Randy has portrayed a heel for about 99 percent of his career. He has built his career around his heelish tactics. The problem is that when someone is a heel for so long, some people start to cheer for him anyways.
The same thing happened with Steve Austin in the 90's. Austin was a full-on heel, but the WWE fans began to cheer him anyways and WWE saw the potential in a blue collar anti-hero character and went for it.
Austin became hugely successful after turning babyface, but what was great about his turn was that his attitude and tactics never changed at all, he simply targeted the bad guys instead of the good guys.
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