Generations of scholars have searched the Compromise of 1850 for insight into contemporary problems, but history’s lessons are never crystal clear. This historio-graphical essay surveys a century of scholarship and traces the evolution of three distinct schools of thought. Celebratory accounts applaud the preservation of the Union and the triumph of moderate lawmaking over political polarization. Critical accounts, in contrast, condemn the compromise as a cowardly act of appeasement. By emphasizing ironic outcomes and the limits of federal influence, an emerging skeptical interpretation departs from the celebrants and critics alike. Writing in a time of political polarization, pervasive racism, and contests over federal power, modern historians have embraced all three of these interpretations, and debates between their respective proponents will continue. This essay reviews their development in an effort to understand where each interpretation of the Compromise of 1850 might go in the future.