The chronically injured worker is perhaps one of the most fascinating psychosocial topics relating to disability. For the chronically injured worker, negotiating the often confusing and sometimes dehumanizing gauntlet of receiving workers’ compensation benefits (WCB) for employees fortunate enough to have coverage may quickly turn into an injured worker’s nightmare (Binder, 1992; Dodier, 1985; Fallenbaum, 2003; Gribich, McGartland, & Polgar, 1998; Willis, 1986). This chapter explores a number of topics related to the world of work, the psychological impact of disability on the disabled worker, the impact of chronic pain, systemic problems in the WCB and Social Security Administration’s (SSA) programs, key players in the gauntlet, the impact on the family of an injured worker, and the discipline of disability management (DM). It briefly explores the anatomy, theory, and assessment of chronic pain.