Orlando Hall, 49, was put to death by lethal injection late Thursday for the 1994 killing of Lisa Rene in Texas.
Rene was abducted with gun threats from her apartment by a group of men and taken to Arkansas where she was killed as vengeance for a botched $5,000 marijuana deal.
Hall is the eighth person to be put to death since the Trump administration restarted national executions in July, ending a 17-year gap.
He is also considered to be the first person killed under an outgoing administration in over a century.
A judge's stay of execution over matters about the execution drug gave Hall freedom, but for less than six hours.
After the Supreme Court flipped the stay, he was put to death just before midnight.
Hall, a reformed man in prison according to his lawyers and a church volunteer who had grown close to him, was comforting his family and supporters at the end.
"I'm OK," he said in a final statement, then adding, "Take care of yourselves. Tell my kids I love them."
As the drug was given, Hall, 49, lifted his head, appeared to flinch momentarily, and twitched his feet.
He appeared to mutter to himself and twice he opened his mouth widely as if he was yawning. Each time that was accompanied by brief, seemingly heavy, breaths.
He then stopped breathing. Soon after, an expert with a stethoscope came into the execution room to check for a heartbeat before Hall was formally pronounced dead.
Hall was between four men sentenced in the kidnapping and death of Lisa Rene in 1994.
According to federal court documents, Hall was a drug trafficker in Pine Bluff, Arkansas, who would seldom buy drugs in the Dallas area.
On Sept. 24, 1994, he met two men at a Dallas-area car wash and gave them $4,700 with the expectation they would return later with the marijuana. The two men were Rene´s brothers.
Instead, the men took their car and the money was stolen. Hall and others figured they were lying and were able to track down the address of the brothers´ apartment in Arlington, Texas.
Hall's lawyers claimed that failures by Hall's attorneys during preparation for his initial trial suggested the jury didn't see evidence - including a long history of family abuse - that may have moved them to save his life.
None of the appeals were accepted.
Rene´s older sister, Pearl Rene, said in a statement that she and her family are very reassured that the matter is over.
"We have been dealing with this for 26 years and now we´re having to relive the tragic nightmare that our beloved Lisa went through."."