5 Most Shocking Heel Turns In WWE History

Steve Austin and Vince McMahon

Throughout the history of WWE, many wrestlers have left the side of good to join villainous factions, or take the easy road to championships and glory. Sometimes, there are months of hints, and for others there seemed to be no indication about what was to come. There are also moments so unforeseen that it shakes the foundations of your fandom. These are the ones we will concentrate on as we look at the five most shocking heel turns ever witnessed in WWE.

5. Stephanie McMahon (1999) – “I’m not Daddy’s Little Girl anymore”

Stephanie McMahon and Test

Stephanie McMahon made a ‘blink and you’ll miss’ it debut on WWE TV in November 1998 as an extra in a backstage segment with ‘Stone Cold’ Steve Austin when the ‘Texas Rattlesnake’ was hunting for The Undertaker. She only spoke a few words before hurrying away down the corridor. A few months later, she began to appear regularly as an on-screen character involved in the increasingly personal feud between her father, Vince McMahon, and The Undertaker who had recently formed his Ministry of Darkness with the intention of taking control of WWE. The Undertaker used Stephanie to torment McMahon, even going as far as kidnapping her and attempting to marry her in an ‘Unholy Wedding’ before Austin saved her from that fate. It was later revealed that the real ‘Higher Power’ behind the Ministry was, in fact, Vince McMahon himself, who was using the group to further his vendetta against Austin. Stephanie was devastated by this betrayal and confronted her father, only to be told it was “just business”.

Stephanie, alongside her mother Linda McMahon, responded by handing their shares in WWE over to ‘Stone Cold’, giving him a stake in the company equal to Vince and his son, Shane McMahon’s. The storyline ended soon after, with the Corporate Ministry, formed from the Undertaker’s Ministry and McMahon’s Corporation factions, falling apart. Austin lost his stake in WWE to Vince, but once again became WWE Champion in an ‘I Quit’ match with The Undertaker at the 1999 edition of Fully Loaded, an additional stipulation also meant that Vince McMahon was banned from television.

Stephanie remained on WWE TV, beginning a relationship with the wrestler Test and eventually, on the first episode of SmackDown on August 26th, agreeing to his marriage proposal. The ceremony took place on November 29th with Stephanie being accompanied by her father after the two were able to reconcile. However, as often happens when weddings take place in a wrestling ring, things did not go as planned when Triple H crashed the party to reveal he had taken an unconscious Stephanie to a drive-through wedding chapel in Las Vegas and tied the knot with her before Test was able to. Vince McMahon was livid and the incident led to a No Holds Barred match between him and Triple H at Armageddon on December 12th, with the stipulations being that the marriage would be annulled if Vince won, or Triple H would get a WWE title shot if he did.

The match was a brutal affair that saw the two fighting in and out of the ring, even going to the parking lot where the ‘Cerebral Assassin’ tried to run McMahon over with a car. Back in the arena, the two climbed part of the stage structure, with McMahon being thrown off a 30-foot tower of scaffolding. McMahon eventually got the upper hand in the ring and was going to attack Triple H with a sledgehammer to end it, when Stephanie jumped into the ring, apparently wanting to do it herself. Triple H grabbed the sledgehammer and used it on Vince to win the match. Stephanie was checking on her father when it looked like Triple H was going to attack her too but when she turned around, he dropped the hammer and the pair embraced instead, with Stephanie raising her husband’s arms over the limp body of her father in front of a stunned audience.

The two had planned the whole thing out to take control of the company and begin the ‘McMahon-Helmsley Era’ going into the new millennium, with Stephanie presumable never having truly forgiven her father for the events of previous months. Triple H would go on to capture the WWE Championship, and Stephanie herself won the WWE Women’s Championship, solidifying their dominance over WWE.

4. Paul Bearer (1996) – “The Undertaker is nothing!”

Undertaker and Paul Bearer

While The Undertaker was brought into WWE by Brother Love in 1990, it was the partnership he began with Paul Bearer in 1991 that became beloved of wrestling fans around the world. With his pale, ghostly make-up, bizarre high-pitched voice, and the iconic urn he carried to the ring, Bearer was the perfect Manager for the ‘Deadman’. The pair became fan favourites in 1992 when Undertaker entered a feud with Jake ‘The Snake’ Roberts, preventing his one-time ally from attacking Randy Savage during Paul Bearer’s talk show segment, the aptly-titled ‘Funeral Parlour’. The ‘Phenom’ would go on to defeat Roberts at WrestleMania VII.

