The majority of the shrinking cities literature focuses solely on instances of population loss and economic decline. This article argues that shrinking cities exist on a spectrum between prosperity and decline. Taking a wider view of population loss, I explore the possibility of prosperous shrinking cities: if they exist, where they exist, and under what conditions shrinking cities can thrive. Examining census place data from the 1980 to 2010 U.S. Census and American Community Surveys, 27 percent of 886 shrinking cities were found to have income levels greater than their surrounding regions. Shrinking and prosperous shrinking cities of all sizes were found across the United States. Shrinkage was most prevalent in the Rust Belt region and prosperous shrinkage in coastal regions. Prosperous shrinking cities were overwhelmingly found within megapolitan regions and were rarely principal cities. Multivariate regression analysis found that both population (city size) and the severity of shrinkage (magnitude of population loss) had no effect on economic prosperity. Talent (location quotient of education) was found to be the strongest predictor of prosperous shrinkage.