Pep Guardiola coaching Christian Pulisic at Milan is a fantasy — but what about another familiar face?
At Milan, the ambitions off the pitch are beginning to mirror the club’s rich history on it. While the squad remains focused on the current campaign, the corridors of Casa Milan are buzzing with high-stakes discussions that could reshape the club’s future. A strategic summit held in London between CEO Giorgio Furlani, RedBird’s Gerry Cardinale, and former Juventus director Fabio Paratici signaled that the club is serious about evolving its project.
Reports from Corriere dello Sport described the summit not as a mere meeting, but “an opportunity to gain a global vision of the club’s projects and intentions.” The idea was to bring Paratici into the fold as sporting director, pairing him with technical director Geoffrey Moncada in a structure designed for long-term planning.
Although Paratici was poised to take on the role despite a 30-month ban, complications have emerged. His suspension, which ends in late July, would limit his ability to influence key summer decisions — a critical period for a club facing a likely managerial transition. According to Gazzetta dello Sport, “talks have reached a sudden stop,” forcing Milan to resume the search.
Paratici had already left his fingerprints on the Rossoneri’s managerial wishlist, reportedly campaigning for a name that turned heads across Europe: Pep Guardiola. Despite the near impossibility of Guardiola leaving Manchester City — where his contract runs until 2027 — to coach Christian Pulisic, the Serie A giant hasn’t ruled out the long shot. Corriere dello Sport admitted it’s an unlikely scenario, yet the mention alone underscores the scale of Milan’s aspirations.
However, one other possibility — less flashy, but steeped in history — has now gained serious traction.
Could the past return to guide the future?
While the Guardiola fantasy flickered, the real intrigue lies in Spain. Following Real Madrid’s 3-0 defeat to Arsenal in the UEFA Champions League quarter-finals, the pressure on Carlo Ancelotti has intensified. Reports from La Gazzetta dello Sport and La Repubblica now suggest that “even a comeback in the second leg may not be enough” to save the legendary coach’s job.
Ancelotti, who led Milan to two Champions League titles during his previous tenure (2001–2009), is reportedly edging closer to the Bernabéu exit door. His relationship with president Florentino Perez has grown fragile, exacerbated by the club’s trophyless trajectory and reported struggles integrating Kylian Mbappe into the team dynamic.
And while Brazil remains a widely reported destination, should Ancelotti leave, Gazzetta notes that “internal obstacles remain” in the Seleção regarding appointing a foreign coach. Which brings us back to Milan — a club that knows Ancelotti, respects him, and now, more than ever, could use his steady hand.
Emotional reunion: Real possibility or wishful thinking?
Both Milan and Roma are reportedly on high alert. “It’s inevitable,” reports Repubblica, “that a coach like Ancelotti, with his history, would attract interest from clubs close to his heart.” The allure of a homecoming is strong, especially with the San Siro outfit searching for a new figurehead and fans nostalgic for better days.
And unlike the Guardiola daydream, the 65-year-old Italian boss represents a realistic, emotional, and tactically sound option — someone who understands the club’s soul and the city’s expectations.
As Milan weighs their options and Real Madrid flirt with a summer shake-up, one thing is becoming clear: Carlo Ancelotti to Milan isn’t just a sentimental storyline — it might be the perfect fit at the perfect time.
