The Current

Author Trevor Cole on the rise and disappearance of Canada's Whisky King

Rocco Perri was once the most infamous mobster in Canada, making millions as a bootlegger in the Prohibition years. But one day in 1944, he disappeared.
Rocco Perri was once Canada's most infamous bootlegger. (Hamilton Spectator Collection, Hamilton Public Library/HarperCollins Canada)

Read Story Transcript

Rocco Perri and Frank Zaneth were about as different as two men could be. Both immigrated to Canada from Italy in the early 20th century, but that's where the similarities stopped.

Zaneth was a homesteader in Saskatchewan before giving that up and becoming Canada's first undercover Mountie, infiltrating unions and gangs. He was honest to a fault and never had much money. 

Perri became involved with organized crime not long after his arrival in Canada, as part of The Black Hand — what we now know as the Mafia. He made millions as a bootlegger during the prohibition years.

The stories of these two men, and how their paths would ultimately cross, is the subject of a new book by Trevor Cole called The Whisky King: The remarkable true story of Canada's most infamous bootlegger and the undercover Mountie on his trail.

Frank Zaneth became Canada's first undercover Mountie. (Courtesy of the Rivers Family/HarperCollins Canada)

According to Cole, Perri was able to make his fortune in large part due to smuggling liquor.

"By the mid-1920s, thanks to Prohibition, which came into Canada in 1916, suddenly there was a vast amount of money to be made in illegal liquor," he tells The Current's guest host Piya Chattopadhyay. 

"By 1924, they were grossing about a million dollars a month — which in 1920s money is, you know, huge."

Perri went into the bootlegging business with his wife, Bessie Starkman — a Jewish woman who he charmed away from her husband and children. They made millions together and gained significant notoriety in the process.

"The authorities were quite happy to turn a blind eye to bootlegging, and also to take payoffs. It was a very corrupt time. And Rocco had all the important police in Hamilton — the important ones — on his payroll.- Trevor Cole

"The authorities were quite happy to turn a blind eye to bootlegging, and also to take payoffs," Cole says.

"It was a very corrupt time. And Rocco had all the important police in Hamilton — the important ones — on his payroll.

The press, he says, "would report on Rocco and Bessie as if they were Hollywood celebrities."

Trevor Cole, author of The Whisky King — the true story of how a notorious bootlegger and a Mountie's paths would ultimately cross. (Fehn Foss/HarperCollins Canada)

Meanwhile, the path of honesty that Frank Zaneth had chosen was proving much more difficult. He had moved his family from the United States north to Moosejaw, Sask., to work the land and build a homestead for themselves.

"It did not go well," Cole says.

"Frank's wife left him, took their child. His life was a real shambles for a while. But while they were in Moosejaw, Frank had heard about the Mounties."

He decided to abandon the farm and join the Northwest Mounted Police, which would later become the Royal Canadian Mounted Police, as its first undercover officer. In his early work, he infiltrated labour unions in search of Bolsheviks.

At one point, posing as a miner in Drumheller, Alta., Zaneth was earning more as a miner than he was as a policeman — but the Mounties forced him to give up his mining wages to the government, leaving him frustrated and poor.

"Poor Frank — he had trouble with money throughout his career," Cole explains.

"He was a guy who was trying to do the right thing all the time. So he was scraping by."   

Zaneth and Perri would cross paths later on, when Zaneth was working against organized crime. But before they met, Starkman, Perri's wife, would meet a grisly end.

She had convinced Perri to get involved in narcotics, which she saw as the way of the future after the end of Prohibition. But she was murdered in a contract killing over a territory dispute — and Cole, through his research, thinks Perri may have been in on it.

There are multiple theories about Rocco Perri's fate: that he was assassinated by rival gangsters, or that he was able to escape to Mexico. (HarperCollins Canada)

"I kind of feel as though Rocco knew, and allowed it to — this was the best solution to a problem. Even though he was devastated by her death," he says.

As the Perris were such prominent figures in Hamilton and Ontario at the time, a huge number of people attended Starkman's funeral.

"On the day of the funeral, 30,000 people — which was a quarter of the city's population — came out to see Bessie's casket drive by."

Zaneth was on Perri's trail by then, but Perri's arrest would ultimately be thanks to the actions of another Italian — Benito Mussolini, when he declared war in 1940.

One day he just walks out of the house where he's staying, and is never seen again.- Trevor Cole

Cole suggests that allowed the police to round up all the Italians they suspected of being involved in organized crime, under the pretense of them being fascist sympathizers.

Perri spent more than three years in an internment camp in Petawawa, Ont. And in that time, his territory was taken over by a rival gang. Not long after his release one day in 1944 he disappeared.

"One day he just walks out of the house where he's staying and is never seen again," Cole says.

There are multiple theories about Perri's fate: that he was assassinated by rival gangsters, or that he was able to escape to Mexico. Cole prefers the latter.

"I don't know. Maybe it's a romantic desire to see Rocco survive in some way," he says.

"That's what I'd like to think happened."

Listen to the interview with Trevor Cole at the top of this web post. 

This segment was produced by The Current's Howard Goldenthal and Julian Uzielli.