Devil’s Advocate: Milan walk into self-created nightmare as Maignan holds all the cards

9 hours ago 31

Usually a decisive MVP-worthy performance from your captain to win a derby is only positive. For AC Milan with Mike Maignan, though, there is a bit more nuance to things. 

Make no mistake about it, what Maignan did on Sunday night in the 1-0 win over Inter was something that will be talked about for years to come. Wearing the armband, he produced not just one but multiple match-winning contributions, in addition to Christian Pulisic’s goal of course.

The acrobatic leap to deny Marcus Thuram’s header and the fingertip save to thwart Lautaro Martinez in the first half would be deemed a good night’s work as it is, but he surpassed all that with a derby folklore moment, keeping out Hakan Calhanoglu’s penalty.

A clean sheet, three points and Derby della Madonnina bragging rights, thanks to the man wearing the armband. Everything is rosy, right? Sadly that is not the case, and the situation is almost entirely of Milan’s own creation.

Emotions are always high after big games, especially one with lots of controversial incidents, so it is important to let the dust settle and for the media extremes to cool down. Even a few days on though, Maignan remains the buzzword in the newspaper columns.

Depending on which sources you believe, the Frenchman is angry with Milan and is heading for Juventus, Inter or the Premier League, or he is in love with Massimiliano Allegri and his goalkeeping coach so he could change his mind about leaving.

One thing remains true no matter what the narrative: Maignan’s deal expires next June, meaning that in a few weeks he will be able to negotiate a pre-contract with another club, and Milan risk losing a crucial player on a free transfer.

maignan saves lautaro calhanoglu

How did we get here?

What led to the current impasse is a rather complicated situation that has played out since the beginning of the 2025 calendar year, a tale of two parties who started with a common goal before a great frost developed that shows little sign of thawing.

According to reliable sources such as Matteo Moretto and Fabrizio Romano, Milan actually began discussions with Maignan and his agent over a renewal back in September 2024, which the goalkeeper was very much open to.

These meetings intensified in the coming weeks, with things heading in the right direction. Then, in February 2025, Milan and Maignan reached a verbal agreement and even shook hands on a contract renewal until 2028 (plus an option for another year) at €5m net per year plus bonuses.

That would have made the former Lille man one of the highest-paid players in the squad alongside Rafael Leao, a salary reflective of his leadership status. It seemed as though it was just a matter of time before he would be called to Casa Milan for the customary renewal snaps.

The contracts were drafted, Maignan was ready and willing to sign, to commit his long-term future to Milan. Yet the management – led by CEO Giorgio Furlani – put the agreement on hold for various reasons.


At the midway point in the season, the Rossoneri hierarchy realised that no European football in 2025-26 was not only a worrying possibility but a nightmarish likelihood. So, they revisited certain negotiations with new financial parameters, including Maignan’s renewal.

It is in this period up until the end of the season that the Frenchman and his representatives become understandably hurt, angered and disillusioned with Milan’s top brass. To have everything agreed and for the offer to then be pulled or revised downwards (depending who you believe) was seen as insulting.

So, to say that ‘Magic Mike’s’ head was turned would be an understatement. When the window reopened ahead of the Club World Cup at the start of the summer and Chelsea came along, he was pushing for the move to the London club.

The Blues offered around €15m in the end, to try and get him in before heading to the United States, but Milan said no and asked for much more despite the player’s wishes and a lack of contractual leverage.

Massimiliano Allegri arrived on the scene amid all of this. The new coach made it clear from day one how much he rates Maignan and so – together with the club – the goalkeeper was taken off the market. The mini-window closed, and Maignan remained.

Allegri had private conversations with his new No.1, asking him to remain professional and give his all while he is still wearing a Milan shirt. A pact was reached, but it didn’t result in anything remotely resembling the reigniting of talks over a new contract.

Maignan ChelseaPhoto by Yasser Bakhsh/Getty Images

Why has the magic returned?

At the moment, it feels like whatever dressing Allegri applied to the wound that is the Maignan situation is holding up pretty well. It is not just the derby performance that gives reason to believe that he is back to his best.

Having felt the trust of the new coach right from the start, work began on the training ground to drastically improve the dire defensive record from 2024-25. It started with the foundation of a three-man defence, with Fikayo Tomori, Matteo Gabbia and Strahinja Pavlovic the chosen trio.

Some goalkeepers can be good enough to win points on their own, and there is a strong argument that notion applies to Maignan. At the same time, that isn’t sustainable in every game, so having a solid rearguard ahead is the best way to consistently keep the ball out of the net.

How does this directly help Maignan? For starters, Milan have a much lower centre of gravity (49.2 metres as the average line height) compared to last season, while they are much more compact in terms of space between the departments (32.5m).

As confirmed by the PPDA index (Passes Per Defensive Action) metric – which measures a team’s aggressiveness in pressing – the Rossoneri are now playing the opposite of the gung-ho style that they deployed in 2023-24 under Stefano Pioli, and under both Paulo Fonseca and Sergio Conceicao in the last campaign.

When not in possession, the 3-5-2 usually transforms into a 4-5-1. Everyone drops in to do their bit, creating a ‘double barrier’ that has made Milan impenetrable in eight out of 14 games so far this season.

Effectively, Maignan is less busy. He is facing less shots, there is no longer a huge amount of space behind the defensive line that could see him need to rush out, and the centre-backs – particularly Gabbia and Pavlovic – are dealing with any aerial bombardment like anti-aircraft guns.

All of the aforementioned means that Maignan is able to focus on the one thing that sets him apart from his peers: his ability to keep out the shots that do make it through, which are often the most challenging ones.

