Billie Coble, a 70-year-old convicted of killing his estranged wife's family, was executed Thursday in Texas. This image shows the death chamber from the witness room at the Southern Ohio Correctional Facility in Lucasville, Ohio, Aug. 29, 2001. Mike Simons/Getty Images

Almost 30 years after he killed his estranged wife’s parents and brother, Billie Coble was executed at Huntsville, Texas, on Thursday. Coble, 70, was the oldest man to be executed in the state.

He was administered a lethal dose of pentobarbital at the Walls Unit of Texas Department of Criminal Justice. His family was present at the time of his execution. His death was confirmed at 6:24 p.m. local time (7:24 p.m. EST) and Coble’s last words were, “Yes Sir, that will be five dollars.”

His son and grandson were arrested during the execution after they started thumping the glass and screaming “No” loudly enough for them to have to be removed from the witness room. They were both charged with resisting arrest and were sent to jail.

Coble was convicted of murder in the 1989 killings of his estranged wife’s family in McLennan County. He was married to Karen Vicha for just over a year when she told him she wanted a divorce. When Karen came home from work one day, she found her children tied up and Coble told her he had killed her parents, Robert and Zelda Vicha and her brother Bobby, who was a police sergeant. After this, he led Karen at gunpoint to his car and tried to flee with her. He crashed into a parked car as he tried to stab her while driving. A police deputy followed them and he was eventually was arrested. Karen survived the attack.

During his trial, the court was informed of Coble’s extended history of brutalizing and molesting women, including his two former wives and several young girls. The prosecution also presented evidence of Coble’s traumatic childhood, his life in a state home for more than a decade and his mother who was institutionalized. He also enlisted in the army to fight in the Vietnam War at the age of 17. In June 1990, he was found guilty of all three murders and was sentenced to death.

However, in 2008, the 5th U.S. Circuit Court of Appeals said the changing standard on how explicitly jurors weighed the mitigating evidence, like Coble’s childhood, could have made them give a lesser sentence to life in prison. When the jury looked at the evidence again in 2008, Coble was sentenced to death again. Prosecutors described him as a man “with a heart full of scorpions.”

His lawyers asked the U.S. Supreme Court to delay his execution. They argued that Coble’s original lawyers neglected to concede his guilt since they failed to present an insanity defense before the jury in both the trials. The request was rejected and his execution date stayed the same.

In the appeal, Coble’s attorney, A. Richard Ellis, said, “Coble does not deny that he bears responsibility for the victims’ loss of life, but he nonetheless wanted his lawyers to present a defense on his behalf.” In a petition to the Board of Pardons and Paroles, Ellis claimed Coble suffered from post-traumatic stress disorder after his time as a marine in the Vietnam War and was convicted due to misleading testimonies from two expert witnesses on him being a danger in the future.

Coble was the second person executed in Texas this year. The oldest person executed in the U.S. was Walter Moody, a serial bomber who was put to death in Alabama in 2018 at the age of 83.