MONTREAL—Flashy fall guy or drug kingpin? These are the duelling portraits a jury will see when a 33-year-old Quebecer goes on trial in June on charges of running a lucrative smuggling ring with links to the highest ranks of the Mafia and the Hells Angels.

Jimmy Cournoyer makes no apologies for his playboy lifestyle. Before his arrest early last year, he drove a car valued at $2 million, dated glamorous Brazilian-born model Amelia Racine and partied with stars like Leonardo DiCaprio and ultimate fighting champion George St-Pierre.

But a list filed in a New York court claiming to outline “Cournoyer’s extensive criminal contacts” is much more sinister, according to American prosecutors, who have disclosed that they will call an expert witness to testify about the workings of Italian organized crime in the U.S. and Canada.

The list includes Montreal Mafia boss Vito Rizzuto, Hells Angels leader Maurice “Mom” Boucher, and the leaders of Montreal’s infamous West End Gang.

The hundreds of names that appear on the court filing were produced last week by the U.S. States Attorney also includes former Canadian boxing champion Arturo Gatti, now dead, and Martino Caputo, a Toronto man arrested last month in Germany on charges that he helped orchestrate the daylight murder of a man outside a College Street bar in Toronto’s Little Italy last summer. The killing was reportedly due to a drug dispute.

Caputo, and his twin brother, Antonio, who together ran a Spadina Avenue restaurant that was a regular stop when Rizzuto visited Toronto, were also arrested in 2001 during a sweep on illegal gambling operations in Ontario and Quebec.

The charges against Cournoyer and five others are the result of a probe that began in 2007 into drug-trafficking operations worth almost $ 1 billion headquartered in Montreal that had formed a cartel to smuggle marijuana into the U.S., set prices and distribute the drugs to users.

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Cournoyer is alleged to have coordinated the shipment of some 50,000 kilograms of marijuana south of the border, arranged for the profits to travel from New York to California and overseen the purchase of cocaine that was then brought back into Canada, according to court filings.

He allegedly outfitted his underlings with high-security Blackberry devices that could be remotely disabled if lost or seized by police and smuggled 9-mm handguns across the Canada-U.S. border for protection.

The list of Cournoyer’s co-conspirators includes other alleged and convicted drug traffickers, bikers, enforcers and numerous residents of Cornwall’s Akwesasne native reserve — the alleged embarkation point for the drug shipments.

Cournoyer’s attorney, Gerald McMahon, said more than a dozen of the names on the list point to the real culprits in the smuggling operation, a point he will try to make to a jury when the trial begins on June 3.

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Chief among those responsible is New York attorney Stanley Cohen, whom Cournoyer has claimed in pre-trial hearings is giving evidence to the authorities in order to protect himself and his clients on Mohawk territory from prosecution.

Cohen worked closely with the Mohawk Warriors during the Oka Crisis and has represented a number of accused Mohawk drug traffickers over the years. He is primarily known in the United States as the lawyer of choice for accused terrorists and for Hamas.

“This is like the fifth different person that the (U.S.) government claims is the head of this consortium. Whenever Stanley Cohen decides to knife somebody, he’s the new head of the consortium,” McMahon said in an interview.

“It’s a moving target. Jimmy Cournoyer is not the head of any consortium. He’s not involved in any marijuana trafficking and he’s simply a target of opportunity for Stanley Cohen.”

Prosecutors have repeatedly denied that Cohen is at the heart of the criminal charges.

“Mr. Cohen is not a government witness and has never been an informant for the government,” U.S. attorney Loretta Lynch wrote in a letter to McMahon last month.