David Bentley arrived at White Hart Lane from Blackburn Rovers for £15 million in 2008. The ex-Arsenal winger had earned himself a good reputation as a footballer and dead ball specialist, as well as senior England recognition. He was expected to develop at Spurs and become an even better player. It simply didn't happen for him at Spurs and one memorable 43 yard dipping volley against former club Arsenal was just about the only decent thing he'll be remembered for. He performed poorly and didn't really seem to care about that fact. He became the clubs 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 didn't impress in any of those spells and found himself back at Spurs in 2013 - five years after he'd first arrived and still having failed to make much of an impression. All in all, he made 62 competitive appearances for Spurs and scored just five times. He was released in 2013 - but that was several years too late, as Spurs were paying his inflated wages for far too long. He has now retired.