John Adams vs. Thomas Jefferson
In 1800, President John Adams ran for a second term against fellow Founding Father Thomas Jefferson…who was also the vice president serving under Adams at the time. Jefferson went negative quick, and despite being a gifted writer (he wrote the Declaration of Independence, after all), he hired writers to essentially slander his opponent. In one piece of campaign literature, Jefferson called Adams a “hideous hermaphroditical character which has neither the force and firmness of a man, nor the gentleness and sensibility of a woman.” In other words, Jefferson claimed that the president was, in the language of today, transgender (and that that was a very bad thing). Adams responded with leaflets proclaiming that a Jefferson presidency would lead to “your dwellings in flames, female chastity violated…and children writing on the pike.” In the end, voters went with the chance for arson, assault, and murder—Jefferson won.
John Quincy Adams vs. Andrew Jackson
When Adams’ son, John Quincy Adams, ran for his second term in 1828 against Andrew Jackson, the campaign got almost as dirty. Adams’s campaign claimed that Jackson was so dumb (he wasn’t formally educated) that he spelled Europe without the “E” at the beginning, and that his wife, Rachel, was…divorced. That was true, but it was a scandalous, private bit of information. (Adams’s people also called her “a dirty black wench.”) Jackson’s campaign didn’t stoop so low as to go after Adams’s wife, but they did claim that he sold his wife’s lady’s maid to the Czar of Russia for use as a concubine. (Jackson won the election.)
Al Smith vs. Herbert Hoover
In 1928, the Democratic nominee for president was New York governor Al Smith, despite the fact that he was Catholic in a period in which adherents of the religion still faced strong prejudice. Smith faced an uphill climb to the presidency, especially after a bizarre rumor spread (likely from somewhere in the Herbert Hoover-supporting Republican opposition) that while governor, Smith had authorized the building of the Holland Tunnel in New York in part to cover up the construction of a secret, 3,500-mile-long tunnel from the U.S. to the Vatican. The tunnel would then be used, according to the rumor, for the Pope to travel through so as to advise a President Al Smith on all of his decisions. Hoover won the election.