4 – He Made a Fortune during Prohibition
By 1957, Joseph Kennedy was named as the 12th wealthiest man in America according to Fortune magazine. There is a great deal of speculation, and mystery behind how he made so much money. Joseph joined Hayden, Stone & Co, in 1919. The job paid a handsome salary of $10,000 a year, but this was only the beginning for Kennedy who had already worked as a bank manager at Colombia Trust Bank. His position afforded him the unique opportunity to learn about the stock market and more importantly, to make a lot of money in the process.
For all his stock exchange wizardry, there is a strong suggestion that he earned a significant sum of money by bootlegging liquor during prohibition. He was never caught of course, and most of the evidence against him is anecdotal. For instance, classmate Richard Whalen said that Joseph supplied all the liquor for the class’ tenth reunion in 1922. Raymond Wilkins was another classmate and said Kennedy brought the liquor in via boat.
One of Meyer Lansky’s lieutenants, ‘Doc’ Stacher, said that Joseph was involved in the hijacking of a whiskey shipment that had been sent to Boston from Ireland in 1927. According to Conspiracy in Camelot, Joseph once attempted to ship his bootlegged whiskey through Detroit without the requisite underworld permissions. The Jewish ‘Purple Gang‘ ordered his assassination, but Joseph was able to get his contacts in Chicago to cancel the hit. He was relieved but now owed a debt to Frank Costello. When Costello called in the debt, Joseph refused, and another contract was put on his life.
On this occasion, he escaped with the help of Sam Giancana but he owed the mob boss a significant debt. Costello later told writer Peter Haas that he was in the bootlegging business with Joseph Kennedy. To put Kennedy’s reputation in perspective, Giancana once described him as “one of the biggest crooks who ever lived.” Bootlegging liquor wasn’t the only illegal venture that helped Joseph grow his fortune.