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Rocco Perri (Italian: [ˈrɔkko ˈpɛrri]; born Rocco Perre;[1] December 30, 1887 – disappeared April 23, 1944) was an Italian-Canadian organized crime figure in Hamilton, Ontario. He was one of the most prominent Prohibition-era crime figures in Canada, and was sometimes referred to as "King of the Bootleggers" and "Canada's Al Capone."[2]

Key Information

Born in the Italian town of Platì in Calabria, Perri immigrated to the United States, and later to Canada, in 1908. In the early 1910s, he started work in construction and in a bakery. Perri and his common-law wife, Bessie Starkman, began a business in bootlegging when the sale and distribution of alcohol was prohibited in both Canada and the United States. Starkman dealt mainly with the finances of the business.[3]

In 1928, Perri was charged with perjury after a Royal Commission testimony, and served five months of a six-month prison sentence. In 1930, Starkman was ambushed in her garage and killed; no one was charged with her murder. In 1940, Perri was arrested and sent to internment at Camp Petawawa as part of the Italian Canadian internment; he was released three years later. Perri disappeared in Hamilton on April 23, 1944, when he went for a walk; his body was never found, and this caused speculation surrounding his purported death.

Early and family life

[edit]

Perri was born Rocco Perre[1] in Platì, Calabria, Italy, on December 30, 1887.[4] His family were poor shepherds, and he dropped out of school in grade 5.[5] In the late 19th century, 80 percent of the people in Calabria were illiterate and Perri stood out in having at least some literacy.[6] Like many other Calabrians of his generation, Perri as a young man longed to go to "America" with the United States being seen as a land of hope, opportunity and prosperity.[6] He immigrated to the United States in 1903, then to Canada in 1908.[7] Perri left for Boston in April 1903 abroad the ocean liner SS Republic on a third-class ticket.[8] Perri soon moved to New York City, and then settled in Massena in St. Lawrence County, New York, where he worked as a general labourer.[9] In May 1908, he moved to Montreal in search of work.[10] In November 1908, Perri moved to Ontario and settled in Cobalt where he worked in a stone quarry owned by the railway.[11] Perri who disliked the harsh winters in northern Ontario lived a semi-nomadic life as he lived in Cobalt in the spring and summer while spending his falls and winters in Toronto.[12] Perri later said of his early years in Canada: "We were treated worse than the Blacks but, unlike them, we couldn't speak English".[13]

During this period, Perri began to engage in crime as he wrote coded letters in Italian full of references to "furniture" and "stuff" that he was always selling and buying to men with criminal records.[12] In May 1912, Perri hired a man, Camillo Tuzoni, to burn down a house in North Bay that was owned by Donato Glionna as a part of extortion bid.[14] Tuzoni after his arrest for arson named Perri as the man who hired him.[13] In the spring of 1912, Perri settled in Toronto permanently.[12]

In 1912, Perri met Bessie Starkman, a Polish Jew who had immigrated to Canada circa 1900, while he lived as a boarder in her family home in The Ward, Toronto, Ontario, with her husband Harry Toben and their two children.[15] Shortly after, Perri began an affair with Starkman, and when he got a job working on the Welland Canal in 1913, she left her husband and children to move in with Perri in St. Catharines and begin a common-law relationship.[15][16][17] After a few weeks of living with Perri, Starkman attempted to return to her husband, who refused to accept her.[13] Starkman later said of her life with Perri in St. Catharines: "We had no friends. We ate bread and swallowed insults. We were marginalized among those who, as immigrants, were already marginalized".[18] In a letter to his mother in Italy, Perri wrote: We used to work risking not only our health, but in many cases our lives".[19]

When the Canadian government cut funding to the Welland Canal project due to World War I, Perri became unemployed. After working in a bakery, he was hired as a salesman for the Superior Macaroni Company. However, Perri and Starkman found a better means of income when the Ontario Temperance Act came into effect on September 16, 1916, as it restricted the sale and distribution of alcohol.[15] The couple began bootlegging; using Starkman's business acumen and Perri's connections, they established a profitable enterprise. It was Starkman who suggested bootlegging, but Perri used his network of his Italian friends to create the Perri-Starkman gang.[20] Alcohol was still legal in Quebec, and Perri used his network of friends in Montreal to buy alcohol to smuggle into Ontario.[21] By this time the two lived in Hamilton, Ontario, and by 1920, moved into a larger home at 166 Bay Street South.[22][23] Perri and Starkman also opened brothels in Hamilton, at the time the city with the highest percentage of its women engaged in prostitution in North America.[24] On March 9, 1917, the Hamilton police raided the house at 157 Caroline Street North owned by Perri and Starkman and arrested Starkman for keeping a bawdy house after the police discovered a prostitute, Mary Ashley, engaged in her trade at the house.[24] Starkman was convicted and fined $50.[25] On November 17, 1917, Starkman gave birth to a son by Perri, but the child died after only two days.[25] On April 1, 1918, the Dominion government banned alcohol everywhere in Canada, a law that remained in effect until December 31, 1919.[26] Perri and Starkman had to smuggle alcohol from the United States into Canada to maintain their business.[27]

In 1918, Perri began an affair with Sarah Olive Routledge, with whom he had two daughters; Autumn (born in 1919), and Catherine (born in 1921).[28] After Autumn was born, Perri had refused to marry Routledge, but he did maintain a home for her in St. Catharines and paid child support.[29] Their affair resumed in 1920.[29] Perri's job as a macaroni salesman required travel across Ontario; he also used those trips to arrange the sale of liquor.[30] Starkman, busy running the finances for their organization, did not question Perri's outings.[31] In February 1922, Routledge was falsely told by Perri's lawyer that he was already married to Starkman. Despondent, Routledge committed suicide by jumping from her lawyer's seventh-story office window of the Bank of Hamilton; her parents took custody of their children.[32][29] In the 1930s, Perri asked to see his daughters on weekends, although their grandmother would always accompany them for fear that he would take them.[33]

