We analyze Milton Friedman's two visits to Chile, in March 1975 and November 1981. We rely on a number of sources, including Friedman's archives, press archives in Chile and the rest of the world, interviews, and the papers and recollections of some of those who accompanied Friedman during his meeting with Pinochet. Although Friedman's 1975 visit has been widely discussed, his 1981 visit has been largely neglected. However, this visit was particularly important as it preceded a severe currency and banking crisis, stemming from an overvalued fixed exchange rate. The crisis put at risk the influence of the "Chicago Boys" and the political and economic liberalization process. We analyze Friedman's views regarding Chile's pegged exchange rate strategy followed between 1979 and 1982, and his position on economic and political freedom.