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A.C Milan Transfer Mayhem In The Last Decade

A.C Milan transfer- It is amazing how far the Rossoneri had fallen down the years. The Serie A club are very far from the quality and class they displayed in the glory days. A.C. Milan used to be one of the top clubs in Italy and Europe but they gave become a shadow of themselves. A team with multiple Scudetti and UEFA Champions League titles now barely makes the cut in the UEFA Europa League.

A lot of factors were responsible for this but one of them is the A.C Milan transfer approach over the last 10 years. The San Siro club bought players that should not have been bought and sold the ones they should have retained. They ultimately began to decline after winning the Serie A in the 2010/2011. Here are some of A.C Milan transfer mistakes in the last decade.

1. Thiago Silva

How the powers that be allowed the Brazilian to leave for PSG in 2012. Silva was virtually the best central defender on the planet when he was sold for €42 million to big-spending PSG. They did retain Mexes and co. but their defense has not had a leader like Silva since he the Brazilian left. The lack of discretion by the management to let him go definitely cost them their place amongst top clubs.

2. Klaas Jan-Huntelaar

MILAN, ITALY – MAY 01: Klaas Jan Huntelaar of AC Milan in action during the Serie A match between AC Milan and ACF Fiorentina at Stadio Giuseppe Meazza on May 1, 2010 in Milan, Italy. (Photo by Valerio Pennicino/Getty Images)

Huntelaar was a proven goalscorer in the Netherlands in the early 2000s. He began his career at PSV in 2002 and went on to play for Ajax from 2006 to 2009. Huntelaar scored 76 goals in 92 league appearances within that period before moving to Real Madrid in January 2009. After half a season, he somehow opted for an A.C Milan transfer from Real Madrid with a record of 7 league goals in 20 appearances in Spain. His time in Italy was not productive too as he made just 25 league appearances scoring seven goals. He left for Schalke at the end of the 2009/2010 season.

3. Robinho

Robinho left Manchester City after an A.C Milan transfer in 2010. He joined the crop of Pato and Ronaldinho to make up the Brazilian contingent at Milan in 2010. He did help them to win the league in 2011 with 14 goals including the one that clinched the title. Three years on he would score 17 goals across all competitions. For a player in his prime, much was expected of Robinho but he could not deliver before leaving in 2015.

4. Kevin Constant

Kevin Constant was an unknown entity in football but the guys in charge of A.C Milan transfer somehow signed him in 2012 from Genoa. His signing showed how much Milan had succumbed to mediocrity. Constant was pacy but he had poor ball management and consistently makes the wrong decision when on the ball. He was sold to Trabzonspor after two years with the Rossoneri

5. Antonio Cassano

MILAN, ITALY – APRIL 22: Antonio Cassano of AC Milan shows his dejection during the Serie A match between AC Milan and Bologna FC at Stadio Giuseppe Meazza on April 22, 2012 in Milan, Italy. (Photo by Marco Luzzani/Getty Images)

It is impossible not to talk about Antonio Cassano when talking about wasted talents in football. The Italian’s career was never stable as he moved from one team to another from club to club. He joined Milan from Sampdoria after a good goalscoring run but he only managed 7 goals in his one year there before moving across to Inter. One cannot but wonder why he was signed in the first place.

6. Andrea Pirlo

This one A.C Milan transfer that shocked many football fans. Max Allegri somehow sanctioned Pirlo’s move to Juventus and Galliani did not help the case either. Pirlo was an artiste of a midfielder but the gaffer then preferred destroyers and enforcers. The technically told Pirlo he was not needed anymore and we all knew how the story ended. The 2006 World Cup winner became a major player in Turin and even added goals to his game.

7. Zlatan Ibrahimovic

MILAN, ITALY – MAY 13: Zlatan Ibrahimovic of AC Milan looks on during the Serie A match between AC Milan and Novara Calcio at Stadio Giuseppe Meazza on May 13, 2012 in Milan, Italy. (Photo by Claudio Villa/Getty Images)

Ibrahimovic is back with A.C. Milan for the second time. The Swede who has also played for Inter Milan and Juventus joined Milan from Barcelona on loan before the deal was made permanent in 2011. He made 32 league appearances scoring 28 goals from 2011 to 2012 and somehow Milan let him go after such feat. They have not had a prolific striker since.

8. Pierre-Emerick Aubameyang

Aubameyang was not given an opportunity to prove himself during his time at the San Siro. The Gabonese forward has no Serie A appearance to his name. He was instead sent on loan spells till he landed at Borussia Dortmund where he scored a hat-trick on his Bundesliga debut in 2013. Milan tried to bring him back before he moved to Arsenal but it was a little too late. The Gunners were much better and financially strong than their Italian counterparts so it was no surprise he moved to London instead of an A.C Milan transfer.

9. Sokratis Papastathopoulos

Unlike Aubameyang, Sokratis made 5 league appearances for Milan but they all came in one season (2010/2011) as he was sent on loan to Werder Bremen for the 2011/2012 season. Werder Bremen would later make the deal permanent the following in 2012/2013. Sokratis like Aubameyang also moved to Dortmund where he gave a good account of himself before moving to Arsenal. Milan lost a gem of a defender.

10. Krzysztof Piatek

Piatek is the latest casualty on our discourse of the A.C Milan transfer crisis. Piatek’s journey at the San Siro was a loss to both the player and the club. They signed him in January of 2019 for a reported fee of €35 million. He showed flashes of brilliance but it was not enough to convince the management. He was sold to Hertha Berlin in January 2020 for €27 million in January 2020.


An interesting fact is that their City rivals (Inter Milan) also experienced a decline with many transfer errors. However, they have bounced back with a top manager in Antoni Conte and top-notch signings that have enabled them to mount a title challenge this season. Milan can also get it right. The ultimate question is- when will that be?

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