Kennedy and Capone, Esposito, and Detroit’s Purple Gang in the 1920s
c. 2018 Ellen NicKenzie Lawson Ph.D.
[Chapter Five of unpublished manuscript Kennedy and Prohibition]
Stories about Joseph Kennedy meeting “Diamond” Joe Esposito and Al Capone in Chicago, and fearing Detroit’s Purple Gang, appear in underworld histories of the Prohibition era, but are usually not acknowledged in biographies of Kennedy.
The Purple Gang
Canadian liquor smuggled to the Midwest was usually taken across the mile-wide Detroit River from Windsor to Detroit. Along with Vancouver to the west and Toronto to the east, Windsor was a major Canadian liquor depot during Prohibition. More liquor reputedly was smuggled across the Detroit River than any other entry point. In the early twenties, no one controlled the river but eventually a group called the “Little Jewish Navy” operated there controlled by the Purple Gang.
This little-known gang began before Prohibition with Jewish teens stealing from merchants in their neighborhood. In 1920, they began selling refined sugar to bootleggers and were called the “Oakland Sugar House Gang.” When they began following bootleggers to stills and demanding “protection” money or hijacking the liquor, they became known as the Purples. This was probably because at first they wore purple jerseys in imitation of a boxer they admired who worked out in a local gym in a purple jersey. Their name has also been traced to a gang member named Sammy Purple Cohen or to the possibility they threw purple dye on clean laundry when trying to intimidate laundries into buying their protection.
In 1926, the Purples made Detroit headlines for the “Milaflores Apartment Massacre,” the murder of Italians from St. Louis friendly with Capone in Chicago. The Italians were trying to take over control of Detroit as the crucial entry for Canadian liquor. Before this or afterward, Capone acknowledged the Purple Gang as agents and paid them. The Purple Gang prevailed because it had political and police protection in Detroit and a lawyer named Edward Kennedy, Jr. defended them.
“Diamond” Joe Esposito and Kennedy?
The Purple Gang has also been connected to Boston’s Joseph Kennedy during Prohibition according to a biography of Sam Giancana, an unimportant teenager in the 1920s who later ran the Chicago “Outfit” in the 1950s and 60s. According to Giancana recalling this story years later, the Purple Gang had a contract out on Kennedy during Prohibition for smuggling Canadian liquor through Detroit without their consent. The authors of the biography, both in the Giancana family, admit in the preface that they wrote the biography to entertain and knew this might offend historians but also no research could equal the personal of a participant like Sam Giancana himself.” This written account of the death contract on Joseph Kennedy deserves scrutiny even though the authors refuse to do this because it has been repeated as true in several books as true, even one written for American middle school children, and because it supports the long view that Kennedy was dealing with the Chicago Underworld for decades before the West Virginia Primary and Presidential Elections of 1960.
Sam “Mooney” Giancana is the only original source for this story. He was an eye-witness, but he also had only an elementary level education, English was his second language, and he was an observer, not a participant. In addition, he recalled the story decades after the fact. All of these could mitigate the truthfulness of the story.
At the time, young Giancana was in Esposito’s 42 Gang in Chicago. Giancana recalled that This is what Giancana recalled that the Purple gang had put out a contract on Kennedy’s life and Kennedy went to Chicago to beg Esposito to use his influence with the Purples to end the contract. Paul Ricca and Murray Humphrey, both major leaders in the Chicago “Outfit” after Capone’s era were present at the Kennedy-Esposito meeting. When Esposito agreed to phone Detroit, Kennedy became, according to Giancana, in Chicago’s debt forever after that.1 In a later passage, Giancana refers again to this event saying Chicago gangsters saved “the arrogant mick’s ass.”
This “mick” according to Giancana was Harvard-educated Joseph Kennedy, assistant manager during the recent World war of 22,000 workers at a ship-building concern south of Boston, and a stock broker who had already made almost a million dollars on the stock market using insider knowledge, then entirely legal.
Giancana’s biographers gives no date for this Esposito-Kennedy meeting. As Esposito was shot and killed in front of his Chicago home in March 1928, while wearing his trademark $5000 diamond belt buckle, the date for this meeting was before then. Who was this man named Esposito and why would Kennedy have gone to Chicago t to resolve a deadly threat from Detroit?
