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Joseph multiplied his fortune through stock speculation; he was a master of the stock pool, a then-legal arrangement in which a few traders conspired to inflate a stock's price, selling just before the bubble burst. Some attribute these market manipulations as being in part responsible for the Stock Market Crash of 1929 which triggered the Great Depression. Ironically, a short time later he was appointed the first chairman of the Securities and Exchange Commission, where he oversaw the banning of these practices. During Prohibition, Joseph was reputedly a bootleger, selling for several British alcohol distillers. He had a large inventory that he sold for a gain of millions of dollars when Prohibition was repealed in 1933. He invested these gains in residential and commercial real estate, the Merchandise Emporium in Chicago and Hialeah Race Track.

Joseph's first active involvement in a national political campaign occurred during Franklin D. Roosevelt's bid for the Presidency. He donated, loaned, and raised a substantial amount of money for FDR's presidential campaign. President Franklin D. Roosevelt rewarded him, with an appointment as the inaugural Chairman of Securities and Exchange Commission. Some attribute a quote to the then President that he had "sent a thief to catch a thief."

http://www.reference.com/browse/wiki/Joseph_P._Kennedy,_Sr.