AC Milan's 5 Most Recent Transfer Window Failures

Adam DigbyFeatured ColumnistJuly 8, 2014

AC Milan's 5 Most Recent Transfer Window Failures

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    Claudio Villa/Getty Images

    There was a time when AC Milan were the most feared team in Europe, revered not just in Italy but across the continent as they swept all before them in the pursuit of glory. With names like Franco Baresi and Marco van Basten in their line-up, the Rossoneri were envied and unrivalled anywhere in the world.

    After the early 1990s, when those Arrigo Sacchi-inspired teams dominated the game, manager Carlo Ancelotti led stars like Kaka, Paolo Maldini and Andrea Pirlo back to the summit. The Champions League triumphs of 2003 and 2007 were the pinnacle of that team, although they would cling on to add the 2011 Serie A title to their bulging trophy cabinet.

    Even now that seems like a distant memory, the team torn apart by a combination of age, expired contracts and a desperate need to cut costs. While both Massimiliano Allegri and Clarence Seedorf have seemingly carried the burden of responsibility, the management above them must also be held to account.

    Money may well be much tighter than it was when Silvio Berlusconi first arrived, but Milan’s spending on the transfer market has been difficult to understand and often extremely wasteful. Over the following slides is a chronological look at the five worst examples of that profligacy, looking at their worst deals over the last two seasons.

May 2014: Not Completing Deal for Adil Rami

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    Antonio Calanni/Associated Press

    While last season was an unmitigated disaster for Milan, Adil Rami was one of the few bright spots, excelling in a particularly poor Rossoneri defence. The Frenchman was brought in on loan from Valencia in October but was only eligible for selection once the January transfer window opened.

    Scoring three goals and adding an assist, the 28-year-old averaged 1.6 tackles and the same number of interceptions across his 18 appearances, according WhoScored.com. Initially viewed as yet another out-of-favour addition to the squad at San Siro, Rami proved to be an excellent acquisition.

    The loan agreement Milan had secured with the Spanish club included a buyout clause set at €7.5 million, according to Football Italia, and by the end of the season that looked like an extremely favourable deal for the Rossoneri.

    They failed to activate it, however, seeking a discounted price in a stunning display of the club’s failure to secure vital players even when it appears simple. He may yet sign, but stalling after getting a chance to complete the deal early seems like bad business.

January 2014: Signing Michael Essien

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    Antonio Calanni/Associated Press

    In recent years, Milan have garnered a reputation for picking up aging players on free transfers, a practice the January arrival of Michael Essien embodies. No longer the marauding force of nature he was at Chelsea, the 31-year-old managed just seven league appearances, looking a shadow of his former self.

    That he was given an 18-month contract despite reports he had failed large portions of his medical, according to Football Italia, only adds to the nonsensical nature of the move. With players like Bryan Cristante further marginalised by the Essien signing, the club’s promise to “focus on youth” became a distant dream.

August 2013: Signing Alessandro Matri

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    Marco Vasini/Associated Press

    When it comes to poor transfer decisions, perhaps no move by Milan generated as much ridicule as their purchase of Alessandro Matri last summer. With gaping holes in defence and midfield, vice president Adriano Galliani spent €11 million to bring the out-of-favour Juventus striker to San Siro, per the Turin club’s official website.

    What makes the purchase worse still is the fact Matri was a Milan youth product, released in 2007 for less than half that sum. That he managed just one goal in 15 appearances before being loaned out to Fiorentina only compounded that misery, as did seeing Juve spend the proceeds on Carlos Tevez.

    The Argentinean would net this stunning strike past the Rossoneri on his way to 19 league goals, piling yet more regret on the Rossoneri. That Tevez had previously agreed to join Milan, according to Galliani, per Yahoo Sport, only made the move even more erroneous.

July 2013: Extending Robinho’s Contract

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    Paolo Ferrari/Associated Press

    If Milan have mistakes in signing players, they have also held on to many they should have released, with Robinho perhaps the best example. Having paid €18 million to bring him from Manchester City, they saw the Brazilian net just 27 goals in his first three seasons, yet Milan somehow came to the decision to extend his contract in July 2013.

    By handing him a new three-year deal, the Rossoneri ensured they were committed to paying a player who was consistently failing to deliver.

July 2013: Buying Kevin Constant Outright

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    Antonio Calanni/Associated Press

    Perhaps one of the most infuriating aspects of Milan’s current transfer policy is paying for players who, like Robinho, have already proven to be not good enough. Kevin Constant proves that to be the case. The Guinean failed to impress in his first season with the club, with Who Scored showing he had a miserable 2012-13 season.

    He completed less than 80 per cent of his passes and made three times more fouls than accurate crosses, and yet the Rossoneri would pay Genoa a further €6 million to sign him outright. That took the total cost of the 27-year-old to an unbelievable €10 million.

    Much like Matri, Constant was a player not good enough to wear the famous red and black stripes, only for the club to splash out an eight-figure sum to secure his services. With money scarce, these financial missteps are ones Milan can ill afford, which is why we have seen them fall further and further behind Serie A’s best clubs.