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Heading into the summer transfer window, the AC Milan management knew they had a lot to do. And a lot they did…
The three months that followed the arrival of the Igli Tare-Massimiliano Allegri duo as the new sporting director and head coach were among the busiest in recent memory. Between 35 and 40 operations were completed, depending on who you want to count.
This is a good time to remember what Giorgio Furlani said, when foreshadowing what was to come. The CEO spoke alongside Tare at a press conference held at Casa Milan on June 25, and his words have now become infamous.
“There will be no need for a total revolution, but we will add some pieces to the squad to be ready for the new season. Our objective, on a sporting level, is the same as before: we must be competitive to win trophies,” he declared.
A revolution was to follow, by pretty much every definition of the word. The biggest upheaval was in the midfield department and it was mostly forced by the sale of Tijjani Reijnders to Manchester City, the first divisive move of a chaotic 12 weeks.
With criticism to come, praise must also be fairly given out. Tare and co. did a good job of rebuilding the midfield: a world-class player in Luka Modric arrived, while Adrien Rabiot would bookend the business as another experienced name.
Yunus Musah departed for Atalanta in an operation most seemed in favour of given his San Siro struggles, especially after Samuele Ricci and Ardon Jashari had joined from Torino and Club Brugge, respectively, to inject some youthful energy and (hopefully) some technical quality to the department.
With the middle part of the jigsaw teasing a beautiful picture, just how did the rest of the puzzle get so scrambled? Despite record proceeds from sales, things would go drastically wrong in terms of squad construction.
Centre-back catastrophe
Going from back to front, many expected Milan to do very little (relative to the rest of the squad) in the centre-back area. If anything, it was presumed that a sale would result in a replacement, and that would be the extent of the business.
In a broad sense, that’s how it went. The issue is the specifics. Milan made the decision to sell Malick Thiaw to Newcastle United three weeks before the end of the window, which – while not ideal from a timing point of view – was enough time to put the €40m to good use.
The necessity became very simple with that amount of money in hand: Tare, Giorgio Furlani and the rest of the directors had to satisfy Allegri’s request: sign an experienced, starter-level centre-back. In essence, they sold for €40m, so they had to buy for €40m.
Instead, they chose to sign Koni De Winter for half the money from Genoa. De Winter is not a bad player; he knows the coach from their time at Juventus, and he has been solid in Serie A so far. So, the issue is not necessarily him specifically as a player. It was the missed opportunity to make a splash.
Realising that Allegri wanted to use a three-man defence and that the central area was light on cover, Milan scrambled as late as they possibly could to try and get another player in to give five centre-back options. Manuel Akanji or Joe Gomez would have satiated the clamour, yet neither arrived.
When news spread early on deadline day that the 19-year-old David Odogu was jetting in for a medical, pundits and fans began to realise the magnitude of the desperation. That is not meant as a slight on Odogu – who, as we highlighted, is an interesting talent to develop – but rather what he represents: another huge gamble, not an instant fix.
It was widely documented by reliable sources that Allegri wanted a leader for the back, and we don’t see one. The oldest player is Fikayo Tomori at 27, and he is coming off three seasons of very patchy form. Matteo Gabbia is 25 and has rightly been made the bedrock of the back line, but Strahinja Pavlovic at 24 is still incredibly raw, and the two new additions are 23 and 19, as mentioned.
Age is not the only determining factor of leadership, of course, because someone like Akanji would have raised the technical level and would have provided a different kind of experience, having played for years under a world-class coach in a world-class team.
So, he could have helped set standards, but now he is doing so for the Rossoneri’s fiercest rivals in what was an embarrassing saga that almost requires a separate discussion. Even the Gomez pursuit was handled badly: hanging on for another operation to be complete (Marc Guehi to Liverpool) with hours of the window left was a risk they could not afford to take.
What should have been done differently? The supporter base at large seemed conflicted on whether spending €40m on Giovanni Leoni was a good idea or not. If Milan had paid the money, then they would have secured a crystalline gem for the future, and his addition would have generated a real buzz given the hype around his talent.
For those who doubt that, Liverpool did not. And they are in a far better state defensively than Milan are. Pietro Comuzzo of Fiorentina was a solid alternative target, but it seems no concrete attempt was made. Since the window has closed, their sporting director has suggested €35m would have got the deal done.
Thus, Milan went into the summer with a need to address, sold a player for €40m, recruited fourth and fifth-choice options as replacements and kept €10m in change. Consider the centre of defence unimproved, and potentially weakened.
Full-back foolishness
Perhaps the flanks were strengthened to improve the health of the defensive unit after all? Sadly, this is an area that the management got even more horribly wrong, despite having almost a blank canvas to work with.
