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#1. John C. Calhoun

Too Much Man for One Party During the Peloponnesian War, Alcibiades made himself a legend by switching between the Athenian, Spartan, and Persian sides. Calhoun is his American equivalent. In 1824, no presidential candidate won a majority of electoral votes, resulting in John Quincy Adams defeating Andrew Jackson in the House of Representatives. Divisive as the election was, everyone agreed on one thing: South Carolina's John C. Calhoun should be the Vice President. He served under Adams for four years, during which he decided he didn't really see eye to eye with Adams on most things and worked to undermine him. In 1828, it was a Jackson vs. Adams II, only this time Calhoun ran with Jackson. The Jackson/Calhoun ticket breezed to victory, and Calhoun vowed things would be different second go-round; instead of seeking to impede his president, he would strive to tear apart the entire nation. Calhoun championed nullification, whereby if states didn't like a federal law, they could just ignore it (and yes, this did lay the groundwork for secession, the Civil War, and 600,000 dead Americans). Jackson disagreed completely with this policy, leading to the two men becoming estranged. Sadly, by this point Calhoun had run out of presidential candidates to switch his allegiance to and had to resign the vice presidency. For the rest of his life Jackson expressed regret over not executing his former running mate as a traitor, making the backroom conflicts between JFK and LBJ seem pretty trivial.