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Well, I recall reading various accounts that suggest he thought he was going to win, and few (if any) where he seriously considered the prospect of losing. But obviously, it's difficult to know for sure.
However, if you combine that mindset with Cameron's all-too-familiar complacency, then you've got a scenario where you enter negotiations half-heartedly, and leave yourself too little time to do any fixing if it starts to look like it might not go your away.
boristrump
1) That was not the case though was it? He was pissed off that the rest of the EU wouldn't listen to him and would only give "meagre" concessions.