10 Transfers AC Milan Should Not Have Made over the Past 5 Seasons

Anthony LopopoloFeatured ColumnistApril 12, 2014

10 Transfers AC Milan Should Not Have Made over the Past 5 Seasons

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    Claudio Villa/Getty Images

    Over the past few seasons, AC Milan have gone from champions to has-beens. They built up a team and sold it away, leaving just the bare bones. In came mediocrity—players who would never play for Milan in the days of their Champions League glory.

    And there really was no plan. CEO Adriano Galliani spent money to get Zlatan Ibrahimovic and a cast of champions, only to let them go a couple of years later. The team did not anticipate the cost of high wages, and they did not care for the future.

    Paolo Maldini said in an interview with La Gazzetta dello Sport last month (h/t Football Italia) that he saw the start of this long decline in 2007, back when they won the Champions League. They did nothing to rebuild. Instead, they bought Ronaldinho and Ibrahimovic, borrowed David Beckham, and Milan looked healthy enough with these bandages on them.

    They sacrificed long-term health for short-term gain. At one point, per the Swiss Ramble, they had a wage bill upwards of €200 million—the highest of any Milan team ever. They won the Scudetto in 2011, but who really cares now?

    Let’s look back five years and examine the mistakes made. Starting from 2009, here are the players they should not have bought—or sold.

Klaas-Jan Huntelaar

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    Valerio Pennicino/Getty Images

    When Milan bought Klaas-Jan Huntelaar, we immediately thought of Marco van Basten. Van Basten coached the player at Ajax and on the national team, and Huntelaar had the same goalscoring knack as his compatriot.

    But Huntelaar did not turn into anything in Italy. Milan created an environment in which he could not thrive, Coach Leonardo even played him out of position on the wing. Huntelaar was hardly a regular starter and scored just seven goals in that single 2009-10 season.

    One particular game against Manchester United made van Basten mad enough to speak for Huntelaar. When Leonardo replaced the Dutchman with Pippo Inzaghi, the fans booed.

    “I don't know why he (Leonardo) replaced him,” van Basten said, per TMW. “Inzaghi is a great player, but we must remember that he is almost 37-year-old. You can't aim on him for the future. Klaas-Jan is younger.”

    A year later, Ibrahimovic and Robinho came to Milan, and Huntelaar had no choice but to leave. He was forced out of a team that never nurtured him.

    Of course, he began scoring buckets of goals at Schalke. They respect him there.


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    Claudio Villa/Getty Images

    Ah, the eternal underachiever. Milan bought Robinho from Manchester City for £15 million, per transfermarkt.com, and they bought him with the intention to produce the best attack in Italy. They had already signed Zlatan Ibrahimovic, and they still had Pato and Ronaldinho. It was a Brazilian affair.

    Robinho scored 14 goals—as much as Ibrahimovic and Pato—in Serie A the year Milan won the Scudetto, and he scored the crucial, match-winning goal against Brescia that all but clinched the title. He has scored 17 goals in all competitions in the three years since.

    He is not a bad presence or a bad person. He is often the joker in training, and he’s always smiling. Surely they love him in the dressing room. But he makes the easy look so, so difficult. He misses so many chances.

    Robinho is too inconsistent for Milan, and he really is just a passenger on this team. Milan can’t afford to carry anyone.

Antonio Cassano

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    Marco Luzzani/Getty Images

    Antonio Cassano himself probably wishes he never went to Milan. Another one of those quick-fixes, Cassano came into the team in the middle of the season and won the only Scudetto of his career.

    Galliani jumped on a discount for Cassano after the player had an argument with the owner of Sampdoria, where he was playing. He scored the third goal in a famous 3-0 win over Inter, his childhood team—and the club that would later take him from Milan.

    He was not necessarily a bust at Milan. He suffered a life-threatening heart condition, and the doctors from the club saved him. “I was afraid to die,” he told Studio Sport (h/t beIN Sports,) “and then past that, I thought about retiring from football.”

    Instead he was full of regrets, and he only played for the team for 18 months. He complained about the promises Milan made—and broke. He seemed to hint at Galliani, who had sold Thiago Silva and Ibrahimovic that summer. The team was falling apart.

    Per Forza Italian Football, he told reporters in 2012 that he wasn’t the guilty party:

    When I joined Milan, I said that if I got it wrong there then I ought to be locked up. Well, this time I’m not the one who got it wrong. I had to leave. There was someone above the coach who did something wrong and I can’t stand it when people take me for a ride. When I was ill, my teammates were very close to me, but this person promised so much. He was all mouth and no trousers.

Pierre-Emerick Aubameyang

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    Frank Augstein

    Milan never gave Pierre-Emerick Aubameyang a chance. Now he is likely the future of Borussia Dortmund, where the speedy winger scored a hat-trick on his debut.

    He played with Milan’s youth teams at 17 years old, and he told The Guardian that he once ran 30 metres in 3.9 seconds while in Italy. He learned how to press and attack from a great, one of Milan’s youth coaches, Filippo Galli. They should have spotted the talent there.

