The Cult of Calcio
·30 May 2025
Max Allegri Returns – Milan Gamble on Results Over Style

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Yahoo sportsThe Cult of Calcio
·30 May 2025
Milan dropped a bombshell yesterday when they decided to sack Supercoppa Italiana-winning manager Sergio Conceicao and bring Massimiliano Allegri back to the club. Numerous Italian media outlets detailed how the 57-year-old tactician met the San Siro hierarchy to define the final details of a multi-year contract yesterday afternoon.
Despite securing Italian Super Cup glory for the first time since 2016 and reaching the Coppa Italia final, Sergio Conceicao failed to earn Milan’s trust. Milan sacked the former Porto manager after only six months, confirming his immediate departure with a 25-second video followed by a brief statement (via The Sun).
Conceicao replaced Paulo Fonseca in January and inspired the Rossoneri to the Super Cup title in his first two games in charge, beating Juventus and Inter to the throne. However, Milan struggled across the board in other competitions, with their Serie A campaign proving particularly disappointing.
After four consecutive top-four finishes in Italy’s top flight, Milan had to settle for a dreadful eighth place despite massive investments in the last two transfer windows. That’s their worst result in Serie A since finishing tenth under Filippo Inzaghi in 2014/15.
Mlan deemed missing out on European football for the first time since 2019/20 unacceptable. However, Conceicao still had a back door open, only for Bologna to shut it down in the Coppa Italia final, sealing the Portuguese coach’s fate in Italy.
Someone had to pay the price for Milan’s epic downfall, and Conceicao couldn’t dodge the axe. With the former Inter winger gone, Massimiliano Allegri has been selected to fill the vacancy and try to inspire the Rossoneri back to the heights of Italian and European football, aiming to restore pride at San Siro after a season to forget.
Allegri is no stranger to the red-and-black half of Milan, having previously led the Rossoneri between 2010 and 2014. He won the Scudetto in his first season in the dugout, but in all fairness, that squad would’ve probably strolled to the title under any other manager.
Milan finished runners-up to Juventus the following year. However, Allegri’s managerial shortcomings would only come to the fore after Zlatan Ibrahimovic and Thiago Silva departed the club in the summer of 2012. Indeed, they were third in 2012/13 before slipping to eight in 2013/14, which was Allegri’s last season at San Siro.
During his previous stint at Milan, Allegri racked up 91 victories, 49 draws, and 38 defeats. In addition to the abovementioned Scudetto, he led the club to the Super Cup triumph in 2011.
Unfazed by the eternal rivalry between Milan and Juventus, Allegri swapped allegiances in 2014. Whether it was his way to get back the Rossoneri for relieving him of his duties or simply a career-driven move, his decision to join Juventus raised eyebrows across the Italian football landscape.
Regardless of motive, Allegri went on to establish a dynasty in Turin. His first stint at the Allianz Stadium was an utter success. He won the Serie A title in all five seasons in charge while guiding Juventus to two Champions League finals. Despite losing both, he cemented his status as one of the most accomplished Italian managers.
Juventus deeply regretted the decision to re-appoint Allegri in 2021. Instead of re-establishing the Bianconeri as viable Scudetto contenders, the ex-Sassuolo boss was lucky to guide the record-time Italian champions to the Champions League.
Writings were on the wall after the first two seasons. Juventus followed a dismal fourth-place finish in Allegri’s comeback campaign with a disastrous seventh place in 2022/23. Despite steering the club to a third-place finish and Champions League qualification in 2023/24, they decided to part with one of the most defensive-minded managers today.
A consolation Coppa Italia win in 2023/24 wasn’t enough to disguise Juventus’ ‘hard-to-watch’ football during Allegri’s second spell at the club.
Allegri bases his football philosophy on a defensive, often destructive approach. Stale, risk-averse, and frankly unwatchable at times, Allegri’s sides have never been among the most exciting. Worryingly, his cautious method reached new levels toward the end of his second spell at Juventus.
Often booed off by the home fans, Allegri appropriately earned a tag as an ‘entertainment killer.’ Juve’s best scoring record in a Serie A season was 57 during his last three years at the helm, accounting for an average of only 1.5 per game. For instance, Milan have not netted under 60 goals per top-flight campaign since 2018/19.
Therefore, for football enthusiasts and, particularly, passionate Italian fans accustomed to attacking, progressive football, Allegri’s rigid system feels outdated. In an era of Jurgen Klopp’s famous gegenpressing and Hansi Flick’s ‘total’ football, Allegri’s style stands in stark contrast.
Even his victories leave supporters underwhelmed due to a notorious lack of attacking intent. In essence, the incoming Milan manager appreciates results but at the expense of spectacle. After an embarrassing season, the last thing the Rossoneri need is to kill the fun. If nothing, they had several remarkable moments in 2024/25.
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