Gleason says it's not because he wants to die, but rather because he knows he will kill again if he's not executed. He was already serving life in prison when he killed his cellmate then vowed to continue killing unless he was put to death. When the system wasn't moving fast enough, he strangled another inmate and warned that the body count would rise if they didn't heed his warnings. Gleason waived his appeals, and he remains in a legal battle with his former attorneys as they file last-minute appeals to try to save his life against his wishes.
"Why prolong it? The end result's gonna be the same," Gleason said from death row in his thick Boston accent in one of numerous interviews he's given to The Associated Press over three years. "The death part don't bother me. This has been a long time coming. It's called karma."
Gleason is scheduled to die at 9 p.m. Wednesday at Greensville Correctional Center in Jarratt. Condemned Virginia inmates can choose between lethal injection and electrocution, and Gleason is the first inmate to choose electrocution since 2010.
The unusual choice follows a series of other shocking moves.
Deputies had to use a stun gun on him during a violent outburst in court in 2008 before he pleaded guilty to a shooting death that sent him to prison for life. Despite there being little evidence against him, Gleason admitted to shooting Mike Jamerson, whose son was cooperating in a federal investigation into a methamphetamine ring that Gleason was involved in.
A year later he got so frustrated when prison officials wouldn't move his new, mentally disturbed cellmate, 63-year-old Harvey Watson Jr., that Gleason hogtied, beat and strangled the older man. Gleason remained in the cell with Watson's lifeless body for more than 15 hours before officers discovered the crime.
"Someone needs to stop it. The only way to stop me is put me on death row," he told AP at the time, repeating his threats in court on numerous occasions.
While awaiting sentencing at a highly secure prison in the mountains that is reserved for the state's worst inmates, Gleason strangled 26-year-old Aaron Cooper through the wire fencing that separated their individual cages on the recreation yard.
Gleason claims he's killed others - perhaps dozens more - but he has refused to provide details. He claims he's different from the other men on Virginia's death row for one important reason: he only kills criminals.
Watson was serving life for killing one man and injuring two others. Cooper was a carjacker with gang ties.
"I ain't saying I'm a better person for killing criminals, but I've never killed innocent people," Gleason said. "I killed people that's in the same lifestyle as me, and they know, hey, these things can happen."
Gleason says he only requested death in order to keep a promise to a loved one that he wouldn't kill again. He said doing so will allow him to teach his children, including two young sons, what can happen if they follow in his footsteps.
"I wasn't there as a father and I'm hoping that I can do one last good thing," he said. "Hopefully, this is a good thing."
Cooper's mother, Kim Strickland, put aside her religious beliefs in opposition to the death penalty when Gleason sent her Bible verses that preached an eye for an eye before his sentencing. She testified that he deserved to die for killing her son. She is suing the prison system over the death.
"May God have mercy on his soul," Strickland told AP. "I've been praying and will continue to pray that his family can heal from this ordeal."
Gleason, 42, was born in Lowell, Mass., a proud Yankee who still signs his letters "Bobby from Boston." After going to art school in North Carolina, Gleason became an award-winning tattoo artist in shops up and down the East Coast. He settled down for a while outside of Richmond, owned a tattoo shop and embraced religion. He later said he was feigning interest in religion to benefit his tattoo business.
In court papers, attorneys detail his "profoundly disturbed and traumatic life" marked by abuse as a child and depression and other mental health problems as an adult. Gleason starting drinking alcohol as a teen and later abused cocaine, meth and steroids, among other drugs. His long criminal record dates back to armed robberies as a teen. He looked up to an older brother who died in a Massachusetts prison during a botched escape attempt.
Attorneys who continue trying to intervene on his behalf claim Gleason is severely disturbed. They argue his competency has deteriorated over the year he's been in isolation on death row, and that he suffers from extreme paranoia, delusional thinking, severe anxiety and other mental afflictions that leave him with "a nearly overwhelming urge to end his own life."
"...his mental illness is causing him to be suicidal, and he is enlisting the government's help to end his life," attorney Jon Sheldon wrote in court documents asking a federal appeals court to require a new competency evaluation. Two other evaluations deemed Gleason capable of making his own decisions.
While those closest to Gleason acknowledge he's had a troubled life, they also describe a man who dressed up as a big, purple dinosaur for his young son's birthday and comforted him when he was scared of the costume, who organized a motorcycle run to raise money for a child with cancer and who is fiercely protective and supportive of those he loved.
"It's a shame," one friend told attorneys of Gleason's death sentence, according to court papers, "because there's a lot of goodness in him."
But there's no mistaking Gleason's dark side.
Prison and jail officials have intercepted letters and calls in which he either discussed killing or directly threatened judges, attorneys, jurors and mental health experts tied to his criminal cases. He told investigators that killing was "like tying a shoe" or "going to the fridge to get a beer."
Those on both sides of the death penalty debate have seized on Gleason's case to prove their point.
Death penalty supporters say that keeping Gleason alive puts others at risk. Opponents of capital punishment argue that the prospect of being executed gave him incentive to kill Watson and Cooper.
Gleason agrees with death penalty opponents on at least one point: that it's likely individuals feel immense pain during a lethal injection. That's partly why he chose electrocution.
The other reason: He just can't imagine going out lying down.
"I can't do that," he said. "I'd rather be sitting up."