By examining the demands of labor strikes in the private sector, this article claims that Chilean trade unions have experienced a politization process from the transition to democracy to our days (1990–2019). Assuming a Marxist perspective on the labor process, we propose operationalizing politization into three levels based on the nature of demands: (1) remunerative, (2) related to work conditions, and (3) related to the organization of the labor process. The study regards these three levels as a latent variable ranging from less to more control over the productive process, but, also, as a continuum ranging from more legal demands to more illegal demands according to Chilean labor regulation. The results show an increase of politized demands (i.e. more control and less legality) through the years. This case study sheds light on the consequences of a rigid and ineffective regulation and on the necessity to rethink politics in the workplace.