A remorseful hitman apologised to his victim's family before he was executed by lethal injection for killing a Texas woman in a life insurance scheme.
Rolando Ruiz, 44, was convicted of killing Theresa Rodriguez, 29, in exchange for $2,000 (£1,644) in 1992.
Ms Rodriguez's husband and brother-in-law, who were beside her when she was shot dead, ordered the contract murder to collect life insurance benefits.
They were both sentenced to life in prison for the crime.
Ruiz was pronounced dead at 11:06 pm local time (05:06 GMT) on Tuesday night.
Despite a five-hour delay to try to stop the injection, he became the third inmate to be executed in Texas this year and the fifth nationally.
Before his death, Ruiz looked at his victim's family members and said: "Words cannot begin to express how sorry I am and the hurt I have caused you and your family."
"May this bring you peace and forgiveness," he added, reports AP news agency.
He also thanked his family for their support.
Ms Rodriguez's mother, Susie Sanchez, said: "It's not going to bring her back, so it really doesn't mean very much."
The US Supreme Court had rejected three appeals by Ruiz's attorneys, who argued his extended time on death row, multiple execution dates and two reprieves were unconstitutionally cruel.
His lawyer, Lee Kovarsky, also contended that Ruiz did not receive competent legal help in his earlier appeals.
Michael Rodriguez, the victim's husband of nearly seven years, stood to collect at least a $250,000 (£205,000) in insurance benefits from his wife's death, evidence showed.
At the time, he had recently applied for another $150,000 in life insurance for her.
Ruiz, then 20, gunned down Ms Rodriguez outside her San Antonio home as she was getting out of the car with her husband and brother-in-law. He was arrested nine days after the shooting.
The Rodriguez brothers accepted life prison terms in plea deals.
Michael Rodriguez later joined Ruiz on death row as part of the Texas 7, a group of seven inmates who escaped from a Texas prison in 2000 and killed a Dallas-area police officer.
The scheming husband was executed in 2008.
Mark Rodriguez, the brother-in-law, was paroled in 2011.