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Based on participant observation and interviews with staff and sex workers at two non-governmental organizations in San José, Costa Rica, I argue that sex workers have gone from being seen, and seeing themselves, as workers and subjects of labor rights in the 1990s, to victims that can be remade as entrepreneurs in the 2000s. In the context of neoliberal Costa Rica, this shift away from demanding workers’ rights toward saving victims and empowering entrepreneurs has had a significant impact on future possibilities for the recognition of sex workers as workers. Sex workers involved with both organizations participate in various forms of what I am calling “pragmatic penance”, the strategic performance of victimhood. This paper demonstrates that the ways that sex workers are helped has been impacted by the broader neoliberal context in Costa Rica, including a decline in class politics and in labour organizing.