Spurs signed David Bentley from Blackburn Rovers for the princely sum of £15 million in 2008. The former Arsenal man had become one of the Premier League's better players in his time at Ewood Park and had developed something of a David Beckham-esque reputation when it came to taking set-pieces. He'd scored 13 times in 84 starts for Rovers - a good record for a winger - and had also broken in to the England squad and much was expected of him. It wasn't to be at White Hart Lane, however, as Bentley had a treacherous time. Aside from one memorable 43 yard dipping volley against former club Arsenal, his time at Spurs will only be remembered for spectacular failure. He performed poorly, seemed to lack drive and effort and never really made his mark. He became the club's forgotten man and was loaned out no less than four times to Birmingham City, West Ham United when they were playing in the Championship, FC Rostov in Russia and the team he joined Spurs from, Blackburn Rovers. He failed to impress in any of his loan spells and returned to Spurs, before being released on the 7th of June in 2013. He has now retired completely from the game, in spite of the fact that he is still only 30, having failed to find a new club since his release.