Voters in almost every state elect county sheriffs but political science has only recently turned its attention to this important office. In this paper, I trace the historical processes that led Americans to begin electing sheriffs in the 18th and 19th centuries, as well as modern reforms to reverse that trend. Pairing newly-collected data on the timing of reforms that democratized local offices with narrative history, I show that the institution of elected sheriff spread gradually across the country and, in many states, Americans were deeply conflicted about subjecting this important office to popular choice. One finding is that sheriffs, in most states, became elective sooner than prosecutors and judges. I also provide evidence of the institution's slow retrenchment: today, there are four states and thirteen counties, home to over 20 million Americans, that do not elect sheriffs. The paper concludes with a discussion about the national importance of this local institution in American politics.