Berlusconi: Condemned to Win

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September 16, 2025

2h 30m

Overview

Three-part series for ESPN capturing the rise of Silvio Berlusconi from his humble beginnings to the very top – from cruise ship crooner to AC Milan owner to Prime Minister of Italy.

Director

Sam Blair

Cast

Silvio Berlusconi

Self (archival footage)

Adriano Galliani

Self

Fedele Confalonieri

Self

Alexander Stille

Self

Ruth Ben-Ghiat

Self

John Foot

Self

Carlo Ancelotti

Self

Paolo Tarozzi

Self

Pippo Russo

Self

Carlo Pellegatti

Self

Vittorio Dotti

Self

Paolo Taveggia

Self