#2. Why it won't fail: His character works well as a babyface

Here is another side to the last point. The best kinds of babyface turns are the ones where a superstar doesn't necessarily completely change their character, but simply maintains the same character and directs their anger and frustration and harsh words towards heels.
It has worked that way for some of the greatest babyfaces ever and simply based off the episode of SmackDown, it's perfectly clear that Kevin Owens has that kind of a character. He's brash, he's cocky, he's rude and he's a straight-up shooter.
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Rather than directing that at the crowd, he simply directed it towards the heels and the crowd absolutely loved him for it. Audiences will always take to a babyface who knows how to spit fire against heels and Owens has that in him and has it to succeed.