Chelsea - I know, sounds odd, but...
Twice in 2 seasons they have had English clubs which are far weaker in general progress further in major competitions. Guess another £50m plus needs to be spent.
However, notable mentions to:
Graeme Souness - Spent and spent and actually had Newcastle take a step backwards.
Shola Ameobi - Had a chance to finally prove himself and merely proved what people thought all along.
Darren Fletcher - As above.
Paddy Vieira - Left a club to progress his career and actually missed out on a European Cup final getting beaten by his old club in the first leg, getting booked and missing out on the 2nd leg all together.
SWP - Could have gone to Arsenal or Liverpool and been a God, instead claims competition will make him play better, then takes steps backwards and becomes 4th choice at Chelsea. Gets 1 game back against Newcastle and does his cause no good by revealing he is infact a diver.