Perri and Starkman survived financially in the few years after 1915 from his income as a macaroni salesman and the grocery store on Hess Street. After the
Ontario Temperance Act was passed in 1916, making the sale of alcohol illegal, the couple started selling shots of
Canadian whisky on the side. Bootlegging became a larger and more profitable enterprise when
Prohibition was declared in Canada nationwide on April 1, 1918, and the
Eighteenth Amendment that prohibited sale of alcohol in the United States in 1920. Through the 1920s, Perri became the leading figure in
organized crime in
Southern Ontario and was under constant surveillance by police. The government allowed for numerous exceptions, allowing various
breweries and
distilleries to remain open for the export market. Perri specialized in exporting liquor from old Canadian distilleries, such as
Seagram and
Gooderham and Worts, to the United States, and helped these companies obtain a large share of the American market — a share they kept after Prohibition ended in Ontario in 1927, and the United States in 1933. Perri sold alcohol to the Chicago Outfit via
the Purple Gang of
Detroit, and he was described as the largest source of Canadian whiskey in Chicago. He has also been linked as a distributor of Canadian whisky to
New York City's
Frank Costello and
Chicago's
Al Capone, yet when Capone was asked by
Daily Toronto Star reporter Roy Greenaway if he knew Perri, Capone said "Why, I don't even know which street Canada is on." Other sources, however, claim that Capone had certainly visited Canada, where he maintained some hideaways, but the
Royal Canadian Mounted Police states that there is no "evidence that he ever set foot on Canadian soil." Perri also sold trainloads of liquor into Chicago and Detroit through
Niagara Falls and
Windsor, Ontario. Stefano Speranza, a member of the Chicago Outfit, described Perri as "the most powerful boss in Canada". Around 1920, the Ontario underworld was dominated by three crime families, the Scaroni family based in
Guelph, the Serianni family based in Niagara Falls and the Gagliardo family based in Toronto. Perri managed to remain on good ties with all three families for a time, but came to be aligned against the Scaroni family when two Serianni family members, Domenic Speranza and Domenic Paproni, killed a Scaroni family member, Joe Celona, in his presence. On June 18, 1921, James Saunders, the bodyguard-chauffeur for the Scaroni family was founded murdered outside of Welland via a knife; in his coat pocket was a piece of paper with Perri's home address on it. On May 10, 1922, the boss of the Scaroni crime family, Domenic Scaroni, was killed after being invited to a meeting of organized crime figures in Niagara Falls. At Scaroni's funeral on May 13, 1922 in Guelph, Perri served as one of the pallbearers along with Antonio Deconza, Frank Longo, Frank Romeo and the D'Agostiono brothers. On June 15, 1922, Salvatore Scaroni, the cousin to Domenic, was wounded in a failed murder attempt in Niagara Falls. Scaroni's brother Joe Scaroni along with Salvatore Scaroni were killed on September 4, after being driven to a bakery by Perri associates John Trott and Antonio Deconza. Perri was linked to the murders, though no evidence was found. With the Scaroni brothers eliminated, Perri formed an allegiance with the Serianni crime family to keep the Ontario market out of the hands of the
Magaddino crime family in
Buffalo,
New York. Perri soon diversified into
gambling,
extortion and
prostitution. By 1924, when the average wage for a construction worker was $42 per week, Perri and Starkman made an annual profit of $1 million. Perri employed about 100 men and was in charge of the operational aspects of the gang. Starkman, who was more literate than Perri, handled the financial aspects of the business and chose the suppliers of alcohol. Starkman mastered Italian and usually spoke to Perri in the Calabrian dialect of Italian that was his preferred means of speech. By contrast, Perri never learned Yiddish, which was Starkman's first language. Starkman made the alliance with
Clifford Hatch, the owner of the Gooderham & Worts distillery that had relocated to Montreal in 1916, after the Temperance Act. Hatch wanted to keep selling alcohol in Ontario where his brand had been well known ever since Gooderham & Worts had been founded in 1832 while Starkman saw the importance of selling high quality and safe alcohol to allow the Perri-Starkman gang to seize market share from other bootleggers. Bootleggers often brewed alcohol under unsafe conditions and diluted their alcohol with mineral oil, formaldehyde, acetone, formic acid, sulfuric acid, and creosote. Death and blindness from drinking tainted alcohol were major problems in the 1920s, and drinkers sought out bootleggers who sold safe alcohol. Perri very much wanted British citizenship (until 1947 a separate Canadian citizenship did not exist) and on March 13, 1922 applied for British citizenship in
Wentworth County. Perri's citizenship application made the front page news of the
