William Jennings Bryan was the Democratic Party's Presidential Nominee in 1896, 1900 and 1908. He lost all three times. William McKinley won in 1896 and 1900, and William Howard Taft won in 1908.
Related trivia : William Jennings Bryan was the youngest person ever to receive presidential electoral votes (36 years & 9 months of age in Jan 1897).
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Buckley ran unsuccessfully for Mayor of New York City in 1965, but I don't believe he ever ran for President.
If he has only run once, he can run for a second term. However, If he has run twice, he cannot become president a third time.
A candidate for vice president of the U.S. does not run separately. The VP candidate is selected as a running mate by the candidate for president, and they run as a team. Back in the beginning, they did run separately: the person with the most votes was president, and the one with the second most was vice president. That system didn't last very long; rivals who'd fought for election didn't usually team up too well. (But it could happen within a party!) A VP can run for president later if the person's party selects him or her as the candidate or if the person decides to run independently.
The Speaker of the house will become President.