Members of the Hells Angels biker gang put millions gained from an underground gambling ring into cash, cars, a motorcycle and even waterfront land they hoped to develop, according to allegations in court documents obtained by CTV News Toronto.

Authorities are trying to seize what they claim are ill-gotten gains from the $160-million sports betting operation in a civil forfeiture application that offers a rare window into the operation itself and what they say happened to the cash.

Officers have been following the money to what they say are several connected enterprises, including numbered companies and a trust, and are even after a multi-million dollar insurance settlement they say came after allegations of arson on some of those properties.

The investments described in the documents are expansive enough that some observers say more needs to be done to make sure funds gained through potential criminal activity aren’t funnelled into what seem like legal businesses.

“The responsibility would fall upon provincial as well as the federal government to make sure we don’t see illegal dollars procured through criminal activity and then washed out the system so you can’t recognize it on the other end,” said Kristyn Wong-Tam, the Ontario NDP’s critic for the Attorney-General.

The sports betting operation was surveilled and infiltrated by officers in an investigation known as Project Hobart, which involved 14 police agencies starting in 2018.

An affidavit by OPP Detective Sgt. Debra Walker describes a pyramid-like structure with hundreds of agents at every level who were assigned code names and solicited bets—taking commissions and passing a percentage of the take up the organization.

“Collection of debts was enforced through violence,” Walker says in the affidavit. One of the group’s alleged enforcers, Michael Deabaitua-Schulde, was being watched when he was shot dead by a rival gang outside a Mississauga gym — a witness account crucial to convicting the gunmen.

At the top, Walker said in the affidavit, were two alleged ringleaders, full-patch member of the Montreal Chapter Robert Barletta who controlled an account code-named “SAHARA”, and full patch member of the Niagara Chapter Craig McIlquham, who authorities linked to an account code-named “XJ-A”.

An officer discovered a picture of McIlquham and Barletta among several other figures in the Niagara Chapter, gathered around a distinctive motorcycle — one of many pictures of the group’s activities found on electronic devices that became evidence in the case.

Some involved pleaded guilty, many charges were stayed, and charges against Barletta and McIlquham fell apart thanks to delays at the Brampton courthouse, the affidavit says.

The pair’s lawyer in the case didn’t respond to questions from CTV News Toronto, but has indicated in court documents he intends to contest the seizure.

Police alleged cash controlled by the pair was stashed in a Yorkville condo, and a police search found a bundle of $50 bills worth $20,000 in a search of McIlquham’s condo.

Officers claim they tracked millions used to purchase seven properties around southern Ontario, purchased by via a network of straw owners, including McIlquham’s wife, two girlfriends and associates. One associate worked at a London strip club, and police claimed her salary there didn’t explain her sudden wealth.

Three properties were the site of suspicious fires, one of which prompted a $7.9 million insurance payout that authorities say was put into the purchase of more properties, the documents say.

Two properties in the Blue Mountains were slated for subdivision and development to become a “gated waterfront enclave,” the project materials said, including a map of potential lot boundaries.

Also targeted are several vehicles, including two Chevrolet Camaros, a 2016 Ford Mustang Shelby, a 2019 Dodge Challenger CTV, two Can Am off road vehicle, a 1985 Alfa Romeo, and a 2018 Harley Davidson RXN motorbike.

About $35,000 in cash, a diamond ring, diamond earrings, a Rolex watch and a Audemars Piguet watch are also among the assets authorities are trying to keep. All of the properties or the proceeds of their sale are being preserved, according to a court's order.

Even in the absence of convictions, the provincial government can use civil forfeiture to disrupt what it believes are criminal operations, because the standard of proof in a civil hearing is much lower, said lawyer Ari Goldkind.

"If you stop the gravy train and the money train, you may be more likely to stop the illegal enterprise just by stopping the flow of money or seizing the assets than by getting a criminal activity," Goldkind said.