Maldini’s Presence Lingers Over Struggling Milan as Top-Four Spot Slipping Away

Posted on: 05/12/2026

AC Milan fans hold up a Paolo Maldini shirt inside the stadium before the Serie A match between AC Milan and Atalanta

Fans held up a Paolo Maldini shirt near the executive section in protest, but stewards quickly escorted them away.

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With over seven minutes remaining in a crucial end-of-season match, plus stoppage time, San Siro was already half-empty. Milan’s ultras had left the Curva Sud early to arrange a post-game demonstration, but even the more forgiving supporters couldn’t be bothered to stay for the final whistle of yet another humiliating defeat. The team trailed 3-0 to Atalanta, and the result came as little surprise. That loss, which felt inevitable, meant Milan collected just seven points from their last eight Serie A matches. Only three teams in the league had a worse record over that period: Verona and Pisa, both relegated, and Lecce, dangerously close to joining them.

Milan, despite still sitting fourth in the table, are now clinging to a Champions League spot. It might sound absurd, but before their recent slump, they were keeping the Serie A title race alive. They were the last team to beat Inter – later crowned champions – back on March 8. The gap between them and Inter now stands at seven points, a cruel symmetry.

Little wonder the few fans who endured until the end on Sunday felt nostalgic. As their beleaguered team struggled to play out from the back against Atalanta’s pressing, they began singing for Paolo Maldini. One of the greatest defenders ever, he won seven Serie A titles and five Champions Leagues as a player, extending the legacy started by his father Cesare. But supporters weren’t just recalling his on-field achievements; they were remembering his recent tenure as a director. Appointed in 2018 as director of sporting strategy and development, then promoted to technical director, Maldini played a key role in recruitment, building the squad that won the 2021-22 Scudetto – the club’s first league title in 11 years.

His position was initially confirmed when RedBird Capital bought Milan in 2022, but he was fired a year later. After a fourth-place finish, Maldini had called for further investment to compete at the highest level. However, Milan’s most expensive signing that summer, Charles De Ketelaere, failed, and CEO Giorgio Furlani said RedBird’s goal was to make the club self-sustaining. The decisions were layered, with each side offering different accounts of strained relationships. But Maldini’s view resonated with fans wanting to see their team fight for trophies. Milan finished second in 2023-24, then fell to eighth last season.

The appointment of Massimiliano Allegri last May was supposed to restore order. Italian media framed him as a guarantee of Champions League football. An aggressive summer followed, headlined by Luka Modric’s arrival, plus significant spending on Christopher Nkunku, Ardon Jashari, Samuele Ricci, Koni De Winter, Adrien Rabiot, and Pervis Estupiñán. Without European distractions, Milan seemed ready for a strong domestic campaign.

Massimiliano Allegri reacts with disappointment during the Serie A match between Milan and Atalanta

Milan fans use their mobile phone flashlights to spell the letters G.F. OUT before the Serie A match between Milan and Atalanta