Historicist: The Bootlegger's Bravado
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Historicist: The Bootlegger’s Bravado

Every Saturday at noon, Historicist looks back at the events, places, and characters—good and bad—that have shaped Toronto into the city we know today.

Front page of The Star on November 19, 1924.

In the heady 1920s, Ontario was a dry province. After the war, the Ontario Temperance Act, which originally prohibited public consumption and sale of alcohol as a wartime measure, had been strengthened to close a variety of loopholes to become outright prohibition. It was, of course, a widely flouted law that gave rise to an underground economy of thriving bootleggers who supplied beer and whisky to blind pigs and speakeasies—as well as to Americans suffering through the decade-long thirst of the Volstead Act south of the border. Rocco Perri, an Italian immigrant to Hamilton, was one of many once-small-time crooks who were emboldened and enriched by the smuggling trade.
The underworld’s escapades provided great fodder for journalists like Dave Rogers, a rising star among the stable of Daily Star reporters who gave that paper the best and most sensational crime coverage in town. The Columbia-educated Nova Scotian was only twenty-three years old when he scored a major coup: an exclusive interview with Perri. Although Perri was known to police, he had hitherto remained a mysterious figure to the public. But by flattering the gangster’s ego in a telephone call—telling him that A.H. Lyle, secretary of the Hamilton Temperance Federation, had labelled Perri the biggest bootlegger in Ontario—Rogers secured a sit-down interview. That very evening, November 18, 1924, he knocked on the door of Perri’s ritzy mansion in a fashionable Hamilton neighbourhood.
Whether it was his elite society connections, the rumoured pay-offs to Hamilton police and judges, or the fact that he’d been bootlegging for eight years without any serious legal repercussions, Perri seemed supremely confident that he was immune from the law. His forthright responses embarrassed the authorities and made outstanding newspaper copy. Indeed, the article turned him into the public face of Ontario bootlegging as the self-styled “King of the Bootleggers.” But he would later come to regret the numerous incriminating comments he flagrantly made.

Coverage of the interview’s fallout from The Star on November 21, 1924.

After ushering the reporter into his lavishly appointed and ultra-modern home, the immaculately groomed gangster calmly sunk into the cushions of his elegant chesterfield while music gently wafted from the radio in the background. Despite the mellow atmosphere, Rogers launched into the interview with a hard-hitting question. “Who killed Joe Baytoizae and Fred Genesee?” he asked, in reference to bodies that had recently been discovered in Hamilton. As James Dubro and Robin F. Rowland wrote in King of the Mob (Viking, 1987), Perri shrugged off the question with a laugh and replied: “Rocco Perri did it, I suppose. Everything that happens they blame on Rocco Perri.” Rogers persisted, insisting that rumours linked the deaths to an Italian bootlegging ring. A more serious Perri furrowed his brow and, although he claimed ignorance, speculated that Baytoizae had been “put out of the way because he was a squealer” who’d assisted police on a number of cases and that Genesee might’ve been killed over a woman. On a number of occasions over the course of the interview, Perri would matter-of-factly reveal the brutish undercurrent of violence in the business.
When again Rogers persisted, asking directly whether the two had been collateral damage in a bootleg war, Perri remained silent. Bessie Starkman, Perri’s common-law wife who was present for the entire interview and occasionally interjected, patted her husband’s back supportively and told him, “You tell them, Rocco, that there is no war. You are the king of the bootleggers. That is what they say. You should know.” Regaining his swagger, Perri echoed, “There is no bootleg war.” Such moments led the media to speculate whether Starkman was the real brains behind the bootlegging ring. These rampant rumours were emphatically quashed by crime writer Antonio Nicaso, who insists in Rocco Perri: The Story of Canada’s Most Notorious Bootlegger (John Wiley & Sons, 2004), that “Perri was not a puppet [or] controlled by a ruthless woman.”
Next, Rogers asked about the OTA and rumours—denied by Perri—that the debonair millionaire had donated $40,000 to the temperance movement. Revealing an apparent social conscience, Perri saw the unenforceable OTA as the root of, not solution to, many social problems. It lured young men and women towards booze through the illicit, but romantic, appeal of the speakeasy. Moreover, although he claimed his own men didn’t carry guns, Perri blamed the OTA for crime as small-time bootleggers engaged in cut-throat competition. “They have no principles,” he said of his competition. “They will sell anything, they will do anything to get the business of their competitor. That makes more crime.” Starkman chimed in with a self-serving rationalization: “Yes, we admit that we are bootleggers, but we do our business on the level.” Perri saw himself as a businessman like any other—and Rogers compared the gangster’s assertions that product quality, “fair prices, and square dealing” were essential in the booze trade to “a college lecture on business administration.”

