John C. Calhoun
Though he initially aspired to the nation's highest office, John Calhoun quickly learned to settle for — and even strive to be — number two. He was so intent on the Vice Presidency that before the election of 1824 he offered his support to both John Quincy Adams and Andrew Jackson, who were running against each other. When Adams won, Calhoun filled the office proudly, despite the fact that he was adamantly pro-slavery while Adams was a Northern abolitionist. In fact, he later became known as the "Arch Nullifier" for his ill-conceived proposal to allow any one state to nullify an Act of Congress — effectively an effort to protect slavery in the South. (It was rejected by Northerners and Southerners alike.) When Jackson won the following election, Calhoun continued to serve as Vice President. But he seemed to forget the cardinal rule of the second-most-powerful job in the land — keep your boss happy — and his relationship with Jackson hit the rocks over Calhoun's decision to ostracize a Washington woman accused of adultery. The social boycott so irked Jackson — a fierce defender of the lady in question — that he fired his entire cabinet and booted Calhoun as well.
—By Tiffany Sharples