It's hard to imagine a point where Vince McMahon didn't think Shawn Michaels as WWE Champion, but according to Bruce Prichard, such a time did exist.
Prichard appeared on the Sam Roberts Wrestling Podcast and detailed Vince's thoughts on The Heartbreak Kid, not only being the company's champion, but also being an effective babyface as well.
"There [are] a lot of situations where we pitched big, sweeping, just simple things like, ‘Shawn Michaels is going to be a babyface.’ [McMahon replied] ‘that little son of a b—h? He’ll never be a babyface in this company!’ And he didn’t see it till after WrestleMania 11. Vince gets in the car and says, ‘Goddamnit, guys, we have a babyface on our hands! Why am I the only one that sees this?’ And Pat [Patterson] and I are looking at each other, going, ‘we were told never to bring that idea up ever again.’ It’s crazy, but I just, God, Pat especially, and Pat was probably the first one that actually made the statement, ‘I can see Shawn Michaels as WWF Champion.’ Yeah, Vince didn’t see Shawn as the WWF Champion at that time. In particular, he didn’t see Shawn as a babyface. But there was an undercurrent there that here you’ve got a guy that is going out, stealing the show every night with whoever he worked with, and the audience after a while began to respect him, so Shawn was doing that every night. It’s kind of like, even Bret Hart, who no matter who Bret was in the ring with, Bret was going to get his match out of him and Bret was going to get that match over no matter what he had to do and they respect that."
Vince obviously eventually changed his mindset regarding Michaels, as he enjoyed three reigns as WWF Champion, one reign as World Heavyweight Champion, six total tag team reigns and two Royal Rumble victories in 1995 and 1996. Michaels effectively became one of the best heels and faces in WWE history after he split with former tag team partner Marty Jannetty in 1992.