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Sheriffs have had an outsized role in the history of law enforcement in America, something that often goes unnoticed by the wider public and scholars. As elected officials, and the only law enforcement in rural areas, they control full counties with little to no accountability. This essay argues that although the Office of Sheriff has been one of the most overlooked and least understood positions in law enforcement, holders of the office dramatically shaped the experiences of localized racial injustice and exacerbated the failures of the legal system for historically marginalized populations, specifically African Americans in the American South, during the early 20th century. To prove this, three Supreme Court cases that demonstrate their abuse of power will be examined; United States v. Shipp in 1906, Mack Claude Screws v. United States in 1943, and United States v. Cecil Price, et al in 1964. A half-century after the end of the period examined in this paper, problems with sheriffs have not disappeared but instead have taken on additional forms, such as mass incarceration in jails, especially of Hispanic and Black people.