Why It's So Hard to Leave Milan

Fans know the scenario all too well. Players are brought in, perhaps they were never Milan quality, perhaps they were young and unproven, or maybe they were even proven elsewhere. Yet they fail to deliver when called upon, especially when they have inexplicably found favor with a coach and are called upon often. The ones who do not get time may agree to go on loan to other clubs to play, but stay on the roster and create a burden for sporting directors to try to offload each mercato. We have seen Milan lose money on players who never lived up to their transfer fees, or who were signed to a five year contract when they should have never been given more than one or two. Then there are the players who simply refuse to leave, taking up a valuable space in the team. Why is it so hard to leave Milan?


Why leave when you start every match?

The obvious answer is that this is AC Milan. A club with history, class, and worldwide recognition. Even after ten years of demise, the club is quickly returning to glory. Milanello features state of the art training facilities, and the San Siro is one of the most famous stadiums in the world. Casa Milan features a beautiful modern museum, including the elegant trophy room, showcasing the club's seven Champions League trophies, amongst others. 


Just another day at Milanello...

Also, our sporting director is some guy called Paolo Maldini, someone who even the stars are in awe of. He comes to training often, sometimes bringing a friend or more like Zvonimir Boban, Alessandro Nesta, Andrea Pirlo, Massimo Ambrosini, Massimo Oddo, Gennaro Gattuso, Andriy Shevchenko, or others. The club has always been described as a family, even at its most dysfunctional times. You may have heard former players have a negative experience with specific people at the club, but you would be hard-pressed to find anyone who had anything bad to say about the club itself.


I ask you: If you had a contract with a club like this, why would you leave?


Theo Hernández: "It's fantastic that he comes and hugs me"

Obviously, players come and go, and many, particularly youth players, have been forced out. Most recently, the head-scratcher was sending Hauge away when we still have certain other unnamed players in the squad who are less talented and less deserving of a spot in the squad. But Hauge was marketable, the club stands to possibly make something on his deal. Could we have waited longer and made more?


Today, Hauge. Tomorrow Roback? Could Milan have cashed in bigger by waiting longer? 

Capital gains on player sales is something they have a hard time with. More specifically, for decades, Milan have struggled to develop young players, something that was also discussed on a podcast last MayWe saw Cutrone pushed out for money, a rare instance where a youth player was sold for complete profit at €20 million, but also millions of tears worldwide. He has struggled to settle in at Wolverhampton, and is probably a purchase that they regret, constantly going on loan. (He just came back to Serie A on loan to Empoli, by the way.) However, with Locatelli, Milan made €14 million by pushing him out only two years ago, while he is now in talks to go to a rival club for more than double that. Many think that with a little more patience with players from the youth sector or players like Hauge, Milan could do better.


How often does selling a player affect his career trajectory? 

We saw Maldini make the tough call to bring in Maignan when Donnarumma went glory hunting, but that was a massive setback to lose a homegrown player who is already world class and should have demanded a sizable transfer fee. It's difficult to argue that it may have gone down differently without COVID, since proper negotiations were not able to be held last year when they should have been. Gratefully, at least we learned that the new technical sector is acutely aware of costs ahead of individuals, which is good business going forward.


If only this could have happened a few years earlier, we could have at least cashed in

However, when you have a player like a spindly, hardworking Spanish winger who just doesn't have the skillset we need, but he doesn't want to leave, what can you do? The club needs to recoup €8 million for that guy, but who will pay that much? Meanwhile there are other players who score one incredible goal, and are versatile and well-liked by Pioli, but have disciplinary issues that include very dangerous and rash tackles, even in friendlies. Yet no one is really interested in them. We can't have 60 players in our squad, we need to be fiscally responsible. Each one of these players takes up a spot on our roster, and we need to build the best team possible.


For the last 3 years, we have had both of these players on our roster.

I like to believe that the new technical director is doing everything he can to change years of negative momentum within the youth sector, and also by investing in young players for very low fees, hoping to have significant gains down the road. But all of that takes time. In the meantime, we are still just barely getting rid of players from our roster such as those who are still fully committed to wearing braids. Playing for Milan, or even having a chance at returning to the first team is the dream of a lifetime. That is why it's so hard to leave Milan.


This post inspired by the music of Front 242's "Headhunter"


Our next match is a Friendly
AC Milan vs. Panathinaikos FC
Saturday, August 14 • 20:30 CEST (2:30pm EDT)
This match is NOT being broadcast in the U.S.


Why It's So Hard to Leave Milan Why It's So Hard to Leave Milan Reviewed by Elaine on 11:30 PM Rating: 5
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