Although seldom the subject of systematic analysis, congressional deliberations about granting statehood to Alaska and Hawaii constituted one of the definitive legislative disputes of the immediate post–World War II era, engaging partisan and ideological cleavages, the divisive racial/sectional politics of the time, the “Red Scare,” economic interests, and institutional differences between the House and Senate. Although by the mid-1940s strong support for statehood existed among the public and within most of the advocacy community, admission did not occur until the waning days of the Eisenhower administration, nearly 15 years later. This article clarifies the factors associated with the impasse, including changes that occurred over the 1940s and 1950s, continuities with earlier episodes of national expansion, and the implications for current discussions about statehood for the District of Columbia and Puerto Rico.