“Socalj” for Borderland Beat
Quebec organized crime kingpin Gregory Woolley was gunned down Friday near Montreal, Canada. Woolley, who had connections to the Hells Angels, Syndicates, Montreal Mafia, and several street gangs, was shot in broad daylight in front of multiple witnesses. Last year, his house was shot at.
Who was Gregory Woolley?
Considered one of Quebec’s most powerful organized crime figures, Woolley was seen as a bridge between local street gangs and the Hells Angels as well as Montreal Mafia figures.
|Woolley with Hells Angels leader “Mom” Boucher.|
Originally from Haiti, in the 1990s Woolley was the leader of the Syndicates, a street gang that worked for the Hells Angels. He later became a member of the Rockers motorcycle gang, a subsidiary of the Hells Angels. Police say that Woolley was a close confidant of the late Hells Angels boss, Maurice Boucher.
“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 rise to the top.”
Woolley’s criminal record as an adult began in 1995 when he and a group of accomplices tried to extort $100,000 from a man who was involved in a bitter divorce. The men pointed a gun at the man’s 12-year-old son while they tried to collect the money. Woolley was a member of the Master B street gang before forming the Syndicates.
Quebec Biker Wars
In 2005, Woolley pleaded guilty to being part of a general conspiracy to kill rival gang members during the biker war and was sentenced to a 54-month prison term. According to Parole Board of Canada records, while he was serving that sentence Woolley was captured on video, in January 2007, assaulting a fellow inmate. Minutes later, two other inmates stabbed the same man with shivs. The inmate survived the attack but had to be treated at a hospital.
When he appeared before the parole board in 2008, Woolley admitted that he “enjoyed a certain prestige” among other inmates and that he was considered an influential person because of his reputation.
|Woolley attended the funeral of Montreal Mafia leader Vito Rizzuto.|
In 2005, while he was serving his sentence at a penitentiary in Ste-Anne-des Plaines, he forged a relationship with Vito Rizzuto, the then-Montreal Mafia leader who was awaiting extradition to the US. Woolley probably helped the Rizzuto organization survive the challenges it faced by forging an alliance with the Hells Angels.
In 2017, Woolley’s Lawyer Loris Cavaliere pleaded guilty to gangsterism and weapons possession and was sentenced to 34 months in jail. Cavaliere was described as a bridge between organized crime groups who held meetings with gangsters at his St-Laurent Blvd. law offices. He was also the lawyer for the Rizzuto family and defended Nicolo Rizzuto before his murder in 2010.
|Chenier Dupuy was killed after slapping Woolley and refusing to align his street gang with the Hells Angels.|
“He (said) would never work for the bikers or their dick suckers,” added a friend of Dupuy’s, an apparent reference to Wooley’s Syndicates. The Bo-Gars leader also reportedly beat up a Syndicates member in front of a Montreal car dealership.
|Jimmy “Cosmo” Cournoyer was arrested in Cancun, Mexico for organizing a US-Canada cocaine and marijuana operation.|
|Mafia leader Leonardo Rizzuto.|
Woolley and Cadet were leaders among a group of drug traffickers who were referred to as the “Bronzés” by the people who purchased cocaine from them. Woolley’s group controlled the supply of cocaine trafficking in Hochelaga Maisonneuve. A major drug trafficker who was operating in that part of Montreal later became a collaborating witness for the Crown and revealed his organization had to pay “taxes” or “rent” to sell on the territory.
He also had to make “deposits” while purchasing kilos of cocaine from the group. He estimated he purchased 90 kilograms of cocaine from the Bronzés over four years. Woolley was sentenced in October 2018 to 8 years in prison after pleading guilty to gangsterism, conspiracy to murder, and drug trafficking charges. But minus time served, he was released on parole in 2021, two-thirds through his sentence after being denied in 2019.
|Desjardins pleaded guilty to conspiring to kill the former Bonanno Acting Boss Salvatore Montagna who looked to take over the Mafia drug trade from the Rizzutos.|
Woolley had also been charged with plotting to kill Montreal Mafia figure Raynald Desjardins following the natural death of Vito Rizzuto. The plot was hatched by former Hells Angel Maurice (Mom) Boucher after he learned that Desjardins was expected to be transferred to a federal penitentiary where Boucher was already serving life sentences for murder.
Boucher used his daughter Alexandra Mongeau to allegedly transmit messages to Woolley on the outside. The police believed that it was up to Woolley to find out if a hit on Desjardins could proceed. In July 2015, Mongeau visited Boucher inside the penitentiary and appeared to have transmitted the message from Woolley.
|Late Mafia boss Vito Rizzuto.|