Maldini's Legacy Haunts Struggling Milan as Champions League Dreams Fade

The Collapse of a European Giant

There were more than seven minutes left to play in a crucial end-of-season match, yet San Siro was already half empty. Milan's Ultras had deserted the Curva Sud to prepare a post-game protest, but even the more forgiving parts of the club's fanbase could not be bothered to stay until the end of another humiliating defeat. Their team was losing 3-0, at home, to Atalanta, and it hardly even felt a surprise.

With this loss, inevitable as it now appeared, the Rossoneri had collected just seven points from their last eight games. Only three teams in Serie A had done worse over the same stretch. Two of those – Verona, and Pisa – have been relegated. The third, Lecce, are perilously close to joining them.

The Maldini Factor and Management Decisions

Watching their beleaguered team struggle to get the ball out from the back against Atalanta's persistent press, fans started to sing for Paolo Maldini. One of the all-time great defenders, he won seven Serie A titles and five Champions Leagues as a player, extending the legacy of success begun by his father, Cesare.

Appointed as a director for sporting strategy and development by Milan's then owners, Elliott Management, in 2018, Maldini was promoted to technical director a year later. He played a central role in player recruitment, helping build the team that won Serie A in 2021-22 – the club's first Scudetto for 11 years.

Maldini's position was initially confirmed after RedBird Capital bought Milan in 2022. But he was fired one year later, despite having just overseen a fourth-place finish. The Rossoneri had just finished fourth, and Maldini spoke about a need for further squad investment to stay competitive at the highest level. But Milan's most expensive signing of the previous summer, Charles De Ketelaere, had been a flop, and their new CEO Giorgio Furlani said the objective given to him by RedBird was to get the club "living within our means."

The Summer Investment and Early Promise

The appointment of Massimiliano Allegri this summer was supposed to get things back on track. Here was a man defined by Italy's sporting press as a "guarantee" of Champions League football. An aggressive summer transfer window followed, headlined by the arrival of Luka Modric, and featuring significant outlays on the likes of Christopher Nkunku, Ardon Jashari, Samuele Ricci, Koni De Winter, Adrien Rabiot and Pervis Estupiñán.

With no European distractions, Milan looked well equipped for a strong domestic campaign. Up until March, they delivered. The performance to beat Inter was classic Allegri, controlling the game while surrendering possession. Estupiñán scored before half-time, and Milan barely gave their opponents a sniff after that. This had been the mode all season: just win, it does not need to be pretty.

The Tactical Breakdown and Player Issues

But the problem with focusing always on the outcome is that you have nothing to fall back on once that part goes wrong. Milan's form early this season was built on the performances of talented individuals – Modric, certainly, but also Rabiot and especially Christian Pulisic, who had eight goals and two assists in the league, despite missing five games, by the end of December.

Allegri's innovation was to move the American inside to operate as a centre-forward. He pulled the same trick with Rafael Leão after the Portuguese returned from a calf injury. Both thrived at first, but as their goals tailed off, Milan have struggled to replace them. Too many square pegs forced into round holes? Or is the picture a little more nuanced? Both Pulisic and Leão have been affected by physical issues as the season progressed.

Atalanta were excellent, pressing selectively and executing ruthlessly. Giacomo Raspadori, signed from Atlético Madrid in January, brought a typically high-energy bustle behind the attack and it was his blocked shot that rebounded to Éderson inside the box for the opener. Nikola Krstovic, in the No 9 role, pinned his man expertly before laying the ball off to Davide Zappacosta to make it 2-0 before half-time.

Fan Protests and Management Response

What stood out in these moments was the clarity of purpose: each player performing the role they are best suited to and understanding what was required. The contrast with Milan's disjointed assembly of talents was stark. Absent the injured Modric, there was no glue to bind them together.

Ultras had already made their feelings known before kick-off with a protest outside the ground then a choreography in the Curva Sud, using their bodies and mobile phone flashlights to spell out the letters "G.F. OUT" – Furlani's initials. Reporters saw a pair of fans attempt a protest, holding up shirts with Maldini's name on the back in front of the section where executives sit, but stewards ushered them away.

By leaving early, they almost missed an improbable turnaround. Milan pulled a goal back in the 88th minute, Strahinja Pavlovic heading home from a Ricci free-kick. Nkunku, on as a second-half substitute, then won and converted a penalty. Suddenly the deficit was down to one goal. In the seventh minute of injury time, Matteo Gabbia almost equalised, flashing a header wide from another set-piece.

Uncertain Future for Italian Football's Powerhouse

Milan exist in a different orbit, still fourth in the table, even if their grip on a Champions League spot looks very loose indeed. It feels absurd to say it now, but before this miserable run they were the team keeping the Serie A title race alive. They were the last team to beat Inter, since crowned as champions, on 8 March. The gap between them, with mocking symmetry, was seven points.

The layers to these decisions are complex, each party with their own version of how working relationships grew strained. But Maldini's assessment resonated with fans who want to see their team fight for trophies. Milan finished second in 2023-24 but fell all the way to eighth last season, and now find themselves once again struggling to maintain their position among Europe's elite.

With the season approaching its conclusion, the question remains whether this is merely a temporary setback or a sign of deeper structural issues at the club. The contrast between the clear, purposeful football of Atalanta and Milan's disjointed performance suggests that tactical clarity may be as much a problem as player quality or management decisions.