2. David Bentley
David Bentley is a classic example of a player who floundered following a big money move. After spending three years at Blackburn Rovers, six months of which were on loan, Bentley
secured a £15 million move to Tottenham Hotspur in 2008. During his time at Blackburn, Bentley had become the first player to score a Premier League hat-trick against Manchester United when he put three past the Red Devils on February 1st 2006. A series of promising performances continued to push Bentley's profile higher as he managed to force his way into the England squad, with then England manager Steve McClaren hailing him as
the 'new' David Beckham. Such comparisons prompted Tottenham to break their transfer record for the player and he started well, scoring a 40-yard goal against his first club Arsenal. Unfortunately that was as good as it got for Bentley as Harry Redknapp looked to Aaron Lennon to use pace and speed rather than the skills of Bentley. A
drink driving offence and a
falling out with Redknapp following Tottenham's qualification for the Champions League would see Bentley fall further still down the pecking order, resulting in him being sent out on loan to Birmingham City, West Ham, FC Rostov (Russia) and Blackburn before finally being released in 2013. Now 29, a number of clubs have passed on signing him, and he remains a free agent.