Devil’s Advocate: How Milan should deal with the eight players currently set to leave in June 2021

By Oliver Fisher -

Despite the fact the ‘summer’ window only concluded early in October, the AC Milan management have had no time to rest and now their time will be consumed by a number of tricky negotiations.

As it stands, there are eight players who are set to depart the club at the end of the season unless some action is taken by Paolo Maldini and co., and here we take a look at each situation and what Milan should do.

Antonio Donnarumma

Antonio Donnarumma has spent the vast majority of his time with the Rossoneri as a third-choice goalkeeper, but is remarkable still a bit of a cult hero among the fanbase having never conceded a goal in his three competitive starts, which includes a 1-0 Coppa Italia win over Inter after extra-time.

It is frankly too easy to simply say “let him go” because it must be considered that Antonio is 30, is happy to be a back-up to the back-up and is a useful leveraging tool in the negotiations for his brother.

There will be those clamouring for Alessandro Plizzari to come back and be the third-choice, but it quite simply does not make sense to devoid him of playing time at such a crucial time in his development.

Therefore, give Antonio Donnarumma and extra couple of years but at a lower salary than his current €1m net per year (as per La Gazzetta dello Sport) if at all possible.

Gianluigi Donnarumma

There is absolutely no question that everybody wants to see Gigio stay in a Milan shirt for a very long time. With 217 competitive games under his belt at the age of 21, he really has a chance to break all kinds of club appearance records and maybe even league records.

The question of course is under what terms the deal should be done. Recent reports have suggested a lot of optimism, and Milan should be happy to commit to a figure of €7m net per year, a slight pay rise from the current €6m he earns.

However, there should also be some leverage on this because it sounds like his agent Mino Raiola wants a release clause. It is genuinely worth raising his salary to €7.5m – perhaps even €8m – to ensure a silly release clause like €50m is not inserted.

Even though the world of football is different now, Chelsea’s signing of Kepa Arrizabalaga shows there is still a market for expensive goalkeepers and Donnarumma would offer quality in that position for a guaranteed 10+ years.

The bottom line: give Donnarumma and Raiola what they want to avoid a release clause within reason, and be creative with bonuses like Champions League qualification.

Mateo Musacchio

Since joining as part of the 2017 summer spending spree under Yonghong Li, Marco Fassone and Massimiliano Mirabelli, Mateo Musacchio has gone on to make 73 appearances for Milan in all competitions and was actually very important during his first two seasons.

However, since then things have gone downhill. He now appears to be the fourth-choice centre-back behind Romagnoli, Kjaer and Gabbia due to a combination of injuries and poor form, and it seems Milan are focused on bringing in another young defender to grow alongside the current group.

Therefore, it only seems fair to let Musacchio escape what has become a pretty difficult situation and allow him to leave on a free transfer, which will in turn save Milan €2m net per season.

Zlatan Ibrahimovic

It seems that the decision will be taken out of Milan’s hands on this one. If Ibrahimovic feels like he can continue then he will, and the club are likely to offer him the same salary again or perhaps slightly lower – which he is absolutely worth.

At some point the issue of what happens after Zlatan will have to be addressed, but for the time being the focus should be to get as much out of the eternal Swede as is possible before he strolls off into the sunset. Another year would do no harm.

Hakan Calhanoglu

This is perhaps the most contentious of the seven situations discussed, as Calhanoglu seems to divide the fan base more and more with each week of speculation.

What seems to filter from the most reliable sources is that the Turkey international wants at least double the €2.5m net per season he currently earns, and there is no way that the should be paying anything like that.

We have already written a feature comparing the potential cost of renewing Calhanoglu vs. signing a new No.10 like Dominik Szoboszlai, but it would also be naive to discredit the important of the former to the way Milan currently play.

The line of stats doesn’t read terrible: 27 goals and 40 assists in 143 appearances in all competitions, but his upturn post lockdown is not enough for Milan to agree to a potentially €40m+ gross contract.

The club seem to have gone up to €3.5-4m max as a last offer, and they should not go further than that. Too much work has been done on trimming the wage budget for the club to now be held to ransom. If he wants more, let him go and get straight on the phone to replacements.

Brahim Diaz

Having arrived on a dry loan from Real Madrid at the start of the season, the overall impressive from Brahim Diaz has been good, and Ricky Massara confirmed before the game against Fiorentina that he plans to hold talks with Real Madrid over keeping him for longer.

Although a number of different possibilities have already been mentioned in the media, one sticks out as being by far the most sensible and that is the extension of his loan for another year (until 2022) with the insertion of an option to buy.

That gives Milan another season of his services guaranteed and means Real Madrid do not lose control of the player, while the option to buy could be set at the €20-25m mark so Los Blancos know they can make a nice capital gain on a player who is unlikely to feature in their plans.

A subsequent buy-back in their favour should be avoided at all costs if possible, but if they insisted then it should be at around €30m so essentially Milan get some form of development fee.

Sandro Tonali

There doesn’t seem to be an awful lot of discussion that needs to be had regarding Tonali’s future. While he has had a somewhat shaky start to life as a Milan player, there is no doubting either his potential nor the belief that the management have in him.

That is exactly why they pursued him so aggressively when Inter’s stalling left the door open, and the €10m loan fee means that an investment has already been made.

There is a €15m option to buy at the end of the season that is almost certain to be triggered at this stage, because Tonali is one of the brightest prospects in Italian football and will be a very important component in this team for years to come.

Diogo Dalot

Finally we come to perhaps the most contentious of the loanees in Diogo Dalot, who came on a season-long loan from Manchester United with no option or obligation to make it permanent.

There has been conflicting speculation about whether or not United are willing to sell, as Fabrizio Romano has claimed that United are convinced that he will become a top full-back, hence why they did not want to include any option whereby they lose control of him.

However, if Milan have a chance to sign him then they absolutely should. Ultimately he became third-choice at Old Trafford so there should be no delusions that he was a valued member of their squad, and he is so useful to Milan’s.

His ability to play on both the right and the left side of defence is a real luxury as he can come in to give Calabria and Theo Hernandez rest, and who knows he could even knock on the door for a starting spot if the former dips again.

With no guarantees from Conti or Kalulu and no current natural back-up left-back, it is a no-brainer to try and keep a very talented young player and of course a friend of Rafael Leao.

🤔 What do you think? Did we get the assessments right? Tell us in the comments below! 👇

Tags AC Milan Antonio Donnarumma Brahim Diaz Diogo Dalot Gianluigi Donnarumma Hakan Calhanoglu Mateo Musacchio Sandro Tonali


  1. Man United is cutting cost – getting Dalot for a decent price is certainly a possibility as he’s not in favor there. He’s only on 40k a week and will be out of contract in ’23. Covers two positions and is a decent player w/ potential to be good (maybe not starter good).

    Sell Conti. He’s dead wood.

  2. Chalhanoglu is replaceable and his form is not consistent
    some games he is awesome and some days he is very slow and bad and his stamina is not that great and every game around the 70th minute we can see that he is very tired even though some players that run more than him are still looking fit
    I personally like his football when he is having a good day and I want him to stay but he shouldn’t take advantage of the fact that his contract is expiring
    and with the way manchester is playing I don’t think that he would be making an upgrade by moving there and he wouldn’t fit that well with a team that only knows how to run
    4 million should be more than enough for what he can do for the team
    Dalot is not worth buying just yet
    he is good but both calabria and theo are much better than him and they are both young and paying more than 10 million for a backup player is not such a good idea even though having a good backup player like him is always a welcomed idea

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