3 transfer mistakes Milan have made in recent years


BIG PLAYERS Milan made the mistake of letting go: Pirlo and Huntelaar are two of them, believes Daniel Gutman.

There have been many questionable transfers made by Milan lately, most recently Matri being purchased at the expense of letting go Boateng. But these aren’t the only, and by no means the biggest transfer mistakes that Milan have made.

They have, in the past several years, let go of players who are now stars at other clubs because they weren’t “good enough”.

Galliani on Berlusconi, injuries, the market and more…
Video: Story of Livorno-Milan

1. Andrea Pirlo
This one is fairly obvious. Pirlo joined Milan from Inter in 2001 for a sum of €18 million. After a decade of service which yielded two Champions Leagues, two UEFA Super Cups, two Scudetti, one Club World Cup, one Coppa Italia, and one Italian Super Cup, he switched Milan for Juventus in 2011 after only appearing 17 times for the Rossoneri in his last season. Why did he leave? Because he was being frozen out of the team, due to the fact that Allegri preferred the now retired Mark van Bommel in Pirlo’s position. Obviously, Pirlo was not in fact at the end of his career, which apparently was Allegri’s mindset. He is playing great football at Juventus and is still plying his trade for the Azzurri. Had he not left, Milan would possess a playmaker that undoubtedly would see to the club sitting a lot higher in the table.

2. Klaas-Jan Huntelaar
Huntelaar joined Milan from Real Madrid in 2009 for €15 million. After establishing himself as one of the Eridivise’s top players, things didn’t go quite right after his transfer to Madrid. He scored 8 goals in 20 appearances after signing in January. He was offloaded to Milan, where he went on to play second fiddle to first Marco Borriello and then Filippo Inzaghi in his only year at the club. In his limited 25 appearances, a bulk of which were substitutions, he scored 7 goals. He was then sold to Schalke for €14 million after being deemed surplus to requirements. But hey, it’s not like he is doing well at Schalke, so it’s ok right? Well, not exactly. In his first season he scored 13 goals. But in now his second he went bezerk, going on to score 48 goals in 48 appearances for Schalke. He is Schalke’s record goalscorer in European competition, with 17 goals. Huntelaar is also a prolific international scorer, with 34 goals from 59 caps. Not bad for a 3rd choice Milan striker…

3. Pierre-Emmerick Aubameyang
The Gabon international was a product of the Milan youth academy. In his three years playing senior football, he was loaned out 3 times, eventually signing with Saint-Etienne in 2011, who he played for on loan the previous season. Not given a chance at Milan whatsoever, he went on to score 35 goals in two seasons for the French club, earning a transfer to CL finalists Borussia Dortmund. In his first match, he scored more goals than the amount of appearances he had for the Milan senior team. He has so far scored 10 goals for the German giants. For Gabon, Aubameyang has scored 12 goals in 34 matches.

These are just players that come to mind when I think about transfers I would reverse if I could. But there are other transfer mistakes Milan have made. What are your picks? Let me know in the comments!

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In my 17 years of watching Milan there are so many that you can not remember them all.

German Milan-Fan

No, i am of another opinion. Pirlo didnt play well in his last Milan season. Furthermore he was one of the players with the highest wage in the squad. Huntelaar had one really good season at Schalke 04 (11/12 – Bundesliga Top Goalscorer), nevertheless he was injured most of the time at Schalke. Currently he is injured again for more than half a year. He also has a really high salary (~ 4 Mio.€ net per year). Aubameyang: When he was at Milan, he has shown nothing great and there were players like Ibra, Cassano, Pato and Robinho in the… Read more »


I am torn with Huntelaar but Pirlo and Aubameyang were not necessarily transfer mistakes. Since winning the Champions League in 2007 Pirlo has been very inconsistent and I daresay fairly average, yet the team continued to rely on him and he was always the first choice on the team sheet….simply because he was Pirlo. It was clear that he needed a new challenge and there was simply nothing more he could offer to Milan, and the hunger was evidently simply not there. I didn’t like it, but for Pirlo moving to Juventus was only fitting to rejuvenate his career. He… Read more »


Thiago Silva, worse than letting Sheva and Kaka go combined!


