Some call him straightforward, others uncompromising, and some even impossible. In any case, Paolo Maldini’s story is marked by difficult relationships and clashes. Those who frequented Arcore, for example, recount a complex relationship even with President Silvio Berlusconi. Legend has it that during a dinner, the Cavaliere said he could never give up having Maldini the player on his team, but outside the field, he would think long and hard before even entrusting him with managing a kiosk. Gossip, some might think, but the fact that the career of the greatest defender in football history has often been accompanied by quarrels and misunderstandings is a reality.
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Maldini, after all, has never been an ordinary man. Neither as a player, nor even less so off the field, where the talent, prestige, and credibility built in an extraordinary career on the green pitch with the Milan jersey coexisted with a strong, inflexible character not at all inclined to compromise. Because that same temperament that as a player helped make him an inter-generational reference seems today to represent the main obstacle in his career as an executive. The role of technical director of the National Team, just accepted, was supposed to mark the beginning of a new stimulating challenge: to revive the fortunes of Italian football. Yet, once again, the feeling is that it was his personality that complicated everything, turning the Azzurri adventure into a dull and forgettable episode.
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DISPUTES
Let’s be clear, Maldini the player is unquestionable. Nor can the man, in his integrity, be questioned. If anything, it is the character that is divisive, at least thorny. The Milan curve knows something about this, with whom there were no shortages of disputes. Sparks culminated with the “incident” of the whistles on the day of his last match as a player at San Siro, on May 24, 2009, when the whole football world should have given him the farewell that a legend deserves. Instead, Maldini experienced one of the bitterest moments of his extraordinary career, with part of the Curva Sud bidding him farewell with whistles and two polemical banners. The first read: «Thank you captain: on the field an infinite champion, but you disrespected those who enriched you». During the final lap of honor, a second appeared: «For your 25 years of glorious career, thanks from those you called mercenaries and paupers». A protest – definitely avoidable (the rest of the Meazza, of course, applauded Maldini) – rooted in the now deteriorated relationships between Paolo and part of the organized fans, worsened by some statements from the defender and mutual misunderstandings developed over the years. «I am proud not to be one of them,» Maldini replied that day.
DEFEAT
And to think that the clashes with the Rossoneri supporters during his playing career were not limited to some members of the Curva Sud. A famous argument also took place between the captain and some fans at Malpensa airport, returning after the heavy defeat in the 2005 Champions League final against Liverpool (on penalties, after the Rossoneri had ended the first half leading 3-0). One Milan supporter, in particular, shouted at the team to apologize, and Maldini went to speak to him face to face. «I give my soul, I could even die on the field. But once I do that, you must not tell me “Try harder” or “Shame on you, you must apologize.” I went in front of that fan. As captain, I could not accept it,» Maldini recounted years later, commenting on the episode.
A complex character, in short. But if during his playing career these episodes did not affect his trajectory, the thorny temperament inevitably penalizes his life as an executive, where compromise becomes essential. The experience leading Milan from 2018 to 2023 is proof of this, as current events confirm. Because problems were not lacking even as a Rossoneri executive, first with the Elliott ownership, then with Gerry Cardinale’s RedBird.
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Maldini wanted free rein, but often had to clash with the slippery dynamics of the American fund. A few weeks ago, Cardinale himself called Maldini a “one man show,” a figure incompatible with teamwork (Maldini replied: «Cardinale? He answers himself»).
A real shame, considering the skills Maldini showed even behind the desk and the charisma capable of attracting important players (see Maignan, Theo, he almost got Olise). After all, Paolo took over a Milan in full crisis in 2018, bringing it back to the Champions League in the 2021/22 season, with the cherry on top being the Scudetto won in a sprint over the cousins Inter on May 22, 2022. In the National Team, instead, the extraordinary ambition to bring the greatest coach in the world, Pep Guardiola, albeit with questionable media management (why tell the press?). Perhaps a bit more diplomacy would have sufficed.
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