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“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.”