The art of selling at the right moment: Milan to face a big conundrum

By Christian Montegan -

Nearing the end of the Silvio Berlusconi ownership period after dominating both Italian and European football for the past two decades, the ‘banter era’ truly came into existence as the club spiralled into arguably its longest period of darkness over the course of its proud history.

Die-hard Milanisti will want to cover their eyes before reading out some of these past players: Michael Essien, Cristian Zaccardo, Alessio Cerci, Kevin Constant, Mario Yepes. There are so many more to name, but let’s spare the blushes and embarrassment.

Signing free agents and players well past their prime became a constant theme in the work of former CEO Adriano Galliani. Clearly, that strategy to save costs did nothing but damage the club.

In 2016, Yonghong Li bought the Rossoneri under Chinese ownership, implementing the opposite strategy which led to big-money transfers. It was rash from the very beginning as no real plan was evident from the very beginning in terms of structuring the squad.

Not long after, transfer values would begin to diminish such as Leonardo Bonucci (equalling the club record for the most expensive transfer of €40m) witnessed his stock fall dramatically.

Copying the model of Paris Saint-Germain and buying as many players as possible (only of lesser quality) was deemed another failed strategy.

Yonghong was unable to repay loan instalments and thus Elliott Management – the US-based vulture fund he borrowed from – seized control of the club. Another new era was ushered in, one that quickly saw Milan banned from European competitions for one season after violating Financial Fair Play (FFP) regulations.

They achieved what no previous ownership could accomplish : convincing Paolo Maldini to be part of the project as technical director, aligning the vision of creating success through youth and smart buys, whilst witnessing player values skyrocket over time.

Working alongside former director of football Ricky Massara, Milan all of a sudden regained a sense of identity and self-worth in the way they were handling their business.

As per Transfermarkt, the following signings made since Elliott’s takeover are as follows:

➤ Rafael Leão – Purchased for €34.5m / Current market value of €90m
➤ Theo Hernandez – Purchased for €22.8m / Current market value of €60m
➤ Mike Maignan – Purchased for €15.4m / Current market value of €45m
➤ Fikayo Tomori – Purchased for €31.6m / Current market value of €40m
➤ Malick Thiaw – Purchased for €8.8m / Current market value of €30m
➤ Ismaël Bennacer – Purchased for €17.2m / Current market value of €38m

As you can see, the scouting and networking done behind the scenes to identify raw talent and develop them astronomically should be viewed as a success for the club’s long-term project.

It can be argued that what’s even tougher, however, is knowing the right time to sell your brightest assets at their peak for the best possible price.

Milan has already fallen victim to the expiration of contracts relating to high-performers and regular starters such as Gianluigi Donnarumma, Hakan Çalhanoglu, Alessio Romagnoli and Franck Kessié; all of which drew differing levels of anger from the fanbase.

We understand how the modern game is nowadays. Loyalty is very rare to come by due to the financial standing of some of the best clubs in the world who can afford to splash the cash.

Timing is absolutely everything when it comes to understanding when the most productivity has been exacted from a player and having the sense of awareness and maturity to offload at the right time.

Leão’s name seems to always resurface in these types of debates. The talent is obviously there for all to see and when the Portuguese star is on, he is virtually unplayable with his pace and the seemingly effortless strides he takes with the ball.

Consistency, consistency, consistency. If only that keyword would be a fitting description for the 23-year-old. For as reliable as the team is on him to perform at maximum capacity, that over-reliance is part of the problem for a player who is still yet to prove that he can be reliable every week.

Despite putting pen to paper on a new deal lasting until 2028 with a reported €175m release clause, is it time to ponder whether Leão is worth rejecting big money for?

Well known for his attacking flair and lightning speed down the left-hand side, Theo Hernandez has been an explosive phenomenon partnering Leão. Since his arrival from Real Madrid in the summer of 2019, the Frenchman has contributed a mind-blowing 25 goals and 30 assists to act as a real threat to any opposition defence, good enough to see him transition into a regular starter in the France national team setup.

