Drug Kingpin Gregory Woolley Killed, Brought the Canadian Mafia & Hells Angels Together

"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, a Molotov cocktail was thrown at his house, and his neighbor's house was mistakenly shot at. 

Around 10:30 AM local police received reports of gunfire in the parking lot outside the Vallée-des-Forts health center in Saint-Jean-sur-Richelieu, a city about 40 kilometers southeast of Montreal. Upon arrival, officers found Woolley, 51, with gunshot wounds. Sources also told CBC that Woolley's wife and 3-day-old newborn witnessed the shooting that took place at his white Lamborghini Urus. He was pronounced dead at the hospital in the same area.

Seven shots were reported to have been fired, and six of those were believed to have hit Woolley. Witnesses told police they saw a black SUV flee the scene, and a vehicle matching this description was found an hour later on fire in Montreal's Pointe-Saint-Charles neighborhood. 

The burning Range Rover SUV was found an hour later near Montreal.

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. 

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.

"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 [support club] that Maurice 'Mom' Boucher used during the famous biker wars [of the] the 1990s," retired Montreal detective Phillipe Paul said. 

According to Paul, Woolley went on to become the first black full-fledged Hells Angels member in Canada. This is disputed, however. While he was part of the overall Hells Angels umbrella, but as a member of the Rockers MC. Also, it should be noted that the Hells Angels had several black members in the 1960s in California and currently have chapters around the world.

"I actually arrested him myself in the early 2000s, in his car, we found guns and bulletproof vests," said Paul. "While he was in the cell, I received a phone call at my office saying to let him go or I would probably not survive the day. I had protection to go to court, we went to court and he was found guilty and did time."

"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.

Woolley came to notoriety in Montreal during the 1990s when he was first charged with being part of a small group of men accused of murdering a drug dealer the Hells Angels wanted eliminated. Shortly after his acquittal, he became a member of the Rockers, a support or puppet club for the Quebec Hells Angels.

Quebec Biker Wars

The Quebec Biker Wars, beginning in 1994, was among the most violent biker and gang wars at the time. The primary battles were between the expanding Hells Angels Canada, based in Quebec, and the Rock Machine MC who later patched over to become part of the Bandidos (the club has since been revived following a separation from the American Bandidos MC.) 

The two motorcycle clubs fell out following the US incarceration of the Rock Machine founder, Salvatore Cazzetta, a longtime friend of Boucher, as the Hells Angels sought to control street-level drug sales in Quebec. Cazzetta served 10 years in the US for importing cocaine. 

Hundreds of murders, bombings, and shootings occurred, including a car bomb that resulted in the death of a young bystander. The war left 162 people dead, including civilians. There were also 84 bombings, and 130 cases of arson. The war ended after the Rock Machine was decimated and patched over to the Bandidos, Boucher was arrested and imprisoned for ordering the deaths of two prison guards.

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.

Woolley was a man connected to many corners of the crime underworld and 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.

Mafia-Biker-Gang Alliance

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. 

A conversation secretly recorded between Woolley, Rizzuto’s son Leonardo, and Stefano Sollecito in August 2015 revealed that the two alleged Montreal Mafia leaders considered Woolley to be equal to them in terms of his influence. “He watches my back, I watch his,” Sollecito said of Woolley in a conversation captured by investigators in the office of former criminal lawyer Loris Cavaliere during the Magot-Mastiff investigation.

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.

Antonio Nicaso, a Toronto-based author and organized crime expert, said the Mafia, the Hells Angels, and street gangs have been working together to gain a better hold on organized crime." They were forging a strategic alliance to control some important sources of revenue such as drug trafficking," he said.

In 2012, as the Alliance was forming, a gang leader who rebuked Woolley and disrespected other organized crime figures was killed. "Big" Chenier Dupuy, head of the Bo-Gars street gang, a Mafia-linked outfit whose members also reportedly claim allegiance to the Bloods street gang.

A source says Dupuy had slapped Woolley in the face during a Hells Angels-sponsored summit north of Montreal aimed at uniting several street gangs under their banner. The summit meeting was organized by Woolley.

"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.

Cocaine-Marijuana Operations

In 2012, Mexican authorities arrested a Quebec man named Jimmy "Cosmo" Cournoyer. He was arrested as he was disembarking from a plane in Cancun, Quintana Roo because he was wanted by US authorities. He was flown back to Canada, but arrested during a stop in Houston, Texas. In the US, he faced charges of orchestrating a large drug network that brought BC Bud marijuana to the US and cocaine from Mexican cartels into Canada.

The marijuana was transported in vans and mobile homes across Canada with the help of the Hells Angels. Then the Montreal Mafia and Hells Angels transported drugs to New York, where trucks would take them to a warehouse in Brooklyn, according to the investigation by the New York Post.

The millions generated by the sale of Cournoyer's marijuana was used to purchase cocaine from the Sinaloa Cartel, at that time led by "El Chapo." The cocaine was then sold on Canadian streets by the Syndicates gang members and others. That money would go back into the marijuana operation, funding more hydroponic farms in British Columbia.

Mafia leader Leonardo Rizzuto.

Project Magot, an investigation that also produced the arrests of alleged Mafia leaders Leonardo Rizzuto and Stefano Sollecito in November 2015, revealed that Woolley had become a very influential figure among Montreal’s criminal organizations. In 2013, he was seen attending the funeral for Vito Rizzuto, held at a church in Little Italy after the longtime leader of the Montreal Mafia died of cancer.

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.

“Yes. Euh, he said yes, do it,” Mongeau was recorded telling Boucher. Despite the evidence, the case against Mongeau was also stayed, in May, when her father admitted he orchestrated the plot. Boucher was sentenced to a 10-year prison term in addition to his life term.

 

Possible Repercussions

According to police sources, Woolley had been warned by the authorities that there was a price on his head. "He recently had a lot of warnings: shootings in and around his house, a fire in his house, and unfortunately for him today he got shot and killed." He had been out of prison only a couple of years.

Woolley with his newborn the day before his murder, posted from his wife's Instagram.

The Montreal Mafia had given Woolley part of the profits from illegal sports betting and loan operations, commonly called the “Book” in the community. More recently, Gregory Woolley had become close to members of the South section of the Hells Angels and had been observed by the police during one of their events.

Woolley's house was attacked several times in the past few years.

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.

Late Mafia boss Vito Rizzuto.

Crime expert and author Antonio Nicaso addressed Woolley's killing saying, "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. Violence amplified against the Rizuttos since the mid-2000s when Montreal Mafia boss Vito Rizzuto was imprisoned in the US on charges of killing three Bonanno Family capos.

Both Vito's father and son were murdered, as well as a Bonanno Acting Boss deported from the US and many others over a battle for the Montreal organized crime trade between the traditional LCN Mafia, Calabrian 'Ndrangheta Clans, and other figures. His successors, have been subject to murders and attempted murders as well.

"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."

Sources CTV. CBC, Montreal Gazette, Borderland Beat, CBC, CBC, Toronto Sun, La Presse