James’ time of death was 9:27 p.m. local time Thursday, according to the press release. James was convicted and sentenced to death for fatally shooting Smith, 26, whom he had dated in the early 1990s. Earlier this week, Smith’s daughter Terlyn Hall told CNN’s WBMA that the family hoped James would be sentenced to life in prison without parole. “She was a loving and forgiving person,” Hall said of her mother. “I’m sure if he was here today, or if he was in this situation, he would want to forgive.” “We don’t think (execution) is required because it won’t bring her back,” he added. Helvetius Hall, Smith’s brother, also pushed for a prison sentence instead of death. “He did a horrible thing,” he told the local news outlet. “He’s suffered enough and I don’t think taking his life will make our lives any better.” The execution came after more than 25 years of legal challenges in James’ case. Alabama Gov. Kay Ivey did not respond to a request for comment from CNN about the execution. James and Smith had a “volatile” relationship, and after they broke up, he stalked and harassed her, went to her home uninvited and threatened to kill her and her ex-husband, according to a U.S. Court of Appeals filing summarizing the case. In 1994, he followed her to a friend’s house and then shot her three times, killing her, the affidavit states. A jury in Jefferson County found him guilty of Smith’s murder and recommended the death penalty in 1996, but the Alabama Court of Criminal Appeals overturned the conviction based on an erroneous admission of hearsay evidence, the appeals court says. Before the retrial, James’ legal team arranged a deal with prosecutors in which he would receive a life sentence in exchange for a guilty plea, but James rejected that plan, the filing said. “James explained that he was doing very well on death row — he had his own room, his own television that he could control to watch whatever he wanted, and plenty of reading material,” the affidavit says. “He didn’t have to worry about other inmates attacking him, because he was always one-on-one with the guards.” In the retrial, a jury again convicted James of murder and sentenced him to death in 1999, and the appeals courts upheld the decision. In 2020, the US Court of Appeals upheld the conviction and dismissed James’ claim of ineffective counsel. A motion to stay his execution was denied by the U.S. Court of Appeals for the 11th Circuit on Tuesday. The state of Alabama last executed a man in January after the Supreme Court voted 5-4 to overturn a lower court’s decision to block the execution. Matthew Reeves, who had been convicted of robbing and killing Willie Johnson in 1996, was executed less than two hours later. Alabama currently has 166 death row inmates. The state’s next scheduled execution is for Alan Eugene Miller on Sept. 22, according to the Death Penalty Information Center.