Coverage of Rocco Perri’s appearance before the Royal Commission from The Star on April 5, 1927.

“You think you have a right to carry on the illicit traffic in liquor?” Rogers asked. “The law—what is the law?” Perri responded philosophically. “They don’t want it in the cities. They voted against it. It is forced upon them. It is an unjust law. I have a right to violate it if I can get away with it. Men do it in what you call legitimate business until they get caught. I shall do it in my business until I get caught. Am I a criminal because I violate a law that the people do not want?”
Asked whether he found it difficult to evade the police and customs officers, Perri laughed, then added: “They are like a lot of schoolboys learning to play ball.” Furthermore, he felt that he and other bootleggers were being lazily blamed for any crime the authorities couldn’t solve. By 1924, Perri was wealthy enough and had a sophisticated enough operation that the occasional loss of a shipment, or having to pay a fine, had little impact. He brazenly suggested that, if authorities were serious about curbing bootlegging, jail time would make a bigger dent on his operations. His ego aside, Perri understood the realities of the business in which he engaged. “If I am put out of business tomorrow,” he stated bluntly, “there will be others to take my place.” As the clock struck ten, Rogers double-checked that Perri authorized The Star to publish his views. “They blame everything on me now, anyway,” Perri politely responded. “I have no good name to lose. My reputation is long since blackened. I am a bootlegger. I am not ashamed to admit it. And a bootlegger I shall remain.” Nevertheless, when city editor Harry Hindmarsh looked over Rogers’s story back in The Star‘s newsroom, he insisted that Rogers return to Hamilton and have Perri sign the galley proofs as an indication of his approval.
The front page story was a sensation on November 19, 1924. News boys were mobbed, and the paper’s entire run was soon sold out. By the end of the day, copies of the two-cent paper were being scalped for $2. Reaction was swift. Armed with this public admission, a group of Protestant pastors called for Perri’s deportation to Italy as a threat to Canadian society. Having been scooped on their own turf, the Hamilton Spectator and Herald and other newspapers lined up at Perri’s door. Ever the self-promoter—unlike other prominent bootleggers in Ontario—Perri graciously agreed. He elaborated on the stories and philosophical positions he’d shared with Rogers and boasted of prominent Hamilton citizens being amongst his best customers.
Police and government officials on both sides of the border took notice. Within days, Attorney General William Nickle had discussed the interview with Victor Williams, chief of the OPP, and issued a statement. “It is not a breach of the OTA for a person to say that he is a bootlegger,” he said. “The mere declaration is not actionable.” In the absence of specific evidence, despite his bold proclamations in the newspaper, Perri could not be touched.
The law finally caught up with Perri when the federally appointed Royal Commission on Customs and Excise began its in-depth investigation of Canada’s bootlegging trade in 1927. He and Starkman were subpoenaed to testify at the commissions hearings in Toronto in April 1927. Although Perri calmly side-stepped many direct questions with claims of faulty memory, Rogers’s interview was presented as evidence he was lying. Perri claimed that his bravado with Rogers had been mere showmanship. “The Star reporter came to me and wanted to give them a little news,” he testified. “They bothered me every day, so I had to give them a little news.” Nevertheless his lies—compounded by evidence of illegal phone calls to distillers and Starkman’s lies about the couple’s bank accounts—prompted the commission to recommend Perri and Starkman be charged with perjury. To save Starkman a prison term, Perri cut a deal with authorities on April 23, 1928, and served five months at Guelph. Upon his release on September 27, 1928, Perri returned to bootlegging and continued to generate headlines with a colourful gangster lifestyle before quietly, and mysteriously, disappearing in the 1940s.
Additional source consulted: C.W. Hunt, Booze, Boats and Billions: Smuggling Liquid Gold! (McClelland & Stewart, 1988)