Of course it was, because selling Kaka when we did was such a beautiful piece of business.

abdul sgg

ibrahimovic t.silva all at PSG


I’m actually okay with them leaving, except for Pirlo, I mean they’re attackers, and we’ve been fine in the attacking department for several years now and have a great future with it as well (if the management doesn’t screw this up either). I’m more concerned with the fact that we keep on bringing in so many mediocre players. If you look at our squad between 02-07, you will find world class players in almost every position, the pinnacle was probably 04/05 or something like that, where there were only three mediocre squad players, or something like that. Now it’s kind… Read more »


Thiago Silva… It really did break my heart… He was our main man… The heart of this AC Milan side… I still remember hearing for the first time him officially leaving Milan… A sad day indeed for ALL true Rossoneri…. I still get sad every time I see him wear that PSG jersey… He never wanted to leave us… I have the biggest feeling he loves Milan more than PSG.


** biggest feeling he STILL loves Milan more than PSG**


Don’t be so overreactive. I never believed Zlatan and Thiago wanted to leave Milan. I’m really damn sure they will be at pleasure to walk out of Milan if the price wasn’t right because they are two of the hottest properties in transfer market.


Ofc thiago silva is the worst ve was our spine.


I especially agree about kjh. Many thought he wasent good enough but the truth is he was very effective in the limited playong time he was granted.

jame xtra tabat

Movic, parto nd silva


Gourcuff had some success after leaving Milan as well. Paloschi has been pretty good at Parma. I didn’t like losing Merkel either..

pato rash

aubameyang was d bigest milan transfer mistake.. Imagine balo, aubameyang nd el shaarawy hmm..


More mistake to come because they’re don’t like young players wait to see next month how many of them gonna leave


“plying his trade for the Azzurri” think you can only ply your trade for a football club, not your country of birth.

This is more about the players they let go that they shouldn’t have, but if you include transfers in, I’d say Kevin Constant, Silvestre and Matri. Don’t know if Birsa should be included or not, but I’m still yet to be convinced that he is good enough to wear a Milan shirt.

I think that Allegri must now rate his decision to let Pirlo move on as one of the worst he has ever made.


don’t let Saponara join the mistakes list

Tafiardo Cardoso

we had so many mistake about transfer like giovane elber, patrick viera, patrick kluivert, roberto baggio


Just to add to that list: Gourcuff, who went from Milan to Bordeaux and became their best player when they won the French league. Not as good anymore maybe, but could have been a real champion. Sokratis, the CB/RB who is now at Dortmund and playing fairly regularly. He played only very few matches in Milan but for some reason they didn´t think he was good enough even though he was a regular in the Greek defence, which isn´t exactly a great team, but one of the best defensive ones. There was also no reason to sell Acerbi, who definitely… Read more »


The Sokritis in Dortmond isnt the man that played in Milan


Got that wrong..its the same player.

Olalekan Mojeed

Look at nigeria born Nnamdi Oduamadi he has been a loan player up to 3 or 4 times but the end he will be sold out DImao kaka junior again and so

Olalekan Mojeed

Mbaye Niang for jujac kucka why did we have Allegri has coach why Berlusconi did not let uncle fester to leave wosrten every day by day galliani says honda @27 is sure in january milan will swap Niang for kacka then why blaming Mrs B for quarellng with Galliani, Allegri is not a coach why hateing this guy bcos he lost a goal lasts eason agaist barca to hell with the coach when will this furniture called himself a coach leave


selling ibra was worst, he makes other players to play better, example: noce,robinho, kpb , they were playing very good with ibra.