Hamilton Herald newspaper, leading to objections from Thora McIroy, the president of the Hamilton chapter of the Citizenship Committee of the Local Council of Women. McIroy wrote a public letter stating that Perri "is not a man of good moral character and is not a fit person to be naturalized in Canada". On March 24, 1922, William Whatley, the Hamilton police chief, wrote to the Dominion government that Perri had criminal convictions for leaving the scene of an automobile accident in 1918, for lying to a police officer and a breach of the Temperance Act in January 1919 and another conviction in July 1919 for allowing "a ferocious dog to be at large". On April 12, 1922, Perri's citizenship application was denied. On May 6, 1922, Perri launched an appeal where he presented himself as misunderstood and maligned. On May 15, his appeal was rejected with his explanations for his behavior be ruled "not very convincing". On November 19, 1924, in an exclusive interview with the
Toronto Daily Star, he stated, "My men do not carry guns ... If I find that they do, I get rid of them. It is not necessary. I provide them with high-powered cars. That is enough. If they cannot run away from the police it is their fault. But guns make trouble. My men do not use them." He also did not view himself as a criminal, believing that Prohibition was "a law that people did not want." Perri openly admitted that he was a bootlegger as he told an American journalist: "All I ever did was to sell beer and whisky to our best people...They call me a bootlegger, and some people call bootleggers criminals. I am simply supplying the demand of millions of law-abiding and law-making citizens. I sell liquor to judges, bankers, senators, governors, mayors, and I have preachers I sell wine to. It is not more criminal to supply this liquor than barter for, possess and consume it. I am willing to be classed in the same category with judges, bankers, senators, governors, mayors and other well known people, call them what you like". Perri typically shipped his illegal alcohol into the United States overland, but also owned a boat for crossing
Lake Ontario. On December 1, 1926, a boat owned by Perri was seized in Hamilton harbour with 100 cases of Canadian whiskey meant for the American market. He had a limited business relationship with bootlegger Ben Kerr, who also owned a home on Bay Street. Kerr was described by the some as "King of the Lake Ontario rum-runners" (smugglers who typically used boats). Kerr was operating within Perri's territory, but the latter required Kerr to smuggle raw American alcohol into Ontario, and may also have allowed Kerr to sell alcohol in a certain part of
New York State in return for the payment of a commission. These ventures enabled Kerr to expand his operations and to remain a solid customer of distilleries such as Gooderham & Worts and
Corby's. Kerr and his boat
Pollywog disappeared in February 1929; weeks later, his body and some wreckage from his boat were found on the shore of Lake Ontario near
Colborne. Based on his research, author C.W. Hunt theorized that Perri was likely responsible for Kerr's death, perhaps using his own, more effectively-armoured boat, the
Uncas. Hunt conceded that there were two other possible causes: "misadventure" (a marine accident) as stated by the coroner, or an act by the Staud brothers with their well armed/armoured boat. One report estimates that in the mid-1920s, Perri and Starkman were generating
C$1 million per year through criminal endeavours and had a hundred employees. In that era, Perri was a "big spender" and the couple lived an opulent lifestyle. Nonetheless, Perri paid only $13.30 in
income tax based on employment as a macaroni salesman and his "export/mailorder" business in 1926; Starkman, who claimed to be supporting him, paid $96.43. At about that time, some reports indicated that she had between $500,000 and one million in deposits at various banks. When Perri turned himself in to face the manslaughter charges in Hamilton on July 31, 1926, it was the biggest news story in the American and Canadian newspapers that day. Even the United States president
Calvin Coolidge spoke about Perri's arrest at a press conference at the White House, which he used as evidence that the Canadian authorities were trying to stop bootlegging into the United States. A woman involved in bootlegging, Mildred Cooney Sterling, told an undercover policeman on August 26, 1926: "No one would ever dare to go against Rocco Perri. He is entirely too powerful". About the tainted alcohol that had caused the deaths of 45 people in Ontario and New York state, she added that Perri had smuggled in the toxic alcohol, but he "...would under all circumstances, prevent the poison liquor from coming in...Rocco Perri and other millionaire rum-runners do not have to handle poisonous liquor because they can make more money with less trouble by handling the straight goods". On 13 January 1927, Perri was acquitted when the Crown was unable to establish that he was aware that the alcohol was tainted. On June 1, 1927, alcohol was legalized in Ontario again. However, the Ontario government forced bars and liquor stores to close early, which still made bootlegging in Ontario profitable as many people wanted to drink past the early closing time. In 1927, Perri was compelled to testify at the Royal Commission on Customs and Excise inquiry, focusing on bootlegging and smuggling, and also at a hearing on