Bearer continued to be at Undertaker’s side throughout the next few years, rallying the ‘Man From The Darkside’ with the urn when he seemed to be flagging in the ring, and leading him to victory over the likes of Kamala, Giant Gonzales, and Papa Shango. At the 1994 Royal Rumble, Undertaker took Yokozuna on in a casket match. Yokozuna was aided by multiple wrestlers in defeating him by sealing him in the casket. Undertaker would not be seen for seven months after the incident, and while the ‘Million Dollar Man’ Ted DiBiase claimed to have brought him back, it was in fact a fake, with the wrestler Brian Lee taking on the moniker. Paul Bearer was incensed by this and brought back the real Undertaker at that year’s SummerSlam to reclaim his place in WWE.

Over the next two years, Undertaker continued to see success, among other things getting his revenge on Yokozuna by defeating him in a return casket match at Survivor Series, battling Kama (the future Godfather), and entering a feud with Diesel which saw him continue his legendary WrestleMania success at the 12th edition of the ‘Grandaddy of Them All’ when he defeated ‘Big Daddy Cool’.

Things were to change when Mick Foley joined WWE, debuting as the deranged Mankind and immediately setting his sights on Undertaker. After several weeks of ambushing Undertaker in various arenas, Mankind cost the ‘Deadman’ his chance at the Intercontinental Championship in a casket match with Goldust at ‘In Your House 8: Beware of Dog’. When Undertaker looked to win the match by rolling Goldust into the casket, Mankind jumped out and locked in the Mandible Claw, dragging Undertaker into the coffin and handing Goldust the victory.

Undertaker and Mankind finally met in a singles match at King of the Ring. Mankind would emerge victorious after Paul Bearer accidentally hit his charge with his urn when trying to attack Mankind. This would not be the end of things as Undertaker accepted Mankind’s challenge to a Boiler Room Brawl at SummerSlam 1996, a match which would start in the arena’s boiler room, with the two having to fight their way to the ring and claim the urn from Bearer. The match was as brutal as you would expect in this heated rivalry, with the two men throwing caution to the wind as they attacked each other with wooden two-by-fours, pipes, and trashcan lids. They also used the unique environment to their advantage, slamming each other against walls and the boiler itself. They eventually battled their way to the ring, where Undertaker threw Mankind to the exposed arena floor. With victory in his grasp, he dropped to his knee and reached for the urn, but in one of the most unexpected and surprising moments in wrestling history, Bearer refused to give him the urn, instead turning his back on his long-time ally. This allowed Mankind to recover and lock in the mandible claw. Undertaker was not yet defeated, so Mankind held him back while Bearer began his own assault, slapping and kicking the former WWE Champion before landing the final blow of the match and their partnership by cracking the urn over Undertaker’s head.

Undertaker and Mankind, with Bearer in his corner, continued their rivalry for months afterwards, competing in ever more extreme matches, from the Buried Alive match at the eponymous PPV, to the Revenge of The Taker event where Undertaker not only defeated Mankind but burned Bearer’s face with a fireball for a measure of vengeance.

3. Seth Rollins (2014) – “There’s always a Plan B”

The Shield

Seth Rollins, alongside Dean Ambrose (now AEW’s Jon Moxley), and Roman Reigns burst onto the scene at Survivor Series in 2012 by attacking Ryback and John Cena. Calling their group “The Shield”, the trio were a tight-knit team who ran roughshod over the company. They remained undefeated for over six months, with Rollins and Reigns capturing tag team gold and Ambrose winning the United States Championship along the way. The group came to the attention of Triple H and Stephanie McMahon, who brought them into their newly formed ‘Authority’ faction as enforcers in August 2013.

Things started going wrong for the group soon after. Rollins and Reigns lost their tag team championships that October and Survivor Series almost resulted in humiliation for their team when an Elimination Tag match saw Ambrose being the first to go and Rollins being taken out with a roll-up by Rey Mysterio. Only Reigns saved them from a complete humiliation when he managed to win the match as the sole survivor. However, CM Punk defeated all three members of The Shield in a 3-on-one Handicap Match at TLC 2013 a few weeks later when a miscommunication led to Reigns landing a Spear on Ambrose allowing Punk to get the pin.

Even during their less successful period, the team continued to gain in popularity, and eventually gave in to the fan’s adulation and turned on The Authority, first feuding with, and defeating, Kane and the New Age Outlaws at WrestleMania XXX. This led to Triple H reforming Evolution with Batista, Orton, and Ric Flair in an attempt to finally defeat The Shield. It was to no avail as Triple H’s once-feared faction was defeated twice, first at Extreme Rules in May 2014 in a Six-man Tag match, and then a few weeks later at Payback in a No Holds Barred Elimination match, The Shield successfully wiped out Evolution with a clean sweep.