On December 31, 1918, Perri and Starkman were hosting a party where two of the guests, Alberto Naticchio and Antonio Martino, become engaged in a dispute.[34] The two men went outside and Naticchio shot Martino who died later that night of blood loss.[35] Perri gave the police the false name of Rocco Suseno, which led him to be charged with lying to a police officer when the police discovered his real name.[36] Perri was charged with selling alcohol on January 3, 1919, and three days later, was convicted.[37] Perri was fined $1,000, but his lawyer, Michael O'Reilly, had the fine reduced to $700 on an appeal.[38]

Starkman was the head of operations and the duo's negotiator and dealmaker,[39] until August 13, 1930, when she was ambushed at around 11:15 p.m. as she got out of Perri's car in the garage of the couple's home.[39] Perri ran down the street after the assailants before retreating back to Starkman, who had been killed with two shotgun blasts.[23] With tears in his eyes, Perri told reporters the next day "I'd give up all my money just to have Bessie still here with me. I've lost my best pal".[40] Police found two double-barreled shotguns and the getaway car without fingerprints. The investigation eventually resulted in no criminal charges being brought despite a $5,000 reward offered by Perri.[23][41] However, it was thought that Calabrian compatriot Antonio Papalia, leader of the Papalia crime family and father of Johnny Papalia, played a role in the murder.[42][43] The stolen license plates used on the car that Starkman's killers had fled were taken from a car parked in an automobile repair shop where Antonio "Tony" Papalia worked.[40] Papalia told the police when questioned: "I've got nothing to do with it. But even if I knew something, I would certainly wouldn't tell you about it".[40] Perri told the reporters about Papalia's possible involvement: "If it were true, I wouldn't be surprised".[40] Two weeks after Starkman's murder, Perri had a will written up, saying he was in fear of his life and "I don't trust anybody".[44] Perri added the clause to his will: "I direct that in the event of my death occurring under any unnatural circumstances that my executor investigate same and if any of my beneficiaries are in any way suspected of having anything to do with my unnatural death, their share of my estate shall be forfeited".[44]

On August 17, about 20,000 people[39] lined the street for the funeral cortege of hundreds of vehicles; Perri fainted at the gravesite.[41] At the funeral, as the rabbi said kaddish (the prayer for the dead), Perri broke down in tears and fainted.[45] Starkman's headstone in Hamilton's Ohev Zedek Cemetery, commissioned by Perri, referred to her as "Bessie Starkman – Perri", but the "Perri" part was later removed by persons unknown.[46] Part of Starkman's estate went to Perri, and the rest to her children. By 1933, Perri was living with another woman, Annie Newman, who helped him to improve his criminal enterprise.[39] The couple profited from enterprises such as bootlegging and drug trafficking. "Annie was just as corrupt and business-like as Bessie," according to one source. In 1943, Newman was imprisoned for smuggling gold.[47]

Criminal operations

[edit]

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.[23] Their bootlegging was done on a small scale, with their kitchen as the centre of operations.[48]

Bootlegging became a larger and more profitable enterprise when Prohibition was declared in Canada nationwide on April 1, 1918,[49] 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.[50]

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.[51] 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."[52][53] Other sources, however, claim that Capone had certainly visited Canada,[54] where he maintained some hideaways,[55] but the Royal Canadian Mounted Police states that there is no "evidence that he ever set foot on Canadian soil."[56] Perri also sold trainloads of liquor into Chicago and Detroit through Niagara Falls and Windsor, Ontario.[17] During Prohibition, "The authorities were quite happy to turn a blind eye to bootlegging, and also to take payoffs ... and Rocco had all the important police in Hamilton ... on his payroll" according to author Trevor Cole.[57] Stefano Speranza, a member of the Chicago Outfit, described Perri as "the most powerful boss in Canada".[52]

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.[58] 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.[59] 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.[60] 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.[61] 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.[62] On June 15, 1922, Salvatore Scaroni, the cousin to Domenic, was wounded in a failed murder attempt in Niagara Falls.[62] 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.[63] 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.[64]

Perri soon diversified into gambling, extortion and prostitution.[65] He and Starkman were also reported to have taken part in the narcotics trade as early as 1922, when the Royal Canadian Mounted Police suspected Perri of "dealing in narcotics on a large scale."[66] By 1924, when the average wage for a construction worker was $42 per week, Perri and Starkman made an annual profit of $1 million.[67] Perri employed about 100 men and was in charge of the operational aspects of the gang.[67] Starkman, who was more literate than Perri, handled the financial aspects of the business and chose the suppliers of alcohol.[67] Starkman mastered Italian and usually spoke to Perri in the Calabrian dialect of Italian that was his preferred means of speech.[68] 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.[69] 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.[69] Bootleggers often brewed alcohol under unsafe conditions and diluted their alcohol with mineral oil, formaldehyde, acetone, formic acid, sulfuric acid, and creosote.[70] Death and blindness from drinking tainted alcohol were major problems in the 1920s, and drinkers sought out bootleggers who sold safe alcohol.[70]

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.[71] 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.[71] 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".[72] 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".[72] On April 12, 1922, Perri's citizenship application was denied.[72] On May 6, 1922, Perri launched an appeal where he presented himself as misunderstood and maligned.[73] On May 15, his appeal was rejected with his explanations for his behavior be ruled "not very convincing".[74]

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."[75] 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".[76]

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.[77] 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).[78] 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.[79] 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.[80][81][82]

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.[23] That same year, Perri faced criminal charges in the death of 17 people who died after drinking illegal liquor, but was acquitted of the charges.[65] 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.[83] 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.[84] 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".[85] 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".[85] On 13 January 1927, Perri was acquitted when the Crown was unable to establish that he was aware that the alcohol was tainted.[85]

Gooderham and Worts, one of Perri's suppliers, as it appeared in 1896

On June 1, 1927, alcohol was legalized in Ontario again.[86] 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.[87] 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.[87] 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."[88] On May 26, 1930, Giuseppe Pennestri, who used the alias Joe Leo, vanished in Sudbury.[89] 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".[89] The body of Leo was never discovered.[89]

