2. David Bentley
Nigel French/EMPICS SportGranted, David Bentley had absolutely no choice in the matter, as he simply hadn't performed in a Spurs shirt, but he must be ruing the fact that he was released from the club. A lot was expected of the former England international when he arrived at White Hart Lane from Blackburn Rovers, for what was then the third largest sum Spurs had paid for a player - £15 million - after Darren Bent and Luka Modric. He was touted as the next David Beckham - a right winger with a wand of a right foot and a reputation for scoring from long range and from set-pieces. Sadly, it would not work out that way, as Bentley flattered to deceive. Aside from a 43 yard dipping volley against former club Arsenal, his time at Spurs will only be remembered for spectacular failure. He 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 his loan spells and returned to Spurs, before being released on the 7th of June in 2013. Having not found a new club for over a year, he announced his retirement from professional football on the 13th of June in 2014. He has spoken out about his retirement, stating in an interview that he had fallen out of love with football. He said the modern game had become "robotic", thanks to the influence of social media and money, and called it "predictable and a bit too calculated". He said he wanted to spend time with his family, but the fact is he had no choice - nobody wanted him. Bentley's attitude was often questioned in his time as a professional footballer and it was generally perceived that he thought he was better than he was. Had he applied himself more, his career might still have been in full swing (he's only 29 years old now) and he might not have had to leave Spurs - a forced move that he surely regrets having happened.