Besides an inch-perfect cross for Oliver Giroud to head home the winner against Paris Saint-Germain two weeks ago, the 26-year-old has been rather underwhelming by his high standards as of late.

For all of his brilliant work going forward, Hernandez is still vulnerable defensively, especially in one-on-one scenarios. Looking at his discipline record, it’s not good viewing with a total of 47 yellow cards and three red cards accumulated in a little over four seasons at Milan.

Frankly speaking, his childish acts when going to ground after the barest of touches brush his body needs to be stamped out of the full-back’s game in an instant. In the 2-2 draw against Lecce, Hernandez was clutching his leg on the floor after a challenge with minimal contact in the hope of gaining a free-kick. Instead, a goal was conceded at the other end with Milan essentially a man down.

And wouldn’t you know it, Hernandez got straight back up to his feet and continued playing as if nothing happened, except, conceding a costly goal in the process. Yunus Musah copped the full brunt of the blame, but Hernandez has not been pulled up on his antics enough to the point where Stefano Pioli doesn’t want to address the issue.

Would it really be the end of the world if Milan pocketed a hefty fee in the near future?

It certainly felt like the world was coming to a halt when Donnarumma walked out on a free transfer until the signing of Maignan has since proven to be a masterstroke. Yes, some of his saves have been crucial along the way, but should injuries and a potentially high transfer sale be enough to justify a potential sale within the next year or so?

This season, Fikayo Tomori has demonstrated the same level of quality and consistency that made him a household name in his early days under Pioli to hold the defence like glue. Perhaps, he may fancy a move back to England to cement his place in the England team to further convince Gareth Southgate that he is in fact the real deal.

Then there’s the possibility of Bennacer’s reported €50m release clause being triggered, albeit not playing a single competitive match since May. Although the Algerian’s quality in midfield has been sorely lacking which is crying out for some control both on and off the ball, the tough questions will need to be asked.

In order to compete long-term and nail down a long-term project, the depth within the squad will be fundamental when comparing Milan to their rivals both domestically and in European competition.

That said, there comes a time when the financial implications of the game outweigh the talent side of the equation. Of course, selling multiple big names in one window or even letting stars go in consecutive summers would draw scrutiny, threaten the stability of the project and require individual consideration.

Arms were frantically waved in the air after learning about the sale of golden boy Sandro Tonali to Newcastle United for a reported €70m plus bonuses. As the dust settled, and with the way things have worked out since, most didn’t care to bat an eyelid.

It has the feeling of an important 12 months coming up for Cardinale and the Milan management to swallow their pride and make the difficult choices required to consistently compete at the top.

The Rossoneri can ill-afford to make the same costly mistakes.

Tags AC Milan


  1. Sold a core starter to fund complete revamp of the team. Across the street Inter are putting in missing puzzles to their cemented core. Tell me, who’s doing better and who’s struggling more? Tell me, what selling more of our core players will bring us? Severe lack of continuity. We’re on a good path to become the Arsenal of Italy with this plan. You think they won’t sell any of newcomers if they start banging? Everyone is for sale in Milan nowadays.

    1. @Ted. Rubbish. Inter loss Skriniar on a free transfer and they sold Onana for 60m to United and Alexis Sanchez was sold to Marseille. Prior to that they sold Lukaku to Chelsea.

      So Inter loss players on free transfer and they also sold players. The difference between Milan and Inter is that Milan are not signing players who immediately improve the squad.

      We are taking too much chances on betting on young players and players who are not playing well in other clubs like Thiaw, Kalulu, Romero, Origi, Jovic, and Pellegrino.

      While inter are signing Acerbi, Thuram, Augusto, Fratessi, Sommer, Klassen, and Asllani.

      There’s a major difference in the quality of players Inter signs compared to Milan.

      1. I’d prefer to involuntarily lose players on frees than to voluntarily sell star players….

        The thing about involuntarily losing players is the club has tried to keep those players and if they choose greed over loyalty (and in some cases success) then f$%k them. See Donnarumma and Çalhanoğlu – both left on a free, both missed out on a Scudetto!

        In that case the focus of my anger is the player.

