The boos that echoed around San Siro on the final match day of the season told the story before the official statement arrived. AC Milan’s season, once filled with title ambition and Champions League hope, ended in chaos after a crushing 2-1 defeat to Cagliari. Less than 24 hours later, Massimiliano Allegri was gone.
For much of the campaign, Milan looked secure. They spent months in Serie A’s top two and appeared capable of mounting a genuine Scudetto challenge. Yet football seasons are often remembered for how they end, not how they begin.
Milan’s collapse was brutal. After losing only once in their opening 25 league matches, the Rossoneri suddenly unravelled. Seven defeats in their final 13 games dragged them from third place to fifth, leaving them outside the Champions League for a second straight season.
The final blow came at home against Cagliari. Milan entered the last day knowing victory would secure a return to Europe’s biggest stage. Instead, they surrendered a 1-0 lead, watched rivals Roma and Como leapfrog them, and walked off the pitch to angry whistles from their own supporters.
RedBird Capital did not hold back in its response. The club’s ownership called the season “an unequivocal failure” and confirmed a sweeping overhaul across the football department. Alongside Allegri, CEO Giorgio Furlani, sporting director Igli Tare, and technical director Geoffrey Moncada all left their positions.
“The final stretch was completely inconsistent with the performance up to that point,” the club statement read. “It is now time for change and a comprehensive reorganisation of football operations.”
For Allegri, the dismissal carries extra weight. His return last summer was meant to restore stability and reconnect Milan with past success. During his first spell between 2010 and 2014, he guided the club to the Serie A title and Italian Super Cup, bringing back memories of Milan’s golden years.
This second chapter never reached those heights. Though Milan collected 70 points, their highest tally ever for a team finishing outside the top four, inconsistency proved fatal. Even Opta’s expected points model suggested they should have finished fourth, showing how costly their late-season slump became.
The wider picture makes the failure even harder for supporters to accept. Next season’s Champions League will feature neither Milan nor Juventus for the first time since the competition’s 1992 rebrand. Meanwhile, Como’s remarkable rise into Europe’s elite has added further embarrassment for two Italian giants now heading to the Europa League.
Questions now surround what comes next. Club legend Zlatan Ibrahimovic remains in place as a special adviser and is expected to help shape the rebuild alongside RedBird owner Gerry Cardinale. Antonio Conte has already been linked with the role, while Allegri himself is reportedly in contention for the Italy national team job.
For Milan fans, however, the wounds are still fresh. A season that once promised redemption has ended with uncertainty, frustration, and another painful reminder that history alone guarantees nothing in modern football.
