Death Of An Anomaly: Gregory ‘Picasso’ Woolley

Mid-morning, November 17, 2023, coming out of a CLSC health clinic in the town of St-Jean-Sur-Richelieu in Quebec. Gregory Woolley at the age of 51, took his final breaths next to his white Lamborghini truck, in front of his wife and 3 day old baby.  He was struck by 6 bullets. Most can say this is the downfall of the unspoken ‘Code Of Honor’. The perpetrator, a hooded figure in a black Range Rover sped off and later torched the vehicle in the Pointe St-Charles neighborhood of Montreal on Sebastopol Street, where the Rockers MC had set up their first clubhouse. Was this intended to be a message, or is it plainly a coincidence?

The scene of the shooting.
Gregory Woolley just days before with his newborn.

To understand why this event is so critical to the future of the criminal playground in the province of Quebec. We need to understand the history of Woolley, his connections in the streets, Motorcycle Clubs and various other organizations that lurk in Montreal and what he ultimately achieved. 

Born in Tabarre, Haiti on February 26th in 1972, emigrating to Canada and joining a street gang known as Master B., who bought their supply off the Hells Angels. Woolley formed a strong bond with notorious biker Maurice ‘Mom’ Boucher, who had originated from a motorcycle club named the S.S. MC. Seeing Woolley being a big earner and very loyal, Mom made Woolley president of the Rockers MC, an HA puppet club, at just the age of 24 in 1996 after the murder of a Rock Machine MC member.

Gregory ‘Picasso’ Woolley (Left), Mom Boucher (Right)
Gregory ‘Picasso’ Woolley
Mom Boucher (Towards the left, facing the camera) and the face of Gregory Woolley (To Mom’s left).

Woolley, being black and of Haitian decent, was non-admissible to be a member of the HA, so he decided to leave Master B. and take up the position of president for the Rockers MC that Boucher had offered him, frequently sporting red and white colors in solidarity of the Angels.

Gregory ‘Picasso’ Woolley

Master B. eventually crumbled with Beauvoir Jean, a member of the Master B, forming another gang named the Bo-Gars and preaching propaganda against Woolley, painting him as an ‘Uncle Tom’ figure. Meanwhile the Bo-Gars were taking work from the Rizzuto clan at the time , which wasn’t any better than what Woolley was doing for the HA. Choosing colors, Woolley decided to opt for blue, teaming up with the Crack Down Posse and becoming Crips, while the Bo-Gars decided to go for red, becoming Bloods. In 1998, Woolley created a street gang named Syndicate, mixing the Crack Down Posse along with members of the Rockers MC.

Beauvoir Jean
Syndicate member photographed.

As Woolley’s relation with Mom Boucher grew, he eventually became Boucher’s bodyguard earning him the nickname ‘Picasso’. Being no stranger to killings, taking his first life at 17, Woolley took aim at the Rock Machine MC in the mid 90’s.

Woolley had gotten arrested coming back to Haiti with a revolver in his luggage.
The Rockers MC tagged duffle bag Woolley was arrested with at the airport on his round trip going and coming back to Haiti. Notice his name being stitch out on the bag.
A letter written and signed by Mom Boucher while Woolley was incarcerated.

In 1996, he murdered Rock Machine member Pierre Beauchamp, gunning him down in Beauchamp’s vehicle. Later bragging about the killing to Rocker MC member, Stephane Sirois, and numerous other members indicating the hit was allegedly ordered by Mom Boucher. In 1997, Woolley sent Rocker member, Aimé Simard, on a mission to complete a hit. The target; a Rock Machine member by the name of Jean Marc Caissy. The hit was successful, but a month after, Simard was arrested and turned police informant. Gregory was charged with first degree murder, but later acquitted, as Simard was not a reliable witness in court.

Aime Simard

In a major attempt by police to sweep bikers off their feet. The SPVM (Service de Police de la Ville de Montreal) launched the infamous Operation Springtime in 2001. Arresting numerous bikers in Montreal including Woolley. He was charged of drug trafficking conspiracy and the murder of Pierre Beauchamp that occurred 5 years earlier. The Rocker member, Stephane Sirois, he had bragged to the night of the Beauchamp murder, had turned crown witness. Acquitted of the Beauchamp murder twice thanks to his lawyer’s defence, Woolley took a plea bargain in 2005 and was convicted for conspiracy to commit murder, and conspiracy to traffic drugs. He was sent to Kingston Penitentiary and was paroled in 2007.

Throughout the 2000’s and the turn of the decade, Woolley was responsible for changing the face of the Montreal underworld. Building an alliance with the Hells Angels, the Rizzuto family and various black street gangs. Woolley’s relationship with Vito Rizzuto stemmed from a prison courtyard in Sainte Anne Des Plaines in 2004. Vito was trying to contest extradition charges for his part in a triple homicide committed in 1981 in New York City. The crime was portrayed in the movie ‘Donnie Brasco’ starring Johnny Depp. Woolley, on the other hand, was housed there during his trial, before he was convicted and sent to Kingston Penitentiary. They would frequently be seen together in the courtyard.

Vito Rizzuto
Vito Rizzuto (Left)
Vito Rizzuto (Left).

The RCMP and the SPVM formed a joint task force named Operation Axe in early 2009. It was aimed to take down the Syndicate along with supporting MCs. The authorities seized multiple different types of drugs, in kilos, weapons, Kevlar vests, cash and electronic devices. During Operation Axe, Woolley was arrested and charged with gangsterism. He became the first person to be charged twice with gangsterism in the history of Canada. Nevertheless, he was convicted in early 2011, then released on parole later in that same year. 

