ive heard countless references to joe being a big bootlegger back in the day, which means he was a gangster or racketeer at least. what confuses me is how he got to be the us ambassador to england. wouldnt a background check of been done of him before he could become a politician??!! crazy!!
Joe Kennedy made plenty of legit money in the stock market (the guy was a Harvard graduate) boom of the 1920s, along with some investments in Hollywood studios. He donated a lot of money to Rossevelt's presidential campaign in 1933. After that he was appointed the Chiarmen of the new Securities and Exchange Commission by Roosevelt. He made his reputation doing that because before SEC was set up, the stock market was virtually unregulated and Kennedy made a good pick because he knew the ins-and-outs of Wall St. and made some of the same dirty tricks and swindles that had made himself rich in the 1920s illegal afterwards.
As for the stories of bootlegging, there two things that have led to speculation that he was a bootlegger:
1. He (supposedly) supplied his Harvard class reunion with a truckload of booze after prohibition. But it wasn't uncommon for the ultra-rich (and Kennedy would have been a billionare in today's money) to hoard liquor before prohibition so it wouldn't have been usual for a man like Kennedy to have a stash sitting around. Plus his father had made his money as a saloon keeper and liquor distributor so it probably wouldn't have been hard for him to get a hold the stuff.
2. After prohibition he bought an exclusive franchise with some high-end Enlgish/Scotch Whiskey makers. During prohibition many bootleggers bought directly from British distributors and after prohibition they were able to buy exclusive franchises (like the Bronfmans of Canada-started in bootlegging-ended up legit with Seagrams). Since this contract was worth a lot of money, it fueled the bootlegging rumors even more after prohibition.
Other than the few stories of "I saw Joe Kennedy unloading huge shipments of booze on a cape cod beach", there's really not much proven evidence that Joe Kennedy was involved in bootlegging.
That's not to say that he had criminal contacts, most politicians back then were even more crooked than they are today, for example the Governor of Louisinana, Hughie P. Long, was a mob boss in his own right and Harry Truman was "owned" by Tom Pendergast, who ran Kansas City like a mob boss and had contacts with the Kansas City LCN.