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Based on National Hockey League club and league correspondence, congressional transcripts, newspapers, and government documents, this essay examines the first attempt to organize a National Hockey League Players' Association. For just over a year, the NHLPA struggled to overcome the resistance of NHL owners, the uncertainty of its own members, and the confusing legal environment created by overlapping transnational, interstate, and inter-provincial jurisdictions. These issues make the NHLPA a compelling case study of the way in which the borders between business and sport began to shift in the 1950s, a time when new forces-technological (television), legal (congressional investigation and judicial decisions), and social (player activism)-were preparing the way for the struggle for free agency.