The following night on Raw Evolution imploded as Batista quit the group and WWE when Triple H refused to allow him a WWE World Heavyweight Championship match against title-holder Daniel Bryan. It looked as if The Shield had sealed their victory over Triple H and The Authority. Later in the night, before Reigns was scheduled to take on Randy Orton, Rollins claimed that the reason Evolution was defeated and imploded was that, unlike The Shield, they didn’t work as one. Reigns added that they also weren’t brothers like he, Rollins, and Ambrose.

‘The Game’ accompanied Orton to the ring with a sledgehammer in hand and said that the match at Payback was ‘Plan A’, but there’s always a ‘Plan B’. This was Rollin’s cue to shatter the brotherhood he had just been celebrating when he attacked Reigns from behind with a steel chair, then set to work on Ambrose, hammering his former friend repeatedly with the chair before ramming his face into it with a Curb Stomp. He then left the ring to let the ‘Viper’ do the same to Reigns.

The following weeks and months saw Rollins go from strength to strength as part of The Authority. Not only defeating his former teammates Ambrose and Reigns but also winning the Money in the Bank briefcase. He would go on to use the contract to insert himself into the main event of WrestleMania 31, originally a singles match between Reigns and Brock Lesnar, Rollins made it a triple threat and pinned Reigns to win the WWE World Heavyweight Championship for the first time.

2. Shawn Michaels (1992) – “Is there a problem with The Rockers? I don’t think so!”

The Rockers

By the time Shawn Michaels entered WWE in 1988 with his tag team partner in The Rockers, Marty Jannetty, the duo had already begun to make a name for themselves. They had wrestled across the USA in Mid-South Wrestling, Central States Wrestling, WCCW, and the AWA, capturing the Tag Team Championships in several of the promotions.

After joining WWE full-time in 1988, the duo’s popularity as fan favourites only grew. They had a heated rivalry with The Brain Busters – Tully Blanchard and Arn Anderson – which included a classic bout on the monthly ‘WWE on MSG Network’ show that garnered a 4.25 star rating from the Wrestling Observer Newsletter. They continued to go from strength to strength while battling through feuds with the likes of The Fabulous Rougeaus, The Powers of Pain, and The Hart Foundation. At the 1989 Survivor Series, Jannetty and Michaels were part of the main event Elimination Tag match alongside Jim ‘ The Anvil’ Neidhart and The Ultimate Warrior, as ‘The Ultimate Warriors’, where they defeated Heenan Family members Bobby ‘The Brain’ Heenan, Andre the Giant, Haku, and Arn Anderson.

While The Rockers never officially held the WWE Tag Team Championships, they did defeat the champions, Bret Hart and Jim Neidhart in 1990 in a 2 Out Of 3 Falls match which was advertised as being for the titles. However, the top rope broke during the bout and the footage was deemed unusable, so WWE didn’t recognise the title change.

In 1991, cracks started to appear in the long-running partnership as issues between the pair began to mount. From Michaels flirting with girls in the crowd instead of at his post when Jannetty wanted to tag out, to Jannetty accidentally slamming one of the Nasty Boys into Michaels during a Survivior Series elimination match, things were heating up. The final straw came when, during a match against the Legion of Doom, Michaels dropkicked Animal from behind when he was about to slam Jannetty, this led to Animal falling on top of his foe for the 3-count. This led to more bickering between the pair, and it would turn out to be their last match as a team.

A few weeks later on Brutus ‘The Barber’ Beefcake’s ‘Barbershop’ interview segment of Wrestling Challenge, Jannetty and Michaels were brought together to try to resolve their differences. Jannetty gave Michaels an ultimatum, either walk away and do his own thing or try to work things out. To the delight of the audience, Michaels turned Jannetty around and the pair hugged, seemingly resolving to reconcile. However, Michaels suddenly superkicked his now-former partner before throwing him through a window on the set in one of the most iconic heel turns seen in wrestling. He then tore the poster of his old team in half and smirked while he uttered the line, “Is there a problem with The Rockers? I don’t think so!”. Michaels then sauntered off the stage leaving Jannetty bleeding on the floor.

The incident worked out well for the man now known as the ‘Heartbreak Kid’ as he became a cocky and vain heel who could also back up his arrogance in the ring. He would soon find himself in singles title matches, and while it took a few months for him to win his first championship in WWE – when he defeated the British Bulldog in November 1992 – there was no doubt that his star was rising fast and the future Hall of Famer never looked back.

1. ‘Stone Cold’ Steve Austin (2001) – “Stone Cold has sold his soul for the WWF title!”

