Evan Spencer Ebel's life seemed to have spiraled out of control in the spring after his 16-year-old sister was killed in a car crash -- a descent that is recorded in the flurry of court cases in 2004 that led him to prison.The 28-year-old parolee was fatally shot in the forehead in a shootout with Texas law officers in Decatur only weeks after his release from a Colorado prison Jan. 28.Authorities are investigating whether Ebel is linked to Tuesday night's shooting death of Tom Clements, the director of the state's prison system, and the killing two days earlier of a Domino's Pizza deliveryman."A lot of people go to prison and come out and lead useful lives," said Scott Robinson, an attorney who represented Ebel in the early cases."It's clear this young man's sentence to prison was a delayed sentence to death."Ebel's documented decline began Oct. 26, 2003, when as a 19-year-old he pointed a gun at the head of an acquaintance and demanded cash.He then went to the man's home and robbed several people watching a Broncos game."I'm not playing. ... This is not a joke," Ebel said while pointing the gun at one man's head. "I'll blow your ... head off."A week later, police found Ebel hiding in the back seat of a car with a handgun whose serial number had been scratched off. He gave them a phony name, a felony."He had been a difficult kid, not enormous problems," Robinson said. "At the time, I thought there was hope for him and thought he was salvageable. I could talk with him. He didn't have any attitude."Robinson got the judge to agree to sentence Ebel to three years of community corrections instead of prison on the first arrest."That was his one big break," Robinson said.But it didn't help.In spring 2004, Ebel's life began to unravel -- a series of violent events that make Robinson wonder whether Marin Ebel's fatal car crash on Jan. 31, 2004, shook the already troubled teen.On April 26, 2004, police say, Ebel carjacked a stranger, hitting him with the butt of his gun and stealing a 1998 Ford Mustang before crashing it 10 blocks away and fleeing.A week later, they say, he knocked on a front door and pointed a gun at the woman who answered, demanding football jerseys that he said belonged to a friend.That June, Ebel shot himself in the stomach, an injury that required him to get a colostomy bag. Twenty days later, he shot himself in the leg, later telling a cellmate that he was handling the gun carelessly.His ride ended when he was sentenced to eight years in prison after pleading guilty to second-degree assault in the carjacking. He entered prison in June 2005 and wouldn't be released until January 2013.