A double murderer smiled and laughed at the family of his victims moments before he was executed in a "botched" procedure that took nearly two hours.
Joseph Wood was convicted of the murder of his ex-girlfriend Debra Dietz and her father Eugene Dietz on August 7, 1989 after walking into their family-owned car body store in Tuscon, Arizona and shooting them.
Debbie, 29, had issued a restraining order against Wood after a turbulent five-year relationship between the two, including alleged acts of domestic violence against her.
Wood, who was 31 at the time, fatally wounded Eugene in the chest with a .38 calibre gun, before catching and restraining Debbie in a hold.
She was then shot twice; once in the stomach and once in the chest.
The police arrived on the scene after the killings and fired at Wood, injuring him only, after he pointed his gun at the officers.
Wood was executed 25 years later in July 2014 at Florence State Prison, Arizona for his crimes, but his last words caused anger among the Diez family, the Daily Star reports.
He reportedly looked at them and said: "I take comfort knowing today my pain stops, and I said a prayer that on this or any other day you may find peace in all of your hearts, and may God forgive you all."
However, after being injected with a sedative and painkiller, his subsequent execution lasted one hour and fifty-seven minutes. The procedure should have lasted 10 minutes, experts claimed.
He reportedly gasped more than 600 times as his jaw dropped and chest moved up and down.
His legal team requested an emergency stay of execution while he was strapped to the bed over concerns about the efficacy of the type of drugs being used in the procedure.
Notes in legal documents read: "He has been gasping and snorting for more than an hour. He is still alive."
But the State Department of Corrections Director Charles Ryan insisted that Wood felt "no pain" and added: "Throughout this execution, I conferred and collaborated with our IV team members and was assured unequivocally that the inmate was comatose and never in pain or distress."
One of his lawyers, Dale Baich, said at the time that the prolonged death could have been prevented and called it a "cruel and unusual punishment".
The state of Arizona temporarily halted all executions following the Wood incident. Executions were not resumed until May of this year.
The Diez family told Sky News at the time of his execution that what they saw was incomparable to what the victims had to face.
Jeanne Brown, Debbie's sister, said: "What I saw today with him being executed, it is nothing compared to what happened on August 7, 1989.
"What's excruciating is seeing your father lying there in a pool of blood, seeing your sister lying in a pool of blood."
Richard Brown, Debbie's brother-in-law, added: "I saw the life go out of my sister-in-law's eyes.
"You guys are blowing it all out of proportion about these drugs.
"This man, he conducted a horrifying murder, and you worry about the drug and how it affects him.
"Why don't we give him a bullet? Why don't we give him some Drano?
"Now my family can rest in peace."