Several candidates have run multiple times — William Jennings Bryan in the early 20th century, for example, and former California governor Jerry Brown in 1976, 1980 and 1992. But perhaps the one who best matches Biden’s longevity is Henry Clay, who starting in 1824 ran multiple times over a quarter-century. Biden has also identified with Clay, who, like him was elected to the Senate at 29 and earned a reputation as the “great compromiser.”