Joseph P. Kennedy Sr.

Born into East Boston politics on September 6, 1888, Joseph Patrick Kennedy made his first fortune as a stock and commodity investor, then pivoted to reorganizing Hollywood studios in the 1920s - work that helped form RKO and left him rich enough to own Chicago's Merchandise Mart, the largest privately held building in the country. Franklin Roosevelt, whom he'd met during World War I at a Bethlehem Steel shipyard, appointed him the first chairman of the Securities and Exchange Commission in 1934, then sent him to London as Ambassador to the United Kingdom in 1938. When war broke out, Kennedy grew pessimistic about Britain's chances and declared in November 1940, "Democracy is finished in England. It may be here." The controversy forced his resignation. He turned his attention to his nine children with Rose Fitzgerald: John became the 35th president, Robert attorney general and a senator, Ted a senator for nearly half a century, Eunice the founder of Special Olympics. He died November 18, 1969, having built the machine but not lived to see it break.