Updated

A man once called the "Houdini" of Alabama's death row for escaping seven past execution dates through legal challenges was put to death early Friday for a 1982 murder-for-hire shooting.

Tommy Arthur, 75, was pronounced dead at 12:15 a.m. CDT Friday at a southwest Alabama prison after a lethal injection, authorities said.

Arthur was convicted of killing riverboat engineer Troy Wicker, who was fatally shot as he slept in his bed in the north Alabama city of Muscle Shoals.

Wicker's wife Judy initially told police she came home and was raped by a black man who shot and killed her husband. After her conviction, she changed her story and testified she had discussed killing her husband with Arthur, who came to the house in makeup and an Afro-style wig and shot her husband. She said she paid him $10,000. Arthur was in a prison work-release program at the time for the 1977 slaying of his sister-in-law, a crime he admits to committing.

His first two convictions in the Wicker case were overturned, but the third one was not. Arthur asked jurors to give him the death penalty. The decision was strategic, he said, to open up more avenues of appeal.

The state set seven execution dates for Arthur between 2001 and 2016. All were delayed as a pro bono legal team fought his sentence. In 2016, Arthur came especially close to the death chamber.

"We were fixing to go into the room and they were going to put the needle in my arm," he said, when the U.S. Supreme Court gave him an unexpected reprieve shortly before the death warrant expired at midnight.

"He's a Houdini," said Janette Grantham, director of the Victims of Crime and Leniency. "He always finds a way to escape."

She called the years of execution delays exceedingly painful for the family of Troy Wicker to bear.

Arthur's attorneys filed court papers Wednesday with the 11th U.S. Circuit Court of Appeals, calling the lethal injection procedure cruel and unusual punishment. The lawyers have argued that the opening sedative in Alabama's execution protocol — midazolam — wouldn't properly anesthetize him before he's injected with other drugs to stop his heart and lungs.

In December, inmate Ronald Bert Smith coughed for the first 13 minutes of his execution and moved slightly after two consciousness tests. Arthur's lawyers argued that Smith was awake during his execution. The state responded that there was no evidence Smith experienced pain.

Both the state of Alabama and Arthur's lawyers have pointed to his case as an example of what they see wrong in death penalty cases.

The state attorney general said Arthur used perpetual litigation to avoid his sentence for years.

"The case of Thomas Arthur is an egregious example of how a convicted murderer can manipulate the legal system to avoid justice," Attorney General Steve Marshall said recently.

But Arthur's lawyers have argued that the state has resisted additional DNA testing on the wig in addition to the questions raised with Alabama's lethal injection procedures.

Arthur, in a round of phone calls to reporters earlier this week, maintained he's innocent in the Wicker shooting.

"I'm terrified, but there's nothing I can do," Arthur told The Associated Press in a telephone interview Monday. "I've got hope in my legal team."