A child of the American Revolution, Henry Clay became a leader as one of the “Great Triumvirate” with John C. Calhoun and Daniel Webster. He ran unsuccessfully for President three times and was passed over for his party’s nomination twice more (ouch). He wasn’t a winner, but he also wasn’t a loser. His skill and relentless ambition put him on the political stage and made him a legend in the House and Senate.

Despite being seemingly cursed from becoming president, Clay didn’t shy away from politics. He was called the “Great Compromiser” because he played a significant role in three landmark compromises: the Missouri Compromise of 1820, the Tariff Compromise of 1833, and the Compromise of 1850.

After his first presidential defeat in 1824, he became Secretary of State (1825-1829) and was nominated to the Supreme Court (which he rejected). After losing the presidency in 1832 to Andrew Jackson, he authored the Compromise Tariff Act. Again in 1844, he was defeated by James K. Polk for the presidency and returned to the Senate.

He didn’t let his losses stop him; instead, they stoked his ambition. He kept vying and kept compromising, becoming an essential force in the 19th century.

Ironically, compromising was most likely his personal political tragedy. His compromising nature and the impression that his principles were negotiable made him unelectable.

Although it doesn’t seem like something he would say, Clay famously remarked, “I’d rather be right than be President.” People rarely remember the Presidents he lost to – Adams, Harrison, Tyler, Taylor, Fillmore (who?), or Pierce- and far more remember Clay. His losses seem more like successes. He failed greatly.