Grégory Woolley
Grégory Woolley
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Grégory Woolley

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Grégory Woolley

Grégory "Greg" Woolley (26 February 1972 – 17 November 2023) was a Haitian-born Canadian gangster and outlaw biker associated with the Hells Angels motorcycle club in Montreal. Woolley was the protégé and bodyguard of Maurice "Mom" Boucher, a controversial senior Hells Angels leader who led his chapter in a long and extremely violent gang war against the Rock Machine, in Quebec, from 1994 to 2002. Woolley was known in Montreal as the "parrain des gangs de rue" ("Godfather of the street gangs").

Woolley grew up poor in the Saint-Michel neighborhood of Montreal, the child of Haitian immigrants. His parents had fled the poverty of their native land and the tyranny of President-for-life Jean-Claude Duvalier, known to the Haitians as "Baby Doc" to distinguish him from his father, President-for-life Dr. François Duvalier, the "Papa Doc". From his teenage years, Woolley was involved in a street gangs in Saint-Michel. He committed his first known murder at the age of 17 when he killed a rival Haitian-Canadian street gangster, which gave him the nickname of "Picasso".

Woolley was the leader of a street gang known as Master B., who bought drugs from the Hells Angels' Montreal chapter led by Maurice "Mom" Boucher. Boucher had once belonged to a white supremacist biker gang known as the SS that existed to beat up non-white immigrants. Boucher's son, Francis Boucher, is an avowed Nazi who had started the Aryan Fest musical festival in 1992 for fascist and white supremacist musical acts and which existed only to glorify Nazism. The Aryan Fest remained the premier annual musical gathering for racist bands and singers. Despite this background, Woolley was very close to Maurice Boucher and served as a bodyguard. Although the Hells Angels are a whites-only group, Boucher made Woolley a member of the Rockers puppet gang. The journalist Jerry Langton wrote: "He [Boucher] appears to have been right about Woolley, who became a very big earner (he became wealthier, in fact, than many Hells Angels and several Nomads) an enthusiastic intimidator, and a loyal member who never informed on anyone". The Rockers were not like the other Hells Angels puppet gangs like the Evil Ones, the Rowdy Crew, and the Condors, which merely performed the same work as the Hells Angels. The Rockers were exclusively the enforcement arm of the Hells Angels divided into a "baseball team", which committed assaults and arson, and the "football team", which committed murders.

Woolley served as the bodyguard for Boucher and was the best assassin working for the Angels. Woolley was known as "Picasso" in the Montreal underworld because it was said that he was such an "artist" when it came to killing, having first killed at the age of 17 when he killed another Haitian immigrant and gang member. Woolley was said to have done such an "exquisite" job at carving up his rival that he earned the nickname "Picasso", and he was ultimately made the president of the Rockers by Boucher, becoming the first black man to ever head an outlaw biker club in Canada. Francis Boucher joined the Rockers with the aim of following his father into the Hells Angels, which put him under Woolley's authority. Besides for the Hells Angels, Woolley's closest allies were members of the "Young Turk" faction of the Rizzuto crime family, such as Francesco Arcadi, Lorenzo "the Skunk" Giordano, and Francesco "Chit" Del Balso.

On 20 December 1996, Woolley murdered a Rock Machine biker, Pierre Beauchamp, whom he shot and killed when he was using his pager inside of his truck, which was parked on the street. Woolley fled in an automobile with stolen license plates, which he later abandoned to take the Metro. The get-away driver was another Rocker, René "Balloune" Charlebois, whom Woolley was to be closely associate with. Found abandoned near the metro station was the gun used to kill Beauchamp along with a toque, which had some hair samples. Afterwards, Woolley went to a bar to tell several other Rockers that he had just "gotten one" for the Hells Angels. Woolley told another Rocker, Stéphane Sirois, who later turned Crown's evidence, that the orders to kill Beauchamp had come from Boucher, who told him not to take any money from Beauchamp as Boucher did not want Montrealers to think that the murder was a drug deal gone bad.

The Royal Canadian Mounted Police (RCMP) informer within the Rockers, Dany "Dany Boy" Kane, reported to his handlers in February 1997 that the Hells Angels had taken control of almost all of the Rock Machine's former drug markets. Kane further reported that the Hells Angels were set upon taking control of the Rock Machine's last strongholds of Pointe-Saint-Charles, Verdun, Lasalle, Saint-Henri, Lachine, Ville-Émard, and Côte-Saint-Paul. Kane continued that the Rockers had set up a death squad whose principal members were Woolley, Pierre Provencher, Normand Robitaille, Stephen Falls, and Stéphane "Godasse" Gagné. Kane added that the members of the Rockers death squad were to receive 30% of the profits from drug sales once the Hells Angels had taken control of the last Rock Machine drug markets.

On 28 March 1997, the Rocker hitman Aimé "Ace" Simard, acting under Woolley's orders, murdered a Rock Machine biker, Jean-Marc Caissy, as he entered a Montreal arena to play hockey with his friends. After Simard was arrested in April 1997, he turned Crown's evidence and named Woolley as the man who gave him the orders to kill Caissy. Woolley was charged with first-degree murder, but Simard proved to be a poor witness on the stand, and Woolley was acquitted.

Woolley was little known to the public until 1998 when he came to public attention as the chief security officer at a Hells Angels funeral. At the funeral, Woolley was seen giving orders to Francis Boucher. A Montreal police officer stated in 2002: "When you're in a position to boss around Maurice "Mom" Boucher's kid, you're somebody." Although the Hells Angels official policies are not racist, experts say many Hells Angels members are racist, and it is rare for individuals of African heritage to join Hells Angels chapters. Woolley, an Afro-Haitian, was described as a rare instance of an individual with black African heritage to rise to a senior position in the Hells Angels. As a black man, Woolley had no hope of ever being allowed to join the Hells Angels, but he seemed very determined to make a career in the Rockers.

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