5 AC Milan Summer Transfer Flops of the Past 10 Years
This summer could prove vital to AC Milan. The club maintains ambitions of returning to the top of Italian football after three successive years without achieving European qualification, but to do so, they will need to reinforce the squad.
Unfortunately, the club’s transfer policy has let them down on a number of occasions in recent times. They have frequently lavished cash on big names who were past their best and have also failed to get the best out of a number of expensive additions.
Here Bleacher Report recounts five of Milan’s biggest summer transfer flops of the past decade.
Honourable Mentions
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The below were all poor summer signings for Milan but didn’t quite make it into the top five.
Alessandro Matri (£8.25 million from Juventus, 2013).
Oguchi Onyewu (free transfer from Standard Liege, 2009).
Bakaye Traore (free transfer from Nancy, 2012).
Yoann Gourcuff (£3.38 million from Rennes, 2006).
Francesco Acerbi (£3 million from Chievo, 2012).
5. Taye Taiwo
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Taye Taiwo joined Milan on a free transfer in the summer of 2011 and was expected to prove the long-term solution to a problem position. The Nigerian joined to fill the club’s left-back gap, as Marek Jankulovski had left and Luca Antonini was not considered to be of the required quality.
However, in his two years with the Rossoneri, he made just eight appearances in all competitions.
A powerful and athletic full-back with attacking intent, Taiwo enjoyed six solid seasons with Marseille prior to leaving the French giants at the age of 26. At the outset. he seemed a bargain signing for Milan given he didn’t cost a transfer fee. And he showed promise in a pre-season friendly against Bayern Munich, keeping Arjen Robben quiet.
But for reasons that were never made clear, he never established himself as a first-team player with the club.
Taiwo spoke out about his disappointment at his being frequently omitted from the lineup, telling L’Equipe (h/t Metro):
"I am suffering every day because I don’t get to play football. I don’t understand how things work in Italy. Sometimes I even have to watch from the stands, but I really need to play in order to show what I can do. It looks like [then-coach Massimiliano] Allegri doesn’t have faith in me.
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Taiwo spent time on loan at Queens Park Rangers and Dynamo Kiev before leaving Milan the same way he came: on a free transfer. He now plays for Finnish club HJK Helsinki.
4. Emerson
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Emerson was regarded as one of the finest ball-winning midfielders in the world during his time with Roma. In four seasons with the Giallorossi he won one Scudetto before following coach Fabio Capello to first Juventus, in 2004, and then to Spanish giants Real Madrid, in 2006.
However, early on in his time at the Santiago Bernabeu, the fans turned on him. And despite gaining form as his first and only season with the club went on, he was sold to Milan in the summer of 2007 for £3.75 million.
At the time, Emerson was still just 31 years old and retained an excellent reputation in Serie A because of his performances for Roma and Juve. The Rossoneri had just won the Champions League, and his signing was seen as a good, experienced reinforcement for the squad, but he didn’t recapture his best form at the San Siro.
Injury problems and competition for midfield places from Andrea Pirlo, Gennaro Gattuso and Massimo Ambrosini meant the Brazilian made just 15 league appearances in his first season with Milan and 12 in his second before leaving by mutual consent in 2009.
3. Klaas-Jan Huntelaar
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Klaas-Jan Huntelaar joined Milan from Real Madrid for a fee of £11.25 million in August 2009 having failed to settle in Spanish football. The Dutch striker scored eight times in 20 outings for Los Blancos before moving to Serie A in a bid to rekindle his career.
Still only 25 years of age, he was regarded as one of the most clinical finishers in football after his prolific spell with Ajax, which saw him score 76 goals in 92 Eredivisie appearances. But he never lived up to expectations with the Rossoneri after making his debut in a 4-0 defeat to city rivals Inter Milan in the Derby della Madonnina.
Leonardo, Milan’s head coach at the time, preferred to partner Alexandre Pato with Marco Borriello. And with the latter in good form, Huntelaar often found himself having to come off the substitutes' bench.
In all competitions, he made a mere 13 starts, with a further 15 substitute appearances, scoring just seven times and earning a poor 6.48 average rating for his Serie A displays from WhoScored.com.
Huntelaar left Milan after just one year, signing for Schalke in 2010. He has stayed at the German club ever since, hitting double figures in four of his six seasons in the Bundesliga.
2. Ronaldinho
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For four years, Ronaldinho did his utmost to defy physics. Between 2003 and 2007, the Brazilian playmaker weaved his magic for Barcelona, mesmerising supporters and embarrassing opponents. He was untouchable at his best, a beautiful combination of explosive power, quick feet and audacious skill.
However, by the time he signed for Milan in 2008, his decline had already begun.
As per the Daily Telegraph's Matt Lawless, the Rossoneri beat Manchester City to the player’s signature, bringing him in for an initial fee of £19.8 million. But the simple fact Barcelona were willing to sell the icon should have been evidence enough the then-28-year-old was no longer the same force.
Ronaldinho’s time at the San Siro began promisingly enough, as he leaped to fire home a headed goal in a 1-0 win over rivals Inter Milan. But he failed to build on that, ending his first campaign in Italy with just eight league goals to his name.
He appeared rejuvenated throughout much of his second season, scoring 12 goals and assisting 18 in 36 Serie A outings, but after a deeply underwhelming start to the 2010-11 campaign, he left Milan and returned to Brazilian football with Flamengo.
Carlo Ancelotti, who worked with Ronaldinho during his final year as Rossoneri head coach, once told Corriere della Sera (h/t Football Italia): “I am not surprised by the decline of Ronaldinho. I saw it coming. His physical condition has always been precarious, while nobody could doubt his talent.”
1. Ricardo Oliveira
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In the wake of Andriy Shevchenko’s departure for Chelsea in the summer of 2006, Milan were desperately in need of a striker to replace the Ukrainian, who had been the club’s top scorer for the past three seasons. They opted for Ricardo Oliveira. It was a poor choice.
The Brazilian had scored 22 goals in 37 appearances to help Real Betis to Champions League qualification through a fourth-place finish in La Liga in 2004-05, but after injury issues stunted his second season, he went on loan to Sao Paulo in the hope of winning a spot in his national team’s squad for the 2006 World Cup.
He joined Milan for an £11.25 million transfer fee that summer but didn’t come close to filling Shevchenko’s boots.
Oliveira scored on his debut, against Lazio, to seal a 2-1 win, but he scored just two more goals in 25 further Serie A displays. And having failed to settle, he was sent out on loan to Real Zaragoza one year after arriving at Milanello.
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