tax evasion charges against Gooderham and Worts. Later that year, at the Gooderham and Worts tax evasion hearing, Perri admitted to buying whisky from the distiller from 1924 to 1927. Gooderham and Worts was convicted of tax evasion in 1928 and ordered to pay a fine of $439,744. Perri and Starkman were charged with
perjury after their Royal Commission testimony, but in a
plea bargain, the charges were dropped against Starkman; Perri served five months of a six-month sentence and was released on September 27, 1928. On June 15, 1929, an undercover officer of the Royal Canadian Mounted Police,
Frank Zaneth, reported to his superiors that he had learned "that Rocco Perri was the big gun in the smuggling and distribution of narcotic drugs in this province." On May 26, 1930, Giuseppe Pennestri, who used the alias Joe Leo, vanished in
Sudbury. Leo left behind a note in a safe deposit box which warned that if he vanished, it would be a case of murder as he accused two Perri associates, Domenico and James D'Agostino of plotting his murder so they "can take my wife and my money". The body of Leo was never discovered. On August 2, 1930, Perri and Mike Serge were charged with illegal possession of of liquor, but nine days later, both men were acquitted. Starkman was murdered on August 13, 1930. Perri started relations with Joe Leo's widow, Maria Vincentia Rossetti, who used the alias Jessie Leo. In October 1930, Jesse Leo confirmed her relationship with Perri to journalists and hinted she would marry him. By 1931, the
Great Depression had led to a 31 percent unemployment rate in Ontario, and the Canadian authorities openly tolerated Perri's bootlegging into the United States as a way to reduce unemployment. In response to threats from the United States government to raise tariffs on Canadian goods, the Canadian government banned the export of alcohol. In turn, the bootleggers took to smuggling Canadian alcohol into the United States via Cuba and Mexico, a choice of routes that hurt Perri financially. Perri's bodyguard/chauffeur Frank Di Pietro later stated: "He felt cornered, as if everyone was plotting against him. He acted in a strange way. In one day alone he lost $100,000 at the racetrack". On October 5, 1932, the Hamilton police raided a hose on Concession Street where of whisky meant for the United States was seized. Charged were Mary Latika, Perri's maid, and Tony Marando, Perri's cousin. The raid costed Perri $28,000 in inventory. On December 5, 1933, Prohibition ended in the United States as the new president,
Franklin Roosevelt, shepherded the
Twenty-first Amendment to the United States Constitution which made alcohol legal again in the United States. The end of Prohibition ended Perri's main source of income, and led to engage in new crimes such as counterfeiting. By the 1930s, Perri had become legendary figure in his native Calabria with popular rumor having it that he "was the richest man in Canada". In 1937, Perri returned to Toronto where he purchased a house with his new common-law wife, Annie Newman. To support himself, Perri turned to running a network of illegal gambling houses in Toronto. Between 1937 and 1939, Perri owned a brewery on Fleet Street in Toronto. In 1938, two attempts were made to kill Perri: on March 20, his
veranda was destroyed by
dynamite that had been placed underneath it, and on November 23, a
bomb under his car detonated. Perri was not injured in either attempt. Perri was the prime suspect behind the murder of a Toronto bookie, James Windsor, who was competing with his gambling houses. While interviewing Perri, two Toronto police detectives, Orrie Young and Herbert Witthun, noticed a .25-calibre pistol in the living room. Annie Newman claimed that gun was hers and she was fined $25 on January 12, 1939 for owning an illegal gun. On August 30, 1939, Perri was charged with the corruption of public officials with the Crown alleging that he had bribed seven customs officers in Windsor to assist with his struggling across the border. One of the Customs officers, David Armaly, had agreed to turn Crown's evidence and testified that Perri had bribed him as he received $25 for every one of Perri's cars that were allowed to cross into the United States uninspected. On the same day that he was arrested, Perri was interviewed by journalists with the discussion turning to the
Danzig crisis. Italy signed the
Pact of Steel with Germany earlier that year, and several journalists asked what Perri would do if Italy were at war with Britain. Perri replied: "Canada is my country. Canada is part of the British empire. I would fight for it. I left Italy more than twenty-five years ago. I don't remember much about it". The next day, the
Daily Toronto Star ran as its headline "War worries Rocco, he's ready to fight". Perri was defended at his trial by
Paul Martin Sr., who always so well informed about the Crown's case that it was believed that one of the Crown Attorneys was selling information, but which Crown Attorney was never established. Martin made much of the fact that Armaly had engaged in welfare fraud, which he used to paint him as a man engaged in perjury. On February 1, 1940, Perri was acquitted. ==Internment==