it was cool when he was a semi-main eventer with the intercontinental title.
until they tried to make him the face of the company. he just wasn't top guy material - heel or face.
and the shane douglas "Syracuse" bullchit made matters worse.
then they proceeded with the boyhood dream bullchit(knowing dam well he was from NWA country), which resulted in the "big" iron man match with bret hart taking place in front of a crowd where half the people decided to leave early instead of watching the main event.
bret hart wasn't a good top guy either, but at least he was convinceable.
Shawn was such an unlikable scumbag, he was getting cheered for workrate and being a cool heel, turning him into happy go lucky white meat babyface and stripping him of all the attitude that got him over was lol. Vince never learned because it's 2020 and he's still doing it with all the top faces who got over as heels or cool bad asses. The only two who got to keep what got them over as heels when they turned top face were Austin and Rock. That's literally it over the past 25 fukking years.
true
but even when they turned him back heel & started DX, it still didn't work out.
hell, DX got hotter after he left.