Gleason said he only requested death in order to keep a promise to a loved one that he wouldn't kill again. He said doing so would allow him to teach his children, including two young sons, what could happen if they followed in his footsteps.
"I wasn't there as a father and I'm hoping that I can do one last good thing," he said previously. "Hopefully, this is a good thing."
Gleason had fought last-minute attempts by former attorneys to block the scheduled execution. The lawyers had argued that he was not competent to waive his appeals and that more than a year spent in solitary confinement on death row had exacerbated his condition. Two mental health evaluations done before Gleason was sentenced in 2011 said he was depressed and impulsive but competent to make decisions in his case.
Late Wednesday, the U.S. Supreme Court rejected a request for a stay.
Use of the electric chair remains rare in Virginia. Since inmates were given the option in 1995, only six of the 85 inmates executed since then have chosen electrocution over lethal injection.
Cooper's mother, Kim Strickland, witnessed the execution. She has sued the prison system over her son's death and said she hopes Gleason's family can have closure.
"May God have mercy on his soul," Strickland told AP before the execution. "I've been praying and will continue to pray that his family can heal from this ordeal."
Waton's sister, Barbara McLeod, said in an email she had "mixed feelings" about the execution but "didn't want him to be able to kill more people." She, nor anyone else from Watson's family, witnessed the execution.
Gleason did not visit with family before his execution. Inmate's families are not allowed to witness executions in Virginia.
He did meet for two hours with his spiritual adviser, Timothy "Bam Bam" Spralding, a church deacon he had known for some time. Gleason had even done some of Spralding's tattoos.
Spralding said Gleason had expressed remorse and had repented.
"When he came into that room and nodded at me and gave a thumbs-up, I knew he was OK. I knew he was at peace," Spralding added.
Some protested outside the prison on Wednesday, saying Gleason's threats to continue killing should not be a reason to justify execution.