Thomas Jefferson

A scientist, an Enlightenment philosopher, and one of the most accomplished—and complicated—personalities in American history, Thomas Jefferson authored the Declaration of Independence and served his country as statesman, diplomat, and president. In 1803, during his first term as president, he orchestrated the Louisiana Purchase, which doubled the size of the United States and established the nation as a continental power. This expansion, more than any other, forced politicians to confront the U.S. economy’s dependence on slavery. Jefferson, who enslaved more than six hundred African Americans in his adult life, wrestled with the rift between his philosophical beliefs and his reliance on bondage.

Gilbert Stuart was not only early America's most admired portraitist but also an eccentric known for procrastinating. After sitting for this portrait in 1805, Jefferson had to wait sixteen years before it was finally delivered.