Steve Austin joining forces with Vince McMahon at WrestleMania 17 marked the end of the Attitude Era and led to a decline in viewership.
Dean Ambrose's heel turn in 2018 was poorly executed, with a wacky character that resulted in him leaving WWE for AEW.
Jim Ross turning heel in 1996 was disliked by fans, as he was beloved and not suitable for a villainous role.
Michael Cole's heel turn in 2011 created negative stigma around his commentary and affected fan enjoyment.
Big Show's constant alignment shifts throughout his career diluted his character and made it hard for fans to take him seriously.