3. Glenn Hoddle
Glenn Hoddle is a Spurs legend - of that there is no doubt - but his managerial career has been questionable at best and he certainly comes with some controversies weighing him down. The once-brilliant midfielder had an infamous spell in charge of England that was blighted by some questionable decisions and actions - such as not taking Paul Gascoigne to the 1998 World Cup, appointing "faith healer" Eileen Drewery as part of his staff and claiming that disabled people were being punished for sins in a previous life. He did, however, have a 60% win record whilst in charge of the national team - a record only bettered by Sir Alf Ramsey and Fabio Capello. His previous spell in charge of Spurs came between 2001 and 2003, where his two full seasons in charge led to disappointing 9th and 10th place finishes and a 2-1 League Cup final defeat to Blackburn Rovers. Today, his name is being linked to Spurs, with the likes of Gary Lineker calling for him to be given another shot at the top level - and if he can gets Spurs playing to anywhere near the standard that he was capable of playing in his prime it would be a stellar appointment. But his time has probably passed.