Woolley getting arrested.

Meanwhile, an internal conflict was brewing in the Rizzuto family. Raynald Desjardins along with his brother in law, Joe Di Maulo were backed by Ontario’s ‘Ndrangheta family and were at odds with Vito Rizzuto. With the Rizzuto clan losing Nicolo Rizzuto, the founder of the Rizzuto clan and father of Vito. Assassinated in 2010 in his own residence from a single sniper shot. Vito decided to turn to Woolley and the part he played in Motorcycle Clubs for back up. Soon enough the Rizzuto clan were backed by the Hells Angels.

Joe Di Maulo (Right)
A Young Raynald Desjardins.
Joe Di Maulo
Raynald Desjardins (Left) with protege Vittorio Mirarchi.

Woolley had even bigger plans to make this alliance between the mafia and the Motorcycle Clubs prosper. He called a meeting for various black street gangs in Montreal and the surrounding regions to form an alliance in August of 2012. Not all street gangs were keen on his idea to form unity. Mainly, gang leader Chénier Dupuy, leader of the Bo Gars gang, and his right hand, Lamartine Severe Paul. Who were both murdered consecutively, one after the other on the same day only a few hours apart in August of 2012. With both the HA and Rizzuto clan supporting Woolley actions, the Desjardins-Di Maulo faction would lose 12 members to murder throughout the next 5 years.

Chenier Dupuy
Chenier Dupuy

Woolley was arrested and convicted once again in 2015 as part of Operation Magot and Operation Mastiff; two police operations aimed at crippling both motorcycle clubs and the Montreal mafia. Gaining immense power as the years went on, Woolley had served as a mediator to the outlaw biker gangs, the Rizzuto family and certain street gangs. Operation Magot-Mastiff began in January of 2013 and resulted in 48 arrests throughout Quebec and Ontario. Woolley was charged with conspiracy to murder Raynald Desjardins, a contract proposed by Mom Boucher from prison. He served 5 years in Bordeaux prison, being released in 2021.

Woolley, surrounded by patched-in members.
Woolley during his interrogation in Operation Magot-Mastiff

Woolley fiancé’d reality TV star Christelle Huot who participated twice in the Quebec reality TV show ‘Loft Story’; once in 2007 and again in 2009. The couple had been dating for close to 10 years. They had bought a 3.8 million dollar house in Saint Jean-sur-Richelieu on Rue des Trembles. Woolley and Huot almost lost the house, which was in Huot’s name to the Revenue Quebec and the Canada Revenue Agency. The house had a 400 bottle wine cellar, as well as an in ground pool and 70 000 square feet of bush surrounding it.

Woolley with Christelle Huot.

Two years after his release, on November 17th, 2023; a hooded figure aimed at Woolley in his white Lamborghini truck and managed to pump 6 shots into Woolley. The unknown assailant then sped off in a black Range Rover which was later found torched.

The assailant running away after torching the vehicle.

Woolley’s funeral was held December 1st, 2023 at the Loreto Complexe in the Saint Léonard borough of Montreal. The Loreto Complexe is owned by the Montreal mob. Woolley was denied a church service due to his notoriety. Many underworld figures throughout Quebec and Ontario attended the funeral. There was also a high police presence, who were talking note and checking all of the attendees ID. Ex-HA nomads were present, along with mob lawyer Loris Cavalière, daughter of Vito Rizzuto; Libertina Rizzuto, Richard Mayrand, Jean Philippe Célestin of the Syndicate, Giuseppe ‘Gator’ Focarazzo, Pietro D’Adamo and many, many others. The Godfather Of Street Gangs was buried the day after on December 2nd, 2023.

Gregory Wolley’s funeral.
Gregory Woolley & Loris Cavaliere.
Loris Cavaliere, Woolley’s lawyer at his funeral.
Giuseppe ‘Gator’ Focarazzo at Woolley’s funeral.

So what does Woolley’s death mean to the future of the criminal playground in the province of Quebec? We can’t say this early on, but there are multiple theories that could sprout. Frederick Silva, a hit man for the Montreal underworld, was apprehended in 2022. Silva decided to turn informant. The SQ and the SPVM have said that his file is the biggest one they’ve seen, with Silva being part of or being the perpetrator of around 65 murders. Silva might be spilling secrets of the Rizzuto clan, several MC’s or street gangs. Which might have had something to do with Woolley’s murder. Might it be damage control? Although Woolley had been under numerous high pressure situations with the law, even if he had been apprehended, one would highly doubt Woolley would crack.

Hitman Frederick Silva
Brandon Jean Celestin (RIP) at Woolley’s funeral.
Libertina Rizzuto at Gregory Woolley’s funeral.

There is also the theory, that just a week after Woolley’s murder, Michel ‘Doune’ Guerin, a close associate of the HA and former president of the Mercenaires MC was murdered in a shooting in Charlesbourg sector of Quebec City the 27th of November, only 10 days after Woolley’s assassination. Most theories of Guerin’s murder lead to one thing. Street gangs and independent dealers are sick and tired of paying the HA their cut; a 10% tax on all dealings. Might this be the same reason Woolley was murdered? Are street gangs tired of sitting at the heels of the immense powerhouse that the HA and the Montreal mafia have built within the last 2 decades? Only time will tell.

Michel ‘Doune’ Guerin
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