8) James Monroe
Pros: The youngest of the Founding Fathers and the last of the so-called Virginia Dynasty to assume the presidency. Served as a teenage officer during the war, fighting in the battles of Brooklyn and Trenton. He is the man holding the flag in the painting of Washington crossing the Delaware. Served as both Secretary of State and Secretary of War for most of the War of 1812. For better or worse, shaped much of Latin America with his Monroe Doctrine, which attempted to keep the fallout from the Napoleonic Wars from reaching this hemisphere. Under his watch, Mississippi, Illinois, Alabama, Maine and Missouri (controversially) all became states.
Cons: Plantation owner (though famously bad at it). Bought Florida from the Spanish.
