May 26, 2020 – Well-known Montreal mob associate Gregory (Picasso) Woolley was recently denied his request for parole and the opportunity to walk free more than a year early from a drug-dealing conviction due to Coronavirus concerns. Woolley was busted for possession of methamphetamine and marijuana inside the Montreal Detention Center two years ago awaiting trial.

The 48-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.

With his current sentence, he could still be released to a halfway house by December. Before his 2015 pinch, he had served two previous prison stints, one connected to a series of attempted murders tied to the Quebec Biker War.

In the 1990s, Woolley was closely aligned to notorious 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.

Rizzuto died suddenly of cancer in 2013 at 67, allegedly turning over power in his crime family to his son, Leonardo. 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 Montreal gangland factions.

Woolley is of Haitian descent. He headed the Master B Gang, a Haitian street crew, as a teenager in the 1980s.

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