Unseating a president is never easy, and Jefferson decided he needed a little "push" in his run against Adams. So Jefferson hired James Callender, a pamphleteer and journalist with a reputation for being a "scandalmonger." Over half of all internet comments involve disparaging the size of a man's equipment, and you'll be happy to hear the same was true of presidential politics in 1800. In a 183-page anti-Adams pamphlet (the equivalent of a mid-length Twitter rant), Callender described the president as "a hideous hermaphroditical character which has neither the force and firmness of a man, nor the gentleness and sensibility of a woman." Since Adams' Sedition Act had recently made it illegal to diss the president, that little burn earned Callender nine months in jail.
It worked, though. Jefferson won the 1800 election, even if his victory soon became a lesson in remembering who got you where you are. Callender wanted a job in Jefferson's administration, but ol' TJ was not about to elevate a hack writer that high in society. So Callender turned his trolling back at the new president. On top of sharing letters which proved they'd colluded during the election, Callender spread the rumor that Jefferson slept with his slaves, and fathered children with one named Sally Hemings. You know, that little centuries-long scandal. Jefferson was furious, but hey, at least the ensuing controversy inspired possibly the greatest portrait in history: