[1][2][3] Woolley was the protégé and bodyguard of Maurice 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.
[7] Woolley was the leader of a street gang known as Master B. that bought drugs from the Hells Angels' Montreal chapter led by Maurice Boucher.
[8] The Hells Angels are a whites-only group, and Boucher made Woolley a member of the Rockers Motor Club puppet gang.
[8] 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".
[7] 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.
[7] Francis Boucher joined the Rockers with the aim of following his father into the Hells Angels, which put him under Woolley's authority.
[12] On December 20, 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.
[13] The get-away driver was another Rocker, René "Balloune" Charlebois, whom Woolly was to be closely associate with..[13] Found abandoned near the metro station was the gun used to kill Beauchamp along with a toque, which had some hair samples.
[14] The Royal Canadian Mounted Police (RCMP) informer within the Rockers, Dany 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.
[15] 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, St-Henri, Lachine, Ville-Émard and Côte-Saint-Paul.
[15] Kane continued that the Rockers had set up a death squad whose principal members were Woolley, Pierre Provencher, Normand Robitaille, Stephen Falls, and Stéphane Gagné.
[16] On March 28, 1997, the Rocker hitman Aimé 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.
[10] 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.
[18] The Bo-Gars waged a propaganda campaign against Woolley that depicted him as an "Uncle Tom" figure serving the "clearly racist Hells Angels".
[23] In August 1999, a bizarre incident occurred on the streets of Montreal when Woolley was riding his Harley-Davidson motorcycle while wearing his Rocker patch on his vest and was pulled over for speeding.
[25] Later, the judge threw out all of the charges, ruling that this was not a routine pull-over, and suggested it was an unusually clumsy attempt on the part of the police to entrap Woolley.
[26] Bouchard had assigned two detectives, Louis-Marc Pelletier and Michel Tremblay, to see if it was possible to match a list of suspects in various murders provided by the informer Dany Kane with DNA evidence.
[27] Pelletier and Tremblay matched DNA samples from the hair found in a toque discovered alongside the discarded gun that had been used to kill Beauchamp to Woolley.
[27] By February 2001, Bouchard's Major Crimes Unit had enough evidence to charge 42 Hells Angels and Rockers with some 23 counts of first-degree murder.
"[29] By contrast, Woolley's associate, René "Balloune" Charlebois, the Rocker who had been promoted up to the Hells Angels, broke down in tears and wanted to make a deal with the Crown for a lesser prison sentence.
[29] Woolley was charged with conspiracy to traffic in narcotics and with first degree murder for the slaying of Rock Machine biker Pierre Beauchamp on December 20, 1996.
[10] The psychologist also found that Woolley had poor judgement and low self-esteem, noting that he tried to commit suicide at the age of 16 as he was ashamed to be a black man in a society where being white was the ideal.
[30] Woolley was tried twice for Beauchamp's murder and was acquitted both times as the defense lawyers argued that the DNA evidence that the Crown had introduced was planted.
[35] 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.
[17] 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.
[32] The gangster Andrew Scoppa told the journalists Felix Séguin and Eric Thibault that: "He brought in Gregory Woolley to get the bikers on his side.
[41] In turn, the Hells Angels and the Rizzuto family were behind Woolley's efforts to unite all of the black street gangs of Montreal.
[52] In a statement of fact at the plea bargain, it was established that Woolly 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.
[55] 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".
Prior to joining the Hells Angels Woolley's mentor Boucher was in a smaller motorcycle gang called the "SS", which had an explicit white supremacist ideology.