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John Raposo was killed in a daylight shooting in Toronto's Little Italy Monday, June 18, 2012.

John Raposo was a gregarious presence in Little Italy, where he socialized at College Street cafés, tooled around in expensive cars and doted on his 17-month-old son.

The 35-year-old also had a profile with police, running afoul of the law on several occasions over the last 15 years. Next month, he was set to stand trial over accusations he beat up a man following a card game at a suburban club.

But it is still unclear why Mr. Raposo was targeted Monday afternoon, gunned down in an execution-style killing amid a crowd of soccer fans watching the European championship. And a day later, the gunman remained on the loose.

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Mr. Raposo lived with his common-law wife on Willard Avenue, a quiet residential street in the west end. His wife's stepfather said he was good with his little boy, and the couple was expecting a second child.

"All of my encounters with John have been very good ones. He's a very friendly person, very outgoing," said David Hawkins, adding that he didn't know Mr. Raposo very well. "I just can't fathom it, I just can't. … I just hope they catch whoever did this."

Records indicate Mr. Raposo purchased the property in 2004 for $247,000, but neighbours said he had only moved in a couple of years ago, tearing down the old house there and building a new one.

He also co-owned a brick duplex on Crawford Street, a block from the College Street café where he was gunned down, which he had recently renovated for his mother to live in.

He was often seen on the block behind the wheel of a BMW 750i and earned the nickname "Johnny Maserati" for his taste in autos. Neighbours said he told them he made a living flipping houses and renting arcade games.

He also suffered legal entanglements, dating back as far as 1997.

His most recent concerned Mississauga resident Jamal Koussa, who said he met Mr. Raposo on March 24, 2011, at a private gambling club in that Toronto suburb. When Mr. Raposo started to lose at gin rummy, the pair argued, he said, and it eventually came to blows.

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"He sucker punched me," said Mr. Koussa, adding that one of Mr. Raposo's friends then jumped him from behind. "I got knocked down [and] they started beating me with steel boots."

Every time he tried to get up, he said, the men would kick him more. When the beating ended some two minutes later, Mr. Koussa said, his jaw was nearly broken and he had to go to the hospital. He was off work for days afterward.

Mr. Raposo was charged with assault and was to be tried July 3 in a Brampton court. He faced another trial in Toronto on Dec. 21, over a dangerous driving charge.

Despite his record, however, a police source long familiar with both the Mafia and outlaw motorcycle gangs said that he does not believe Mr. Raposo belonged to any organized crime group.

Although he shares a last name with Luis Raposo, a member of the Bandidos motorcycle club murdered in 2006, there is no indication he was related to him. And several lawyers connected with that murder case, as well as former Bandido-turned-author Edward Winterhalder, have never heard of him.

Such a brazen shooting is uncommon on the normally safe College Street strip. The killer approached the Sicilian Sidewalk Café in a white construction hat, a dust mask and an orange safety vest, opened fire, then fled north on foot in front of numerous bystanders.

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The shooter's bizarre garb may make the case hard to crack. Police described him as a six-foot-tall man with shoulder-length blond hair and a medium build.

With a report from Stephanie Chambers

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