Later Political Career
In the 1800 presidential election, Pinckney was the Federalist candidate for vice-president, running with the incumbent president, John Adams. They were defeated by the Democratic-Republicans Thomas Jefferson (who became president) and Aaron Burr (who became vice president). In 1804, the Federalist Party nominated Pinckney to run for the presidency against Jefferson. Jefferson, who was very popular due to the acquisition of the Louisiana Purchase and booming trade defeated Pinckney in a landslide. Pinckney won only 27.2% of the popular vote and carried only two states. In 1808 he was again the Federalist nominee for president, running against Jefferson's Secretary of State, James Madison. Pinckney did not fare much better against Madison, carrying only five states and winning 32.4% of the popular vote. From 1805 until his death, Pinckney was president-general of the Society of the Cincinnati. Pinckney died on August 16, 1825 and was buried in St. Michael's Churchyard in Charleston, South Carolina. His tombstone reads, "One of the founders of the American Republic. In war he was a companion in arms and friend of Washington. In peace he enjoyed his unchanging confidence."
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