Esposito, 48 when killed, was an Italian immigrant, owner of Bella Napoli Restaurant on 850 Halsted Street, and leader of the 42 Gang which he took into into smuggling and bootlegging in 1920. He was also a Republican ward boss and, according to a grandson, Esposito met with Republican President Calvin Coolidge in the twenties and asked for federal “protection” for bootleggers Samuel Bronfman, Joe Renfield, and Joe Kennedy. Ricca and Humphrey were Esposito’s top lieutenants before moving over to join Capone. Ricca, head waiter at Esposito’s restaurant, met Capone who sometimes dined there, and Capone was best man at Ricca’s wedding in 1927. Murray Humphrey, “the Brainy Hood” was American-born of Welsh parents and good at schmoozing with and corrupting Chicago politicians and specialized in labor racketeering. Humphrey moved over from Esposito to Capone in 1926.
Given Esposito’s death, Ricca’s wedding, and the fact Humphrey was with Capone in 1926 narrows the Kennedy-Esposito meeting to before or during 1926. As the Purple Gang did not control Detroit until 1923 or 1924, the date of the meeting was probably sometime between 1924 and 1926. Esposito was then in his 40s, his two lieutenants in their 20s, and Giancana in his late teens, but no innocent as he was arrested 20 times before age 18 and charged with murder in 1926, escaping a trial when the chief witness was murdered. These were tough guys and, with over 100 murders in Cook County in 1926 and 1927, a “hit” on Kennedy in Chicago on behalf of a Detroit gang was not beyond the realm of possibility.
But could this have been someone other than Joseph Kennedy of Boston? Could it have been a Canadian liquor dealer named Daniel Joseph Kennedy who went by his middle name? This Joe Kennedy, in his fifties during Prohibition, was second generation Irish, and lived in Dublin for two years while dealing in European liquor for the American market at the turn of the 20th century. He would have seemed more like a “mick” than Joseph Kennedy, Harvard ’22? This D. Joseph Kennedy founded Joseph Kennedy Limited in Vancouver B.C. c. 1920 and lived in Chicago in the 1890s.. Historians have known for decades about the Joseph Kennedy Ltd. Warehouse in Canada but have mistakenly assumed it was owned by the Boston Kennedy when, in fact, it was founded by D. Joseph Kennedy and sold by him in the mid-twenties to the Riefel family who also owned the British Columbia Brewing Company and the British Columbia Distillery Company but kept the name. Thanks to research done by Jason Vanderhill of Vancouver, more is now known about the Canadian Kennedy, liquor salesman and creator of several drinks named after himself. Vanderhill though was puzzled by this Kennedy sold out to the Reifels. Could it have been because he was the target of the Purple Gang and sufficiently frightened into returning to Vancouver and selling out? 2
Maybe the man begging for his life in Chicago in the twenties was not even named Kennedy and Giancana misheard from the sidelines? Could the man have been the Detroit agent for Joseph Kennedy Ltd. ? A man named Charles A. Savard who lived in Detroit, and was definitely employed by the Reifiels from 1926 on? The Canadian government charged Savard with doing $5 million dollars worth of business for that company in 1926. Surely Savard would have run afoul of the Purples if he refused to make payments to them to get this liquor across the Detroit River and through Detroit?In 1928, Canada charged Savard and 20 others, including Hiram Hatch of the new Hiram Walker Distillery in Windsor, as Canadian “rum” dealers.
Kennedy and Capone?
Another Chicago story involving a Kennedy, again assumed to be about Boston’s Kennedy, is about a 1926 meeting with Al Capone. In this story Kennedy sat down to a spaghetti dinner with Capone at his home in Cicero. The two were overheard by piano tuner John Kohlert preparing Capone’s grand piano for a jazz session. Kohlert was a fly on the wall like Giancana earlier. Kohlert claimed he heard the two men talking about landing liquor on Mackinac Island in Lake Michigan. This would have meant by-passing Windsor and Detroit’s Purple Gang. (Another version is that Kohlert actually ate spaghetti with Kennedy and Capone.)
Maybe this was not the Boston Kennedy but again, as per the Giancana story, D. Joseph Kennedy or Agent Savard for Kennedy Ltd. ? Or could it have been Purple gang lawyer Edward Kennedy Jr. working out an agreement between Capone and Detroit? Supposedly Capone visited Detroit in 1927 to set up his own franchise but was forced to deal with the Purple Gang which was at its height of power in the city.
