This paper concentrates on the meaning of the term “dilemma” and, on the one hand, it offers a discussion concerning Berlusconi’s main political choices (that is, those crucial choices that were made in conditions of uncertainty), and, on the other, it raises those questions that scholars have been addressing in the past few years. Amongst Berlusconi’s choices, the author lists, first of all, the decision to “enter the field”; then to form a coalition able to win the election within the new electoral system framework and the definition of his political programme. Then,once at the opposition, his firm strategy of bipartisanship and protest. Finally, in 2001, the redefinition of his relationship with his political allies. Amongst those questions that have, in the past few years, both raised the political scientists’ attention and constituted themselves dilemmas that are not easily solvable, the author lists: the reasons for Berlusconi’s political victory and personal success; the impact that television has on its viewers, Berlusconi’s relationship with his political allies.