Joe Kennedy : Smuggler or Bootlegger?

Joe Kennedy: Smuggler or Bootlegger?

c. Ellen NicKenzie Lawson Ph.D.

Joe Kennedy, father of U.S. President Kennedy, was rumored to have made money smuggling and/or bootlegging during Prohibition. The rumors were based on  “facts.”

The Word of Bootleggers and Smugglers on Joseph Kennedy

Decades after Prohibition, Underworld figures like gangsters Meyer Lansky and Frank Costello fed the rumor by speaking up in public that they worked with Kennedy to bring in liquor from Rum Row or to transport it on land. Owney Madden, another gangster bootlegger, confided privately to his lawyer that he served Kennedy’s liquor in his Prohibition era night clubs in New York City, which would have included the Cotton Club.

The author of Paddy-Whacked: Untold Story of the Irish Gangster suggests Kennedy may have financed shipments to Rum Row from Europe but not smuggled these shipments to land. Instead, he could have re-sold it to others who then smuggled it in (e.g. Costello?) According to the Dark Side of Camelot , Kennedy smuggled liquor to Long Island’s Sag Harbor. But maybe this was Costello bringing in liquor purchased on Rum Row from Kennedy?  Lansky in the 1970s also said Joe Kennedy disliked him because Kennedy thought he (Lansky)  once hijacked a liquor shipment of his (Kennedy’s) from Boston to New York City during Prohibition. (See Mafia Encyclopedia.)

Any evidence that Joseph Kennedy was indeed a bootlegger or smuggler?

A close study of Coast Guard records at the National Archives shows  some Kennedys smuggled and bootlegged in New York City. But not the famous  Massachusetts Kennedys. These smugglers were Jack and Edwin Kennedy who operated a restaurant in midtown Manhattan. This came to light when the body of Edwin, 25, was found floating in the Hudson River near 84th Street in the fall of 1927. His brother could not explain this death. His widow insisted her husband was murdered by bootleggers. Did Lansky, Madden, and Costello, recalling Prohibition decades afterward, confuse these New York Kennedys with Joe Kennedy who did not have a national reputation in politics until the 1930s when he was the first chairman of the Security and Exchange Commission and then Ambassador to Great Britain? Or did these gangsters believe that the Edwin and Jack Kennedy in the restaurant business in Manhattan were distant relations working for him? It is true that Boston’s Joe Kennedy lived in New York City and worked there as an investment banker after 1926. If these were relatives, did they front for him?

At his tenth Harvard class reunion on Cape Cod in 1922, Joe Kennedy supplied the liquor. Letters among his papers at the John F. Kennedy library document this. Kennedy had access to his father’s legal pre-Prohibition stock of liquor. (His father was a liquor importer to Boston before Prohibition.)  Contrary to modern understanding, drinking was not illegal under the 18th Amendment, only its production, transportation, and sale were illegal. (This is a key difference with current federal marijuana law which punishes users.) Kennedy actually sold the legal liquor, at cost, for the reunion, which would  violate the 18th Amendment, making this an instance of small-time bootlegging. He also sold the liquor left-over from the reunion to a friend at cost. But again, even though he made no profit, this would have been illegal and an instance of small time bootlegging.

Coast Guard records of  boats  seized with liquor during Prohibition include one in Nantucket Sound which had a nautical chart aboard showing liquor drop-offs near Hyannisport where the Kennedy family had a new summer home after 1926. This does not prove Kennedy was a smuggler or bootlegger —only that he probably was a scofflaw like millions of  fellow Americans. And actually Kennedy was a non-drinker, so any liquor he acquired in this way would have been for his guests.

Medicinal liquor was Legal during Prohibition

During Prohibition, medicinal liquor could be acquired with a doctor’s prescription. This was a common way to obtain liquor as the permits were easily acquired and/or faked. In the final year of Prohibition, Joe Kennedy obtained a federal permit to bring in a significant amount of medicinal liquor according to his own admission. (He may have obtained such permits earlier too but most Prohibition permit applications, eventually stored at the National Archives, were destroyed in the early 1950s.) In this case, he may have used existing smugglers’ vessels to bring in this medicinal liquor. Frank Costello’s operation had many trans-Atlantic ships and this may have been when Costello assisted Kennedy.  This would have been entirely legal.  When repeal happened, in December 1933, this medicinal liquor could be freely sold and  would have fetched a very good price from a thirsty public. Is this what Costello meant when, in his final days, he told author Peter Maas, that he helped make Joe Kennedy rich during Prohibition? Technically it could have been true.

More historical background on Joseph Kennedy and his father.

What is the Kennedy family ‘s history with regard to liquor? Before Prohibition, Joe Kennedy’s father imported whiskey to Boston and owned saloons in Boston. In 1934, the year after Prohibition, the son founded Somerset Limited and imported quality liquor, mostly whiskey, for a decade, reputedly making a profit in the millions.

In the 1920s he made millions with insider trading and shorting stocks when this was legal. The stock market in the 1920s was as wild and untamed as the wild west. When President Roosevelt sought to rein in the excesses of Wall Street with the new Security and Exchange Commission c. 1934, he appointed Kennedy as chair because he knew Kennedy, better than most, understood firsthand through personal experience how the market was manipulated by insiders.

