The King of the Bootleggers
Plus a bizarre way to sell beer, summer reading recommendations and more.
One dark October night in 1923, Toronto police got a big tip. It was the height of prohibition and rum-runners had been spotted unloading a boat full of booze on the waterfront. What happened next is one of the most dramatic stories I’ve come across while researching my new online course, A Boozy History of Toronto (which begins this week; you can learn more about it right here). So, last night I turned the tale into a Twitter thread and I thought I’d share it with you as well — along with a few extra details I wasn’t able to squeeze into those tweets.
Here's the story of The King of the Bootleggers and the deadly shootout that erupted at Ashbridge’s Bay that night…
His name was Rocco Perri. He was born in Italy, the son of a goat-herder. But as a teenager, he left home and crossed the Atlantic — just as the 1900s were getting underway. He eventually ended up in Toronto, moving into the city's most notorious "slum."
By then, the neighbourhood known as The Ward had been home to generations of new Canadians. It began in the 1850s, with newcomers who escaped slavery on the Underground Railroad. And in the following decades, wave after wave of immigrants moved in, forced to live in increasingly squalid conditions by landlords who were all too willing to take advantage of their tenants. (The Ward would eventually become the city’s first Chinatown before being razed to the ground to make way for City Hall and Nathan Phillips Square.)
It was there, in a world of poverty and slumlords, that Rocco Perri fell in love.
He got work laying streetcar tracks and rented a room from a poor Jewish family on Chestnut Street. Within weeks, he was having an affair with the woman of the house. Bessie Starkman soon left her husband and children to be with him.
By then, Perri had already gotten his start in the underworld. He had ties to the mob and appeared on the witness stand during the infamous murder trial that first brought Italian organized crime into the public consciousness in Toronto. He’d even contracted out an arson while working in a northern mining town.
But it was with Bessie that his career took off. Together, they would build an empire of crime.
They set up shop in Hamilton. Bessie ran their books and a brothel, using the money to buy fur coats and jewels; her jeweller called her "a diamond fiend." She was known to be ruthless, too; not afraid to strong-arm people into business deals at the point of a gun, or have a pet dog killed to deliver a message.
Rocco was more gregarious, in his pinstripe suits and bright ties, posing as a salesman for the imaginary Superior Macaroni Company as he built relationships and connections across the world of organized crime. His outgoing personality helped him bridge traditional divides, ignoring the old Italian regional rivalries that created so much distrust and unrest.
But behind that friendly exterior, violence lurked.
People around the Perris had a habit of turning up dead. A murder at a New Year’s party. A stabbing. A shooting. A dead cop. Even Rocco's mistress, Olive Rutledge, died in grisly fashion. He’d married her under a fake name and had two kids with her, but she got sick of being neglected in Bessie's favour, jumping out the window of her lawyer's office to her death.
Rocco and Bessie had their fingers in all sorts of illegal pies. And the local police force in their pocket so they could get away with it. But in those early days, it was gambling above that made them the best money, with a network of rackets that reached all the way into Toronto.
As Trevor Cole points out in his excellent book about Perri, The Whisky King, our city was big for bookies. Ernest Hemingway once explained, "For years, Toronto has been known all over the world as the biggest betting town in North America." He figured there were 10,000 wages placed on horse races in the city every day. And the Perris were getting a cut of a lot of those bets.
Still, it was with the arrival of prohibition that business really took off. The sale of alcohol was banned, but thousands of speakeasies and "blind pigs" (their dive bar cousins) sprang up across Southern Ontario. They all needed booze. And the Perris became their biggest supplier.
The couple built a fleet of 50 boats that sailed the waters of Lake Ontario, Lake Erie and the Niagara River, smuggling booze across the border. They didn’t even need hardened criminals to captain them. Many rum-runners were ordinary fishermen looking to make a little money on the side, happy to break a law they didn't believe in. Rocco was so confident in the operation, that he gave interviews of the press. "I am a bootlegger," he told The Toronto Daily Star. "I am not ashamed to admit it. And a bootlegger I shall remain." His smugglers, he boasted, didn’t even carry guns.
There were even legal loopholes to take advantage of. Ontario had banned the sale of alcohol, but for a long time you could still make booze — for export. Major breweries and distilleries like Gooderham & Worts (the company whose old complex is now the Distillery District) were still very much in business. And the notorious Perris became one of their biggest customers.
