TIL William Jennings Bryan ran 3 times for the Presidency (1896, 1900, and 1908) and, each time, lost to another William, McKinley in 1896 and 1900 and Taft in 1908

https://en.wikipedia.org/wiki/William_Jennings_Bryan

https://www.reddit.com/r/todayilearned/comments/15itdxy/til_william_jennings_bryan_ran_3_times_for_the/