Stone Cold Steve Austin

‘Stone Cold’ Steve Austin was a phenomenon in WWE. Despite entering the company as a heel managed by the ‘Million Dollar Man’ Ted DiBiase in 1996, Austin began to gain momentum with the audience after his famous ‘Austin 3:16’ promo at that year’s King of The Ring after defeating Jake ‘ The Snake’ Roberts to win the tournament. He started getting more crowd support as the year went on, but it was his feud with Bret Hart that really put the future WWE Champion on the map. The two fought for months from the end of 1996 into 1997 with Austin as the heel and Hart as the fan favourite. However, Austin’s increasing popularity as a no-nonsense badass led to the iconic Submission match at WrestleMania 13 that saw a bloodied Austin pass out in the Sharpshooter rather than quit. Hart continued to attack Austin after the match leading to the crowd getting fully behind the ‘Texas Rattlesnake’.

Austin quickly became one of the top stars in the company while feuding with the Harts over the rest of 1997. He had captured the hearts of the fans and was in tune with the cultural mood of the time, fast becoming the centre of the WWE’s new ‘Attitude Era’. He won the WWE Championship for the first time at WrestleMania 14 after defeating one of the defining stars of the 1990’s, Shawn Michaels, with a little help from ‘Iron’ Mike Tyson. It was then that his feud with WWE Owner ‘Vince McMahon’ began and thrust the company fully into the mainstream with ‘Stone Cold’ as its most recognisable star. McMahon threw everything at Austin, who he had deemed an unsuitable champion for his company, from The Undertaker, to Mankind, and even a debuting Big Show, but his spot at the pinnacle of the company couldn’t be taken from him and, as mentioned earlier in this article, Austin even managed to take the position of WWE CEO from McMahon for a time.

Towards the end of 1999, the ‘Bionic Redneck’ was forced to take a lengthy leave of absence to get neck surgery for an injury that was the result of a piledriver that went wrong in a match two years prior with Owen Hart. He was written off TV at Survivor Series when an unknown driver ran him over with a car. When he returned late in 2000, it was revealed that Rikishi had been the culprit and had taken orders from Triple H. This ignited a feud with the ‘Cerebral Assassin’ that culminated in February 2001 in a 3 Stages of Hell Match which was won by Triple H when Austin attacked him with a bat wrapped in barbed wire, only for the ‘King of Kings’ to fall on top of him for the pin during the third fall inside a steel cage.

Austin won the Royal Rumble for the third time in 2001, guaranteeing him a spot in the main event of WrestleMania 17 against The Rock, who had captured the gold from Kurt Angle at No Way Out. The Rock’s career had taken a massive upward trajectory during Austin’s time away from the ring, as the ‘Great One’ turned from a cocky heel into the ‘People’s Champion’ who had reached a level of popularity comparable to Austin himself. While the two had faced off before, at WrestleMania 15 two years earlier, this time stage was set for a clash of the ages. However, things were to take a turn nobody would ever have expected.

In the middle of the match and with neither The Rock nor Austin able to get the upper hand, Austin’s old enemy – and The Rock’s old ally – Vince McMahon made his way to the ring, seemingly to watch the match. The WWE Chairman soon made his presence felt, pulling The Rock out of the ring when it looked like he was about to get Austin pinned for a 3-count. Later, after the referee was thrown from the ring, Austin hit Rock with a low blow and then, to the confusion of everyone watching, instructed McMahon to attack The Rock with a steel chair. It still wasn’t enough to put the ‘Brahma Bull’ away and he came back with a Rock Bottom, but McMahon distracted the referee from counting the pinfall. After The Rock kicked out of a Stunner, Austin smashed his head with the chair, The Rock kicked out once more and then Austin snapped and beat him with the chair repeatedly until he could no longer defend himself, then pinned him to claim the WWE Championship. The crowd weren’t sure to make of what was happening, then McMahon and Austin went face to face in the ring and after a moment shook hands. It was now clear that Austin had went to great lengths to regain the championship, in the words of Paul Heyman on commentary, “Stone Cold has sold his soul for the WWF title!”

While it deservedly takes its place in this list as the most shocking heel turn in WWE history, unfortunately, it wasn’t well-received by fans who wanted to continue to cheer on their long-time favourite. While Austin was determined to become the top heel in the company, trying everything from teaming with McMahon and another old rival, Triple H, it was a struggle for everyone involved to make it happen. Austin’s friend Jim Ross explained on the Grilling JR podcast that they were “swimming upstream” trying to make it stick.

“Heel qualities include having enough heat on them that you will pay your money to drive to the arena to watch them get their ass whipped. Nobody’s going to pay their money to come to RAW, a house show, live event whatever you want to call it, to see Austin get his ass whipped. They’re not mad at him.”

In the end, the turn would only last until the end of 2001, when Austin returned to being a fan-favourite and was once again a thorn in Vince McMahon’s side.