Rocco and Bessie would send their men to buy huge amounts of legally-made liquor, bribe an official or two, fake some paperwork, load up a boat, and pretend to be shipping the booze across the lake to the United States… then wait for the cover of darkness to bring the booze straight back into Ontario to fuel the speakeasies and blind pigs.
So that's what they were doing on that bloody October night in 1923.
Bessie ordered more than 2,500 bottles of whisky from a distillery in Belleville. And then she sent four unarmed rum-runners — a young man from Port Dalhousie with his friend, dad and uncle — to go pick up the shipment in their boat and secretly bring it to Toronto.
They slipped into Ashbridge's Bay around midnight, under a cloud sky with a only a thin sliver of moon, quietly sneaking up to a deserted patch of shoreline near the foot of Leslie Street. Rocco and his men were there waiting for them with a couple of trucks (REO Speed Wagons, ancestors of the pick-up truck) ready to be loaded up.
That's when the Toronto police got a telephone call from someone reporting the suspicious activity. Four officers raced down to Ashbridge's Bay, firing a warning shot into the air as Rocco's men dove into the bushes — where they were caught and arrested one by one.
The men on the boat, though, were still trying to escape — throwing the engine in reverse and chugging away into the darkness.
The police called out for them to stop: "Shut off your engine or I will sink your boat!"
There was no response…
The police opened fire.
Rocco screamed, "Don't shoot! There are people on that boat! You could kill them!" The police ignored him. They fired over and over again — at least 15, maybe 30 times. Their bullets couldn't sink the boat, but they tore through the cabin — and through two of the men on board.
One was hit in the jaw; he'd need emergency surgery at St. Michael's Hospital.
And his nephew wasn't so lucky. John Gogo was struck in the chest, the bullet carving its way through his heart and lung. He was dead within 15 minutes.
It was one of the biggest booze busts in Ontario history, but instead of being hailed as a victory in the fight against organized crime, it became a major scandal. Headlines criticized the police for opening fire on defenceless men. An inquiry found the use of force was "without justification." All four officers were put on trial for manslaughter — only spared after two hung juries couldn’t agree on their guilt or innocence.
And that was far from the deadliest chapter in the story of Rocco and Bessie Perri. As the authorities cracked down with new laws and enforcement, the sources of safe, legal booze dried up. Bootleggers were forced to make their own liquor — moonshine — out of poisonous industrial alcohol.
The government made sure that industrial alcohol was the only alcohol available and that it was deadly to drink thanks to lethal additives. So the Perris hired chemists to filter it, using a perfume shop and tonic factory as a front. But that was an incredibly dangerous game.
In the summer of 1926, a rushed shipment turned deadly. It would prove to be 94% pure wood alcohol — too poisonous even to touch, never mind drink. And as it made its way through underground parties and secret bars, it unleashed horrors.
One victim threw up black vomit. A second turned blue. A third foamed at the mouth with a bloody froth. Some died screaming. One woman wondering aloud why the green leaves outside her window had all turned black; her eyesight was going. Many went blind before passing away. By the time it was all over, 45 people had been killed across Ontario and New York State.
The deaths helped bring an end to prohibition in our province. Within months, the premier was running for re-election on a platform promising to introduce government-run stores under the Liquor Control Board of Ontario: The LCBOs we still have to this day.
With prohibition gone, it wasn’t long before the Perris' empire began to crumble. The big blow came suddenly and in bloody fashion. When the couple arrived home one night after a game of cards, two assassins were waiting in the shadows. As Bessie got out of the car, they opened fire with their shotguns; the blasts left her dead in the driveway. Tens of thousands of people came to gawk at her funeral.
Rocco carried on for another decade. He even found a new partner. Annie Newman was a platinum blonde with “the cold, blue eyes of a killer,” who’d once lived in The Ward herself. She took over the books and even launched her own gold racket, buying the Metro Theatre on Bloor Street (the building is still there today; it’s a gym in Koreatown) to serve as a front. She hired miners to smuggle gold flakes out of mines and assayers to mis-weigh gold samples and pocket the difference, melting them down to be smuggled into the United States. It wasn’t until one of her mules was caught at the border into Buffalo wearing a vest filled with gold bars that she was sent off to the Kingston Penitentiary.
As for Rocco, he'd always been able to escape any real repercussions. Even the police had failed to pin anything big on him. He compared them to “a lot of schoolboys learning to play ball.” He just once spent a few months in prison for perjury — and a couple of years in an internment camp for Italian-Canadians during the Second World War. The Canadian government was quick to use the War Measures Act as a way to round up gangsters they’d failed to convict when due process was required.