On August 2, 1930, Perri and Mike Serge were charged with illegal possession of 10 US gallons (38 L) of liquor, but nine days later, both men were acquitted.[90] Starkman was murdered on August 13, 1930.[39] Perri started relations with Joe Leo's widow, Maria Vincentia Rossetti, who used the alias Jessie Leo.[91] In October 1930, Jesse Leo confirmed her relationship with Perri to journalists and hinted she would marry him.[91] 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.[92] In response to threats from the United States government to raise tariffs on Canadian goods, the Canadian government banned the export of alcohol.[93] 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.[93] 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".[94] On October 5, 1932, the Hamilton police raided a hose on Concession Street where 26,000 US gallons (98,000 L) of whisky meant for the United States was seized.[94] Charged were Mary Latika, Perri's maid, and Tony Marando, Perri's cousin.[94] The raid costed Perri $28,000 in inventory.[94] 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.[95] The end of Prohibition ended Perri's main source of income, and led to engage in new crimes such as counterfeiting.[96]

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".[97] In 1937, Perri returned to Toronto where he purchased a house with his new common-law wife, Annie Newman.[98] To support himself, Perri turned to running a network of illegal gambling houses in Toronto.[99] Between 1937 and 1939, Perri owned a brewery on Fleet Street in Toronto.[23] 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.[100] Perri was the prime suspect behind the murder of a Toronto bookie, James Windsor, who was competing with his gambling houses.[101] While interviewing Perri, two Toronto police detectives, Orrie Young and Herbert Witthun, noticed a .25-calibre pistol in the living room.[101] Annie Newman claimed that gun was hers and she was fined $25 on January 12, 1939 for owning an illegal gun.[101]

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.[102] 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.[103] On the same day that he was arrested, Perri was interviewed by journalists with the discussion turning to the Danzig crisis.[104] 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".[105] The next day, the Daily Toronto Star ran as its headline "War worries Rocco, he's ready to fight".[105] 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.[105] 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.[105] On February 1, 1940, Perri was acquitted.[105]

Internment

[edit]

In 1940, Perri and his brother Mike were arrested and sent to internment at Camp Petawawa as part of the Italian Canadian internment, as potentially dangerous enemy aliens with alleged connections to Benito Mussolini's fascist regime.[106][3] The Royal Canadian Mounted Police arrested Perri along with Antonio Papalia, Frank Silvestro, Mike Sergi, John Taglerino, and Charles Delcastro of Hamilton along with Domenic Longo and Domenic Belcastro of Guelph.[107] A group of Mounties arrived at Perri's Hamilton house, where he was arrested without incident.[108] One prisoner at Camp Petawaw, Osvaldo Giacomelli, recalled: "Perri never gave himself airs. He played cards often, but he avoided any conversation concerning activities that he was supposedly involved in".[108] Perri was described as a well behaved and polite prisoner who suffered from depression as 1941 turned into 1942 while he became very nostalgic for Calabria.[109]

During this internment, Perri served some time with Antonio Papalia, who was released two years before Perri. When Perri saw Papalia arrive at Camp Petawawa, he shouted at him in Italian: "I should slap you black and blue!"[110] Papalia replied "just try" and only the prompt intervention of the guards stopped a brawl between the two gangsters.[110] When he returned to his tent, Perri swore like he never been seen to do before as he cursed Papalia as a friend who had betrayed him.[108] Perri was greatly angered by the way that Papalia had allied himself with his old enemy, Stefano Magaddino.[111] Upon his release, Papalia then began to expand his enterprise with his son Johnny, who had some relationship with the Buffalo crime family.[112] On October 17, 1943, the Justice Minister, Louis St. Laurent, ordered Perri released.[113] Perri found that Ontario underworld was now dominated by Papalia, Bordonaro, and Silvestro who were serving as the agents of Magaddino, who did not want Perri involved in the underworld again.[114]

Disappearance and aftermath

[edit]

Rocco Perri was last seen alive in Hamilton on April 23, 1944, at the home of a cousin, Joe Serge, on Murray Street West. According to a Maclean's magazine report from June 15 of that year, Perri was then "working as a doorman in a Toronto theatre."[115] Before lunch, he complained of a headache and went for a walk to clear his head but never returned.[116]

Perri's body has never been found, though it is speculated he was murdered by being fitted with cement shoes and thrown into Burlington Bay—a practice known colloquially as the lupara bianca.[117] It is believed Antonio and Johnny Papalia, along with Stefano Magaddino of Buffalo, played a role in Perri's disappearance to gain better control of the Canadian alcohol market.[118] In 1944–45, the Papalias hunted down and killed all of Perri's allies such as Jouhn Durso and Louis Wernick, which completed Magaddino's control of the Ontario underworld.[119] The Royal Canadian Mounted Police concluded in 1954 that they "won't find his body until the Bay dries up."[120] After Perri's disappearance, three of his former lieutenants, in addition to Papalia and Giacomo Luppino, began answering to Magaddino in Buffalo: Tony Sylvestro, Calogero Bordonaro and Santo Scibetta, known as the "three dons."[121][122]

Later developments

[edit]

In 1992, evidence into Perri's disappearance was uncovered by Mafia expert Antonio Nicaso. A letter shared with him by Perri's cousin in Italy, dated June 10, 1949, and translated from Italian, read, "Dear cousin, With this letter, I will tell you I am in good health. Let them know I'm fine if you've heard the news." It is signed Rocco Perri. Perri's cousin also claims that the gangster died in 1953 in Massena, New York.[123] In 2018, Perri's relatives from Hamilton and Australia, during an attempt to collect on the late mobster's estate, claimed that he had lived in Massena under the name Giuseppe Portolesi before dying of natural causes in 1953. The group's Andrew Monterosso said that he had made a good living through legal ventures such as the ownership of properties in the United States and in Mexico.[124]

In 1998, a will and testament from 1930 surfaced; it was purported to be that of Perri, but there is doubt that he was ever declared dead. A CBC News report in 2012 stated that "there's no death certificate out there for Rocco Perri."[125] The group attempting to access the mobster's estate said in 2018 that there was no social insurance number or death certificate, and that the Canada Revenue Agency had transferred the funds from Perri's estate to Italy in 2008.[124]

[edit]

In July 2014, the first performance of a one-woman play about Starkman's life, Bootlegger's Wife, was staged at Theatre Aquarius in Hamilton, Ontario. The creator and star was Victoria Murdoch; while the Perri character does not appear, "voiceovers" provide his comments.[126] The play was staged again in mid-March 2019[127] and at intervals between those dates.[128]

Stefano DiMatteo portrays Perri in "Parker in the Rye" (January 6, 2020), episode 10 of season 13 of the Canadian television seriesMurdoch Mysteries.[129]

See also

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Books

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  • Nicaso, Antonio (2004). Rocco Perri The Story of Canada's Most Notorious Bootlegger. Toronto: John Wiley & sons. ISBN 9780470835265.

