5 Great WWE Heel Turns That Flopped Badly

John Cena finally turned heel at Elimination Chamber 2025, shocking the entire WWE Universe. Fast forward to SummerSlam, and Cena is back as a babyface for the remainder of his farewell tour.

While Cena's heel turn was great, its execution can be considered a failure due to the absence of The Rock, who was originally part of the storyline. However, it wasn't the first great heel turn that flopped in WWE history.

Here are five of the best heel turns that totally bombed.

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#5. Dean Ambrose turns on Seth Rollins after Roman Reigns' cancer diagnosis

Dean Ambrose attacks Seth Rollins on WWE RAW (Photo source: wwe.com)

One of the most shocking heel turns of the past decade was when Dean Ambrose attacked Seth Rollins after they won the RAW Tag Team Championship on the October 22nd episode of RAW. It was the night that Roman Reigns announced his leukemia had returned and he had to step away.

In terms of heat, it was a great way of generating it for Ambrose. However, his reasoning for attacking his Shield brother was off and poorly executed. It also contributed to Ambrose's unhappiness with Vince McMahon and WWE, leading to his departure and AEW debut.

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#4. Shawn Michaels superkicks Hulk Hogan on WWE RAW

Shawn Michaels returned from a four-year retirement in 2002 and proved that he is one of the greatest in-ring performers of all time. Michaels was a babyface for the majority of his second run, with a short heel run in mid-2005 during a feud with Hulk Hogan.

It was done wonderfully and was fully unexpected at the time. It was a success in terms of creating a shocking moment in WWE history. However, it was a flop because Hogan allegedly didn't want to have a trilogy of matches against The Heartbreak Kid.

Michaels put on a comical showing during their SummerSlam match, overselling The Hulkster's moves just to prove a point and send a message.

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#3. Xavier Woods and Kofi Kingston kick Big E out of The New Day

Big E, Kofi Kingston, and Xavier Woods. (Photo source: wwe.com)

Before John Cena broke a lot of hearts in Toronto, Xavier Woods and Kofi Kingston made several fans cry when they kicked Big E out of The New Day in December last year. It was a surprising turn, considering WWE was planting the seeds of a feud between Woods and Kingston.

While the turn was universally praised, the follow-up was a bit disappointing. They are still fantastic heels, especially online, but they haven't had a significant run as tag team champions outside of their title win at WrestleMania 41.

One culprit is the lack of babyface tag teams on RAW, so a move to SmackDown might salvage their heel run.

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#2. John Cena finally turns heel after more than 20 years

After more than two decades of being the ultimate babyface, John Cena finally turned heel at this year's Elimination Chamber. It's an understatement to describe it as one of the most shocking moments in WWE history. It was unexpected since Cena was on his farewell tour, with his in-ring career ending in December.

The execution of the heel turn was nothing short of fantastic, but the run itself was mediocre at best. The Rock, who had a hand in the heel turn as The Final Boss, failed to show up after Elimination Chamber. There was no follow-up at all outside of Travis Scott's interference at WrestleMania 41.

Less than five months later, Cena is back to being a babyface for the rest of his retirement tour. The heel run could have been something, but the company's failure to find a way for The Rock to address their story doomed it from the start.

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#1. Stone Cold Steve Austin aligns with Mr. McMahon at WrestleMania 17

Mr. McMahon and Stone Cold Steve Austin (Photo source: wwe.com)

There's no denying that Stone Cold Steve Austin was the face of the company during the height of the Attitude Era. When he turned heel at WrestleMania 17 and aligned with Mr. McMahon, it was a shocking decision that ultimately failed.

Austin was still very popular when the heel turn happened, with many fans still cheering him on at events. His personality changed, though his comedic chops were evident with his backstage segments with Kurt Angle and Mr. McMahon, which were very entertaining.

Maybe if Triple H didn't suffer his quad injury, The Two-Man Power Trip could have saved the heel run of The Texas Rattlesnake.