The Supreme Court decided late Thursday not to stay the execution.
Gary Ray Bowles, 57, was pronounced dead at 10:58 p.m. ET, Michelle Glady, communications director for the Florida Department of Corrections, said.
The state argued in its response filed with the court that Bowles’ attorneys didn’t file a proper claim until this week. The matter should be, and was, decided by a lower court of appeals, the state said.
Justice Sonia Sotomayor wrote that she believes there were important questions in the case.
However, “because I do not believe that the questions as presented merit this Court’s review at this time, I do not disagree with the denial of certiorari,” she wrote. It could be different in other cases, she said.
Inmate wanted cheeseburgers for last meal
On Thursday, Bowles woke up at 4 a.m. and was calm and in good spirits, Glady said. His last meal was three cheeseburgers, french fries and bacon, she said.
He also was later featured in an episode of A&E’s show “The Killer Speaks” as the “I-95 Killer.”
Bowles pleaded guilty to first-degree murder in 1996 for killing Walter Hinton in Jacksonville Beach, Florida by dropping a 40-pound cement stepping stone onto his sleeping head. Bowles then strangled him and stuffed toilet paper and a rag in his mouth, court documents show. His body was found inside his locked home wrapped in sheets and bedspreads, the documents say.
A jury sentenced him to death in 1996 for killing Hinton, but the Florida Supreme Court later reversed the death sentence and remanded the case for a new penalty phase. Another jury unanimously sentenced him to death in 1999, and since then, a series of appeals have been denied by courts leading up to Thursday’s expected execution.
In addition, he was convicted of first-degree murder in 1997 for robbing and killing John Roberts by strangling him and stuffing a rag in his mouth, according to court documents. He also was convicted in 1996 of murder for killing Albert Morris in a case in which he struck Morris in the head, beat him, shot him, strangled him and tied a towel over his mouth. He was sentenced to life in prison for both of those cases.
Convicted killer is 99th person executed in Florida
Bowles had several previous charges and was sentenced to prison for beating and raping his girlfriend in 1982.
“Intentionally ending Mr. Bowles’ life is unnecessary,” Michael B. Sheedy wrote in the letter. “Society can remain safe from any future violent actions of his through life-long incarceration without parole.”
CNN’s Steve Almasy contributed to this report.