Smiles, laughter, and free-flowing conversation.
The content of which, of course, remains unknown, but the meeting between Theo Hernandez and Paolo Maldini that took place recently at a downtown Milan venue—one where Paolo has been a regular for years—is, and always will be, news in the eyes of the Rossoneri faithful, especially in difficult times like these, when for fans, seeing those two together in their current respective roles has a certain impact—and not a pleasant one.
One is strongly rumored to be on his way out, seemingly at the end of his cycle with Milan. The other has been gone for almost two years now from the club that defined his life on the pitch and where he later worked as an executive.
There are 29 years between them, but friendship often knows no age.
Reports suggest that Theo Hernandez and Paolo Maldini had a coffee yesterday, a rather long one.
Almost six years have passed between this coffee and the famous one in Ibiza back in June 2019, when Maldini essentially convinced the Frenchman to join Milan.
In football, that’s an eternity. In this Milan, with everything that has happened, it feels like two or three lifetimes. Theirs has always been a special relationship, from the very beginning. Theo was instantly enamored with the idea that a legend like Paolo had come specifically to meet him and explain the project.
Paolo completed one of the most significant signings of Milan’s modern era, a key pillar of the team that would go on to win the Scudetto three years later. They played the same position, though their personalities are vastly different, on and off the pitch. Opposites attract, and perhaps that’s why they immediately clicked.
Scattered across these six years are countless warm gestures and words of praise. Paolo on Theo:
"You are my worthy heir, I care about you," and "What he does, no one else can. He has revolutionized the modern interpretation of the role." Theo on Paolo: "He was crucial in my decision to come to Milan. Our meeting in Ibiza convinced me this was the right place for me." The literature on their bond is extensive, and it grew even more when Hernandez first matched and then surpassed Maldini’s tally of 30 Serie A goals, becoming Milan’s highest-scoring defender of all time. "Happy to reach 30 goals with Milan and make history with this jersey. Sorry, Paolo Maldini, but you told me so. I care about you," the Frenchman wrote on social media. Paolo replied: "Great job, Theo. The small difference is that it took me 25 years—you did it in just five. You’re special!"
"Special" is the key word, just like their relationship. Maldini first welcomed Theo, then protected, guided, and advised him until he became one of the best left-backs in the world. That’s why many believe Maldini’s bitter departure from Milan was a turning point for Theo, who became something of a footballing orphan. Deprived of the guiding light that warns a sailor of dangerous rocks—the very rocks Theo has crashed into this season. Unrecognizable. There is no definitive proof that his struggles stem primarily from Maldini’s exit, but it is reasonable to assume that it played a role.
The extent of that impact?
Only Theo knows. As for what was said between them yesterday, that, too, will remain between Hernandez and Maldini—two men who, in different ways, find themselves orphans above all of Milan, waiting to see what the future holds.
It’s easy to imagine that in a different context, and with a different management team, Paolo would consider a return to Milan’s hierarchy. Theo, however, faces more immediate concerns. By June—regardless of Milan’s stance—he must have clarity on what he wants to do with his footballing future. With different timelines, both Hernandez and Maldini need to figure things out. Who knows if, over that coffee, they spoke about that too?