If asked to pick out the 30-year-old’s best attributes, most would pick out two would pick out two without hesitation: reflex saves and footwork. In Allegri’s system, he plays an active role in build-up, so that is a second tick when it comes to magnifying strengths.

Then, there is the coaching factor. Since the 2021-22 season, Maignan has had the following goalkeeping coaches: Dida, Gigi Ragno, Emiliano Betti, Flavio Roma, Anthony Roberts, Antonio Ferreira, Diamantino Figueiredo and Vedran Runje. Such a carousel is not good for consistency.

As soon as Allegri signed with Milan, there was another change as he called Claudio Filippi to join him. The 60-year-old holds the distinction of being regarded as the best Italian goalkeeping coach, and the mentor to Gianluigi Buffon.

Maignan seems to have improved under the latest coach, especially from a mental point of view. Allegri even said that Filippi was decisive in convincing Maignan to stay at Milan, and the impression is that he’s the key here. Maignan recognises Filippi as a top-notch professional and trusts him.

This switch has helped with things like penalties. This month alone Mike has kept out Paulo Dybala and Calhanoglu, perhaps the two best in the league from 12 yards. Allegri’s nod after the match was unmissable: “Claudio Filippi is the best at this; he’s very good at preparing goalkeepers for penalties.”

It isn’t just about spot kicks, though. Those who are present at Milanello are saying that Maignan’s volume of work in training is down, but the precision and intensity is up. Filippi is a very analytical coach, who pays attention to the goalkeepers’ technical movements and posture.

He’s not a revolutionary, but a coach who follows the great Italian tradition. Mike adds his own way of doing things based on what he knows works well for him and things he has added to his routine from others. Whatever the daily dynamic is, these three months show it’s working.

claudio filippi maignanPhotos: Claudio Villa + Yu Chun Christopher Wong/Eurasia Sport Images/Getty Images

Where do we go from here?

By this point, you have probably seen the reports suggesting that Milan are readying one final attempt to get Mike Maignan to commit his future to the club. It all feels a bit desperate though, doesn’t it?

Ultimately, the management made their bed with this one by reneging on a previous agreement which was reached earlier in the year. The decision not to push forward with that extension is what will most likely end up coming with the cost of losing Maignan without receiving a transfer fee.

Matteo Moretto reported the following in his most recent update: “There’s still great cold and great distance between the parties. All of this makes us think that in the end, Maignan will leave for free.

“I can tell you, adding another detail: the Premier League remains very attentive, but keep an eye on Juventus too. The Bianconeri have started to have this idea in mind in case Maignan doesn’t renew.

“Let’s keep Juventus in mind, let’s keep the Premier League in mind, but above all, let’s keep in mind a future for Maignan that remains absolutely up in the air.”

Imagine that: not only could Milan lose their captain for nothing, but they could drive him into the hands of a rival. Any last-ditch attempts to mend things should be unsuccessful: as a matter of principle Maignan shouldn’t entertain any further talks.

Within all of this, there is a risk of dangerous revisionism too. Maignan has been far from perfect during his time at Milan, having had injury problems and struggles at certain times with different elements of technique.

The decision to revise the renewal offer came at perhaps his most difficult moment with the club, in January-February 2025 when lots of goals were flying in the shouldn’t have been. If a poll were conducted at the time about committing potentially over €30m gross to a new deal, the responds would have been intriguing to see.

Recency bias prevails though, especially seeing Maignan back to these levels, and now the player holds all of the cards. In January he will be free to sign with whoever he wants, perhaps entertaining the riches of the Premier League or maybe even being tempted to deliver a final jab to the Milan management with a Calhanoglu-esque move a rival.

Yet, all hope doesn’t appear to be lost just yet. Just like back in June, there are suggestions that Allegri could yet play the role of manager and director by convincing Maignan to remain a part of his plans moving forward.

Putting forward the head coach as the final chess piece to try and win a losing battle is not something that inspires a lot of confidence nor is it emblematic of a totally competent management. Stranger things have happened though, and if we have learned one thing about Maignan it’s that he has a strong character, so doting on that could force a change of heart. Unlikely, not impossible.

What a competent management would do is make a final offer – perhaps with a little extra on top compared to the previous offer, to boost the chances of it being accepted (€5.5-6m net?) – but also prepare for the worst eventuality.

maignan suzuki caprilePhotos: Yu Chun Christopher + Alessandro Sabattini + Gabriele Maltinti/Getty Images

Of all the names linked to replace the current number one, few inspire much confidence. Zion Suzuki, Elia Caprile and Noah Atubolu are all very talented and appear to be on an upward trajectory. Yet, the impression is that Allegri wants someone at their best now, who is tested on the biggest stages.

So, rather than going for someone who is promising but unspectacular at Parma or Freiburg, it would not be a huge shock to us if links surfaced with options like Emiliano Martinez or even David De Gea, strong characters with a lot of winning experience. That is what Allegri seemed to value most about Maignan: the leadership factor and other intangibles.

Whatever happens from here, we must be appreciative of what Maignan has given during his half-decade at Milan. To win a Scudetto with 17 clean sheets instantly writes you in the history books at a club where the bar is high.

Who knows, he could yet contribute to another bit of silverware before he ventures off to pastures new, or Max’s charm offensive might yield the desired results to kick start a new glorious era with Maignan defending the posts.

If football has taught us one thing, it’s that it moves in cycles which are almost impossible to avoid. It’s always best, therefore, to enjoy the magic while it lasts.

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