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HomeFootballWhy Allegri Failed in His Second Stint at Milan

Why Allegri Failed in His Second Stint at Milan

What started as a bid for the Scudetto ended with a 6th-place finish—following a colossal collapse. That, combined with the underlying issues, has now cost recently returned coach Massimiliano Allegri his job. His next destination could be in the south.

AC Milan’s players and staff had drawn the right conclusions from the chorus of boos on the very first matchday following the surprising 1-2 loss to promoted side Cremonese—led by Massimiliano Allegri, who had only returned to the bench last summer.

From then on, the 58-year-old led his team, featuring Luka Modric and winter signing Adrien Rabiot, to a 21-game unbeaten streak in the league—even the championship title seemed within reach. This was precisely because the Rossoneri looked well-oiled and always well-rested following their disastrous 8th-place finish in the 2024/25 season, which left them without a European spot.

However, after the final matchday and the bitter 1-2 loss—following an early 1-0 lead—against Cagliari Calcio, who were stuck in the middle of the table, the Milanese once again hit rock bottom, culminating in Allegri’s dismissal and the ousting of sporting director Igli Tare and CEO Giorgio Furlani.

Setbacks following Milan’s championship

After just one year, the club parted ways with the 2010/11 championship-winning manager, partly because the internal atmosphere—particularly with club advisor and legend Zlatan Ibrahimovic—had reportedly cooled significantly, with heated arguments included.

Furthermore, the high-profile offense featuring Rafael Leao and the seemingly “sad and helpless” Christian Pulisic never lived up to its reputation, faltering significantly toward the end of the season with just one goal scored between matchdays 31 and 35, and regularly letting down the otherwise stable defense led by goalkeeper Mike Maignan.

Following the radical shake-up at the leadership level—only owner Gerry Cardinale, advisors such as club icon Ibrahimovic, and possibly also President Paolo Scaroni, who is overseeing the new stadium project, are allowed to stay—the proud, traditional club from the fashion capital of Milan is once again in a massive shambles.

And following the failed tenures of coaches Paulo Fonseca, Sergio Conceicao, and Allegri (a record of 22 wins, ten draws, and ten losses in 42 competitive matches), the club must once again present a solution that includes a new leadership team. Ideally, a high-profile solution is needed to quickly calm the extremely tense atmosphere—with Milanisti fans regularly voicing their anger lately—over the summer.

At least the Europa League beckons as a European competition for Allegri’s successor. But is that appealing enough for a truly high-profile coach? Time will tell. Either way, the former Champions League regular and winner (seven titles in the competition—most recently in 2006/07) has reached yet another low point in a modern era already marked by setbacks. This is particularly bitter because many had seen Milan on the rise after the 2021/22 Scudetto under Stefano Pioli—at the time still with an active Ibrahimovic.

Milan’s “catastrophe,” “disaster,” “failure”

The reality, however, is one of scorn and ridicule—especially from the domestic press, where terms like “catastrophe,” “disaster,” and “failure” were in the headlines. La Gazzetta dello Sport was even quite blunt after the loss to Cagliari: “Milan manages to squander the easiest of all match points and bids farewell to its only true goal of the season in the saddest, most painful, and most guilt-ridden way. The music has stopped, the friends are leaving. And with them go the millions from the Champions League. It will be the Europa League—and that is a footballing blasphemy for a team that has been in the top four since Matchday 4.”

Allegri himself, on the other hand, might get off lightly, as he has been considered for weeks—well before the collapse of Milan’s leadership—as a candidate for the position of new coach of the Italian national team, as well as President Aurelio de Laurentiis’s preferred choice to succeed Antonio Conte at SSC Napoli.

Meanwhile, Ibrahimovic is expected to help, in his advisory role, to search for, find, and present the new coach. According to Italian media reports, the club prefers a modern solution like Como’s Cesc Fabregas, who has led the surprise club from Serie B past Milan and into the Champions League in three years with proactive and attacking soccer.

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