>>16054049I think it's basically because Shawn got the life/career Bret was "supposed" to have despite being a massive fuck-up. He was strung out on pills and a belligerent dickhead, Bret "took it seriously"/"did it the right way," and Shawn always came out on top.
Bret signed the 20 year contract, Shawn is the lifer with a cushy backstage job
Bret is loyal to Vince/the company, Shawn "loses his smile" to avoid dropping the belt, Bret gets screwed
Shawn, despite not taking care of his body at all, has arguably a BETTER second half of his career while Bret is essentially retired after the goldberg match and subsequent hardcore clusterfuck on a Nitro no one cared about
Shawn has one of the most beloved retirement matches of all time and puts a cherry on top of his career while Bret gets the vince mcmahon streetfight
And that's not to mention all the personal stuff with Owen. He's probably still unimaginably bitter that Shawn gets all the adoration in the world and a generation of people using him as inspiration for their style while all Bret gets is lipservice from the bald dude in the revial and occasional appearances for AEW in canada.
