This paper analyses three key political economy issues in Chile after the return of democracy in 1990: the prioritisation of learning; teacher's career and evaluation (intimately linked in the case of Chile); and quality assurance. The first issue is divided in turn in two subtopics: the identification of learning as the key educational policy objective and whether educational quality is made a priority by the government. The findings suggest a longstanding and sustained effort of successive approximations to better solutions that address the technical limitations and political restrictions that shaped reforms and policies, in a complicated path dependent process that will be analysed throughout this paper. All three issues are addressed in 26 interviews with key actors, the relevant legislation histories' as well as a national database of written media in the period 2007-2018, with special focus in the time span of legislative discussion of relevant initiatives.