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On August 11, 1972, District of Columbia police shot and killed Gregory Coleman, an African American teenager riding a bicycle that they had planted in front of a grocery store as part of a “bicycle stakeout” sting operation. At his memorial service a little over a week later, Gregory’s father, Lancelot Coleman, said, “The whole thing was senseless that my son had to die for a lousy bike.” Coleman’s death foreshadowed a half-century of escalating law-and-order policies established across the United States for which African American youths would experience the most severe of consequences. Bicycling was implicated in these trends. Officers used mandatory bicycle registration and bicycle stakeouts to patrol racial boundaries in a city where the majority of the population was African American. As a vehicle for physical mobility and a source of play for young people during an era of intense federal attention to juvenile delinquency, the bicycle became a fulcrum for efforts to maintain segregated public spaces in the District.