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This dissertation studies the meaning of workplace democracy by examining San Francisco Class B Longshoremen whose status came into existence in 1958 as part of the automation and containerization plan agreed upon by the waterfront employers and the International Longshoremen’s and Warehousemen’s Union (ILWU). The B-men who toiled at the point of production as second class workers in this transitional period were in a unique position to see problems emerging from the mechanization plan and understand the exploitive nature of new work processes that arose from the abandonment of the old work rules. Although the main motivation for the waterfront employers and the longshoremen’s union behind the recruitment of B-men was to create a flexible but disciplined labor force that would make a smooth transition to automation, by organizing themselves for equal status and better working conditions, the B-men challenged the roles imposed upon them. By focusing on the black longshoremen who disproportionally filled the ranks of B-men and who lost their jobs without just cause and subsequently organized various actions for their reinstatement, this study provides a lens for viewing structural racism in the process of automation and demonstrates the irrepressible self-activism of working people for respect, equality, and control over their working conditions.