Apart from Pompey, which I think was more down to the actions of the owners, I can't think of many clubs who have spent themselves into oblivion. There have been some small non league clubs who have come and gone but not many 'bigger' clubs as there have always been buyers who would step in.
I can't remember who, but someone mentioned Oscar being on the same flight to Barcelona yesterday. It's probably nothing, as he could be visiting family.