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Milan’s biggest regret this season: Antonio Conte could have coached Christian Pulisic – Ends up lifting Serie A title with Napoli

Antonio Conte (left) and Christian Pulisic (right)
© Getty ImagesAntonio Conte (left) and Christian Pulisic (right)

Napoli is a Serie A champion again, securing its fourth Scudetto in club history and restoring pride in a city that breathes soccer. But beyond the celebrations in Naples, this title triumph carries a twist of poetic justice. In a season where other giants stumbled, one man rose above expectations, proving yet again why he’s among the elite of his profession.

The coach at the center of it all? Antonio Conte. A year ago, he was overlooked—left on the outside of elite Italian coaching circles, seemingly past his best. Fast forward to May 2025, and he’s lifted another Serie A title, reinforcing his status as a relentless, winner-at-all-costs leader. What makes it even more compelling is that this very season, he could have been coaching one of Italy’s other top clubs, leading a very different squad… one that included Christian Pulisic.

Milan’s missed opportunity

Last summer, Milan was in need of a new coach. The Rossoneri had finished the 2023-24 season with unfulfilled potential and knew change was necessary. Antonio Conte was interested, even making it known that Milan was his preferred destination. Initial contact was reported between Conte and Milan’s technical director Geoffrey Moncada, but the discussions stopped there.

According to La Gazzetta dello Sport, the Red and Blacks chose a different path. The club, led by Zlatan Ibrahimovic and CEO Giorgio Furlani, made the controversial decision to appoint Paulo Fonseca instead.

“At Milan, you have a coach, not a manager. We didn’t talk with Conte because with the criteria we had, he wasn’t what we were looking for, his name didn’t come up,” said Ibrahimovic at the time. “With all due respect to him, who is a great manager, he’s not what we were looking for.”

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Milan wanted someone more collaborative, less confrontational, someone who wouldn’t challenge the board’s decisions. Conte, famously intense and outspoken, didn’t fit their philosophy. Fonseca, by contrast, was seen as malleable—a coach rather than a manager. The decision seemed rational at the time. In hindsight, it’s one they will likely regret for years.

conte napoli

Conte wins Serie A while Milan collapses

While Napoli surged to the top of Serie A under ConteMilan endured a catastrophic season. Sitting ninth in the league, the Rossoneri were knocked out of the Champions League by Feyenoord and fell short of every domestic objective.

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A recent report by La Gazzetta dello Sport outlined seven key mistakes in Milan’s planning, and “No Conte” topped the list. The club’s hierarchy had prioritized structure and shared decision-making over leadership and grit—qualities that the Italian tactician brings in abundance.

pulisic conceicao milan

Fonseca’s tenure ended in disappointment and disillusionment, and his replacement, Sergio Conceicao’s stint, has been no different. Milan’s final match of the season, a meaningless fixture against Monza, only underlined how far the team and its management have fallen from their ambitions.

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