Another Chicago Rumor
Another rumor about Chicago and Kennedy, not as strong as the Esposito or Capone stories, is that Kennedy had a speakeasy in the new Merchandise Mart built in Chicago in 1930. One source for this is the 1980 memoir of reputable New York Times reporter Harrison Salisbury, then a young reporter for UP in Chicago covering the Capone tax evasion trials of the early 30s. Salisbury stated that Kennedy then owned the Merchandise Mart. But Kennedy did not buy the Mart until 1945, over a decade after Prohibition’s end. Salisbury, a registered Republican who disliked the Kennedys, may have been inclined to believe the worst, e.g. this rumor, without checking it out. Or maybe D. Joseph Kennedy who owned a barroom in the Mart? Or Joseph Kennedy Ltd. Under Savard ran a speakeasy in the new Mart?
In these accounts of Kennedy in Chicago, it actually could have been any number of other men named Joseph Kennedy as 18 lived in Detroit and more than forty lived in Chicago during Prohibition. Any one of these adults could have been bootlegging and wanted to make a deal with Capone or escape the wrath of the Purple Gang?
The Purple Gang did not survive Prohibition. The Licavolis of St. Louis eventually took over Detroit in the 30s, as well as Toledo, Akron, and Cleveland. They worked with the Capone gang in Chicago, but the name survived and was sometimes attached to the Licavolis, perhaps too colorful a name to die. These Licavolis, a.k.a. the Purples, had a contract out on a young man in Toledo named Jack Kennedy shot in 1932. But this Kennedy would have been too young to have been seeking help from Esposito in Chicago in 1926, as he would have been only 17. Was he in business in Toledo with his father and did the father journey to Chicago to beg for help from Esposito? Yonnie Licavolo was convicted of murdering this Kennedy and sent to the Ohio Penitentiary for thirty years. Despite being jailed, he managed to continue running mobs in Detroit, Toledo, and Cleveland.
Gangster Moe Dalitz, who had Prohibition-era ties to the Purples as a bootlegger and who later ran the Desert Inn in Las vegas said his supplier during Prohibition was Kennedy, but again this could have been D. Joseph Kennedy or Savard of Kennedy Ltd. . Jimmy Hoffa, a labor leader for Teamsters Local No. 299 in Detroit in the 1930s, relied on the Licavolis, a.k.a. Purples, to protect picketing union members from company thugs. Hoffa’s nemesis in the 60s, before his disappearance, was U.S. Attorney General Robert Kennedy.
The Reifels, father and son, who owned Joseph Kennedy Ltd. from the mid-twenties were arrested when they visited the United States after Prohibition and charged $17,250,000 for failing to pay taxes on bootlegging income. The U.S. government settled for $500,000 and the Reifels forfeited an additional $200,000 paid when they posted bail and returned to Canada. Somehow these American officials never confused the owners of Joseph Kennedy Ltd. with D. Joseph Kennedy much less Joseph Patrick Kennedy of Boston, New York, and D.C., living three thousand miles distant.
Sam (Mooney) Giancana, protege of Ricca, boss of the Chicago “Outfit, in 1957 was questioned by Robert Kennedy for the McClellan Committee investigating organized crime. Then, as Attorney General, Kennedy had Giancana’s movements monitored and his phone and rooms bugged by the F.B.I. Giancana resented this as it made his personal life, functioning as a boss, impossible. He felt Joseph Kennedy, father of the president, “owed” him given his donation to the West Virginia primary in the spring of 1960 and, felt doubly betrayed because he convinced himself Kennedy’s obligation to the Chicago Outfit dated to Prohibition.
In retrospect, the words of Judge Abraham Lincoln Marovitz, a friend of Mayor Richard Daley in Chicago and a U.S. District Judge appointed in 1963 by President Kennedy, are worth considering. Marovitz, a lawyer for gangsters before his appointment as judge, should have known the Esposito and Capone stories if they were about Joseph Patrick Kennedy. But it is worth noting that when he was interviewed six decades after Prohibition, in his 90s, the judge did not say Kennedy bootlegged in Chicago. He said Kennedy was bootlegging “out there in New England.” 3 [Italics added]