After 42 years of trying, Canada loses another bid to deport alleged top Mafia boss in Toronto

On the 42nd anniversary of Ottawa trying to deport a man who police named as Toronto’s top Mafia boss, the government has again failed to prove he should be deported back to Italy.

The Immigration and Refugee Board (IRB) rejected arguments that Vincenzo DeMaria, better known as Jimmy DeMaria, has been a member of the shadowy and powerful ’Ndrangheta, which is the proper name of the Mafia formed in Italy’s southern region of Calabria, and that he engaged in Mafia activities, including money laundering.

If the Canada Border Services Agency (CBSA) had succeeded, it could have led to DeMaria being deported from Canada.

The government’s latest effort ended in failure with a decision by the IRB’s appeal division quietly released in July after a year of hearings, arguments and deliberation.

DeMaria and the Canadian government have been fighting a monumental legal and bureaucratic war on many fronts over whether he is a Mafia boss and the related question of whether he can remain in Canada.

So far, the war has tilted decidedly in DeMaria’s favour.

Now 72 years old, DeMaria has lived in Canada for all but the first nine months of his life, after he was born in Siderno, Italy, and came to Canada in 1955 with his parents.

Although he has lived here, he never became a Canadian citizen. His eligibility for citizenship ended in 1981 when he shot dead a man who owed him money. DeMaria was convicted of second-degree murder in 1982. He was released on full parole ten years later, but as a convicted murderer he remains on parole for the rest of his life.

He was first ordered out of Canada in 1984, while still in prison. He successfully defeated that deportation — and every other attempt to remove him since.

At immigration tribunals, parole hearings, and in court, DeMaria has mounted well-resourced and successful challenges, rebutting various allegations of involvement in organized crime. By disputing, denying, and delaying, he has remained with his wife and children in Canada.

His latest battle began last summer.

The minister of public safety appealed a 2023 decision by the IRB that the government had not proven that DeMaria is or was a member of the Mafia.

As is typical of DeMaria’s battles, the latest hearing was long and complicated; it stretched over 10 days of hearings in the summer and fall of 2025, followed by lengthy written submission from both CBSA officials and DeMaria’s team of lawyers.

Documentation filed in the case was so lengthy — more than 20,000 pages — that the IRB’s computer system kept crashing at the hearing when more than one of the huge files was opened at the same time.

“There is a long history of administrative hearings and judicial reviews in this case,” IRB member Benjamin Dolin said in a stroke of understatement in his written decision.

At past immigration proceedings, police named DeMaria as an influential member of the ’Ndrangheta, but conceded their inability to prove it beyond reasonable doubt in criminal court. An officer from Peel Regional Police said DeMaria was the “top guy in Toronto” for the ’Ndrangheta.

In 2018, the IRB declared him inadmissible in Canada for having a “high-ranking position within this organization, which engages in criminal activities, including weapons smuggling, drug trafficking and counterfeit products.” DeMaria appealed that decision to the Federal Court and won a new hearing.

The new proceeding in 2023 came to a different conclusion, finding no viable evidence of DeMaria’s link to the Mafia, writing: “The Panel finds the Minister’s evidence to be no more than unfounded suspicions based on flimsy and circumstantial evidence.”

It was then the government’s turn to appeal that decision, which sparked the latest IRB hearing, that featured new controversies.

At the hearing, CBSA entered transcripts of wiretaps that secretly recorded conversations of alleged mafiosi visiting Canada from Italy in 2019. As first reported by National Post, Italian police used spyware to surreptitiously force the visitors’ own cellphones to record and transmit their conversations, regardless of whether the phone was in use or not.

The IRB heard from a police officer from Italy, called by CBSA as a witness, who said the visitors, one of whom was a relative of DeMaria’s, came to Canada to meet with Angelo and Cosimo Figliomeni, alleged to be senior mob figures, to investigate the murder of a mobster in Italy. The Italian officer testified that the visitors talked about DeMaria.

DeMaria’s lawyers argued the wiretaps were illegal, unconstitutional, and unreliable, calling it “foreign interference.” A lawyer for CBSA then said they would no longer rely on the wiretaps to make their case.

The government alleged that DeMaria used the family’s cash services business to launder mob money.

DeMaria testified at the hearing, denying any link to the Mafia and involvement in organized crime. He denied any criminality by the family’s money business, saying he left the family’s cheque cashing business years earlier, and none of the transactions questioned by authorities had been linked to him or to the mob.

In his written decision, Dolin said the government’s evidence of DeMaria’s involvement in money laundering amounted to “nothing more than speculation.”

Dolin rejected the government’s contention that the murder DeMaria was convicted of was related to the ’Ndrangheta in DeMaria’s capacity as a mob enforcer.

Dolin also said evidence heard at the hearing of DeMaria interacting with men suspected of alleged Mafia involvement, including Cosimo and Rocco Remo Commisso, the Figliomeni brothers, and Carmine Verduci, was not evidence that DeMaria was a mobster himself. DeMaria told the hearing the few interactions mentioned were mostly social occasions at ethnic community events.

He also rejected the government’s evidence that various underworld snitches or other gangsters caught on wiretaps alluded to DeMaria as being involved in the mob. Dolin characterized it variously as unreliable or untrustworthy.

“The Respondent is a convicted murderer who came to Canada as an infant from an Italian province associated with the ‘Ndrangheta,” Dolin wrote in his conclusion. The government’s case against DeMaria, he wrote, does not amount to evidence that he is a mobster or criminally involved in the mob.

“In my view, the Minister’s case amounts to no more than conjecture and speculation.” He dismissed the government’s appeal, and confirmed that DeMaria was not deemed inadmissible to Canada.

A request for comment from DeMaria’s immigration lawyer was not responded to prior to publication deadline.

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