10 Wrestlers Vince McMahon Couldn't Get Over
Don't cross (this specific version of) the boss! It hasn't gone well for Austin Theory...

There are evidently way more than 10 wrestlers Vince McMahon can't get over.
One need only look to the WWE Personnel Wikipedia page to find a majority of names that the Chairman has profoundly failed in recent times, and that doesn't include the folk binned off in the last two years - so great in number in fact that they helped make that destination Wiki's most edited link.
This is not that list, but will instead focus on those McMahon has directly included himself in the misadventures of. The talent he's deemed worthy enough of his precious time in between gaslighting midcarders, b*llocking commentators and tearing up Raw scripts. Special cases, and yet not that special at all, because it wasn't his fault when these pushes failed.
In much the same way Hulk Hogan got over in one specific way and McMahon subsequently went looking for a direct replacement, or John Cena reimagined the expectations of a top star and his boss applied them to every wrestler that attempted to headline, the Chairman gets fairly set in his ways with something if it works once.
Austin Vs McMahon worked really, really well. Unlike...
10. Bobby Lashley

Bobby Lashley's 2021 return to television came with an in-built spot in the next pay-per-view WWE Championship match.
Yes, he had to jump through various kayfabe hoops to gain a spot in the multi-man match, but these all contributed to an IRL inevitability. The 'All Mighty' is now a former titleholder himself, and one that looked better with the belt than most that came before him.
It was - in Vince McMahon's defence - this he saw over fifteen years ago when the ageless Lashley arrived in World Wrestling Entertainment, but a combination of wrestler inexperience and McMahon's heavy-handed over-promotion very nearly doomed the standout for good.
A run as ECW Champion for big Bobby was loathed for what it wasn't (a push for CM Punk, another roll of the dice on Rob Van Dam) rather than beloved for what it was (a transparent power play by Vince McMahon in a one-sided war against Paul Heyman). Lashley had chance after chance to beat, brutalise and embarrass McMahon following his Battle Of The Billionaires win over Umaga, but fan sentiment was already skewing south and so too was Lashley's enthusiasm.
After taking time off with injury that summer, he'd leave the following spring as an impossible wasted opportunity. It took both sides a decade to start writing those wrongs.