Paul Wilson: Lawyer chases will of Hamilton's biggest mobster

Rocco Perri, proud to be a bootlegger, vanished one Sunday in the spring of 1944. Some say he left millions behind. Now a lawyer in Dundas wants to take a look at his will.
Rocco Perri, centre, was a broken man at the 1930 funeral of his murdered lover Bessie Starkman. A couple of weeks later he signed a will. Now a lawyer who represents his family wants to take a good look at that will. (Milford Smith Collection, Hamilton Public Library)

Nearly 70 years after Hamilton’s most famous mobster went for a walk and was never seen again, a local lawyer is trying to gain access to the will he left behind.

Rocco Perri wasn’t shy about what he did for a living. "I admit I am king of the bootleggers," he told a reporter in 1924. "I give my men fast cars and I sell only the best liquor, so I don’t see why anyone should complain, for no one wants prohibition...

"Some days I handle 1,000 cases for my customers, and the very best families are among my customers."

They say he made millions. They say he had people killed.

Certainly, some tried to kill him. In the summer of 1930, two men with shotguns missed Perri as he got out of his car.

They gunned down Bessie

But the gunfire did take down the woman with whom he lived, Bessie Starkman. That happened in front of the couple’s posh home on Bay South near Duke, where the Berkshire apartment tower is today.

And 15 days later, Perri visited a young lawyer downtown to sign a hand-written last will and testament.

Rocco Perri in happier times. He declared himself the king of the bootleggers. (The Toronto Archives)

That will came to public attention 14 years ago when a man contacted the Hamilton Spectator to say he owned Rocco Perri’s will. He said he had purchased it a couple of years earlier for $500 from the estate of Hamilton lawyer John Prendergast O’Reilly, who witnessed Perri’s will.

"I bought it just as a part of the history of Hamilton," the man told The Spectator’s Doug Foley. "I am sure it’s the real will. Maybe in the future, we could sell it or we’ll turn it over to a library."

The document showed that Perri planned to leave his estate to his brother Michael Perri of Hamilton. His cousin Mary Sergi was to get $1,000 and a diamond ring. Bessie’s two daughters, Gertie and Lilly Tobin, were to get $1,000 each "if they don’t contest the will and providing our relationships are friendly."

Widow got a call

The man who bought that will died a few years ago. But recently his 75-year-old widow got a call from Dundas lawyer Helen Vukotic. She says she represents family members of Rocco Perri and wants to view the will.

Vukotic has told the lawyer who represents the widow that if Perri’s family wants the will probated, the original would have to be filed with the court.

The Rocco Perri mugshot. He was 55 when he vanished. (Provincial Archives of Ontario)

It’s been public knowledge since 1998 that the will was out there. Who has stepped forward to make a claim on the Perri estate, and why now? Vukotic has not yet responded to voicemail and e-mail requests for comment.

Hali Carlson is the daughter of the widow with the will. "This is causing far too much stress in my mother’s life," she says.

"It’s been made very clear to us that my mother is in possession of a document that she should not have. She’s totally freaked out by the whole thing and just wants this to go away. She is terrified that her name will appear in the news somewhere."

Carlson says arrangements are now being made to have the will turned over to the Dundas lawyer.

Rocco missed lunch

Of course, there’s no death certificate out there for Rocco Perri.

After Bessie Starkman was gunned down, hit men came after Perri again. In 1938, they planted dynamite in his Bay Street home. But he was out with the maid at the time.

Eight months later, on Hughson North, his car blew up. The bomb injured his pals, but Perri was fine. And he had explosion insurance on the new sedan.

He went off to Toronto after that. But in the spring of 1944, he visited the home of his cousin Joe Serge at 49 Murray Street West. On the Sunday morning, April 23rd, he went for a walk.

He didn’t return for lunch. A little after midnight, the police were called. Their bulletin included this description: "The missing man is 55 years of age, five feet, four inches in height, 170 pounds, dark complexion, and an Italian. He was last seen wearing a blue striped suit, black oxfords, light brown spring overcoat, light brown fedora."

Rocco Perri left this house at 49 Murray Street West one Sunday morning in 1944 and was never seen again. David Romanello is now renvoating the home for new owners. (Paul Wilson/ CBC)

Ten months after Perri vanished, Toronto police said they had underworld information that the bootlegger "is in a barrel of cement at the bottom of Hamilton bay." Others think he found himself an ocean view in Mexico.

At the house on Murray where Perri was last seen, David Romanello is now doing major renovations for new owners Meg and Kevin Makins. They know the history. And they know they have a fine house – pine plank floors, nine-foot ceilings, big bay window looking out onto the new condo lofts at the old McIlwraith school.

Joe doesn't know

A few blocks due south of there, Joe Perri is working the final shifts at MacNab Grape on Cannon. At this time of year mountains of grapes arrive here from all over and get dumped into noisy machines to be ground into juice.

Joe Perri, grandnephew of Rocco Perri, has heard the stories of a fortune left behind. He says he's not the one now going after that old will. (Paul Wilson/ CBC)

Rocco Perri was Joe’s great uncle. Rocco was the biggest bootlegger of them all, and here’s Joe in the wine business. He loves the irony. The customers love it too. When they come in for grape juice, it’s Joe or brother Frank they want to see.

Naturally, Joe’s interested to hear that someone’s chasing Uncle Rocco’s supposed fortune. "There was this story going around that he left $21 million," he says.

Joe doubts there’s a dime to be had. He knows for sure that he’s not the one going after that will. He says it’s not his sister or brothers either.

"And we’re the only relatives around here," he says. "Other people say they’re related to Rocco Perri. It seems like everyone wants to be part of the story."


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