References

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Further reading

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Rocco Perri

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from Grokipedia
Rocco Perri (c. 1887 – disappeared 23 April 1944) was an Italian-born figure who operated primarily in , , and became one of 's most prominent bootleggers during the era. Born in , , Perri immigrated to as a youth, eventually settling in where he worked manual labor before entering illicit activities amid 's prohibition laws enacted in 1916. Known as "'s " and the "King of the Bootleggers," he built a vast operation with a fleet of boats transporting across the and to supply speakeasies in and the , forging ties with American mobsters like and exploiting legal loopholes for bulk purchases. In partnership with his common-law wife Bessie Starkman, who managed financial and operational aspects, Perri expanded into gambling, extortion, and narcotics, amassing significant wealth while evading authorities through corruption and violence. Starkman's unsolved assassination by gunfire at their Hamilton home in 1930 marked a turning point, after which Perri faced intensified rivalries, including bombings and legal scrutiny, yet persisted in diversified rackets like counterfeiting post-Prohibition. Interned as an enemy alien during World War II due to his Italian origins, he was released in 1943 before vanishing during a walk in Hamilton on 23 April 1944; his body was never recovered, fueling theories of mob execution—possibly involving disposal in Hamilton Harbour—or deliberate flight to the United States or abroad.

Early Life and Immigration

Origins in Italy

Rocco Perri was born on December 30, 1887, in , a remote village in the , , . He came from a family of modest agrarian means, reflective of the subsistence-level peasant existence prevalent in the Aspromonte mountain area surrounding , where rocky terrain and fragmented land holdings limited agricultural productivity. Calabria in the late 19th century was emblematic of the Mezzogiorno's broader socioeconomic challenges, including widespread , high illiteracy—exceeding 70% in some southern provinces—and entrenched latifundia systems that concentrated land in few hands while leaving smallholders in debt peonage. These conditions fueled social unrest, from sporadic remnants of the post-unification era to the emergence of secretive rural criminal networks like the precursors to the 'ndrangheta, which originated in clans enforcing codes of honor and vendetta amid weak state authority. Perri's upbringing occurred against this backdrop, where family survival strategies often involved seasonal labor migration or reliance on informal ties for protection and economic support. Formal education for boys like Perri was rudimentary at best, typically confined to basic if available through local schools, as resources prioritized wealthier urban centers over isolated villages. The pervasive trend—over 4 million Italians left between 1876 and 1915, disproportionately from the south—shaped worldviews in places like , presenting overseas opportunities as viable alternatives to entrenched destitution and cyclical harvests. Such environmental pressures, rather than direct criminal involvement in youth, likely primed Perri's eventual departure for around age 20.

Arrival and Settlement in Canada

Rocco Perri, born on December 27, 1887, in , , , immigrated first to the before arriving in in 1908 at approximately age 21. Upon entry, he initially settled in but soon relocated to , where he took up demanding manual labor in a stone quarry near Coulbert (close to Parry Sound) to support himself amid the challenges faced by early 20th-century Italian immigrants seeking in industrial sectors. By the early 1910s, Perri had moved toward the area, securing further employment in construction, including work on the and laying streetcar tracks, reflecting the transient job patterns common among unskilled immigrant workers during a period of rapid infrastructure development. In spring 1912, he established more permanent roots in , navigating the era's labor market fluctuations exacerbated by the onset of in 1914, which strained resources and heightened competition for jobs in manufacturing and . Perri's personal life during this settlement phase included forming a relationship with Sarah Olive Routledge around 1918, under a , resulting in two daughters and underscoring the familial adaptations and tensions typical of immigrant households balancing survival with limited opportunities. These years preceded Ontario's implementation of laws in 1916–1918, which imposed additional economic pressures on working-class communities by disrupting legal alcohol-related trades and foreshadowing shifts in underground economies, though Perri had not yet engaged in illicit activities.

Initial Criminal Involvement

Fruit Vending and Petty Crime

Upon arriving in , Rocco Perri initially engaged in legitimate fruit peddling as a means of livelihood within the city's Italian immigrant during the . This occupation provided a modest cover for his emerging involvement in small-scale illicit activities, including minor thefts and operations that leveraged urban networks of fellow immigrants. Perri's petty criminal endeavors expanded to include horse betting and informal loansharking, activities that allowed him to cultivate local connections without resorting to overt in the early stages. These rackets operated discreetly amid Hamilton's growing , where enforcement was lax for minor offenses. By the late , police records document his first significant brush with the law, including a 1916 arrest for , marking the onset of a pattern of misdemeanors that escalated toward more organized petty schemes. Empirical evidence from Hamilton police archives indicates a progression in Perri's activities through the early , transitioning from isolated thefts and to coordinated rackets that laid the groundwork for larger criminal enterprises, though still confined to low-level operations at this juncture.