Edgar Davids


So many players milan have let go. Dont know the reason behind but I still feel sad when I remeber players like Patric Viera, Yohan Goucuff. As at that season they sold kaka seedorf retired milan needed a play maker and then Goucuff was having a fantastic season with Bordeaus and later Lyon . That was sad. Alberto Paloschim his doing well in his present club, Alexander Merkel, he his talented. This guys were deemed surplus and they sold them out. We need to keep the young players together and bring in average age player once in a while to… Read more »

Abu kaka

U will see another mistake in january,they will sell saponara,cristante,niang and vergara to go some where else.


To me galliani is our main problem in the transfer,yeah he did great job at times,but he has clearly shown that he isn’t good in decision making most of the time.I pray that this guy will go comes the end of the season because we are seeking for a new begining.And in the list I will to include astori and where the hell is didac vila to me he is better than both constant and emmernuelson.Most of our problems lies in the middle of the pack,every good team in the world most has an array talented midfielders b/4 they succeed… Read more »

Olalekan Mojeed

Pls do we have a coach? And who is the coach?


When Pirlo left, he wasn’t really playing greatly for us.

Aubameyang left at a young age.

When Huntelaar left we got Ibra, Robinho, and had Pato

Out of this topic: So seems like Vergara, Cristante, Saponara, and Niang will all leave Milan, probably on loan to be replaced by Rami, Kucka, Honda, and Pazzini’s return.

Also the following: Amelia,Zaccardo, Constant, Nocerino, and Matri/Robinho may leave.

Kwabena Adu

I was very sad when Galliani decided to stay,He was once a Guru but he is not the same guy he use to be.The only thing that he cares about these days is balancing the books.After winning many trophies I think he is not as hungry like he used to be.
The kind of players he buy these days is sad,I hope Barbara will watch him very closely,He should be accountable for the players he brings into the team


In galliani’s recent comment,he said there will be a surprise swap deal which himself does not know yet,my feeling tells me its shneider and el-sharrawy.


Matri-Marchetti and Kucka-Niang


Was rumored today that if Lazio dont agree to his demands, they may agree to sell and Milan are interested. They have also followed Matri a lot and will need someone to replace Klose.

hindo rogers

.galliani and alligri are our worst nightmare it is too sad to be a milan fan with broken heart galliani is buy low grade player and selling our best player b cuz of greed.why even think on selling stephan el when he is a feature word class player galliani always goes for player who another clubs have offload because of bad performance besides we have lot of player that are liabilitis to the team after our first eleven there is no one there to help for example constant,muntari zarcado,matri,b cuz i will prefer robinho to him,niag ,bonera, and zapata are… Read more »


I think the most transfer mistakes is Allegri


Niang and possibly SES will be the next.

John Gatjang C.

the only great mistake done by milan is not letting uncle fester and Allegri go.

John Gatjang C.

to avoid those mistake milan should buy in January Luckas of PSG,Countinho from Liverpool and Koke from Atletico Madrid.


whom of the following would you rather have at Milan?

ter Stegen


Why are we suddenly talking about transfers Galiani got wrong? because of Matri? or what? Life is a teacher, even sir Alex Ferguson confessed his regret letting go of Jaap Stam. When someone lose, someone gains and that is life. You cannot get it right all the time because nobody is perfect. Why not write about taking Thiago Silva for next to nothing considering his sold price? How much did we buy Kaka from Sao Paulo? how much did we sell him? and how much did we just pay to have him back? Galiani’s time at Milan is due but… Read more »


Galliani’s main problem is that he has stick so badly with Allegri. Allegri is the reason for many of the most recent transfer fiascos (Pirlo, Matri, Pato etc.) and the worst thing is that he is about to do more damage with Cristante, Niang, even SES.
Out of million calls he has made for Milan keeping Allegri for so long might even cost his position.


I disagree on Huntelaar, he had plenty of chances and even Borriello was clearly better. I can see Niang being the next though, he has all the abilities Aubameyang has and we’re swapping him for Kucka, Allegri’s dream player!


