The Chilean education system is an emblematic case of school management privatization, with the majority of schools operating under government funding, but private administration. This article addresses the incidence of this dimension on school leadership, showing the differences and continuities established among primary school principals in the subsidized private and municipal sectors. The conclusion is that private school administrators do not recruit principals on a competitive basis, as a result of which these principals do not present a more developed professional profile, and that merely having more duties for executing the principal position--as happens in subsidized private schools--is not enough for an effective development of practices evidencing improved school leadership. These conclusions challenge the statement frequently expressed, but lacking sufficient empirical evidence, that the greater autonomy in school management encompassed by privatization will positively impact on school leadership and, therefore, on educational improvement.