Gregory 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.

Criminal career Master B 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. 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.

The Rockers 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 lead an outlaw biker club in Canada, since Rod McLeod of the long defunct Montreal chapter of the Satan's Choice MC in the 1970s. 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. In 2005, Rizzuto and Woolley were often seen talking in French in the prison courtyard. In 2005, Woolley was convicted of other charges and was sent to serve his sentence at Kingston Penitentiary. On 27 June 2005, in a plea bargain, Woolley pleaded guilty to conspiracy to commit murder, conspiracy to traffic in narcotics, and gangsterism while the first-degree murder charges were dropped. Even while held at Kingston Penitentiary, Woolley was described as controlling the drug trade from his prison cell and had a monthly income of $10,000. In 2006, Woolley punched out another prisoner who questioned his authority whom was almost stabbed to death minutes later. In 2008, the National Parole Board turned down Woolley's request for parole under the grounds: "No matter where you find yourself in custody, the power conferred on you by your official status among bikers, and implicitly as the head of street gangs, is of such a scale that no [rehabilitation] program can sufficiently protect the public from the risk you represent".

Rizzuto family On 13 February 2009, Woolley was arrested as part of Operation Axe, and thereby acquired the dubious honor of being the first Canadian to be charged with gangsterism twice. In January 2011, Woolley made a plea bargain with the Crown where he pleaded guilty to the Operation Axe charges in exchange for a lesser prison sentence. During his second sentence at Kingston Penitentiary, Woolley's closest friends in prison were the Hells Angel Harley Davidson Guindon and Juan Ramon Fernandez, the Toronto agent of the Rizzuto family. Guindon stated about Woolley: "He was always smiling. He was always laughing. He was the best chess player I've played".

Later in 2011, he was released on full parole and returned to Montreal. During the civil war that tore apart the Rizzuto family between Raynald Desjardins and Vito Rizzuto in the early 2010s, Woolley supported the latter and he was often called upon for help from Rizzuto, who seemed to had much respect for Woolley's abilities as a leader and as a killer. The renegade faction within the Rizzuto family led by Desjardins and his brother-in-law, Joseph Di Maulo, had the support of the 'Ndrangheta families of Ontario in a bid to topple Rizzuto. In 2010, the murders of Paolo Renda and Nicolo Rizzuto were major blows to Rizzuto's leadership of his crime family, and a number of Rizzuto family capos defected over to the Desjardins–Di Maulo faction, which appeared to be the stronger faction. There was a period in 2010 and 2011 when Rizzuto came close to losing control of his own crime family. The support of the Hells Angels along with Woolley were described as being crucial in helping Rizzuto survive the challenge. The mobster Andrew Scoppa told the journalists Felix Séguin and Eric Thibault that: "He brought in Gregory Woolley to get the bikers on his side. Vito was OK with Woolley because he knew him and he liked him". Scoppa described Woolley as a "pro" who was very useful for Rizzuto in beating back the challenge posed by the Desjardins–Di Maulo faction. Between 2011 and 2017, at least 12 members of the Desjardins faction were killed.

In August 2012, Woolley called for a meeting of various black Canadian street gang leaders in Sainte-Adèle, where he called for a union of all the street gangs under his leadership. In turn, the Hells Angels and the Rizzuto family were behind Woolley's efforts to unite all of the black street gangs of Montreal. One Haitian-Canadian gang leader who attended the meeting, Chénier Dupuy, refused the offer, saying it was a shame that Woolley was working for the racist Hells Angels and slapped Woolley across the face. When Rizzuto died in December 2013, Woolley attended his funeral alongside a number of Hells Angels leaders from Quebec and Ontario, and was given a place of honor at his funeral service despite not being a mafioso, which indicated that he was considered to be an important ally.

The journalist Julian Sher stated: "The Montreal Mafia leaders considered Woolley to be an equal to them". Woolley was often seen with Leonardo "Leo" Rizzuto, the son of Vito, who is described as being his successor along with Stefano Sollecito. In July 2015, Boucher, who was loyal to the Rizzuto faction, ordered from his prison cell for Woolley to kill Desjardins. In August 2015, Sollecito was recorded by a police wiretap as telling Leonardo Rizzuto: "We share business. We share things with Greg. We share big secrets". Sollecito described Woolley as more trustworthy and reliable than some other members of the Rizzuto family. Both Sollecito and Rizzuto described Woolley as an equal to the Rizzuto family. In November 2015, Woolley and 47 suspected underworld leaders were arrested in a sweep. In October 2018, Woolley was found guilty of conspiracy to traffic in narcotics and gangsterism. Project Magot-Mastiff, as the police investigation was known, established that Woolley had sold 192 kilograms of cocaine in the Hochelaga-Maisonneuve borough of Montreal between 2011 and 2015.

On 27 October 2018, in a plea bargain, the Crown dropped the conspiracy to commit murder charges in relation to the Desjardins murder plot against Woolley in exchange for him pleading guilty to the Project Magot-Mastiff charges. In a statement of fact at the plea bargain, it was established that Woolley along with another drug dealer, Dany "Lou" Sprinces Cadet, were part of a select group known as "les Bronzés", who were permitted to buy cocaine at a favorable price from the Rizzuto family. In April 2019, Woolley was convicted of selling methamphetamine in Bordeaux prison, for which he received a light sentence.

In November 2021, Woolley was released on full parole. Woolley was engaged to Christelle Huot, a French-Canadian woman who was a reality television star in Quebec on the Loft Story TV show between 2007 and 2009. Hout is well known in Quebec as "l'exhibitionniste du Loft" ("the Loft exhibitionist") owing to her frequent nudity and general flamboyant behavior. The couple lived in a luxury mansion in Saint-Jean-sur-Richelieu on rue des Trembles worth $3.8 million that had such features as "a 400-wine bottle cellar, a built-in sound system, an in-ground swimming pool, separate accommodation and 70,000 square feet of wooded land". The house was held in Hout's name only, and in 2022, it became the object of a dispute with the Canada Revenue Agency over claims of unpaid taxes. In May 2022, a drive-by shooting occurred, with someone opening fire on Woolley's house. In August 2022, somebody burned down Woolley's garage.

Death Woolley was killed in a shooting in Saint-Jean-sur-Richelieu, on 17 November 2023, aged 51. He was shot dead in a parking lot in front of his fiancée Christelle Huot and their child. His murder was a major violation of the underworld code in Canada, which forbids murders in front of wives and children. The Mafia expert Antonio Nicaso wrote that Woolley's murder was likely Mafia-related, as he wrote on his Twitter account: "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 was buried on 2 December 2023, at the Mafia-owned Loreto funeral home in Laval. The Catholic Church denied Woolley a funeral service in a church on the account of his gangster lifestyle. Woolley's funeral was attended by numerous Hells Angels, Rockers, mafiosi and street gang members. Among the attendants were Leonardo Rizzuto, Pietro D'Adamo, and Giuseppe "Gator" Focarazzo of the Rizzuto family; Mario Brouillette and Richard "Bert" Mayrand of the Hells Angels; and the Haitian-Canadian Jean-Philippe Célestin of the Syndicate.

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