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Rating AC Milan’s Winter Transfer Window 2021/22

An underwhelming one but hopefully the management are vindicated come June.

AC Milan Unveil New Signing Lazetic Photo by AC Milan/AC Milan via Getty Images

AC Milan had a really quiet January transfer window given the desire of the club to fight for the title and secure a top four spot this season.

There were numerous gaps to fill due to injuries and due to poor performance but none moves came to fruition. A centre back was direly needed, as was a central midfielder and a right winger. The defender will likely arrive in the summer given the costs, the midfield has Adli and Pobega in waiting but also a blockbuster target for the summer and the right winger front remained quiet throughout. A striker could arguably have also been added but a long term solution is needed at the end of the season here too.

Calcio e Finanza via are reporting that Milan have cut their wage bill by about 3 million euros from the winter window which is a minor victory.

Here is a summary of the window and our ratings:


Andrea Conti - Sampdoria - Right back - Permanent

A really good deal from Milan’s perspective albeit a little late. We save on six months of wages for a player is not considered to ever contribute to the side again. 8/10

Pietro Pellegri - Torino/AS Monaco - Striker - Permanent

A tough call for the management as they needed to weigh his potential against his poor injury record and they decided it wasn’t worth it without a discount. Not a loss for us at all as he barely contributed. He was directly replaced and the only big loss are the wasted wages and loan fee. Good move overall. 7/10

Milos Kerkez - AZ Alkmaar - Left Back - Permanent

An odd one, I cannot help but feel that Theo’s renewal pushed Kerkez out as the Hungarian youngster expected to get a shot at the first team. This will never be the case as long as Theo is committed as he commands too much influence on the pitch and adoration from the fans. A good 1.8 million euro capital gain is a win. The move is a little short sighted given Ballo-Toure is not convincing but the timing works. 6/10

Alessandro Plizzari - Lecce - Goalkeeper - Dry Loan

This is another tough one, he obviously needs playing time but another loan in Serie B and at a club that has an established starter? He will likely not crack 10 games before he returns and this raises questions around his actual potential given this is the fourth loan. It might be time to sell and promote Jungdal to the third keeper spot. 4/10


Marko Lazetic - Crvena Zvezda - Striker - Permanent

Very tough transfer to judge. On paper, he looks to be a like for like replacement for Pellegri but with much less experience but potentially a larger upside. He can develop under Zlatan and Olivier and play a role with little pressure which could aid his development. A solid long term investment but barely fixes our current problems. 5/10

Cathal Heffernan - Cork City FC - Defender - Loan with option

A purchase for the Primavera to bolster their defensive ranks and add some leadership. The youngster could be coming in to boost the numbers as Kerkez left. He seems to be highly rated and a good link to build between Milan and Ireland. Lots os opportunity for him to develop and he has a point to prove to earn that permanent move in six months. 6/10


The overall window is tough pill to swallow as many Milanisti expected at least one big spend on a key player to replace the likely outgoing Romagnoli or Kessie. The missed opportunity to bolster us at striker or right winger also stings given the recurring fitness issues with Ibrahimovic and the under-performance of Giroud, Messias and Saelemaekers. The biggest failure of the window is by far not selling Castillejo who will see out his contract with Milan pulling a Montolivo-esque move as he knows he cannot play again.

Maldini and Massara could potentially be confident in the current squad and planning for a big summer given the potential question marks around UCL football, some key renewals and potentially a title run.

Overall, I rate this window a 4/10 but focused on the trimming of the wage bill. I am confident Lazetic will offer more than Pellegri did, so we are just slightly stronger but I acknowledge much more should’ve been done.