Devil’s Advocate: Maldini’s deadline day strategy rightly leaves Milan fans scratching their heads

By Oliver Fisher -

Going into deadline day for the 2020 summer transfer window, it seemed obvious that Milan would be active and sign at least one player. Just one.

Yet here we are with the window having slammed shut, and no players have arrived through the doors. There was no routine and efficient business that saw Paolo Maldini and co. secure a target that the media assure us we have been ‘scouting for months’ nor were there any frantic or dramatic last-minute additions that really feed into the frenzy of the final day of the window.

After Sunday’s win against Spezia, Milan’s sixth in six games to start the season and one which continued the perfect start in Serie A, this of course continuing the incredible post-lockdown form from 2019-20.

Following the game, head coach Stefano Pioli made the following remarks: “I am satisfied with tonight’s match. It is true that we are looking for a central defender because we have many injuries and a demanding schedule. It’s a good start, it must give us positivity and confidence for the future.”

It follows on from comments made by Ricky Massara and Maldini which in the days and weeks prior to the close of the window confirmed that a centre-back was Milan’s main priority, given the injury situation which meant Simon Kjaer and Matteo Gabbia were the only options.

So many targets were linked, including the likes of Celtic’s Kristoffer Ajer, Fiorentina’s Nikola Milenkovic and Saint-Etienne’s Wesley Fofana. None arrived as all three were ultimately deemed not worthy of the investment, or the money simply wasn’t there.

Then even on deadline day there were three irons in the fire: Schalke’s Ozan Kabak, Chelsea’s Antonio Rudiger and Strasbourg’s Mohamed Simakan.

Ultimately, not a single one of the over 10 centre-backs linked with Milan ended up arriving, and it has left many fans feeling understandably quite frustrated but mostly underwhelmed.

When a position is such a huge priority and key figures at the club come out and even say so themselves, disappointment should be expected when a player in that position did not join, because it means the problem ultimately was not addressed.

The saying ‘no business is better than bad business’ is one that does hold weight, especially on deadline day and especially in these times given the stresses on finances.

However, we know we had liquidity from the €20m sale of Lucas Paqueta to Lyon and through the €15m+ that Europa League qualification will bring, and also from the confirmation of bids for various defenders that confirms money way there to be invested.

Therefore, we must in a way question the tactics deployed by Maldini and Massara in the final 72 hours of the window. Instead of honing in on one target, they seemed to shift from alternative to alternative and low-ball the asking price repeatedly until every club put up a wall and refused a sale or they sold to a higher bidder.

We do not know what happens in the conference calls between the management and the ownership, it may well be that Elliott Management were only willing to make funds available for investments of certain quality, but not even a temporary solution arrived to plug a quite obvious gap like the loan of Rudiger – which seemed an easy-ish operation to wrap up.

One can then start to point the finger at other parts of the market where Milan did far from ideal business. From being virtually promised a back-up double pivot of Tonali-Bakayoko, the latter has joined rivals Napoli. Looking at the two weak spots heading into the summer – right-back and the right wing – no players arrived to improve the starting XI.

It was very obvious from the moment the collapse of Ralf Rangnick’s arrival was announced and Pioli’s new deal was confirmed that this would be a market of fine tuning rather than radical overhaul.

Once again, doing solid business early is much better than being left in a position where the management are left to panic buy and spend money badly on deadline day, alas the frustrations and the reservations regarding the end to the market are warranted.

Yes, the return of Alessio Romagnoli will feel like a new signing, however the bottom line is Milan are still one injury away from big problems because Leo Duarte and Mateo Musacchio simply will not cut it.

A big piece of the squad that Pioli asked for – one that will play over 50 games this season – did not arrive, and he should receive a frank and honest explanation as to what happened. After all, this is his reward for going 15 Serie A games without defeat with 12 wins.

To end the stream of consciousness with some positivity, the transfer window is a lot like Christmas. It tends to be a month of excitement building up to the hallowed day, which often flies by with nothing other than pure elation or disappointment – there is no in between.

Perhaps though Milan’s Christmas came early, through the marquee signing of Sandro Tonali, through a potential future star in Brahim Diaz (if a permanent deal can indeed be agreed) or through the exciting and bargain deal for Jens Petter Hauge.

Not only that, but there were other important moves that people might forget. Zlatan Ibrahimovic’s renewal was secured after a long back-and-forth, Ante Rebic joined on a permanent deal and there were also departures like that of Lucas Paqueta which are nothing but beneficial.

Let’s just hope that these fine tweaks are enough, and that we are not looking back before the January transfer window with big changes needed like we did last season. Pioli, after all, has shown that he is capable of delivering excellent things with the current squad.

Now, the focus must be on maintaining that core. Get Gianluigi Donnarumma’s renewal sorted, and the same for Hakan Calhanoglu, maybe even Franck Kessie too. Make sure that this current group stays together, because it has fans dreaming again for the first time in a while.

Tags AC Milan


  1. Wait you’re disappointed because Milan wouldn’t overspend on Bakayoko (whose salary was to big and Chelsea wanted to sell outright for €30 million) when Krunic has been a usable backup who’s played well in some big games?
    Gone are the days where Milan were “better served” by throwing big money at a desperate last minute solution. This is a young team that is deep in talent. Shrewdness in the market is what makes teams with poor finances good. Not spending recklessly so the media can feel like spoiled kids on Christmas.

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