>>7738237He wanted to make them both and the company more money.
People didn't get sick of him until 2002 once he abruptly turned face after Survivor Series. Even during the invasion people still wanted him around, just not in the capacity and character he was. He knew he was one his way out. Why bother reinventing yourself when you're already planning your exit?
Why would someone whose character was a dude who got into wrestling to get drunk and fight people without going to jail give two fucks about managing someone?