Cincinnatus’s willing withdrawal from power as dictator twice during the Roman Republic has inspired many. Our first president, George Washington, is considered to be the “American Cincinnatus.” To Lord Byron, Washington was the “Cincinnatus of the West,” in his “Ode to Napoleon,” written upon Napoleon’s defeat in 1814 (verse 19, line 6). But others (e.g., the American Revolutionary General John Starks, Andrew Jackson, Calvin Coolidge, Harry Truman, and Bob Dole) have also been compared with Cincinnatus. Twenty-first-century presidential candidate Tom Steyer nicknamed his supporters “Team Cincinnatus” in 2015 while contemplating a campaign to replace the retiring U.S. Senator from California, Barbara Boxer. After studying the original sources, this case will allow students to examine our ideas about public leadership. Is “rule by amateurs” a good idea? Does character and conduct in and out of power matter? Have our ideas about such positions been sought out of a sense of duty (and not self-serving pleasure)? Has the basis of these ideas changed?