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It was peak of the "smarks being held hostage by Vince because WWE is more or less the only game in town" era.
Bryan was the under-sized indie guy who was seen as very much being everything Vince didn't give a shit about. Small, good in the ring, etc.
And somehow, Bryan was able to get himself over with Vince. McMahon loved Daniel Bryan and Bryan has said many times than he respects Vince more than anyone other than his own father. They developed a great relationship, so not only did he have the fans, but he also had Vince behind him.