    He went on loan looking for more playing time and played for several clubs in France before finding his form at Saint-Etienne. In 2012-13, he scored 19 goals for Saint-Etienne in Ligue 1, where only Ibrahimovic had scored more. He wanted to come back to Milan, per goal.com, but he went to Dortmund instead.

Andrea Pirlo

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    Massimo Pinca

    No one says his name around Milan anymore. It’s like Voldemort.

    Of course, it was Massimiliano Allegri who did not see the need for Andrea Pirlo anymore. They had Mark van Bommel—another quick-fix—and Allegri wanted to use a bunch of destroyers in front of the defence.

    Pirlo understood immediately during a meeting with Galliani that he was no longer useful to them. And all Galliani gave him for 10 years of service was a pen. “My 10 years of Milan,” he wrote in his book (h/t Football Italia,) “gone like that. I smiled anyway.”

    Milan still lack a player of Pirlo’s quality, and it is no help that he is scoring goals like never before with Juventus. In 10 seasons with Milan, Pirlo only scored eight goals from free kicks. He has 12 such goals in just three seasons with Juve. He is now the influential player that Milan no longer saw.

Sokratis Papastathopoulos

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    Martin Meissner

    Remember him? Sokratis Papastathopoulos started just three games for Milan in a single season with the team back when he was just 22 before they sold him to Werder Bremen.

    Now at Borussia Dortmund, Sokratis has realised his potential, deputising for Neven Subotic, who suffered a season-ending injury. He is quick to the tackle and strong on the ball, and he will play in the World Cup for Greece.

    Another defender Milan gave away. Sokratis would look good in the Rossoneri defence right about now. Instead, they have a dangerous cocktail of defenders such as Daniele Bonera and Philippe Mexes.

    Much was made of Thiago Silva, but here is another young player Milan failed to understand. Zero foresight. It’s as if they can’t identify talent anymore—or realise the talent they already have.

Philippe Mexes

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    David Ramos/Getty Images

    No one player on Milan is more harmful to his team than Philippe Mexes. He is a red card waiting to happen. The tackles are almost always late, and he always goes for the spectacular. He is never a safe bet. What’s worse, he is making around €4 million—reportedly as much as Mario Balotelli and Kaka. Mexes does not even play regularly anymore.

    Milan got him for nothing from Roma, who have since built up the best defence in Italy—that is no coincidence. Galliani seems to love his free signings and Roma certainly don't miss Mexes.

    He has served several suspensions while playing for Milan, and the risk is too great with him in the squad. Though he is capable of the odd performance—he was immense against Genoa this past Monday, when he made several crucial blocks. But even then, he almost scored an own goal.

Thiago Silva

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    Claudio Villa/Getty Images

    He is the biggest of them all. Thiago Silva is the most expensive defender of all time, sold for €42 million, but he was worth so much more to Milan. He could have served as their captain, and likely would have. He was the soul of their defence. Thiago Silva does not dive into tackles, he waits for the right time and he anticipates.

    But Milan had to balance the books and Thiago Silva was a quick sale. Weeks before they sold him, Milan signed him to a contract extension. They saw the money and only the money.

    Selling Thiago Silva was a way to resolve the poor state that Galliani and Berlusconi had put the club in. They ran the club in the red for years, and despite knowing they couldn’t afford the wages of players such as Ibrahimovic or Ronaldinho bought them anyway.

    Thiago Silva is a fan of Milan and they believed in him. The Brazilian had contracted tuberculosis while playing in Russia and spent years recovering. Milan bought him for a little more than a bargain £8 million, per transfermarkt.com. Like a stock and as they had done with Andriy Shevchenko, the club sold him high. Except Thiago Silva had a future.

    Encouragingly, he said in an interview with La Gazzetta dello Sport (h/t goal.com) that he wants to return to Milan one day.

Kevin Constant

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    Mario Carlini / Iguana Press/Getty Images

    This player is an example of the mediocrity that Milan have adopted. Who even really knows where Kevin Constant actually plays? Allegri played him as a winger, a midfielder and a full-back. Constant can run, and sometimes he blows past players, but he has no idea what to do with the ball. In no other year would a player like Constant have a chance of playing for Milan.

    Constant is exactly the kind of player Milan have to avoid, but he told Il Corriere dello Sport (h/t Football Italia) that he has shown what he is worth. Clarence Seedorf initially told Constant to train outside of the squad and did not appear to trust him.

    This is the same Constant who played against Barcelona and was ruthlessly exposed. He is out of his element, and if Milan want to get better they have to move past the mediocrity of which Constant is the embodiment.

Alessandro Matri

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    Fabrizio Giovannozzi

    Alessandro Matri scored just once in 15 appearances for Milan. He spent half a season there before joining Fiorentina on loan. They have said they will send him back, per La Gazzetta dello Sport (h/t Forza Italian Football.)

    It is not so much that Matri is a bad player, more what he represents. Milan bought him from Juventus for roughly €11 million, per the Milan Channel (h/t Football Italia.) He was a totally unnecessary purchase, let alone an expensive one. For a team struggling with finances, they spent a lot of money on a player that will more than likely not be playing for them next season.