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Old man Kennedy was in banking and importing go whiskey during prohibition
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See other answers for the amount of wealth, remember we are comparing to-day's paper dollars with real dollars of the 1930's. Joe Kennedy was appointed Ambassador to the Court of St. James (England) and used his connections to smuggle booze under diplomatic immunity, avoiding taxes, it was after Prohibition. He is said to have been a founder of Seagrams by also brining in large quantities of Canadian Whiskey. When in Ireland in 1964 I met an old boy who claimed he helped smuggle Irish Whiskey with Joe Kennedy. It came out of Cork, Ireland to Canada. The Kennedy Dynasty was founded on bootlegging.
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He was perhaps one of the richest. Jefferson was doing pretty well in today's dollars. The Kennedy trust was about 200 million 1950 dollars. But LBJ, RMN, The Bushes, are/were about as wealthy or more. His father Joe Kennedy was a banker and was appointed ambassador to England. Therefore his private yacht "the Cutty Sark" had diplomatic immunity as he smuggled tons of scotch whiskey into the US during prohibition. JFK needed large quantities of medical supplies to function as a naval officer during WWII and daddy made sure there was a sufficient stockpile all over the world for him.
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JP Kennedy made his fortune through stock trading and manipulation, real estate, and possibly bootlegging. He was worth about $400 million when JFK became a Senator.
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How wealthy was JFK when he became president and where did his wealth come from?
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