This article examines the effects of accomplishments on the career paths of big-city mayors. Using data from 104 cities with populations over 160,000 from 1992 to 2012, this study examines the extent to which performance in economics, crime, and recruiting mega-events affects mayors’ decisions to seek reelection or other offices, or retire. Results indicate those mayors of cities with population growth, a decrease in the crime rate, and that host certain mega-events (presidential nominating conventions) are more likely to seek another office than other mayors. A decrease in the crime rate seems to help mayors win reelection while none of the other accomplishments appear to improve their chances of winning campaigns for other offices.