7. Alberto Aquilani – Roma to Liverpool
Alberto Aquilani was a highly rated upcoming talent when Liverpool signed him back in 2009 as a replacement for Xabi Alonso, who had left for Real Madrid. The Italian was worth £18 million, which some thought was a bargain for a player of his talent. However, the Italian struggled during his time in Anfield as he is more of a dynamic attacking midfielder than a deep lying playmaker like Alonso. He was also hit with a series of injuries, which limited his playing in the lone season at England. After playing just 18 league games, Aquilani was shipped back to Italy with loan spells at Juventus and AC Milan. He eventually left in 2012 to Fiorentina on a free transfer, and currently plays for La Liga minnows Las Palmas.
6. Alexander Hleb – Arsenal to Barcelona
Alexander Hleb formed a brilliant midfield trio with Cesc Fabregas and Samir Nasri during his time at Arsenal, which attracted the eyes of Pep Guardiola and Barcelona. He was signed for €15m in the summer of 2008, becoming one of the earliest signings of Guardiola’s charge at the club. However, the relationship between the two turned sour because of Hleb’s attitude, which explains the very little playing time he got in Spain. He only made 19 league appearances in his lone season at the club, and was sent out to a series of loan spells before having his contract cancelled in 2012. Since then, the Belarusian played for several eastern European clubs, and is currently a free agent after leaving Krylia Sovetov Samara in the summer following their relegation from the Russian Premier League.
5. Alex Song – Arsenal to Barcelona
Alex Song, just like Hleb, is another player who had a fantastic time at Arsenal but made the wrong move to Barcelona. Song spent six years at Arsenal and established himself as a regular starter, making 215 appearances in total under Arsene Wenger. He made a jump to Barcelona in the summer of 2012 to become Tito Vilanova’s second signing at the club. However, the Cameroonian failed to earn a regular playing time in Barcelona, making only 39 appearances in his two seasons. He was sent to West Ham United in the summer of 2014 for a two-season long loan, and had his Barcelona contract terminated in 2016. Song currently plays for Russian Premier League club Rubin Kazan.
4. Mario Balotelli – AC Milan to Liverpool
One of the most talented, yet controversial players to ever exist, Mario Balotelli ruined his chance of becoming one of the top strikers in the world when he opted for a move to Liverpool in 2014. He just had a brilliant a year and a half at AC Milan before the move, where he scored 30 goals in 54 games, and looked to be resurrecting his career. However, the £16m move back to England proved to be a disaster as he failed to adapt with Brendan Rodgers’ tactics and scored just four times in 28 games across all competitions. A loan move back to Milan in the 2015/16 did not work out either and Balotelli signed for Nice on a free transfer in the summer of 2016. Speaking about his time in Liverpool, the Italian admitted it was the “worst mistake of his life.”
3. Andriy Shevchenko – AC Milan to Chelsea
Arguably one of the biggest flops in the Premier League, Andriy Shevchenko was shockingly bad at Chelsea. Signed in 2006 for £30 million after a tremendous spell at AC Milan, where he scored 173 goals in 296 appearances, and captaining Ukraine to the quarterfinal stage in the World Cup, the striker was expected to bring Chelsea to the next level. However, he failed to adapt to the physical nature of English football, and scored just nine goals in 48 league appearances. He returned to Milan on loan during 2008/09 season, before leaving on free to his hometown club Dynamo Kyiv. Shevchenko retired from football after playing in the Euro 2012, and is currently the head coach of the Ukraine national team.
2. Fernando Torres – Liverpool to Chelsea
If Shevchenko’s Chelsea career was bad, Fernando Torres’ was even worse. The Spanish striker was labelled as one of the world’s best players after his spells at Atletico Madrid and Liverpool, as well as his role in helping Spain win the 2010 World Cup and Euro 2008. He was signed in January of 2011 for £50 million, which set a new record for a British transfer. However, it took him 903 minutes to score his first goal for the club, which came at the end of April against West Ham United. Although his link up play was brilliant, Torres had trouble finishing chances and was widely criticized for an open-goal miss against Manchester United during the 2011/12 season. His only memorable moments at the club were scoring against Barcelona in the semi final of the Champions League and scoring in the 2013 Europa League final. After the arrival of Diego Costa in 2014/15, he was loaned out to AC Milan, who made his transfer permanent in January 2015 and then let him leave for Atletico. Torres still doesn’t look like himself at his hometown club, and has only scored 32 goals in 138 games during his second stint.
1. Ricardo Kaka – AC Milan to Real Madrid
Third player in this list who left Milan and flopped, Ricardo Kaka arrived to Real Madrid with big expectations in the summer of 2009 following a reported €68.5m fee. He was a Ballon d’Or winner just a year before the move, and played a key role in Milan’s Champions League title in 2007 and Serie A title in 2004. However, his time in the Spanish capital was disastrous as a series of injury issues kept him away from the pitch. He never made more than 27 league appearances in each of the four seasons at the club, and even when he was playing, the Brazilian did not exactly light up the world. He left the club in the summer of 2013 after a chat with the new manager Carlo Ancelotti, who made it clear he is not in the plans, and returned to Milan for a free transfer. After a season back in San Siro, Kaka signed with Major League Soccer club Orlando City for a three-year deal. He recently announced his retirement and will be remembered as a legend, but one has to wonder what more he could had achieved in football if he didn’t sign for Madrid.