Prosecutors are the most powerful officials in the criminal justice system. At least ninety percent of all criminal cases are prosecuted on the state level, and in all but five jurisdictions, the chief prosecutor (also known as the district attorney) is an elected official. Most district attorneys run unopposed and serve for decades. However, in recent years, a number of incumbent district attorneys have been challenged and defeated by individuals who pledged to use their power and discretion to reduce the incarceration rate and eliminate unwarranted racial disparities in the criminal justice system. These so-called “progressive prosecutors” have enjoyed some modest successes, but many have faced challenges—from within and outside of their offices. This Article discusses some of these successes and challenges and proposes guidelines to assist newly-elected district attorneys who are committed to criminal justice reform.