William Jennings Bryan, 1900
A rematch of the 1896 election between McKinley and Bryan, only Bryan didn't do quite so well as the first time, partly because the economy was going like gang-busters and partly because the Spanish-American war had been such a hoot. (Bryan did have some competition for the Democratic nomination in the form of the war hero Admiral Dewey. Dewey promised that as president he would be as diligent in following the orders of Congress as he had been at obeying his superiors in the navy. For some reason, this statement did not win him widespread support.) The Spanish-American War was bravely entered by Americans determined to free innocent Cuba from the tyrannical boot of the Spanish Empire. All this took only four months. Bryan protested vociferously against the war, but that was just plain sour grapes. Teddy Roosevelt, who became McKinley's running mate, said it was "a splendid little war," and that's just what it was.1 This was a wonderful patriotic war and had nothing at all to do with controling Cuba's sugar market or grabbing up Guam, the Phillipines, and Puerto Rico. Afterwards, Cuba was governered by Major General Leonard Wood which just goes to show how even a boy growing up in humble New Hampshire can aspire one day to rule the Free Independent Republic of Cuba.
Result
William McKinley: 292
William Jennings Bryan: 155
1. By the way, Bryan's running mate was Adlai Stevenson, grandfather of future presidential loser Adlai Stevenson and great-grandfather of Senator Adlai Stevenson. There really ought to be rules against that sort of thing: John Adams and John Quincy Adams, George Bush and George W Bush - it just muddles things up. If you want to be president, they should make you change your name to something so off-the-wall, it will never show up again, like Farnsworth E Pinkdoodle or Barack Obama.