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I still 100% believe that Shawn could have worked as early as 2000 but one of two things happened.
Either he was exagerrating his injuries so he could keep his contracts and do drugs.
Or he could have comeback, but Vince was sick and tired of his drug addiction, tired of his backstage politicking, and the simple fact that Austin was a bigger draw then him so he didn't need him.
Also, HHH was suppose to beat Undertaker at Wrestlemania 2000 with Shawn's help because before Mania 2000, HHH beat Austin for literally no reason and the only logical reason would be to set up a title match later.