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PARCHMAN, Miss. – A Mississippi man who confessed to killing a 16-year-old waitress 22 years ago was put to death on Wednesday evening.

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Thomas Edwin Loden, Jr., 58, was executed by lethal injection at the Mississippi State Penitentiary more than two decades after he pleaded guilty to the rape and murder of Leesa Marie Gray, a waitress in Itawamba County.

A coroner pronounced Loden dead at 6:12 p.m. CDT, WLBT-TV reported.

Before he was executed, Loden expressed remorse, according to the television station.

“I’d like a brief moment to express to the Gray family and anyone else I hurt how deeply remorseful I am for everything I did,” Loden said. “I know these are mere words and cannot erase the damage I did.”

It was only the second execution in the state since June 2012, the Clarion Ledger reported. The state has executed 128 people since 1940, according to the newspaper.

Gray was stranded with a flat tire on the side of a road in June 2000 when Loden pulled her into his van, WAPT-TV reported. Prosecutors said Loden spent hours raping and sexually assaulting Gray before suffocating and strangling her to death, according to the newspaper. Loden videotaped most of the crime, prosecutors said.

Earlier this month, a federal judge declined to block Mississippi from carrying out the execution because of a lawsuit from Loden and four death row inmates in the state that challenged the lethal injection protocol, according to The Associated Press

Mississippi’s most recent execution was on Nov. 17, 2021, when David Neal Cox was put to death.