41. James Monroe
Monroe had his fingerprints all over the U.S.’s development far before he ever became president. In the famous painting that depicts George Washington’s crossing of the Delaware, Monroe is seen holding up the U.S. flag. During Thomas Jefferson’s presidency, Monroe helped negotiate with France over the Louisiana Purchase. Later, Monroe served as Secretary of State in James Madison’s cabinet.
We can’t completely fault Monroe for his lack of smarts. After all, a teenage Monroe dropped out of the College of William & Mary to enlist in the Revolutionary War in 1776. Monroe’s best skill in office was perhaps his ability to delegate duties to his cabinet members. In fact, the Monroe Doctrine (written in 1823) was mostly penned by Monroe’s brainy Secretary of State, John Quincy Adams.
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