In this essay, we discuss the impact of Paulo Freire’s stay for almost four and a half years in Santiago, Chile. At that time, the educator distanced himself from his Brazilian experience, and was able to rework his pedagogical ideas by observing, experiencing, and questioning the Chilean social situation in the 1960s. In the year that celebrates the centenary of his birth, we bring questions about the impact of the Freire’s thought for education in Chile, as well as highlight that popular movements, such as the mobilization of High School students and the recent “social outbreak”, are indicative that Freire’s work is current and necessary to think, as a Chilean society, the new directions of education, since the current moment is to face the fear of freedom.