Milan Winter Transfer Mercato: 2024-25 -

Hey everyone, Gillis here to open this post. Lisi is going to handle the new transfers below but wanted to just acknowledge the departure of Davide Calabria, off to Bologna on a permanent deal, and Ismael Bennacer, off on a loan plus option deal with Marseille.

We won’t focus on the other guys but here are the rest of the departures:

Álvaro Morata – Galatasaray 1yr Loan (€6M fee)+€8M Option
Noah Okafor – Napoli Loan (€2M fee)+€23M Option
Kevin Zeroli – Monza Dry Loan
Fodé Ballo-Touré – Le Havre AC Contract Terminated
Marco Pellegrino – Huracán Dry Loan
Luka Romero – Crul Azul €3.4M

Moving on to Calabria and Bennacer, both players were solid contributors as Milan lifted themselves out of the banter era. Calabria, the boy who joined Milan when he was only 9 years old, came up through Milan’s youth system and became a starter on the first team, a rare occasion the last 15 years. A guy who always gave maximum effort, he was also one that many of us, including myself, felt was a liability on a team otherwise performing at a high level during the Scudetto season a few years back.

The most memorable Calabria game for us was when he shut down soon to be Serie A MVP, Khvicha Kvaratskhelia, over 3 games, late in Napoli’s Scudetto-winning season and a few weeks later in Champions League. I’ve always thought Kvaratskhelia was overrated (and still do) and Calabria putting him in his back pocket is something I will always hold dear. Calabria is a Milanista through and through. Maybe our paths cross again in a management role like Abate or Bonera. Always good to have guys around who bleed the red and black.

Bennacer came to us from Empoli and was a little rough that first season. Lots of yellows I remember. But he formed a lethal combination with Sandro Tonali and Franck Kessie in the double pivot and sometimes more advanced as a CAM, proving to be a vital piece of that dynamic trio of midfielders finding their way on the pitch.

Injuries really took their toll on Bennacer, suffering multiple severe leg injuries in back to back seasons. It’s ultimately what prevented him from remaining a top option for Milan. But in the midst of it all, his huge game winning goal in Champions League, also against Napoli, will be one of my favorite Milan memories.

Best of luck to you both. Grazie and forza Milan per sempre.

The Winter Mercato

Where did this come from?! I, like many of you, was blown away by the amount of action at the close of the winter window. Milan is really going for it! (and by it I mean just trying to finish in the top 4)

Lisi will tackle the details below but just wanted to say, as many of you likely know already, that newly signed striker Santiago Giménez has been a life-long Milanista as this photo from his youth has been making the rounds. Like Kylian Mbappe, it’s refreshing to see players as young as these guys rocking Milan jerseys during a time when Milan were starting to come out of their heyday of Champions League trophies of the 1990s and 2000s (both Giménez and Mbappe are photographed in the 2010-11 Scudetto winning season kit). Milan is always world wide, world renown, and always top class. Gotta love it.

On the pitch, the passion of a lifelong fan, often attributed to locals or natives of the town/city/country, can also come from afar. I’m looking forward to seeing this kid play his heart out for his favorite boyhood club.

And now I hand it off to Lisi…

Here we go folks. Your 2025 Christmas/January/Holiday transfer report card for Milan. Each player followed by cost, where they came from and age. A note on the grades: I’ve been really grumply lately. The grades will certainly not be fair and balanced and they might actually be terribly biased. They mostly reflect short term need and filling that need. January transfers are about desperation, not 5 year plans.

Keep in mind this order has nothing to do with who my favorites are or who looks best in red and black. It is simply in the order they arrived. Promise.

Winter Signings

Kyle Walker

34yrs old MANCHESTER CITY Loan+ €5M option

June 2025/€2.5M per year (if option exercised contract until June 2027)

While I will always have respect for Calabria a change was needed. RIP to the Kvaradona killer. Certainly a more reliable player. Royal certainly wasn’t that guy. In fact he was SUPPOSED to be in the outgoing section til he got hurt. Because he got hurt Calabria is gone. So now we go from having an army of guys at RB to only 2. Walker is gonna be solid. He should also be a great partner for Tomori considering a common language and shared experiences in the Premier League and on the English NT. Whether he stays or not is really not important. Be a rock back there sir. Nothing fancy. Just solid. Love it.

Grade : B+

Santiago Giménez

23yrs old FEYENOORD €32M+ ad-ons

June 2029/€2.5M per year

Anyone remember the last time we spent this kind of money on a striker under 25? Yeah ok fine it was CDK but how about before that? Never. Yes he put up big numbers in the Eridivisie. I get that. He also put them up in Europe. Repeatedly. He scores goals with both feet, his head and even cracks in bangers from distance. He’s got some serious grinta and plays with an edge I think other folks on the team will gravitate towards. Right player at the right time if you ask me. He has to be for Ibra. This is his ‘plant my flag’ moment as a sporting director. Playing in the shadow of Ibra? No pressure kid. Personally I love it.

Grade: A

João Felix

25yrs old CHELSEA Dry loan (€5.5M fee)

June 2025/€2.25M per year

Anyone remember the last time we had a dry loan that really worked out? Me neither. Probably Mario Pasalic? That was a while ago. Any chance he stays? No way. He’s signed through 2030 at 12 million a year. He wants to play, It isn’t happening at Chelsea. Essentially he’s James Rodriguez 2.0. All the talent in the world but no position and no real place for him. A fun toy that we can play in lots of places and maybe finds a spark. Worth the gamble considering we need something special to get top 4. There’s a reality where he explodes and the attacks takes off with him involved. Will that actually happen? Probably not. Thing is though all he needs is one or two big moments to make it all worth while. Just like Pasalic.

Grade: TBD

Warren Bondo

21yrs old MONZA €10M

June 2029/€1.5M per year

Fills a big need in deoth at the defensive midfield depth. Would have preferred a vet but also ok with possibly getting a steal from Monza. They are going down and the fire sale starts now. Actually it started last summer but that’s for another post. He’s the vice Fofana we need to rotate down the stretch. Won’t be flashy. Probably no chance he scores. That’s not what we need though. Just go win the ball and distribute it to the plethora of attacking players we are blessed with. Do you know what a plethora is? That’s it kid. Don’t need to be a hero. Could be a sneaky good signing down the road for us. The type of signing that has Golden Tie written all over it. FLY CONDOR FLY!

Grade: B

Riccardo Sottil

25yrs old FIORENTINA Loan (€1M fee)+ €10M option

June 2025/€600K per year

Fills the need of an extra body/winger with Okafor leaving. Fills the spot of Italain on the roster with Calabria leaving. Fills the need of having a good looking fellow (don’t judge) on the squad for the ladies to gaze at. Probably also contributes mightily to Avia’s not WAG post. Honestly if he scores 1 goal the rest of the year it’s a bonus.

Grade: C

Wrap Up

You have to break a few eggs to make an omelette. I’d say we broke a few eggs we no longer needed and the omelette just got a whole lot tastier. Is top 4 in reach now? Hmmmmmmmmaybe? Is that a word? More maybe than a few days ago? Probably. Will I throw a fiver on it? You bet your ass.

Cheers

Lisi