He is one of Winnipeg's most curious criminal enigmas: a longtime biker with a reputation for irrational, often bizarre behaviour.
And now Kevin Sylvester is back in jail, accused of a seemingly random attack that has caught the eye of police, justice officials and organized-crime experts across the country.
"Kevin Sylvester has a long history when it comes to violent crime, and he has a lot of enemies," noted Canadian biker author Jerry Langton told the Free Press this week. He has followed Sylvester's exploits for more than a decade but admits to being puzzled by the most recent events, considering Sylvester had stayed out of the headlines -- and the justice system -- for several years.
Sylvester, 49, was arrested Oct. 1 after allegedly confronting a 32-year-old man and a woman with her one-year-old baby at gunpoint outside a King Edward Street convenience store in broad daylight. The victims fled to a vehicle and Sylvester is accused of chasing after them in his own vehicle for several blocks, repeatedly ramming them. They escaped without serious injury.
Sylvester was arrested later in the day and found in possession of a loaded firearm and two loaded clips. He is being held in custody without bail on numerous charges and has declined interview requests. Police have said there is no apparent motive for the attack and the victims were not known to him.
"If this is a case of mistaken identity, I wouldn't be too surprised," Langton said. That theory stems from Sylvester's well-documented, long-running feud with members and associates of the Hells Angels, his self-admitted paranoia and the current unstable biker scene in Manitoba.
"Violence always occurs in Canadian cities when the organized status quo is altered," Langton explained.
"A long series of raids on the Manitoba Hells Angels and their allies have weakened them considerably. That has allowed an opposition to coalesce under the Rock Machine gang. When two gangs are vying for the same drug-selling territory, there's always violence."
A brief history lesson is required to understand the root of the issues. Sylvester is the younger brother of Darwin Sylvester, the 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.
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 that had dozens of pedestrians and motorists ducking for cover.
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. Provincial court Judge Charles Newcombe said at the time he was "holding his nose" at what many called a "deal with the devil."
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.
Around the same time, the saga involving his missing brother, Darwin, took another twist. Longtime Spartans gang member Joel Maguet died in 2007 after crashing the small plane he used to traffic drugs. The crash occurred at West Hawk Lake. Many people within law enforcement and the criminal underworld believe Maguet was responsible for killing Darwin Sylvester and a second Spartans member, Robert Rosmus, in 1999. But there was never sufficient evidence to charge him.
Sylvester pleaded guilty in late 2007 to the police assault and was given three months in custody and probation.
"I'm sorry for the whole incident. It was a bad scene that I caused. It was embarrassing," he told court at the time. He wouldn't be heard from again, at least not publicly, until bursting back onto the scene last month.
The story behind this latest incident remains to be told.