First Arrests and Influences

Rocco Perri faced his initial arrests in , for petty offenses including shop-breaking and theft during the early years of his residency there. These encounters with law enforcement typically resulted in brief detentions, reflecting the era's challenges in securing convictions against small-scale criminals amid limited investigative resources and evidentiary standards. The imposition of under Ontario's Temperance Act, effective January 1, 1918, profoundly shaped Perri's trajectory by outlawing alcohol sales and distribution, thereby generating acute shortages and elevated black-market premiums. This legislative vacuum supplanted prior state-regulated liquor systems with illicit supply chains, incentivizing individuals like Perri—who possessed street-level acumen from prior hustles—to organize importation and resale operations exploiting cross-border disparities, including the concurrent U.S. national ban starting 1920. Such policies, by criminalizing a previously taxed commodity, predictably channeled entrepreneurial energies into evasion tactics over compliance, amplifying organized distribution networks. Perri's preexisting ties to Italian immigrant networks, forged during time spent in Chicago's , further propelled his pivot toward syndicated . These associations provided access to routes and personnel versed in evading enforcement, transforming sporadic thefts into structured rackets attuned to prohibition's demand surge. Gambling dens, already a staple in ethnic enclaves, offered complementary revenue streams, intertwining with alcohol trades as enforcement gaps allowed vice syndicates to consolidate influence in Southern Ontario's industrial hubs.

Bootlegging Operations During Prohibition

Rise to Prominence

With the enactment of the Ontario Temperance Act in 1918, which prohibited the sale and consumption of alcohol in the province until 1927, and the subsequent U.S. Volstead Act implementing national Prohibition from 1920 to 1933, Rocco Perri identified lucrative opportunities in exporting Canadian-produced liquor to American markets where demand surged amid legal restrictions. Operating primarily from Hamilton, Ontario, Perri sourced liquor from legal distilleries within the province, which continued production ostensibly for permitted export purposes, and directed it toward U.S. buyers despite federal bans on importation. By the early 1920s, Perri had developed a reputation for reliable supply, providing Canadian whiskey to prominent American figures, including Al Capone's network in , thereby establishing himself as a key transborder supplier. His operations emphasized streamlined and distribution, controlling flows from Ontario distilleries through to border handover points, which allowed him to scale without engaging extensively in the violent turf disputes common among U.S. counterparts. This strategic focus propelled Perri to prominence as the "King of the Bootleggers" by the mid-1920s, with his illicit trade generating millions in revenue through high-volume shipments that capitalized on the price disparities created by . Perri's in navigating legal loopholes for sourcing and prioritizing efficient over confrontation enabled rapid wealth accumulation and solidified his dominance in Canada's Prohibition-era underworld.

Smuggling Networks and Innovations

Perri's smuggling networks capitalized on the disparity between Ontario's Temperance Act, which banned domestic alcohol sales but permitted exports, and the U.S. enforcing nationwide . Legally produced liquor from distilleries such as Gooderham & Worts was acquired through bribes to officials and paired with falsified export paperwork, enabling redirection across the border rather than legitimate overseas shipment. A fleet of approximately 50 boats, crewed by unassuming fishermen, transported cargoes across the , , and , primarily under cover of night to evade patrols. Land-based operations complemented maritime routes, utilizing fast trucks like REO Speed Wagons to distribute loads from waterfront drop points to speakeasies and blind pigs. These networks supplied thousands of illicit venues in and U.S. border regions such as Buffalo, with one documented shipment alone exceeding 2,500 bottles of whisky. Adaptation to intensifying enforcement involved scaling up domestic production, employing chemists to distill high-proof spirits when legal distillery access became riskier. While mechanical innovations such as hidden compartments or decoy shipments lack direct attribution in primary accounts of Perri's methods, his operations innovated through systemic exploitation of export loopholes and hybrid legal-illicit sourcing, minimizing traceability. However, the unregulated nature of Prohibition-era supply chains introduced perils, including adulteration with toxic wood alcohol; in July 1926, bootleg liquor containing up to 93.9% wood alcohol caused 44 deaths across and New York, with three fatalities in Allanburg on July 21 and 18 more in Buffalo and Lockport on July 26. Such incidents underscored the causal trade-offs of : black-market incentives drove corner-cutting for volume and profit, yielding contaminated products amid unmet legal demand, yet effectively provisioning consumers in a suppressed economy.

Key Partnerships and Associates

Perri's primary collaborator in bootlegging was his common-law wife, Bessie Starkman, with whom he began a around 1913 that intensified during . Starkman oversaw critical operational elements, including placing orders with distilleries and breweries, laundering proceeds through bank accounts, and conducting negotiations with rival gangsters on liquor and narcotics distribution as well as with politicians and for protection. Her involvement extended to diplomatic functions that bridged ethnic divides in the , leveraging her Jewish background to forge alliances beyond Perri's Italian networks in Hamilton. Perri cultivated extensive connections within Hamilton's Italian immigrant community and its emerging , positioning himself as a leader among local Calabrian figures while expanding southward. These ties included routes that linked to American groups, with Perri reportedly acting as a key supplier and contact for figures like , facilitating cross-border liquor flows from Canadian distilleries into the U.S. during the height of national from 1920 to 1933. Such partnerships relied on Perri's network of drivers, bribers, and enforcers drawn from Hamilton's ethnic enclaves, enabling large-scale shipments via boats and trucks that evaded authorities through forged documents and official corruption. A hallmark of Perri's approach, distinguishing him from more volatile rivals, was his strategic eschewal of personal , favoring and financial incentives to maintain alliances and deter . He publicly distanced himself from Hamilton's rising gangland killings in the mid-1920s, insisting they stemmed from independent disputes rather than his operations, which preserved operational stability amid turf wars. This restraint extended to Starkman, who handled confrontational diplomacy, though it did not prevent her on August 13, 1930, when she was shot multiple times in the couple's garage driveway by unidentified assailants believed to be rivals targeting Perri's dominance. The murder, which drew over 30,000 mourners to her funeral, disrupted immediate activities but failed to dismantle the infrastructure, as Perri reorganized and continued shipments into the early .

