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What Are AC Milan’s Priorities For The Last Two Weeks Of The Summer Transfer Window?

Tick tock for Maldini and Massara.

Real Madrid v AC Milan - Pre-Season Friendly Photo by Jonathan Moscrop/Getty Images

Today is the 16th of August, we are now into the final 15 days of the mercato. AC Milan have already invested significantly over the summer but surprisingly the squad is less complete than before as a result of some big departures. Milan have thus far added Fikayo Tomori from Chelsea FC, Mike Maignan from LOSC Lille. Brahim Diaz from Real Madrid, Fode Ballo-Toure from AS Monaco, Sandro Tonali from Brescia and Olivier Giroud from Chelsea FC.

Here is a look at the five gaps that Milan still need to address, arranged in reverse by priority. I have also added a opinion rating of the likelihood of a deal being closed:

#5: A Right Back (Depth)

Options/Rumours: Alessandro Florenzi (AS Roma)

Milan need to get some cover for Davide Calabria and Florenzi has emerged as an option. The former AS Roma captain has fallen out of favour in the capital and has been out on loan at Valencia and PSG over the past two seasons. He brings Serie A and UCL experience which will be valuable as well as positional versatility as he can play as a right back and a right winger if necessary. The deal seems close and will allow Stefano Pioli to push Pierre Kalulu to play as a centre back which is good in the long run.

Likelihood: 9/10

#4: A Striker (Depth)

Options/Rumours: N/A

The Rossoneri have two veterans in Zlatan Ibrahimovic and Olivier Giroud leading the line at the moment. Both players bring a lot to the table but injury worries have fans sweating given our experience last season. A third striker such as Lorenzo Colombo or Kaio Jorge would have been ideal to train with the duo and provide cover in the Coppa Italia and off the bench in other competitions. There are no strong links at the moment as most tracks cooled down but a deadline day addition would be ideal here to further strengthen the squad.

Likelihood: 3/10

#3: An Attacking Midfielder (Starter/Depth)

Options/Rumours: Nikola Vlasic (CSKA Moscow), Isco (Real Madrid) and James Rodriguez (Everton)

This could arguably be Priority #1 but given the promise shown by Brahim Diaz, I have put it lower as the Real Madrid youngster could be the silver bullet for the season. Regardless of his potential, Milan could do with a more experienced and physical player given the nature of the Serie A. Links to Coutinho, Isco and Rodriguez seem lazy and unliekly given their wages but the track of Vlasic seems realistic.

Likelihood: 4/10

#2: A Central Midfielder (Depth)

Options/Rumours: Yacine Adli (Bordeaux) and Tiemoue Bakayoko (Chelsea FC)

This is a tricky one as the issue could potentially be dealt with in the winter window but a lack of chemistry would hamper it’s effectiveness then. Milan will lose Franck Kessie and Ismael Bennacer for the AFCON in January and February 2022. Miln have a tough stretch of games then hence need a solid cover midfielder to partner with Sandro Tonali. Adli seems close, Bakayoko less so but there is an argument to make for Tommaso Pobega to get the nod. Either way, the Rossoneri need to ensure we are not short staffed in the midfield as it was one of our strongest positions last season.

Likelihood: 8/10

#1: A Right Winger (Starter)

Options/Rumours: Hakim Ziyech

The signing is realistically worth the other four combined. Milan cannot get to the next level without a major upgrade at right wing. If we go into the season with Samu Castillejo, we will be ineffective in attack raising the pressure on the defence. Alexis Saelemaekers is good but is not a starter would can deliver a threat consistently, he is a good utility player and adds energy off the bench. Milan need someone creative who has pace and drive to contribute with goals and assists game in and game out. Ziyech is the name that lingers but this deal seems complicated, my ideal signing would be Domenico Berardi from Sassuolo but it does not seem that he is on the market anymore but anyone good would do the job.

Likelihood: 7.5/10

Below is a snapshot of Milan’s squad as it stands. The ‘?’ represent opportunities for an intervention in the market.


I have excluded Samu Castillejo and Tommaso Pobega from the line up as wishful thinking. Pobega seems likely to go out on another loan in Serie A to develop further if Adli arrives and this will be the best course of action for him. Castillejo has received multiple offers from Spain but wants to remain at Milan, but we need him to leave to be able to upgrade at that position where he has not offered much over the past one and a half seasons.


What Should Be Milan’s Priority #1 To Sign?

This poll is closed

  • 37%
    Central Attacking Midfielder
    (80 votes)
  • 3%
    Right Back
    (7 votes)
  • 52%
    Right Winger
    (113 votes)
  • 3%
    Third Striker
    (7 votes)
  • 3%
    Central Midfielder
    (7 votes)
214 votes total Vote Now