When the Third Time is NOT the Charm

In American political history, only two presidential candidates have ever received a major party nomination on three occasions and lost every time: Henry Clay, who ran and lost the elections of 1824, 1832 and 1844 and William Jennings Bryan, who lost the election of 1896, 1900 and 1908. 

Both men were tenacious firebrands, fierce orators and accomplished in their respective political careers. Yet, perhaps their most apparent similarity was that they were both opportunists, whose pursuit of the Presidency bordered on the pathological. How else could each have come so close to the White House three times?

Although they were of two different eras, Bryan revered Henry Clay and featured a portrait of him in the living room of his home. Bryan, who lost to William McKinley twice in 1896 and 1900, would run for his third time in 1908 against Teddy Roosevelt's hand picked successor, William Howard Taft -- the below cartoon from '08 depicts his yearning for the Presidency as TR interrupts Bryan's daydream.