He has lived the type of life few could even imagine -- and even fewer would wish to follow.
Now one of Winnipeg's most curious criminal enigmas is hoping to reinvent himself as a mentor to troubled youth, believing his checkered past can be a great motivator to stay on the straight and narrow.
"I know about being on the wrong side of the law," Kevin Sylvester said in a forensic report tendered last week at his latest sentencing hearing.
The Free Press reviewed a copy of the report, which gives new insight into Sylvester's background that could produce a stirring plot for a Hollywood crime thriller.
"He would like to work with youth, particularly those who were gang-involved. He reported he would like to take courses, such as psychology, that would allow him to relate meaningfully to this population," wrote Dr. Kent Somers, who described Sylvester's personal story as "remarkable."
Sylvester, 50, is going to have to wait a little while, however. The longtime biker is now facing up to eight years in prison after admitting to terrorizing an innocent Winnipeg family last fall in a case of mistaken identity.
Sylvester admits confronting the couple outside their vehicle, believing they were involved in an attack that saw the mother of his kids beaten and burned. In fact, the pair had no involvement. They had just loaded their children, aged 21 months and nine months, in the back of their car when Sylvester approached and pulled a .45-calibre handgun.
The family fled, with Sylvester in hot pursuit. He chased them for four blocks, ramming their vehicle about 10 times while pointing the gun out his window. The chase ended when the mom, who was driving and calling 911 at the same time, veered off and lost him.
In the forensic report, Sylvester admits he fell into the same trap that has landed him in so much legal hot water over the years: Losing his cool.
"Mr. Sylvester acknowledges being an individual who, absent medication to regulate his mood or use of street drugs such as marijuana to dull his emotional reactions, is prone to hostility, explosive anger and physical aggression," Somers wrote.
The veteran doctor described Sylvester as straightforward and honest, his health failing and his emotional state in disarray due to a "chronic history of depression, with a high degree of anxiety and agitation."
"He presented as somewhat sad and resigned in our interview," said Somers.
The Crown says a lengthy prison sentence is needed as Sylvester remains a "true danger" to the public. Defence lawyer Laura Robinson asked for a maximum of five years. Provincial court Judge Dale Schille has reserved his verdict until Sept. 12.
Sylvester has become a familiar name in Manitoba because of his well-documented, long-running feud with members and associates of the Hells Angels.
He is the younger brother of Darwin Sylvester, who was president of the former Spartans motorcycle gang. Darwin disappeared in 1998 and is presumed dead. Kevin Sylvester narrowly escaped death himself while a member of the Spartans in 1992. He was critically wounded when he got into a gunfight with a member of the rival Los Brovos gang. He underwent a kidney transplant because of the injury.
In summer 2001, he believed he was terminally ill and decided to try to avenge his brother's suspected slaying by waging a war against those he thought might be responsible. He shot Hells Angel Rod Sweeney in the head as he sat in his tow truck with his young son beside him. Sweeney survived the point-blank attack.
Sylvester became a wanted man after the shooting and was the victim of several retaliatory incidents that summer, including three firebombings of his house and a drive-by shooting attempt on Portage Avenue during rush-hour traffic.
Facing dozens of charges, Sylvester struck a deal with justice officials to testify against members of the Hells Angels in exchange for a sweetheart deal of just two years in jail.
But even that didn't make Sylvester happy. He walked away from the witness-protection plan months later and gave an interview to the Free Press in which he blasted police and justice officials for how they'd treated him, claiming they made all sorts of financial promises to him that weren't fulfilled. He said his life was in constant danger.
Sylvester was back in the news in 2007 when he overdosed on antidepressants and made a series of phone calls to a Crown attorney, his defence lawyer and the Free Press in which he spoke about wanting to get into a confrontation with police, his hatred of the system and how they'd failed him. Officers went to his residence, where Sylvester attacked them before being Tasered.
Sylvester pleaded guilty in late 2007 to the police assault and was given three months in custody and probation.
The doctor said a new medication regime has put Sylvester in a better place in recent months, saying he might be able to maximize his next chance at freedom.
"His thinking has been clearer than it has at any point that he could recall in his adult life," he said. "But risk management is a critical issue in the consideration of risk of future offending."