I genuinely think him going to Celtic is a waste of everyone's time to be honest. All he's going to do is pad his record up there. It's a walkover league, Rangers are going to be a few steps off the pace seeing as they just came up. He's proven here, with better resources at his disposal, that he isn't up to the task in Europe. So I don't think he's going to improve the club in that regard. From a professional standpoint I just don't see an upside to this.
Obviously there wasn't interest from Premier League clubs (hence why he went to Glasgow) but I don't see how winning a few titles in that piss poor league will make him a more attractive proposition, it certainly didn't work for Neil Lennon. If he fails to win the SPL then he will be branded a failure and in a career where he failed at Reading, Watford, ultimately failed at Liverpool and was only really successful at Swansea I don't think he can afford to walk around with another F on his record.
Personally I get that he's a Celtic fan apparently, isn't everyone a Celtic fan when they join the club though? Our old mate Robbie Keane can attest to that. I hope he enjoys himself but if I were him I would have looked at one of the stronger Championship clubs like Derby (wealthy owner for that level, good support, already play some pretty football) and tried to rebuild my career from there.
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