        Voluntarily selling star players involves deciding to just allow a top talent go to another club. And if we want to go somewhere, a potential competitor.

        If a player is performing player it also means taking a huge punt on whoever replace that player with performing at the exact same level or higher where there is no guarantee because there are so many variables e.g. tactics, training methods, chemistry, team mates, manager, family, favourite place to have lunch….

        But the media and fans miss this because all they think about is MONEY. And the thing about MONEY is that the more you think about it…..the more you tend to spend…..Milan spent over billion Euros in 10 years (the so called ‘banter era’).

        1. Sorry but I have to disagree (but not entirely).
          It’s true that it is FAR FAR better to keep a star player for as long as possible, as long as this players is well performing. It’s also a fact that, in order to keep a certain amount of continuity and cohesion, we must try to maintain the same backbone of the team. That doesn’t mean that we should keep every player but the most important ones (Real Madrid is a good example of this strategy).
          However, it’s sometimes clear that a player’s mind can be elsewhere, and that player, unless you give him a lot of money (which can be detrimental to the cohesion of the team), is going to leave. In that case, it’s better to sell him, rather than losing him for free.
          Now, I don’t really regret either Donnaruma or Calhanoglu, we did win a scudetto without them, but it’s true that, had we opened their case a season or so sooner, we could have decided to sell them even by the summer of 2020, which could have helped the club A LOT financially wise.
          And in the case of Kessie, we did regret our lack of management both financially and on the field. We kept trusting his words until it was too late, and we neither kept him, we didn’t replace him afterward, and we didn’t benefit from his departure.
          So sometimes, you have to know how to sell your players.

      2. @ZionTrain. Skirinar wasn’t playing much near to the end of the season and Onana was a good sale and with Inzaghi’s tactics they don’t need a ball playing keeper. They replaced him with one of Bundesliga best historically. Sanchez isn’t a game changer and was played sporadically. Those weren’t core players. They refused Barella sale because they knew how important he was to the team. But I do wholeheartedly agree with the last part. While we’re getting the unknowns Inter picking up solid signings.

    2. Milan is doing better because we are financially stable. This season might go to shinter on the field but of the field we are in a much better place.
      Also, don’t act like shinter didn’t sell to finance those missing puzzles. #Onana

      1. I’m not talking financial aspect, that we have best in Italy for sure. Yes they sell and yes they lost on a free but they get adequate replacements (Onana-Sommer, Lukaku-Thuram, Skriniar-Pavard) and left their core untouched while continuing with same formation, system and philosophy. We went on to revamp the squad, formation and philosophy of recruiting. We sacrificed a core midfield player to buy completely new midfield that does not function for our new system. All we needed to do was to replace Kessie in the midfield and add depth not to revamp the squad with 11 new players. Only player Milan adequately replaced was Maignan for Dollarumma.

        1. Yep but you could also argue Maldini let the “core” of the squad go in the first place by letting Hakan Donnarumma Bonaventura Kessie Romagnoli all go for free.

          1. He didn’t have much of a choice since most of them decided to leave of their on (very much) free will.

            So you’re basically blaming Maldini for Busman, and I tend to blame Bosman for Bosman.

            Maldini delivered a Scudetto and back to back Champions League qualifications after a 7 year absence. That’s the level the current mob need to reach. End of.

          2. @ dejan10

            And what would we have done with that money?

            Signed someone better than Kessie?

            How do we know that [imaginary player] would’ve done better than Kessie?

            We know for a fact that Kessie helped us win the Scudetto.

            We don’t know who the [imaginary player] is.

            I think I’ll take the Scudetto!

        2. thing is our “core” did not function. Pioli had the right idea but has since then started doing the same shite he did last season. And here we are, talking how we bought 2 many players and that is the reason why he are shite now. But in fact we were shite even with the previous groupe.

          And we did replace Kessie its just pioli never used the players he got, he elevated Krunić instead.