I think that the worst of all is Vieira (yes the one who used to be the best DMC for almost a decade). He was owned by Milan before he moves to Arsenal. Similar case is Davids. In recent years I cannot forget the fiasco with Pato (we rejected a 35m offer to sell him 15m 1 year later). Similar also was Kaka (City offer 100m in January and we sold him 67m 5 months later). In years when every million was gold (we’ve lost many players because of 1 or 2 millions) Galliani threw away 50m only out of… Read more »


Oliveira, Gilardino, Viera


Biggest mistakes to me we’re letting go of Pirlo, Silva, Kaka and Sheva.

Best signing of Alergies era was definitely Matri – he has one goal but it doesn’t matter because he always works hard for the team! I think Galliani had too much wine when he did that transfer! LOL


My fear now is who is joining d list come january,who knows?


The 3 transfer msitakes as I see it:

1. Signing Allegri 1st yr
2. Renewing Allegri contract a 2nd yr
3. Renewing Allegri contract and signing Matri-3rd yr


Patrick veira



Kwabena Adu

Barbara Berlusconi should chain Galliani during the January transfer window before he causes another severe damage


This problem will never solve if we keep arguing to blame some persons in board of management. I thought reasons behind Milan’s bad market moves were: worsened financial status and lack of intuition regarding those unexpected talents who came up high at their new clubs.


Lets put this into context. You have to condider the large transfer fees we got for ibra and silva, kaka and scheva and the wages saved. What should count as mistakes are letting go of players who turn out to be great eg davids, viera. Also players who are much better than what we have now eg letting antonini go for constant, or letting acerbi and sokratis go and having to rely on silvestre.

As an aside ive never seen a worse bunch of central defenders than the ones we have now.

Andriawan Ludji

Milan mistakes for transfer is among all was Didac Villa, he was the young best talent for a left back, but he never get a chance to prove how best he is.


I was willing to forget all mistakes that galliani did in the past because he was able to make up for them with equally good players, and they were mistakes that anyone would in his position would make, but his recent transfers have all been insane, they reflect the type of team we have turned into under Allegri. For as long as I’ve known Pirlo he has always been consistent, he has always been one of the best MF that a very few people noticed how good he was. He won the WC, two UCLs. WHO IN THIER RIGHT MIND… Read more »


Pirlo is a legend. But… but, if Milan played Pirlo instead of van Bommel that season, they would not had won the scudetto. Simply, he was not motivated, and he player poorly. Now he is one of Juve’s best player, and that is completely understandable, but I would not consider his sale to be a mistake.

Pa ibra

#1 is pirlo. cant get over it. the worse transffer in history ever.

#2 ronaldinho. an unmotivated/unserious ronaldinho is better than anything. chassing him away is one of the reasons i’ll never liked allegri.

#3 didac vila. we’ll be back here again discussing about him just like we’re now discussing aubameyang. letting go of youngsters without really giving them a chance will keep taunting milan.

i saw allegri frustrating pato too, this hurts, but his departure is a little bit understandable.


Didac Vila is on Loan, he is still owned by AC Milan.


This is my future remorsal list. Try to remember it

1. Matteo Darmian
2. Alessio Innocenti
3. Marco Fossati


Loan: Alberto Paloschi, look how often he scored for Chievo last season and he still doing it. Piere Emerick, Sokritis, Pato beasting in Brazil, and Number one Thiago Silva, I didn’t care much once Ibra left, he is good beastly player but you can’t sell silva and get rid of nesta at the same time.


How ’bout not selling Pato to PSG when a 30 Million Euro offer came in!!!!! Their First Choice striker was Pato, since we rejected (Winter 2011), they went for Ibra, according to Bleacher Report. However Pato left later for only 15 Million Euros to some Brazilian CLUB. I think letting go of Sheva and T. Silva were bad ones.


Aubameyang is special
nobody think he’s gonna be this good when he still at Milan

to me Silva is the worst transfer despite the money
look at our defense, we still have the problem while we see many defender come and go
we sold the best defender at the time when a good defender is hard to find

I don’t agree with Pirlo
we have De Jong and Montolivo (if he can find his form just like last season) also Poli