But by then, Perri was already clearly in someone else's crosshairs. A bomb blew apart his porch. Another tore through his car; he had to drag himself out of the burning wreckage. And when he was finally released from the internment camp, he discovered that a notorious Buffalo gangster had moved into his territory. The violence was getting worse.
Once hailed as the King of the Bootleggers, Rocco Perri was now back in Toronto, staying with friends, pretending to be a janitor at the movie theatre, trying to piece his empire back together.
And that's when he disappeared...
It happened during a visit to Hamilton, where he was making plans to move back into the house where he and Bessie had once ruled the Ontario underworld. He told friends he was going for a walk in the rain, slid on his overcoat and his fedora, slipped out the door...
And was never seen again.
Some people think he fled to Mexico where he lived out the rest of his days. But others say he met a grislier end: that he was murdered by hitmen sent by that Buffalo gangster, his body encased in a barrel filled with cement and then dumped into Hamilton Harbour.
Those people say he's still down there now, the King of the Bootleggers in his watery grave.
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The Boozy History of Toronto online course kicks off this week and will be filled with stories like this one. If you’re interested, you can learn more about it here. The courses have been a big hit and are now my single biggest source of income, allowing me to focus on history writing full-time, so it’ll mean a lot if you check it out or are able to spread the word to anyone else you think might be interseted in it.
And if you’re a paid subscriber to this newsletter, you’ll get 10% off as a thank you! You can switch to a paid subscription by clicking here:
I’ll also mention again that Trevor Cole’s written a wonderful book about Rocco Perri, The Whisky King, which is where I came across a lot the details I’ve included. And since I published the thread, I’ve also heard from the co-author of a pair of groundbreaking books on the subject: King of the Mob: Rocco Perri and the Women who Ran His Rackets and Undercover: Cases of the RCMP’s Most Secret Operative. They were both written by James Dubro and Robin Rowland who also made a ten-part radio drama about Rocco & Bessie, which aired on Morningside in the 1980s and starred The Beachcombers’ Bruno Gerussi and As It Happens’ Barbara Budd. Amazing!
A BIZARRE WAY TO SELL BEER
UNEXPECTED MARKETING DECISIONS NEWS — I’m not quite done sharing tidbits I’ve come across while getting ready for A Boozy History of Toronto. There’s one more strange story I thought I’d tell you about.
Last week, I wrote about the propaganda war that broke out over the question of prohibition, with the pro-booze side arguing that it would “kill Toronto.” But that’s not the only tactic they employed. As a crackdown on booze loomed, brewers began pitching their beers as a healthy choice of drink. Some even suggested their products had medicinal qualities.
The most extreme example? The rise of the Invalid Stout.
Many brewers sold one, claiming their stouts were so healthy even medical patients should drink them.
Toronto’s own Dominion Brewery framed their Invalid Stout as “a safe drink even for a dyspeptic” and “liquid food.” It “makes you feel like a boy again.” They even pitched it to nursing mothers. Their local competition, Cosgrave’s, called theirs Convalescent Stout. And even the Hudson’s Bay Company got in on the action, boasting that their version was “very nourishing” and “a tonic [that] tones up the system and is strengthening.”
You’ll be shocked to learn it didn’t work.
SUMMER READING PICKS FOR TORONTO HISTORY BUFFS
HONOURED TO BE INCLUDED NEWS — The staff of the Toronto History Museums have put together a list of recommending summer reading, filled with books about our city’s past. I was delighted to find both The Toronto Book of the Dead and The Toronto Book of Love included, along with a couple of other little books I contributed to: Spacing’s 25 Days That Changed Toronto and 50 Toronto Hidden Gems & Curiosities.
But there’s plenty more on the list that makes it worth checking out, beyond my shameless self-promotion. In fact, I recently started reading one of the other titles, Indigenous Toronto. And only a chapter or two in, I can already tell that it’s going to shape the way I think and write about the city for years to come.
QUICK LINKS
The best of everything else that’s new in Toronto’s past…
MISSING NEON SIGN NEWS — Jack Landau looks into the condo taking over Filmores, and the fate of the strip club’s iconic neon sign in particular since it doesn’t factor into the renderings of the new development. He’s told the developer is “working with the city planning department to explore preservation options right now.” An architectural firm’s report suggests “Discussions with a local Business Improvement Area (BIA) as well as a community-led initiative are currently underway to donate the signage for a potential 'Toronto signage museum.’” Though it does feel like we’ve been hearing about that museum idea of years and years now with nothing substantial ever coming of it…. Read more.
