Berlusconi: Condemned to Win

Berlusconi: Condemned to Win (2025)

Documentary

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.

  • Release Date: 2025-09-16
  • Runtime: 2h 30min
  • Director: Sam Blair

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Trailer

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

  • Andrea Scanzi

    Self

  • Edoardo Maturo

    Self

  • Dejan Savićević

    Self

  • Zvonimir Boban

    Self