5. Arsene Wenger
Fifth place feels a little low for the legendary Arsenal manager Arsene Wenger, but the fact he has not won a trophy since 2005 cannot be ignored.
What also cannot be ignored is the fact that he has won two Premier League titles - one of which the Gunners won after going the entire season unbeaten - plus three FA Cups.
Wenger guided Arsenal to the 2006 Champions League final, but the Gunners were eventually 2-1 by Barcelona in Paris.