Theo Hernandez was sold to Al-Hilal for €25m to bring a six-year era to an end, so a starter was needed for the left side. One of the mitigating circumstances mentioned for Theo’s decline was the lack of a backup, resulting in him being overworked, so one could make a strong case that two left-backs were needed.
On the right flank, there had been almost a systematic clear-out in recent months. Davide Calabria departed, Alessandro Florenzi’s contract expired, Kyle Walker’s loan was not made permanent, and Emerson Royal was sold. This left a grand total of zero natural right-backs in the squad.
Admittedly, the decision to use a 3-5-2 formation and subsequently go with wing-backs moved the goalposts a touch. All of a sudden, Alexis Saelemaekers – returning from his loan spell at Roma – and Alex Jimenez looked like candidates for both positions.
The first new face through the door was Pervis Estupinan from Brighton – risk number one. Why? Injuries have been a big problem for Estupinan in the past couple of seasons, as we highlighted in our player analysis.
Since the start of 2023-24, as per Transfermarkt, the defender has missed 43 games for club and country combined due to various issues. Three of the four long-term absences (30 days or more) are listed as ‘muscle injuries’, while he had an ankle problem that kept Jim out from April to the end of August in 2024, which was 140 days in total.
Staying fit is the first battle, before performance levels come into things. With the latter, a period of adaptation to Serie A is needed, and having to fly out to meet his new team-mates mid-tour was far from ideal.
Estupinan could turn out to be a very astute signing for less than €20m, and if he gives Milan 35+ games per season, he probably will be. Yet, to go from links with Destiny Udogie, Andrea Cambiaso and even Miguel Gutierrez to such a seismic gamble follows a theme that was to be repeated.
Not only that, but the Ecuadorian does not have a natural back-up either, with Davide Bartesaghi the deputy on paper at present. More to come on why that is. The Milan academy product is not only deeply inexperienced, but he seems to be more of a full-back or outside centre-back and certainly not a wing-back.
Did Milan at least ‘balance’ things a bit by signing a right-back with proven quality? You already know the answer. Zachary Athekame was the only signing from Young Boys in Switzerland, and he very much fits into the Odogu ‘wait and see what he becomes’ mould, rather than an instant contributor.
His zero minutes so far prove this, and there are question marks about his role because it appears as though a natural full-back has been signed for a system without any. Once again, that is not to say that the Swiss can not and will not develop into a very functional player in time, but he needs that time, and the Diavolo do not have it.
There have been comparisons drawn with signings such as Pierre Kalulu and Malick Thiaw, but where it falls short is that the defensive department, when they arrived, had become a strength, so they were complementary pieces at best. Instead, Odogu and Athekame arrived instead of what should have come.
Then we come to the seemingly rash decision to let Alex Jimenez go. There was speculation about attitude issues, including arriving late to training, yet waiting until the mercato finale to offload him feels counter-productive. There is a time to get rid of a bad egg when they are important, and that is not with hours to replace them.
Jimenez was not unanimously regarded as a starting quality wide man by any means. However, he covered a lot of ground, had technical quality and most importantly, versatility. Any Milanista who says they would not feel more comfortable with the Spaniard as the back-up wing-back on both sides rather than Bartesaghi and Athekame is lying.
Of course, there was a saga, too. The chaos that erupted surrounding then-Gent defender Archie Brown on the night of July 11 brings back nightmares for many as Milan battled to snatch him from Fenerbahce but ultimately lost. How is Archie doing, you ask? Five goal contributions in seven games.
The same as with the centre-back situation, the money was there to do the job properly. In terms of attainable alternatives, Gutierrez or Maxim De Cuyper would have been better for the left; Marc Pubill (who the Rossoneri turned away from before Atletico Madrid decided he was good), Arnau Martinez, or Givairo Read would have given more guarantees on the right.
Midfield mystery
In the introduction, the work done to reconstruct the midfield was praised, so hypocrisy now would be remiss, and this section will be a bit shorter. That being said, for as much as quality has come into the side, there are arguably more question marks than in any other area.
Modric, Rabiot, Jashari, Ricci, Loftus-Cheek, Fofana. Sounds pretty good, doesn’t it? Or at the very least, more than enough to get through a season with only one main competition to focus on, given the lack of European football. So what’s the issue?
Well, as of September 11, we are left with no idea which two or three players Allegri wants to play. It starts from a simple basis: Modric is undroppable, but not in the role that we all thought he would be, which is as a box-to-box mezzala. Instead, the Croatian has made his home as a deep-lying playmaker – a regista – and has effectively been given the keys to the control room.
There is no issue with Modric playing anywhere – the technical level he has and what he has achieved in the game means he commands the right to have input on that, though it moves the other pieces around in an awkward way.
