law, who were out to collect her life insurance money.

Ruiz was convicted and sentenced to death. Rodriguez’s husband and brother-in-law, Michael and Mark Rodriguez, both received life sentences.

Michael, the husband, escaped from prison in 2000, one of the notorious “Texas 7.” He was sentenced to death and executed in 2008 for a murder the prisoners committed while on the run. Mark, the brother-in-law, was released on parole in 2011 and was recently charged with felony theft in an alleged roofing scam.

In the 25 years since the murder, Ruiz underwent multiple rounds of appeals and had four execution dates.

“He’s actually had three different execution dates before this one, two of which were stayed at the eleventh hour,” said Burke Butler, one of Ruiz’s appellate attorneys with the Texas Defender Service. “That obviously is something that causes immense psychological pain and stress.”

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Ruiz had multiple petitions pending before the U.S. Supreme Court Tuesday night, most claiming his prolonged confinement on death row — about 22 years, or half of his life — qualifies as cruel and unusual punishment.

The Court denied his appeals at around 10 p.m., with Justice Stephen Breyer dissenting in one. Breyer said he would have liked to have used Ruiz’s case to further explore whether extended periods of time on death row qualify as cruel and unusual punishment.

“This Court long ago, speaking of a period of only four weeks of imprisonment prior to execution, said that a prisoner’s uncertainty before execution is ‘one of the most horrible feelings to which he can be subjected.’” Breyer wrote in his dissent. “Here the prisoner has undergone death row imprisonment, not of four weeks, but of 22 years.”

Breyer, the high court’s leading death penalty opponent, has long wanted to look into lengthy death row stays. He said in a 1999 opinion that it is cruel and unusual to leave inmates on death row for decades. Others, like Justice Clarence Thomas, have argued it is the defendant who creates the long confinement by filing and refiling appeals. Breyer said that was not the case for Ruiz.

“The lower courts have recognized that Mr. Ruiz has been diligent in pursuing his claims, finding the 22-year delay attributable to the State or the lower courts,” he wrote.

Though the court ultimately denied Ruiz’s appeal, hours of uncertainty ticked by. Execution warrants are viable from 6 p.m. to midnight. If no appeals are pending, the execution usually proceeds right around 6 p.m., but in Ruiz’s case, the prison had to wait until they heard from the high court. If there was no ruling before midnight, Ruiz’s execution would have had to be reset again.

The first time Ruiz sat in the holding cell on the night of his execution, it was July 2007, 12 years after he was sentenced to death.

He had been trying unsuccessfully to bring his claims of ineffective counsel to court. He argued his trial lawyer didn’t present enough mitigating evidence in court, like an abusive childhood and substance abuse, and that his state appellate lawyer failed to bring up his ineffective trial lawyer in appeals. Although a federal court agreed with Ruiz’s argument and went so far as to call his appellate lawyer’s representation “appallingly inept,” procedural rules kept that court from reviewing his case.

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But after a new, last-minute filing, the U.S. Fifth Circuit Court of Appeals granted Ruiz a stay and agreed to review the case.

Ultimately, the lower federal court ruled that Ruiz’s claims of ineffective counsel were not worthy of a new sentencing trial, and a new execution date was set for July. It was rescheduled to Aug. 31. But five days before that execution, he got another stay, this time from the Texas Court of Criminal Appeals.

Ruiz had filed another appeal a couple of weeks earlier, and the court postponed his execution while it reviewed the case. In November, its judges issued a harsh ruling denying Ruiz’s claims — both of ineffective counsel and of cruel and unusual punishment.

“Rolando Ruiz does not contest his guilt. He just doesn’t want to be executed. Neither did Theresa Rodriguez,” Judge Bert Richardson wrote in the court’s opinion.

At the Bexar County District Attorney’s Office, appellate division chief Rico Valdez said before the execution that Ruiz deserves the death penalty because of his violent nature.

“In Ruiz’s case, it’s just his background. He just had a history of being a violent person,” Valdez said.

Ruiz was a gang member and has had multiple violent encounters in prison with inmates and officers, Valdez said. According to prison records, Ruiz was convicted of aggravated assault on a Bexar County corrections officer while he was awaiting his original death penalty trial.

“From my perspective, whether you’re for or against the death penalty, it is the law,” Valdez said. “... At some point, it’s time for the sentence to be fulfilled.”

Read more on the first two executions in Texas this year:

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