In 1946, he  sold this legal business to former East Coast bootleggers Joe Reinfeld and Abner “Longy” Zwillman. Reinfeld spent much of Prohibition in St. Pierre and Miquelon, the French islands in the North Atlantic which served as way stations of smuggled liquor. Reinfeld’s specialty then was whiskey. Doing business with these two may have tainted Kennedy’s reputation, as in “birds of a feather flock together”?

History of the Rumors

The continuing rumors of Joe Kennedy smuggling and bootlegging may be an instance of the American public wanting to fill in the historical gap (1920-33) by assuming historical continuity between the Pre-Prohibition family business in Boston and the Post-Prohibition Somerset Ltd.

But history isn’t always or neatly continuous. These rumors are  a simple explanation for the Kennedy wealth, first made in the 1920s> But the truth is more complex. Kennedy manipulated stocks, in the days before regulation by the Security and Exchange Commission. He also owned a bank, a chain of new England movie theaters, and investments in Hollywood  films. All this in the 1920s.

According to hearsay reported later by Gore Vidal in his memoirs, step-brother to Jackie Kennedy, Franks Costello and Joe Kennedy lunched together weekly in New York City up to the time of Kennedy’s stroke, during the first year of his son’s presidential term. Lunching  like this with Costello, a former bootleg gangster, may have further tainted Joe Kennedy’s  public reputation, even though this was almost three decades after Prohibition. On the other hand, Gore Vidal was no fan of Joe Kennedy.

Joe Kennedy died in 1969.

Rumors expand in the 70s and after.

In  1972,  gangster  Frank Costello said in public that he helped make Kennedy rich during Prohibition. Then the first of the Godfather series came out of Hollywood.  The central character was based on Costello.

Also in the 1970s   a Congressional investigation committee revisited the assassination of JFK. Conspiracy theorists began writing books.

Some argued the Underworld helped Kennedy win the West Virginia primary in 1960 and thus helped elect him. That state was predominantly Protestant and Kennedy was Catholic. The nation had never elected a Catholic as president. Others argued  the Mob influenced the final vote tally in Chicago that determined Kennedy’s narrow win in the presidential election.

According to either theory,  the Underworld wanted to regain its pre-Castro influence in Cuba in gambling. And the election of Kennedy was supposed to help. When this did not happen under JFK’s watch, they felt betrayed. And they felt further betrayed when Attorney General Robert Kennedy started to prosecute Underworld figures. The assassination of JFK stopped this prosecution. When Robert Kennedy decided to run for President in 1968, he too was assassinated, perhaps to stop his being elected and continuing to persecute the Underworld.

These conspiracy theories rest on the assumption that it was Joe Kennedy who made the deals with the Underworld in 1960, either over West Virginia or over Chicago. To argue this, the theorists resurrect the story that their connection to Joe Kennedy was personal and dated back to Prohibition.

These rumors remain alive in 2017.


Perhaps history will show that Joe Kennedy did nothing illegal during Prohibition. That he was a small time bootlegger for his Harvard reunion and for his friends using his family’s legal supply from before Prohibition.  That he imported medicinal liquor in the last year of Prohibition. And nothing more. So far no serious, scholarly biography of Joseph Patrick Kennedy lends credence to him as a major bootlegger or smuggler during Prohibition. But gangster biographies and autobiographies see it differently and rumors are presented as fact.

Perhaps Kennedy was more like brewer Jacob Ruppert? Ruppert’s  pre-Prohibition brewery in Yorkville was forced to shut down from 1920-33 but resumed business immediately after repeal. Just as Patrick Kennedy shut-down his 30 year old Boston liquor importing business in 1920 and his son Joseph resumed the family business of importing liquor in 1933.

Both Kennedy and Ruppert were legitimate  businessmen from ethnic communities (Irish-American and German-American) which opposed Prohibition. New York City bootleggers and smugglers, like Lansky, Costello, Madden, Zwillman, and Reinfeld, were from similar urban ethnic communities — Irish, German, Jewish, and Italian.

These communities sparked the informal, significant, initial resistance  to Prohibition in its very first year. Eventually politicians caught up with the reality of a continued demand for liquor in America and repealed the 18th Amendment.

[ For more, see Smugglers, Bootleggers, and Scofflaws; Prohibition and New York City (SUNY Press, 2013), available in paperback and as an e-book. It is a scholarly work, less than 200 pages, includes narrative, photos, footnotes, bibliography, index, and primary documents. Joe Kennedy, not mentioned in the narrative, is mentioned briefly in footnotes. ]

Other Kennedy rumors  as yet unexamined:

* a Kennedy penthouse in Albany during Prohibition to oversee shipments by land from Montreal?

* Joe Kennedy  at the Boston docks or in Dorchester, Massachusetts, supervising liquor in the 1920s?

*Joe Bonanno’s hearsay about Kennedy  liquor landing at Sag Harbor during Prohibition?

* Madden’s insistence that he served Kennedy liquor in his night clubs?

*Doc Stacher’s story of Lansky’s hijacking of Kennedy trucks/ships in 1927?

Smugglers, Bootleggers, and Scofflaws: Prohibition and New York City is now available on kindle or paperback at both Amazon and Barnes & Noble!