This paper will draw on the Pittsburgh Police History Association Archives, which detail how Pittsburgh police were trained to arrest, and how they described arrests and explained how arrests went wrong. It will supplement this with accounts of arrests in newspapers and trial transcripts. Most importantly, I will conduct interviews this summer with two dozen individuals who were arrested in Pittsburgh in the period between 1967-1980 to capture what arrests looked and felt like from inside the handcuffs. Pittsburgh writer John Edgar Wideman has described Pittsburgh policing in the beginning of this period as characterized by personal relationships between police and the policed, relationships which often involved coercion and violence. At times, in the late 1960s and early 1970s, attempted arrests dissolved into fights between officers and community members. Informal interviews I have done have made similar points. By the end of this period, policing had come to seem more removed, formal, and bureaucratic, in ways that were undeniably positive, but which some “policed” people from those years also see as having led to a new set of problems.