Greatest Heel Turns In Wrestling

In this edition of The Wrestling Estate roundtable, we discuss the greatest heel turns in wrestling history.

What’s the first heel turn you remember?

David Gibb: The honest answer is I don’t remember. I was watching a lot of WWF from 1998-2001 and TNA from 2006-2010, so I’ve seen too many of them to keep track of.

Chad Gelfand: Stone Cold turning on Team WWF at Invasion 2001. I thought the “Old Stone Cold” was back for good and I was sad when he turned again.

Steven Jackson: Hulk Hogan at Bash at the Beach 1996. Although I watched it retrospectively on VHS, seeing how Hogan changed from the face of the USA to being the most hated man in wrestling, still gives me chills!

John Corrigan: Vince McMahon screwing The Rock at WrestleMania 2000. It was the first pay-per-view my parents ordered and I had to tape the last hour because of my bed time. When I woke up, I asked my dad who won the main event and he said Triple H after Vince hit Rock with a chair. I was so confused because Vince was in Rock’s corner – he wouldn’t do that! I told my dad he must be mistaken, maybe he meant Shane. But sadly, he was right.

Jack Goodwillie: The very, VERY first heel turn I can recall (depending on what came first) was Spike Dudley turning on his friend Rey Mysterio to side with Bubba Ray and D-Von Dudley in order to keep the Cruiserweight Championship around his waist, or Billy Kidman turning on Paul London as part of the aftermath of his Shooting Star Press putting Chavo Guerrero out of commission. I remember watching the latter turn back again just a couple of years ago and remarking about how excellent of an angle it was.

Is there a heel turn that should have happened, but didn’t, that really grinds your gears?

Gibb: Not really. Historically speaking, Hogan should’ve turned heel heading into WrestleMania VIII, but I wasn’t thinking on that level at the time. If you’re baiting me for a John Cena diatribe, I politely decline.

Gelfand: John Cena should have turned heel after losing to The Rock at WrestleMania XXVIII. It makes even more sense with the story heading into WrestleMania 29 being that Cena was having his worst year ever. Could have easily turned him back face after beating The Rock at 29 to redeem himself.

Jackson: John Cena should have turned heel several times in his career. I applaud his integrity and I am a huge fan, but had he turned full-on heel against the likes of Daniel Bryan, AJ Styles or CM Punk, we may have seen a very different outcome.

Corrigan: Stephanie McMahon should have ditched her hubby for Kurt Angle at Unforgiven 2000. Angle would have got a huge boost leading to his WWE Championship run and Triple H could have been the number-one face for when Stone Cold turned heel.

Goodwillie: I feel like this question is a lot more prevalent for face turns. Heel turns, after all, are much easier to pull off, as many of us are able to attest that it’s a lot easier to get people to hate you rather than get them like you, relate to you and want you to succeed. Of course, people will point to John Cena as “the one that got away” as far as heel turns are concerned, but I’m going to go in a slightly different direction with Roman Reigns. When Seth Rollins tore up his knee and had to miss WrestleMania in Dallas, I saw it as the perfect opportunity for WWE to recreate the Deadly Game tournament at Survivor Series with Reigns standing in for The Rock. Doing so would have solved many of WWE’s problems in one fell swoop, such as creating a fresh heel atop the card while preserving Reigns as a long-term main event player. Instead, a lukewarm Sheamus left the show as champion that night, and WWE has been chasing its tail ever since.

What’s the worst heel turn ever?

Gibb: Rikishi. Putting Steve Austin out of action for a year should’ve been a feather to pin to the next big heel’s cap. Instead, the reveal was shocking on all the wrong levels. Fatu certainly knew how to work like a heel from his time in the SST/Headshrinkers, but I don’t know that Rikishi ever figured out how to work like a heel.

Gelfand: One of Big Show’s heel turns. I can’t pinpoint an exact one, but it has to be one of those.

Jackson: I have never been a massive fan of Edge (I have huge respect for Adam Copeland, just not a fan of a lot of Edge’s work) and his 2004-2008 period where he was meant to be this deranged crazy “Rated-R Superstar” never appealed to me. Edge is too much of a nice guy to suddenly act in that manner. It just made me cringe.

Corrigan: Monty Brown. The Alpha Male was poised to be TNA’s breakout star, but instead of capitalizing on his momentum, he aligned with Jeff Jarrett and went from number-one hero to just another henchman.

Goodwillie: This question depends on how you define a bad heel turn. For example, Becky Lynch turning heel on Charlotte at SummerSlam 2018 was technically a failure because the fans never accepted Lynch as a heel. However, it was a catalyst in her becoming one of the company’s top draws to this very day. Other times, heel turns fail because the people behind the characters are actually BAD at being…well, bad. For that reason, Jeff Hardy’s run as “The Antichrist of Professional Wrestling” has to go down as one of the worst of all time. The turn itself was fine, but Hardy’s run with arguably the ugliest looking belt in all of wrestling was inauthentic and so strange with the likes of Hulk Hogan and Eric Bischoff behind him. The whole run was a complete failure and ended in just about the worst way possible.

What’s your favorite heel turn ever?

Gibb: Ted DiBiase in Mid-South. The Junkyard Dog never saw Ted DiBiase’s betrayal coming, but if you go back and watch the footage week to week, DiBiase’s mental turmoil and cowardly fear of losing his career at the hands of a better wrestler (who happened to be his friend) were on display in subtle ways. His donning of the loaded black glove and alliance with the clearly-mean-and-nasty Jim Duggan and Matt Borne made it impossible for even the fans who’d loved DiBiase a few weeks earlier to condone his new path.

Gelfand: Chris Jericho throwing Shawn Michaels through the Jeri-Tron. The buildup is what makes this heel turn so special, leading to one of the greatest heel runs of all time.

Jackson: Hulk Hogan joining The Outsiders and forming the nWo at Bash at the Beach 1996 shattered so many myths and brought the Hulkster straight back to the forefront of wrestling.

Corrigan: Trish Stratus slapping the shit out of Chris Jericho at WrestleMania XX. Nobody saw it coming and evil Trish was sizzlin’. My second favorite was Batista calmly informing Rey Mysterio that he was going to rip his head off.

Goodwillie: A good heel turn should somewhat surprise you, which is why I wasn’t too much of a fan of the MJF turn against Cody. Strictly going off shock factor, the two greatest heel turns would have to be Hogan joining the nWo and Austin aligning with McMahon. That said, one worked marvelously and the other did not, so shock and awe being the only criteria is somewhat of a gamble. The Rockers’ breakup also deserves a mention, just for how iconic of a moment it became. But if you’re looking for a textbook modern example of what a good heel turn looks like, look no further than Seth Rollins spurning the SHIELD to create The Authority. There was certainly an element of surprise involved, with everyone and their mother assuming Dean Ambrose would be the one to inevitably dissolve the SHIELD, and the turn itself resulted in Rollins taking his career to new heights.