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Come Fan with UsFriday, July 3, 2026

The Massimiliano Allegri standoff

With still nothing decided after two lengthy meetings, Max Allegri’s position as AC Milan coach remains unclear.

Claudio Villa

Sitting down to dinner in a Milan restaurant on Thursday evening, it seemed like AC Milan director Adriano Galliani and the club's coach Massimiliano Allegri would finally come to a decision. It has been going on for months, but they still had not yet decided whether or not Max would be the team's coach next season.

Not surprisingly, we’re still none the wiser.

Just as in the aftermath of Allegri's hour-and-a-half long coffee with Galliani last week (with Galliani's explanation being that they "savoured it"), a decision has yet to be made. "Before Sunday evening" is the latest deadline for a resolution, according to club president Silvio Berlusconi. Given the way things have gone so far, it wouldn't be surprising if that meeting was just to arrange their next one, never ever actually reaching a verdict.

The situation is made even more chaotic by the suggestion in Corriere dello Sport that Allegri already has a three-year deal in place to take charge of AS Roma, should he leave the rossoneri. With popular opinion among the giallorossi supporters swinging against their incumbent interim boss Aurelio Andreazzoli, they've moved to bring Allegri to the Olimpico.

On paper, that would seem like a good move. After all, Allegri came to a declining Milan from Cagliari in 2010 and won the title in his very first season. Not only that, but he broke the domination of an Inter Milan side which had won Serie A six-consecutive seasons, overseeing the rossoneri's first Scudetto win since 2004. Even over the last couple of seasons -- where Milan have come up against a comfortably superior Juventus team -- he's ensured Champions League qualification.

Aside from winning the title, young players like Mattia De Sciglio and Stephan El Shaarawy have developed into brilliant talents and have broken into Milan's team under Allegri, and he has managed to shake off his reputation of tactical inflexibility by ditching his beloved 4-3-1-2 for a more appropriate 4-3-3. He has overseen a difficult period of transition at the San Siro, with the rossoneri now having a solid base on which to build for the future.

And yet, Allegri has still never quite managed to convince.

For starters, he's been criticised for failing to impose any real style or identity on the Milan side -- seen as a short-term fix but not a long-term solution. What some would describe as 'pragmatic' is a demonstration to the Allegri-detractors of an example of his limitations as a coach, while his insistence on a combative rather than more aesthetically-pleasing style saw him release Andrea Pirlo after the Scudetto win in 2011.

Even this season, Milan only just squeezed into the Champions League with two goals in the final ten minutes against Siena, having only recovered from a horrible start to the season in November. In some ways, Milan's indecisiveness is understandable. They can thank Allegri for their only league title in almost a decade, but difficult circumstances have made it hard to determine whether he's to blame for them failing to win one -- or at least getting closer to winning one -- since.

Reluctant to let him go but equally reluctant to keep him on, Milan have reached an impasse with Allegri. With Roma joining the chase, it’s a Milanese version of a Mexican standoff -- only considerably more tedious and hopefully with the situation resolved without anyone actually being killed. Maybe this week someone will finally pull the metaphorical trigger.

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