While completion of a college credential is a critical step toward increasing one’s viability in today’s labor market, only about 40 percent of Americans earn an associate’s or bachelor’s degree by age 27. In 2011, the Kresge Foundation launched the National Talent Dividend $1 Million Prize Competition. Leaders of the initiative posited that a city’s per capita income would rise as the number of degree holders rose, and the contest promised to award $1 million to the city with the greatest proportional increase in its college degree completion over a four-year period. Fifty-seven of the nation’s most populous cities participated in the competition; the winner was Akron, Ohio, which increased its degree attainment by 20 percent. This case study examines the efforts of six of the top cities in the competition (Akron; Columbia, South Carolina; Omaha, Nebraska; Orlando, Florida; Portland, Oregon; and Richmond, Virginia) in an effort to build a set of hypotheses around the activities that may have helped these cities increase degree attainment.