Post-Prohibition Criminal Activities

Diversification into Other Rackets

Following the repeal of in on January 1, 1927, which legalized alcohol sales and eroded the profitability of bootlegging, Rocco Perri adapted by expanding into alternative illicit activities to sustain his operations amid shifting economic pressures, including the onset of the in 1929. This diversification reflected pragmatic responses to reduced bootlegging margins, as legal distilleries like those in Windsor supplied markets previously dominated by smugglers, compelling figures like Perri to seek new revenue streams in Hamilton and surrounding regions. By the early , Perri had established involvement in dens, operating underground establishments that catered to wagering on horse races and card games, leveraging his existing networks of associates for enforcement and collection. He simultaneously extended into schemes, imposing protection rackets on local businesses such as restaurants and shops in Hamilton's Italian enclaves, where payments ensured avoidance of or disruption, thereby maintaining territorial control without the need for overt violence. Perri's operations further incorporated narcotics trafficking, with reports indicating participation in the distribution of derivatives and early morphine-based substances smuggled via cross-border routes previously used for , partnering with his associate Bessie Starkman in these ventures during the decade. Additionally, he engaged in counterfeiting, producing fake and documents to launder proceeds and fund expansions, activities that capitalized on the era's economic desperation and lax in industrial centers like Hamilton. These rackets allowed Perri to preserve influence over southern Ontario's underworld, though they yielded lower volumes than peak bootlegging eras, contributing to a gradual erosion of his dominance by the late .

Expansion and Regional Influence

Following the end of in in 1927, Rocco Perri maintained dominance over southern 's underworld from his Hamilton base, extending influence into through operations such as a brewery on and cross-border activities reaching . This territorial control encompassed , narcotics trafficking, and counterfeiting, building on his bootlegging networks to consolidate power across the region without direct expansion into violent turf wars. Perri forged alliances with emerging Mafia figures, notably partnering with Buffalo crime boss in smuggling ventures that facilitated mutual interests across the U.S.-Canada border. These relationships, extending from earlier ties to figures like , allowed Perri to stabilize local criminal dynamics through diplomatic arbitration, reducing overt conflicts among factions in and enabling coordinated operations. However, this structure also perpetuated the proliferation of illegal gambling dens and narcotics distribution, drawing increased scrutiny from authorities while sidelining smaller operators. By the 1940s, Perri's influence waned as he aged beyond 50—born in 1887—and faced mounting pressure, including and wartime restrictions targeting Italian immigrants. Health complaints and internal shifts, such as subordinates aligning with Magaddino, further eroded his grip, paving the way for successors like the Papalia group to inherit fragments of his Hamilton-centric operations.

Arrests, Trials, and Acquittals

In July 1926, Rocco Perri was arrested on charges following the deaths of multiple individuals from consuming contaminated with wood alcohol distributed through his bootlegging network. The batch, containing 93.9 percent pure wood alcohol, resulted in 44 fatalities across by late July. Perri surrendered voluntarily on July 31 in Hamilton, accompanied by his lawyer, amid investigations linking the poisonings to a redistilling operation raided earlier that year. Associates refused to provide testimony, and police records showed no direct references in Perri's ledgers, complicating prosecution efforts. Perri and several co-accused faced , but he avoided due to insufficient establishing personal for the deaths. Only minor figures, such as Bert and James Voelker, were found guilty, with later securing release on retrial. On August 3, 1926, additional charges of illegal importation, , and were filed, each carrying potential sentences of up to seven years. These proceedings underscored the evidentiary hurdles in prosecuting Prohibition-era suppliers, where indirect distribution chains obscured direct responsibility. In 1928, Perri was convicted of stemming from false testimony before a investigating liquor trafficking. He received a six-month sentence but served only five months, marking his sole pre-World War II incarceration. The conviction arose from discrepancies in statements about alcohol sales, following a arrangement that dropped related charges against his associate Bessie Starkman. By 1930, post-Prohibition enforcement persisted, leading to Perri's on August 2 for illegal possession of 10 U.S. gallons of alongside Mike Serge. Both were acquitted just nine days later, highlighting ongoing difficulties in securing convictions against Perri's operations amid claims of alibis and procedural challenges. Throughout , Hamilton police intensified scrutiny on Perri's activities, including dens, but repeated yielded few successful prosecutions, reflecting inconsistent governmental application of and laws.

World War II Internment

In June 1940, shortly after Italy's declaration of war on the Allied powers, Rocco Perri was arrested under Canada's War Measures Act as an "enemy alien" due to his Italian birth and immigrant status, despite lacking any documented ties to fascism or Axis activities. The Act, invoked by the government to authorize broad security measures without trial, enabled authorities including RCMP officer Frank Zaneth—who had long pursued Perri unsuccessfully through criminal channels—to detain him preemptively, bypassing evidentiary hurdles in prior bootlegging cases. Perri's brother Mike was similarly interned, reflecting a policy that targeted over 600 Italian Canadians, often on vague suspicions of disloyalty rooted in ethnic profiling rather than specific threats. Perri was held primarily at Camp Petawawa in , a military facility repurposed for civilian , where conditions included barbed-wire enclosures, military oversight, and restrictions on movement and communication, though internees faced no systematic abuse beyond isolation from family and business. This wartime confinement marked an ironic culmination for Perri, who had evaded violent reprisals and legal convictions for decades through savvy networks; the policy's blunt application inadvertently neutralized his influence without proving criminality, allowing rivals like the emerging Papalia faction to consolidate control in Hamilton's underworld during his absence. Such overreach echoed Prohibition-era dynamics, where federal interventions disrupted immigrant communities' economic adaptations—here, substituting ethnic suspicion for , with causal effects amplifying distrust among toward state institutions long after the war. Perri remained interned for over three years until his release on October 17, 1943, amid shifting wartime priorities and reviews of non-dangerous detainees, though no public petitions explicitly highlighting his non-violent record are recorded in primary accounts. The internment's empirical basis—heritage over evidence—highlighted policy flaws, as subsequent inquiries revealed most Italian detainees posed no security risk, underscoring how powers, when decoupled from individualized threat assessments, generated disproportionate harms to minority groups without enhancing national defense.

