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ESPN Films’ Latest 30 for 30 ‘Berlusconi: Condemned to Win’ Premieres Sept. 16

The three-part documentary explores how Silvio Berlusconi rose from media mogul and AC Milan owner to one of Italy’s most powerful — and polarizing — political figures, showing how his transformation of the club helped set the stage for his decades-long grip on the country.

Clarence Moye by Clarence Moye
September 9, 2025
in Television
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ESPN Films’ Latest 30 for 30 ‘Berlusconi: Condemned to Win’ Premieres Sept. 16
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ESPN today announced that “Berlusconi: Condemned to Win”, the latest installment in its 30 for 30 series, will premiere September 16 on the ESPN app and on ESPN2 at 7 p.m. ET.

Directed by Sam Blair (“Maradona ‘86”, “Make Us Dream”, “Ronnie O’Sullivan: The Edge of Everything”),  and produced by Box to Box Films, the three-part documentary tells the story of Silvio Berlusconi, one of the most significant figures in Italian history over the last three decades. Serving as Italy’s prime minister over three different stints, Berlusconi first rose to prominence as a business and media tycoon who owned one of the country’s most storied football clubs, A.C. Milan. As he turned the team into arguably the world’s most successful club, he used its victories to fuel his own popularity — ultimately propelling him to the highest political office in the land. Yet as the film reveals, Berlusconi’s ascent raised troubling questions about how sport can mask corruption and provide a pathway to power with consequences far beyond the game.

“Silvio Berlusconi is one of the most complex figures of our time,” said Blair. “His story is about more than football or politics — it’s about ambition, power, and the way sport can be used to reframe an entire nation’s identity. With this documentary, we wanted to explore not only how Berlusconi built AC Milan into a global powerhouse, but also how that success became a launchpad for his rise to the highest office in Italy. It’s a story about the seduction of winning, and the price a society pays when victory overshadows accountability.”Added Marsha Cooke, Vice President & Executive Producer, 30 for 30: “Like so many of the best 30 for 30 films, Berlusconi’s story bridges the worlds of sports, politics, and culture in an unforgettable way. It shows us how the drive to win at all costs can impact every facet of society. The film challenges us to think about the true cost of power — and the role sport can play in enabling it.”

Here’s the trailer for “Berlusconi: Condemned to Win.”

 

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Clarence Moye

Clarence Moye

Clarence Moye is a proud co-founder of The Contending where he writes about film, television, and occasionally Taylor Swift. Under his 10-year run at Awards Daily, Clarence covered the Academy Awards, the Golden Globes, the Telluride Film Festival, the SCAD Savannah Film Festival, the Middleburg Film Festival, and much more. Clarence is a member of the Critics Choice Association.

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