Organized crime kingpin Gregory Woolley gunned down near Montreal

Quebec organized crime kingpin Gregory Woolley was gunned down Friday near Montreal, multiple sources confirmed to CTV News. 

Woolley — who had connections to the Hells Angels, Montreal Mafia and several street gangs — was shot in broad daylight in front of multiple witnesses.

Around 10:30 a.m., local police received reports of gunfire in the parking lot outside the Vallée-des-Forts health centre in Saint-Jean-sur-Richelieu, a city about 40 kilometres southeast of Montreal. 

Upon arrival, officers found Woolley, 51, with gunshot wounds. He was later pronounced dead in hospital. 

Witnesses told police they saw a black SUV flee the scene, and a vehicle matching this description was later found on fire in Montreal's Pointe-Saint-Charles neighbourhood.

Provincial police, who have taken over the investigation, said they're working to determine whether the events are connected. No arrests had been made as of mid-afternoon Friday.

Witnesses told police they saw a black SUV flee the scene. A vehicle matching this description was later found on fire in Montreal. (photo: CTV News Montreal / Matt Gilmour)

Considered one of Quebec's most powerful organized crime figures, Woolley was seen as a bridge between local street gangs and the Hells Angels. He was one of few Black men to ever be accepted into the notorious biker gang.

A man connected to many corners of the crime underworld, Woolley also had close ties to the late Montreal Mafioso Vito Rizzuto and his family.

"Gregory Woolley was one of the most fascinating and powerful members of Montreal organized crime," said investigative journalist Julian Sher in an interview with CTV News Friday.

"He had a street sense and a ruthlessness. He started off with the Montreal street gangs and then is able to convince Maurice 'Mom' Boucher —  that famous head of the Hells Angels — to let him join the Rockers, which was really a strike force that Maurice 'Mom' Boucher used during the famous biker wars [of the] 1990s," he said. 

Sher, the co-author of The Road to Hell: How the Biker Gangs Are Conquering Canada, said Woolley's influence couldn't be contained, even behind bars.

"When he was in prison serving time for various charges, he is still, according to police [...] running a massive drug-trafficking ring. So he had the smarts and that bullishness that led him to really rise to the top."

Woolley had been sentenced in October 2018 to eight years in prison after pleading guilty to gangsterism and drug trafficking charges, but subtracting time served, he still had three years to serve. He was released on bail in 2020, two-thirds of the way through his sentence.

At the time of his death, Woolley was living in the Saint-Luc sector of Saint-Jean-sur-Richelieu.

REPERCUSSIONS COULD FOLLOW: EXPERTS

Daniel Renaud, a police and organized crime reporter at La Presse, said in an interview with CTV News that Woolley was considered among the top organized crime members in Montreal.

There will likely be repercussions following Woolley's killing, said Renaud, who agrees with other crime experts that it could be the start of a potentially violent period ahead.

Crime expert and author Antonio Nicaso addressed Woolley's killing on X, formerly called Twitter, Friday afternoon.

"The one in Montreal is an endless war. The latest murder is yet another attack on the power of what was once considered the most powerful crime family in Canada," he wrote, alluding to the Rizzutos.

The one in Montreal is an endless war. The latest murder is yet another attack on the power of what was once considered the most powerful crime family in Canada. 1/2

— Antonio Nicaso (@AntonioNicaso) November 17, 2023

"And everything happens amidst the indifference of a country for which the fight against organized crime has never been a priority," he added. 

Julian Sher said Woolley's assassination, while not totally surprising, will go down in the books.

"I think we're still looking to a rocky period ahead in the streets of Montreal," he said.

"For somebody as powerful as Gregory Woolley, for someone who survived, God, like almost 30 years of the biker wars, somebody who pleaded guilty to conspiracy, to murder, and was involved in so many other murders — for him to finally get gunned down, it just shows how long the reach of the enemies in the underworld can be."  

 

With files from The Canadian Press