    3. Exactly! The money gained from selling Tonali was spent on a midfield that currently doesn’t function. Getting back into the Champions League, winning Scudetto, and reaching the Champions League semi final were achieved because we kept the good players as long as we could instead of selling them. Maldini said it best before the Champions League semi-final, “We are not there with the top teams, but we are here. We need to be brave and smart enough to understand the moment and invest now to reach that level”. Basically, you had a historic club represented by a good young core that proved they were capable of competing for titles. Milan was attractive again, a team that both ambitious and proven players could see themselves winning with. Unfortunately, these new owners didn’t see that and decided to adopt a different strategy. So far, Maldini is being proven right, and the owners who didn’t want to spend, are planning to splash out in January, on more unproven players, in order to stay competitive.

    4. I’m not sure what you’re talking about. Inter have 3 core players: Bastoni, Barella and Martinez. Everyone else has been rotated in or out of the squad over the last 2-3 years. GKs have changed 3 times over 3 seasons. Skriniar is gone. Brozovic is gone. Lukaku is gone. Hakimi is gone. Perisic is gone. Dzeko is gone. Inter have just gone really good at rotating players in and out. They did great at selling players when the price was right.

      1. This is what everyone is explaining. When you sell à player, you should replace with better player but we are recruiting unknown player who will take 2years atleast to adjust to the league. Then your project is lost.

        And Inter didn’t sell their players for fun, they were financially in difficult situation. They dont want to get punished by FFP. They replace with better players and they kept hold of some key players too

      1. What’s the point of your comment? I didn’t talk about financial status. I said we are in best shape financially. I am talking about recruitment and sales, the sporting side. They didn’t sell Tonali to balance the books but to fund transfer campaign. And by now these transfers or should I say 130 millions acquisitions are not bearing fruit on the pitch are they? But if I take into consideration also financial aspect, in my opinion we can expect sales every year cause these bankers are all about profit and capital gains. Don’t forget Cardinale has huge loan and even bigger interest rate on it to pay off. Don’t even want to go about investors who gave him the money to buy the club. They probably expect return on investment soon.

  2. Added note: milan will bring juan miranda i think for theo replacement. Milan will sold him for the highest price at january or summer transfer. Only my prediction.

  3. The sporting results are secondary to financial results at Milan under Redbird, so we will see players leave. I think Pulisic came in to replace Leao this summer, not to fill in on the right – they brought Chuck and Romero for that – but no offer arrived for Rafa.

    The reason we don’t hear complaints about Tonali anymore is because he is banned for the rest of the season and Krunic would have played anyway.

    Theo should be the next name to go, to make room for a “future Maldini” in Bartesaghi. Not really saying he has that potential, but we need Primavera players to come through and become starters. That’s what carried Man United for a generation. So buy Miranda as a starter, sell Theo for the 60 mill he is supposedly worth, and let Bartesaghi compete for Miranda’s spot, while 60 mill is enough to plug the holes in the squad.

    1. Here’s the thing. They clearly haven’t taken a wholistic approach into improving the club because there’s a massive injury crisis going on. What’s the average value of a starting XI spot? €35m? With all the time missed by starters that’s the equivalent of buying like 1.5-2 starting XI caliber players more than some of our competitors. So if Shinter’s sports medicine room are doing their jobs, they’re effectively saving €50m-€70m/yr compared to Milan’s. All the numbers I’m using are just estimates but you can see how excessive time lost (like how an employer would look at lost production) matters financially as well.

  4. If we are funding our campaign mostly with player sales then the next person to go needs to be Leao.

    1. As long as he is the best player on the team he will never improve and his consistency will need improve as there is no pressure or challenge. At Madrid for example he’ll be one of many so he’ll need to consistently improve.

    2. The proceeds from his sale would be the highest since PSG will need to replace M’Bappe and will likely come calling for him. They definitely have the money for it. No other player would bring as much money in.

    3. We won’t need to revamp the entire team, but we can bring in key pieces to elevate the level and depth of the team. Not to mention we’d be able to pay good money for a better coach.

    So yeah, I’m open to selling Leao.

  5. Inter will likely win the scudetto.

    But after 10+ years of the banter era, it beats logic why anyone here would want to be Inter now.