YET ANOTHER MODERN GEM IN THE CROSSHAIRS NEWS — It feels like every week I’m telling you about another celebrated modernist tower being threatening with demolition. This time, it’s the Toronto Professional Building, which has been standing on Edward Street near University & Dundas since 1964. And as usual, you can count on the Globe’s Alex Bozikovic for a thread of informed outrage:
BOOZE NEWS — Turns out there’s a cocktail called the Toronto. (Did you know this? I did not know this.) It’s “a unique mix of Fernet Branca, Canadian rye whisky, and Angostura bitters and sweetened with maple syrup.” And this week, the ad-laden Money Inc. website looked into its mysterious origins for some reason. Read more.
SWEATY NEWS — During this week in 1936 Toronto was hit by one of Canada’s deadliest heatwaves, with temperatures reaching 40°C. It killed about 200 people in the city, and thousands more across the continent — striking when people were already struggling with the hardships of the Great Depression. The Weather Network takes a look back. Read more.
AIR DISASTER NEWS — During this week in 1970, Pearson Airport witnessed one of the deadliest crashes in Canadian aviation history. An Air Canada flight schedule for a brief stop on its way from Montreal to Toronto slammed into the runway at 220 knots, killing everyone on board. Dozens of victims were buried at Mount Pleasant Cemetery, and pilot error was found to be the cause. Read more.
ART DECO DISTRICT NEWS — Jack Landau had busy this week. Not only did dig into the fate of the Filmores sign, he also headed to Eglinton Avenue to check out what he calls “one of the best-preserved collections of Art Deco architecture in Toronto…” Read more.
ABANDONED NEWS — …and explored an abandoned off-ramp in the Don Valley, with the roadway and traffic signs now being reclaimed by nature. Read more.
TORONTO HISTORY EVENTS
THE HISTORY OF CANADIAN WOMEN PILOTS & OTHER AIRBORNE SUPERSTARS
July 14 — 2pm — Toronto Public Library, Taylor Memorial branch
“Discover how Canadian women broke through the sky blue ceiling as Dr. Elizabeth Muir discusses her book, Canadian Women in the Sky: 100 years of Flight.”
Free with registration!
SUMMER HISTORY SERIES: THE KINGSWAY
July 21 — 7:30pm — Online — Etobicoke Historical Society
“One of Canada’s premier neighbourhoods, The Kingsway was the vision of one man, Robert Home Smith. A lawyer by training but a natural-born town planner, Home Smith took 3,100 acres of ordinary Etobicoke farmland and turned it into an elegant series of subdivisions that were deemed ‘A bit of England far from England’. Centered around the Old Mill, they offered not only a new vision of town planning but of upper middle class life in Toronto. So ‘jump on the bus’ with EHS Historian Richard Jordan for an enjoyable virtual journey through this picturesque and historic neighbourhood.”
Free for members; an annual membership is $25.
SUMMER HISTORY SERIES: ETOBICOKE’S HISTORIC LAKESHORE
August 18 — 7:30pm — Online — Etobicoke Historical Society
“Mimico, New Toronto and Long Branch share many things, including the streetcars of Lakeshore Boulevard West and the beautiful shores of Lake Ontario, but they have very different histories. Mimico is an older town, once the home of palatial estates. New Toronto had its start as a gritty industrial suburb. And Long Branch began as a gated, upper class cottage community and resort in Victorian times. Join EHS Historian Richard Jordan as he travels back in time on this virtual historic tour of Etobicoke’s three lakeshore communities.”
Free!
MY UPCOMING EVENTS
THE TORONTO CIRCUS RIOT: A TRUE TALE OF SEX, VIOLENCE, CORRUPTION AND CLOWNS
August 3 — 7:30pm — Online — Toronto Branch, Ontario Genealogical Society
The strangest riot in our city’s history broke out in the summer of 1855. It was sparked by a brawl at a King Street brothel, when some rowdy clowns picked a fight with a battle-hardened crew of firefighters on the most dangerous night of the year. That bizarre encounter would reverberate through the city. The circus performers had made a terrible mistake; those firefighters were members of the Orange Order, the powerful Protestant society that ruled Toronto for more than a century. And they wanted revenge. The circus grounds would soon become the scene of a bloody clash that shook Toronto to its core and laid bare the fault lines that once violently divided our city.
Free with registration!