November 11, 2020 — You could not have painted a better picture for one of Canada’s most notorious criminals. Montreal gangland leader Greg (Picasso) Woolley was paroled early from his drug case with strict conditions this week, walking out of prison eight months before he was scheduled to be because of the COVID-19 pandemic. On Tuesday, he checked into a Quebec halfway house.
The 49-year old Woolley is affiliated with both the Italian mafia and the Hells Angels biker gang in Quebec. He was arrested as part of a narcotics-conspiracy case in 2015 and sentenced to eight years behind bars — awaiting trial in the case, he was nailed for smuggling cocaine and crystal meth into his detention facility. His previous attempt to shake loose from behind bars on a COVID-19 related motion failed back in the spring.
This was Woolley’s third prison term. One of the stints in the can was connected to a series of attempted murders tied to the Quebec Biker War.
In the 1990s, Woolley was closely aligned with legendary Hells Angels boss Maurice (Mom) Boucher and given leadership of a Hells Angels support club called, “The Rockers.” Woolley fought on the frontlines of the Quebec Biker War that engulfed the Canadian underworld between 1994 and 2002 and resulted in dozens of casualties. The war pitted the Hells Angels against the Rock Machine and the Banditos for drug and extortion turf in Montreal. Today, Boucher is serving a life prison sentence for ordering the contract slayings of two prison guards.
While in prison in the early 2000s, Woolley built a friendship with vaunted Montreal mob don Vito Rizzuto. When Rizzuto’s mafia empire came under siege in 2009, Woolley brokered an alliance with the Hells Angels to aid the Rizzuto organization in fending off the insurrection. Mom Boucher put a hit out on Rizzuto’s former right-hand man turned rival Raynald Desjardins upon Desjardines being locked up.
Rizzuto had helped mediate the end of the Quebec Biker War years earlier. Woolley set up a meeting between the Rizzuto clan and Hells Angels bosses in a cemetery chapel at a 2012 funeral, per court records, to cement backing in the Rizzutos war.
The regal and resolute Rizzuto died suddenly of cancer in 2013 at 67, allegedly turning over power in the crime family to his son, Leonardo. The war for control of the Rizzuto mob kingdom continues to be fought today, with a series of recent flareups in Hamilton, Ontario.
A police-wiretapped conversation between the 50-year old Leonardo Rizzuto and Woolley in the summer of 2015, showed Rizzuto fawning over the influence Woolley wielded across multiple gangland factions in Canada. Where he stands in terms of the ongoing strife in the Rizzuto organization is unknown.
Woolley is of Haitian descent. He headed the Master B Gang, a Haitian street crew, as a teenager in the late 1980s.