This three-stage lesson explores Thomas Jefferson’s plans to create an “Empire of Liberty” and the problems he faced in realizing his goals. In so doing, it considers the state of abolitionism in the early-nineteenth century, westward expansion, and the complications posed by the 1820 Missouri Compromise. What links these subjects are the disconnect created by the seemingly incongruous pairing of Jefferson’s progressive vision for his new nation and the preservation of the institution of slavery. More broadly, the issues explored here could help lead students to consider long term causes of the American Civil War in future lessons.