Infamous Canadian Gangland Figure Won’t Be Released From Prison Early

May 26, 2020 – Montreal mob associate Gregory (Picasso) Woolley was denied his request for parole and the opportunity to walk free more than a year early from a drug-dealing conviction because of the Coronavirus pandemic. Woolley was busted for possession of meth inside the prison he’s incarcerated at last year.

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 close to notorious Hells Angel boss Maurice (Mom) Boucher and given leadership of a Hells Angel support club known as “The Rockers.” Woolley fought on the frontlines of the Quebec Biker War that engulfed the Canadian underworld between 1994 and 2002. The war pitted the Hells Angels against the Rock Machine and the Banditos for drug turf in Montreal. Today, Boucher is serving a life prison sentence.

While in prison in the early 2000s, Woolley became close to Montreal mob don Vito Rizzuto. When Rizzuto’s mafia empire came under siege in 2009, Woolley brokered an alliance with the Hells Angels to help the Rizzuto organization fend off an insurrection.

Rizzuto died of cancer in 2013, allegedly turning over power in his crime family to his son, Leonardo. A police wiretapped conversation between Leonardo Rizzuto and Woolley in the summer of 2005, just weeks before Woolley was jailed, showed Rizzuto fawning over the influence Woolley wielded across multiple Montreal gangland factions.

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