What it means is that Samuele Ricci is now facing a battle to get starts or even regular minutes, given that he was also brought in to be that screen in front of the defence. As the first piece of the midfield rebuild, that is far from ideal.
Jashari’s injury could not be legislated for by anyone, though it does provide Allegri with an early headache. Presuming he persists with using a three-man midfield, he has Loftus-Cheek, Fofana and Rabiot to call upon at present for the two box-to-box roles.
The latter has just arrived, so by process of elimination, the coach has found himself having to rely upon the inconsistent Loftus-Cheek and Fofana in the early part of the season. After all of the business is done, such an eventuality seems problematic, to put it nicely.
Allegri said rather worryingly in a press conference that he wants the Englishman and the Frenchman to combine for 15 goals; i.e. the total that Reijnders scored last season. It drew a few laughs, but we suspect it might have been a media ploy to try to highlight what he feels that he is missing.
Rabiot’s late addition may go under the radar, but the end product that he gives might be crucial in filling that void. Given his relationship with the coach from their time at Juve, it feels like a starting spot has been nailed on for him.
That will leave four players for one place, though having an abundance feels like a nice problem to have after years of not having enough. Over to you, Max, to find the magic combinations.
Frontline farce
During his press conference with journalists at Casa Milan, Milan’s sporting director Tare boldly declared that the club are looking for a striker who can provide competition but above all something different skills compared to Santiago Gimenez.
“We are evaluating both in Italy and outside Italy: it is a question of characteristics, and for our team’s game, it is fundamental. He must be a player with completely different characteristics to those of Gimenez, who is not a centre-forward like Giroud: we must be good at completing these two things together,” he said.
Did a striker arrive? No, they did not. Many will view this as the great failure of the 2025 summer transfer window, because of what the hierarchy publicly stated they wished to do and the wild goose chase that then began.
First and foremost, the striker pursuit itself was handled dreadfully. From the hopeless hanging on for Dusan Vlahovic to the Victor Boniface debacle and the Conrad Harder confusion, Milan got right to the finish line several times but never crossed it.
The solution, again right at the end of the window, was to invest heavily in Christopher Nkunku of Chelsea. While a quality signing on paper, his best numbers have come as an attacking midfielder or a second striker, so he is certainly not the new number nine to lead the line.
Rafael Leao and Christian Pulisic were used as the front two throughout preseason, which again felt like a message from Allegri to the management regarding what he was working with. They did, however, look quite bright in the split striker roles.
The one to suffer massively from the centre-forward chaos is Santiago Gimenez. From Tare’s announcement onwards, there has been no shortage of speculation about him being unwanted just a few months into his time at Milan, and it continued until deadline day, when there was talk of a swap deal with Roma for Artem Dovbyk.
We have already written another lengthy column about the mis-profiling and mis-treatment of the Mexican, but things might have been forgotten had Milan managed to sign a striker that got everyone excited and satisfied Allegri.
The end result is that Milan essentially have three natural wingers and one unwanted striker for a two-man attack. Max must choose two to miss out on who will believe they should start. Yet, if the manager wants to use three forwards, then the issue becomes even more critical.
The sale of Noah Okafor was one that the majority of the fanbase did not argue with, given the guaranteed receipt of €20m for a hit-and-miss player, but then to let Samuel Chukwueze leave in the finale has taken away more depth.
As Leao’s absence over the past three weeks has shown, Milan are now one injury away from being in real trouble because they have so little to bring off the bench. Look at the upcoming Bologna game as an example: Leao out, Nkunku not fit yet, then Pulisic and Gimenez returning on Wednesday after over 15,000km travelled.
Trimming down the squad was necessary with no European football, as was offloading players Allegri didn’t see a use for. Despite this, we think that a forward had to arrive with Okafor and Chukwueze let go, because the end product is painfully thin forward depth and the potential for quite a predictable attack.
The hope to be wrong
There is no doubting that some of you will read this and feel that it is a negative and cynical assessment of how things have gone over the summer, and perhaps it is. With writing this comes a genuine hope that it all turns out to be incorrect and the window appears a masterstroke with time.
However, even the most ardent defender of the work done must admit that there is quite a lot of luck required for things to turn out right. The centre-back, full-back and attacking departments must remain injury-free, and Allegri must find the right concoctions across the park.
Admittedly, the mercato has thousands of dynamics that never make it as easy as ‘recoup money then spend it’. Otherwise, everyone would be an expert. That said, it does feel like other clubs are better at reacting to said dynamics, being proactive with business rather than reactive.
Another mitigating circumstance is that Milan do not have the appeal of Champions League football this season, and that this could merely have been a stripping back mission before a more expensive window in a year, hopefully with a ticket stamped for the top club competition and higher revenues on the cards.
For now, though, we are left to reflect on what feels like a missed opportunity.
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