Charles Cotesworth Pinckney, 1804
After two, acrimonious, partisan, edge-of-your seat elections, the US needed someone to ensure a good yawn-inducing
campaign, and Pinckney was the man for the job. Somehow even his impressive record as a general and prisoner of war during the American Revolution wasn’t enough to engender excitement. (Of course it didn't help to be running against the author of the Declaration of Independence.) Even the name: Pinckney. It not only sounds funny, it’s one of those names that after you write it, you have to go back and check your spelling. Which explains why his parents named him Cotesworth. They probably figured, "Hell, his last name is already Pinckney. We can't make it any worse." His running mate was even better: Rufus King of New York. Why can’t we have someone named Rufus in the executive branch? It would not be strictly accurate to say the Federalists “threw” their support behind Pinckney – “tossed” might be closer, or even “dropped.” In 1804, the Federalist Party was too demoralized even to hold a caucus. There were three hot-button issues, or, for the election of 1804, maybe tepid-button issues would be the mot juste. For one, the scandal had broken about Jefferson’s affair with Sally Heming. Social conservatives were scandalized at the thought of their president making mattress magic with a black woman. The thought of a president owning a black woman didn’t seem to trouble them. The other issue was the Louisiana Purchase, which the Federalists argued was unconstitutional. They had a good point, but when the president doubles the size of the country by writing a check, carping about constitutionality seems like sour grapes. The Indians in the new territory might have had something to say about it, but they didn’t show up to vote. The other thing, which seems like it should have been a bigger issue than it turned out to be, was that the Vice President Aaron Burr shot and killed political rival Alexander Hamilton. (Those were the days - don't bother with a smear campaign, just pop a cap in his ass!) Having a murderer as veep didn't make Jefferson's Democratic-Republican Party weaker, if anything, the Democrat-Republicans became unstoppable after this. (In those days, people appreciated a good shot. Dick Cheney was another Vice President who shot someone in office, but that's not the same thing, because he wasn't aiming.) The result was a landslide with Cotesworth and Rufus underneath it.
Result
Thomas Jefferson: 162
Charles Cotesworth Pinckney: 14