Devil’s Advocate: A month of opportunity for Milan amid a winter of discontent

By Oliver Fisher -

Many view January – in terms of the transfer window at least – as a dangerous period with regards to the buying and selling of players.

The general consensus is that it is a time for panic-buying; an opportunity for clubs to overprice their assets in the hope of getting a bite from a club desperate to add that missing piece to the jigsaw and help them achieve their objectives for the season.

This is where Milan must think differently, especially given the situation they have found themselves in. In many ways they are fortunate; after a dismal start to the season – which saw the Rossoneri down in 12th place prior to Saturday’s win – a lot of players were perceived to be out of form and out of favour.

The usual suspects were hung out to dry by the media and the fanbase. Hakan Calhanolglu, Franck Kessie, Suso and Krzysztof Piatek have all been jeered by supporters at San Siro and persistently berated by the Italian press, and arguably with good reason given their contributions so far this season (or lack thereof).

Despite the aforementioned, there are still plenty of clubs sniffing around the names in question. West Ham continue to be linked with Kessie and Piatek, the latter also a target for Spurs, while Calhanoglu and Suso have admirers from overseas too if the speculation is to be believed.

This is where a winter of discontent could turn into a month of fresh opportunity for the Rossoneri. If head coach Stefano Pioli decides to proceed with a defined two-striker system with two wingers and two midfielders, there is the potential to raise funds through sales and really put his stamp on this group.

Despite what leading bookmakers like MarathonBet are suggesting, the fight for a top four finish is not yet dead and buried – there are still 57 points to play for and the gap to Atalanta stands at just 10 points. Stranger things have happened.

Back to the January market though, and there are seemingly a few key moves that Paolo Maldini and Zvonomir Boban are keen on making in order to give more balance to the squad.

Letting Mattia Caldara return to Atalanta was ultimately the right call regardless of the structure of the deal, but even when factoring in the addition of Simon Kjaer it still appears as though the centre-back department is a bit threadbare.

Given Mateo Musacchio’s inconsistency and Matteo Gabbia’s inexperience, the Diavolo should be looking at bringing in another leader at the back with experience at the top level. They could do worse than the likes of Dejan Lovren or Jerome Boateng – both of whom have physicality-based skill sets which should in theory complement Romagnoli’s, just as Alex and Gabriel Paletta’s did.

Looking at the full-back situation, Ricardo Rodriguez’s departure forces the need for a back-up left-back to Theo Hernandez. Layvin Kurzawa could be a good pickup for the right price, while it is worth noting that Paolo Ghiglione is having a superb season and can play either flank.

On the wings, Milan should see if Samu Castillejo can build on his positive showings on the right flank and stick with him if he deserves it, especially if Suso is sold. Speaking of which, the Spaniard’s sale could fund a move for Matteo Politano, who can play on either wing and would provide something different to the current group.

On the left side, Calhanoglu doesn’t seem to be a natural winger so it may be worth trying Giacomo Bonaventura out on the left one again. If the Turkey international is sold for the €20m figure being widely reported, Milan should try and bring Gerard Deulofeu back to the club. It seems as though the team has been lacking his pace, skill and direct approach since his departure.

Ante Rebic’s future is a puzzle which needs solving too: the Croatian is struggling for game time and if there are no plans to use him, he should be allowed to leave so his salary can be saved.


The central midfield department is perhaps the most interesting area. Ismael Bennacer and Franck Kessie played well together against Cagliari but there is still doubts about the consistency of the latter. If Monaco are still interested in the Ivorian, proposing a swap deal for Tiemoue Bakayoko would be an intriguing hypothesis given that he is a much more natural double pivot.

Rade Krunic can certainly do a job in midfield when asked and can offer that bit more penetration and attacking creativity, but that leaves a problem with Lucas Paqueta. The Brazilian cannot play in a midfield two and is unlikely to be shifted to wide midfield, so you can make a solid argument that Maldini and Boban should look at cashing in.

If they do decide to sell – and they get the €35m+ they are reportedly asking for – that money should be used to sign a real difference-maker to go alongside Bennacer in midfield, such as maybe Ivan Rakitic or Arturo Vidal from Barcelona.

Then we look at the striking department. Rafael Leao and Zlatan Ibrahimovic seem to be the established pairing after bright early signs, and with Piatek seemingly destined for the exit door the attention will turn to a replacement.

Andrea Petagna of SPAL has been mentioned. He scored 18 goals in an average side last season which cannot be ignored and would likely accept a role as a rotation player, but Milan must think beyond Ibrahimovic.

With money raised from sales, they could formulate a serious offer for Andrea Belotti either in January or in the summer. The Torino striker is still only 26 and is one of the most complete strikers in the league, meaning he could work well either alongside Leao or paired with a target man.

He likely wouldn’t carry a €100m price tag anymore, either, and the opportunity to play for his boyhood club could be enough to get him to force a move.

The bottom line is this: a lot of Milan fans are looking at the current squad as one with many holes and not enough money or time to address them, but there is reason for optimism.

There are opportunities out there, and a simple one-in-one-out policy could see Pioli stamp his mark on this team with some clever business while shifting out players no longer deemed central to the project.

Moreover, the fixture list is kind to Milan up until the derby in early February. Wednesday night’s game against SPAL should be a passage through to the next round of the cup, while league games against Udinese, Brescia and Hellas Verona follow.

As William Shakespeare said: “There is a tide in the affairs of men, which, taken at the flood, leads on to fortune.”

Tags AC Milan