On May 31, 2009, Toronto's world-beating hip-hop star Drake was enjoying an evening at a restaurant in Little Italy at the corner of College and Beatrice streets.

He was on the verge of huge artistic and commercial success, loved by fans, admired by critics, seen by corporations as a crossover artist who could make a mint in endorsement deals. But with his burgeoning fame and success came the kind of threat that music superstars sometimes face, a threat that would make him feel unsafe in the city that gave him his start.

Drake left the restaurant that night with a woman named Chantal Brown, according to a synopsis drawn up by police, and they walked down Beatrice Street to his parked SUV. Drake was either sitting in his seat or about to slide in when two men walked up.

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They drew handguns and pointed them in Drake's face. They demanded he give up his jewellery and cash. Drake had little choice but to comply.

He handed over his gold and diamond necklace, his several-thousand-dollar Audemars Piguet watch, and $2,000 in American bills.

Ms. Brown was sitting in the passenger seat. A third person, Nicholas Carino, walked out of the restaurant and saw the robbery in progress. He yelled at the gun-toting thieves "to get the fuck back," according to police.

Startled, but with the bling already in hand, the thieves hopped into a waiting getaway car, heading south on Beatrice Street. Shortly after, the getaway car was stopped by police for going the wrong way on a one-way street. Two men dove out, trying to evade arrest.

One, Soccerties Cotterell, was chased down and put in handcuffs.

Another man, Paul Lucian Lelutiu, was allegedly driving the vehicle and was arrested without a struggle.

He was prosecuted along with Mr. Cotterell. They were charged with armed robbery, conspiracy to commit armed robbery, three counts of pointing a firearm and possession of stolen property.

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All of this helps make Drake's startling quote in the New York Times this week, that he feels "unsafe at all times" in Toronto, a little more understandable. Drake will be in town next week for the MuchMusic Video Awards, a gala event, but one where last year, at an after party Drake hosted, three firearms were seized by a heavily armed police squad.

In January, all of the serious charges against Mr. Cotterell and Mr. Lelutiu were withdrawn. They pled guilty only to conspiracy to commit robbery, not armed robbery, and possession of stolen property. Although the police investigation alleged they pointed a weapon at three people with witnesses present, those charges were dropped. The men were sentenced to time served plus one day, and so were out of prison and walking the streets by January of this year. They spent a little over six months in jail.

According to a lawyer involved in the case, Mr. Cotterell was the alleged gunman and Mr. Lelutiu the alleged driver. But the police synopsis names a second gunman, whose identity can't be printed. It's not known what happened to him. An officer and lawyer familiar with the case said their belief is the man escaped arrest.

So what happened? At the time, Drake was being dissed by another Toronto rapper for being a so-called "snitch" for co-operating with a police investigation. Although Drake's roots are in the genteel Forest Hill neighbourhood, he must still contend with a strain of hip-hop culture that, through a twisted "street" logic, vilifies speaking to police.

It raises the question, though, of whether the case collapsed because Drake refused to co-operate. A lawyer close to the process said the withdrawal of the charges was agreed before anyone had to testify, but all indications were that Drake was available to take the stand. He said the artist was "not exactly forthcoming, put it that way," but that he didn't refuse to help the authorities at all.

Although police recovered the necklace, the watch and $1,330 (U.S.) cash, no guns were found, which may have presented an obstacle for the Crown. Also, Drake has said he was set up that night, which a lawyer corroborated.

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"[Someone]might have been the source of information as to where Drake was for these guys to locate him," the lawyer said.

Drake still comes to Toronto for recording sessions and owns a condo in the city, and though he subsequently downplayed his remarks, saying that they were taken out of context, he might be inclined to tread cautiously.

As he told the Times interviewer, "There's no one else you can hate as much as me if you hate money, or you hate success."