Personal Relationships and Public Image

Family and Romantic Partnerships

Perri's earliest documented romantic involvement was an affair with Sarah Olive beginning in 1918, which produced two daughters: Autumn, born in 1919, and Catherine, born in 1921. Despite Routledge's repeated requests for , Perri refused, maintaining his relationship with Bessie Starkman; Routledge died by suicide on July 3, 1922, after a falsely informed her that Perri had wed Starkman. Perri's primary long-term partnership was with Bessie Starkman, a Polish-Jewish immigrant whom he met around 1912 while boarding at her home; Starkman abandoned her husband Harry Tobin and their two infant daughters, Lillian and Gertrude, to join Perri full-time by 1917. The couple cohabited as common-law spouses without formal marriage, relocating from to and later to Hamilton in the early , where they maintained a family-like household incorporating Starkman's daughters. Starkman was murdered by in their Hamilton garage on August 13, 1930; her estate, valued at approximately $12,000, passed to Perri and her daughters Lillian Shime and Gertrude Maidenberg. Following Starkman's death, Perri entered no known subsequent marriages or equivalent long-term romantic partnerships, prioritizing personal autonomy amid ongoing legal scrutiny. His own daughters from received limited direct involvement from him, and after his disappearance, estate claims surfaced among extended relatives rather than , underscoring the absence of a formalized nuclear unit.

Lifestyle and Avoidance of Direct Violence

Perri resided in a prominent mansion on South in , where he cultivated an image of affluence amid the era's underworld. The property served as a hub for his operations and social engagements, reflecting his accumulation of wealth from bootlegging, estimated at handling up to 1,000 cases of liquor on peak days. He maintained a that catered to high-profile clientele, emphasizing quality merchandise—"only the best liquor"—to sustain elite patronage and business stability. Perri publicly espoused a non-violent personal code, asserting in a 1924 Toronto Star interview amid rising gangland killings: "While I admit that I am king of the bootleggers, I can assure you that I have nothing to do with these deaths." He delegated enforcement to subordinates, prioritizing logistical innovations like souped-up vehicles and boats for over hands-on brutality, and claimed zero direct murders attributed to himself. This approach aligned with a calculated of , where of police and politicians supplemented muscle to resolve disputes. Critics, including law enforcement contemporaries, contested this detachment, linking Perri indirectly to the era's violence through his command of enforcers during Hamilton's turf conflicts, where rivals were eliminated to protect routes. Despite surviving multiple attempts—such as shotgun ambushes in 1938—his survival into the 1940s contrasted with shorter-lived U.S. counterparts like , whose impulsive personal killings invited retaliation and downfall. Perri's longevity stemmed from diplomatic maneuvering and rational prioritization of profit over vendettas, enabling dominance in southern Ontario's rackets without the self-destructive prevalent south of the border.

Disappearance and Unresolved Mysteries

Circumstances of Vanishing

On April 23, 1944, Rocco Perri visited relatives in Hamilton's north end, where he shared a meal before complaining of a and deciding to take a walk to alleviate it. He donned a brown and was last seen walking away from the residence, after which he vanished without trace. Perri's cousin reported the disappearance to Hamilton police on April 25, 1944, prompting an investigation that yielded no body, demands, or eyewitness accounts. Authorities conducted searches but described their efforts as brief and superficial, ultimately deeming the case inconclusive and considering possibilities such as or without sufficient evidence to pursue further. This event occurred amid Perri's post-World War II internment decline, marked by reduced criminal influence after Prohibition's end, accumulating debts from failed ventures, and deteriorating health that had limited his activities in the preceding years.

Prominent Theories and Evidence

The predominant hypothesis regarding Rocco Perri's fate posits that he was murdered by associates or rivals, likely due to mounting debts, territorial disputes, or retribution for prior betrayals in the . Perri had accrued significant financial obligations following his release from in 1943, including loans from figures connected to the , which controlled cross-border smuggling routes and viewed his operations as encroaching. Threats against Perri intensified in the months before his disappearance, including warnings from local enforcers like and , who were rising in Hamilton's criminal hierarchy and had motives tied to unpaid protection money. A specific claim emerged in 1992 when historian Antonio Nicaso obtained a letter from Perri's cousin in , dated shortly after the vanishing, alleging that Perri was fitted with concrete shoes and dumped into Burlington Bay—a method aligning with mob disposal practices to eliminate high-profile liabilities without recoverable evidence. No forensic remains have surfaced despite searches of and surrounding waters, consistent with such a disposal but offering no direct corroboration; causal analysis favors this scenario given Perri's history of surviving two attempts in 1937 and the pattern of violence against his associates, including the unsolved 1924 of his wife Bessie Starkman. Alternative theories suggest Perri orchestrated his own escape, leveraging a purported hidden fortune to flee to the , , or , motivated by foreknowledge of a hit. Biographer Trevor Cole, in his 2017 account The Whisky King, argues Perri may have been tipped off about an imminent plot—possibly by a corrupt contact—and relocated under an alias, citing the absence of a body and Perri's demonstrated cunning in evading during . Nicaso has similarly proposed a flight to , shortly after hearing of threats, with one unverified conjecture identifying a "Giuseppe Portolesi" who died of natural causes in New York in as Perri in . These escape narratives on anecdotal reports of Perri's amassed wealth from bootlegging, estimated in the millions adjusted for inflation, but lack substantiation: Canadian Revenue Agency records show no evidence of holdings or large transfers, and archives yield no confirmed sightings or entry documents post-1944. Motives for flight appear plausible given Perri's declining influence amid post-war crackdowns on Italian syndicates, yet the theory's evidentiary void—coupled with the improbability of a 56-year-old with issues sustaining —renders it speculative compared to the documented enmities preceding his last known outing on , 1944. Fringe hypotheses, such as induced by personal impotence or overwhelming debts, have circulated informally but lack primary sourcing or witness accounts, undermined by Perri's resilient persona and absence of a note or body in accessible locations. Overall, verifiable leads tilt toward foul play by criminal elements, as mob retribution aligns with the era's causal dynamics of power consolidation, whereas escape claims rely on without archival or testimonial backing from neutral parties.

