Also, another interesting question about Bryan that is more applicable since it's there in any scenario where Bryan keeps going heel.
Should Michael Cole hate heel Bryan?
It's an interesting dilemma. Character consistency demands he does it, and the WWE should do everything it can to actually have consistent personalities, since that's rather rare. But then you have the problem where the entire announce team will be constantly burying him, which doesn't sound like it could possibly work out well.
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Mistake you're making - overlooking the fact that we might not want to be saved.