  6. I still have nightmares seeing Yepes and Constant at the back and Cerci on the right wing. I hope Jovic doesn’t turn into another Matri but at least he cost us peanuts as opposed to Allegri’s boyfriend.

    1. I have nightmares about having unqualified managers like Seedorf, Inzaghi, Brocchi and Gattuso.

      I am not sure how you judge the players who played under these managers.

      PS Yepes won the Scudetto putting him in the top 0.0001% of people to have played football…..

      (I do love how people just sort of take it for granted any old donkey can win championships….).

  7. With 10 new signings the depth-issue was supposed to be fixed. And here we are AGAIN in a situation where we only have one CF and one LW available for the next 2 matches. How crazy is that?!!!

    And even if we ignore the injuries, out of those 10 signings only 4-5 has made an impact. All the others have failed to raise the level of the bench. Maybe it’s time to buy domestic? I’d prefer Italians but since that is no option, how about Serie A proven players so it wouldn’t take 2-3 seasons to “get used to” living and playing in Italy? Or actual pros who hack it where ever, when ever?

    1. Yes, with Amrabat and Scamacca we would at least solve two of the weakest and crucial roles in this system. Sadly they are after growth decree thus buying abroad.

      1. With those two we’d be challenging Inter for scudetto for sure. I wouldn’t have objected to getting them even if they cost more than the ones we got. Well…. That’s wasn’t fair. Let’s not “compare” Jovic to anyone. As Costacurta said, he prefers Camarda to start against Viola and that says a lot. A 15-year-old kid is better than Jovic.

      2. poor Amrabat, sitting at united most of the time. He does earn double now tho..
        Hjulmand would’ve been nice as well, 18M for a proven serie a def mid. No brainer

  8. you are all turning out to become real good masters of finger-pointing and judges too all because of what? we are having some games not going as planned? i remember many of you here congratulating moncada and furlani for bringing in ‘adequate reinforcements’ all of a sudden you all are questioning and berating them for selling tonali…with all the time the new signings have adapted we still remained third and if u all forgot many of the matches we came away witha draw, we actually dominated and even went ahead in those games, so i belieev its something the coach and the sporting team will fix in due time..

    1. Bro, ALL those people who got excited over the summer signings haven’t commented recently because they’re seeing the disaster which we warned them about. I feel no remorse for that because you try to warn people in the summer that the signings weren’t all that but get called hater and said this was the best transfer window in a decade. Yet here we are talking about January signings in order to cover up the mess that was the summer. Look at who’s commenting above? The same ppl who warned those excited fans that we didn’t have depth and that the signings weren’t as cracked up as they think it was. I for one said it had potential but we didn’t have depth..yet the same mantra was repeated here and even with Pioli and management. I remember asking how Okafor will get game time as Leao plays on the left and Puli on the right while at CF Giroud will be preferred…and I got bashed for that. Turns out it was exactly what happened. Alot of people thought he’d walk into the CF role or even get time on the wings. Smh 🤦‍♂️. This is the third transfer window which I’ve been correct about. No, I don’t have any remorse because people will reply with a bunch of nonsense. We can see past the smoke and mirrors bro, respectfully

  9. Its hilarious to me not seeing any of those people who drooled over the summer signings. Crickets and thumbleweeds right now. The big shame is trying to argue with them. Not sure if they’re more fans or not but I noticed lot of veteran fans knew this was coming.
    Anyways on the article, I do believe we’re going to have to sell pieces to make the squad whole. Miranda comes in for cheap and Theo leaves for instance. But the way they buy players I’m not a fan of. These guys are injury prone (RLC, Puli and Chuk). Two of which are great when they’re not injured but alas they are….another point we talked about in the summer. I don’t believe we upgraded on Tonali when it takes all three to match what we get out of him.

  10. “For as reliable as the team is on him to perform at maximum capacity, that over-reliance is part of the problem for a player who is still yet to prove that he can be reliable every week.”

    Yes, we saw how it goes without Leao. I mean it would be cool if Milan did great without Leao, but in reality it is like a different team…

Comments are closed

Serie A Standings

Live football scores . Current table, fixtures & results.