Enduring Legacy

Influence on Canadian Underworld

Rocco Perri's operations during the era established the foundational structure for in , positioning him as the founding godfather of the through a network of bootlegging, , and alliances that emphasized business-like expansion over overt violence. His disappearance on April 23, 1944, created a power transition that integrated Hamilton's rackets into the broader influence of Buffalo boss , who assumed control over Ontario's underworld by the mid-1940s, leveraging local lieutenants to maintain continuity in vice operations such as and . This shift debunked notions of a complete collapse in following Perri's absence, as verifiable successors like Antonio Papalia, one of Perri's key lieutenants, assumed leadership in Hamilton, founding a dynasty that persisted until the late 1990s. Perri's model of non-confrontational empire-building—relying on and diversified rackets rather than territorial wars—influenced the operational style of subsequent figures, including the Papalia family, who operated under Magaddino's oversight and expanded into narcotics and labor while inheriting Hamilton's entrenched economy. This continuity fostered economic growth in illicit sectors, with Hamilton remaining a hub for activities that generated millions in unreported revenue through controlled dens and schemes by the 1950s. However, the vacuum left by Perri's exit also precipitated spikes in rival violence, as competing factions, including American interests, vied for dominance, leading to assassinations and turf conflicts that contrasted with Perri's earlier stabilization of the . These dynamics underscored Perri's indirect role in shaping a resilient yet volatile Canadian , where his foundational networks enabled long-term entrenchment despite intermittent disruptions.

Economic and Social Impacts

Perri's bootlegging operations during Ontario's era (1918–1927) generated substantial underground economic activity in Hamilton, fostering an illicit market that employed dozens in , distribution, and related rackets across the Niagara region and . His network, which included a fleet of boats for cross-border alcohol transport and deals with corrupt officials for falsified export permits, amassed personal fortunes estimated at around $1 million annually for Perri and his partner Bessie Starkman at their peak, injecting untraceable wealth into local economies through dens and informal labor. This shadow economy provided opportunities for low-skilled workers, including Italian immigrants, but diverted resources from legal sectors and entrenched dependency on volatile black-market cycles. Socially, Perri's supply chains contributed to crises, exemplified by the July 1926 incident where "bunk hooch"—adulterated traced to his operations—poisoned and killed dozens in , highlighting the risks of unregulated, often in prohibition-driven markets. Such events underscored broader societal costs, including heightened rates and from turf wars, as bootleggers like Perri prioritized volume over quality to meet demand suppressed by legal bans. Perri's rise illustrated Prohibition's policy shortcomings in , where moral suasion failed to curb consumption and instead incentivized the formation of hierarchical crime syndicates capable of evading enforcement through and international ties, as seen in his legal alcohol exports repurposed for U.S. . This entrepreneurial adaptation to regulatory voids—rooted in Perri's immigrant background rather than innate criminality—challenged stereotypes of ethnic predisposition to vice, framing his success as a rational response to artificial scarcities that rewarded organization over compliance. Post-repeal, these syndicates persisted, evolving into narcotics and , demonstrating how prohibition-era figures like Perri entrenched long-term infrastructure.

Modern Reflections and Estate Disputes

In recent biographical works, such as Trevor Cole's 2017 The Whiskey King, Rocco Perri is portrayed as a figure whose criminal empire was primarily a direct response to the created by U.S. (1920–1933) and Ontario's restrictive liquor laws, rather than an inevitable product of innate criminal predisposition; this perspective emphasizes how state-imposed bans on alcohol production and distribution incentivized smuggling networks, benefiting operators like Perri who capitalized on cross-border demand without initial reliance on violence. Similarly, Nicoletta Grassie's 2005 analysis in Rocco Perri: The Story of Canada's Most Notorious Bootlegger underscores Perri's operations as emblematic of policy-induced underground economies, where enforcement failures and public demand sustained bootlegging fortunes estimated in the millions by the 1920s, challenging narratives that attribute solely to immigrant cultural factors. These reassessments highlight causal links between legislative prohibitions and the emergence of figures like Perri, who amassed wealth through fleets involving up to 50 vessels, rather than portraying his activities as detached from broader regulatory missteps. Estate disputes have persisted into the , fueled by claims of hidden assets from Perri's Prohibition-era gains. In 2018, descendants pursued legal action in courts to reclaim alleged U.S. holdings purportedly valued at millions, accusing Canadian authorities of withholding records or seizing properties post-disappearance; however, the maintained no verifiable documentation of such a fortune exists in public or seized records. Earlier efforts, including a 2012 probe by Paul Wilson, sought Perri's unprobated will and rumored offshore accounts, estimating potential s from bootlegging proceeds hidden in safe deposit boxes or under aliases, though no distributions have materialized due to lack of concrete evidence. These claims remain unresolved, as Perri left no formal will and his assets were reportedly liquidated or concealed amid wartime scrutiny, complicating under 's intestacy laws. Despite intermittent searches and speculation, no physical remains of Perri have been located since his April 23, 1944, disappearance from a Hamilton residence, with theories of burial in or escape abroad unverified after decades of inquiries by police and . The absence of a —required for estate finalization—has perpetuated legal limbo, sustaining true-crime fascination through podcasts, documentaries, and local lore without forensic closure. This enduring ambiguity underscores how Perri's legacy interrogates official accounts of "" as primarily a of prohibitionist policies that birthed black markets, rather than exogenous threats, with empirical patterns showing similar syndicates dissolving post-repeal in jurisdictions that legalized alcohol distribution.

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  39. https://quillandquire.com/review/rocco-perri-the-story-of-canada-s-most-notorious-bootlegger/
  40. https://therealdeal.com/new-york/2018/08/12/family-of-1920s-mobster-and-bootlegger-searches-for-lost-real-estate-fortune/
  41. https://www.cbc.ca/news/canada/hamilton/talk/paul-wilson-lawyer-chases-will-of-hamilton-s-biggest-mobster-1.1136050
  42. https://www.cbc.ca/news/canada/hamilton/talk/paul-wilson-hamilton-mobster-graces-her-mantel-and-virgin-mary-too-1.1200347
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