How broken contracts, rebranding battles, and stock market moves led to the most infamous moment in sports entertainment history 25 years ago.
“I think I’m cute, I know I’m sexy.”
Female fawning and the lyrics to “Sexy Boy” boomed through the PA system at Molson Centre, overpowering a packed house charge by boos of both spellings. All at once, a look of shock washed over the face of Bret “The Hitman” Hart.
Staring back was an arena full of fellow Canadians who had just seen their local legend lose. Panning closer to the ropes was WWF bossman Vince McMahon, suddenly fully aware of what he’d just done.
Only moments before Shawn Michaels’ theme song overpowered the arena, McMahon had screamed, “Ring the bell! Ring the bell!” as a means to reroute the title match.
“I got the looks, that drives the girls wild.”
In a state of awe, Hart knew exactly what had just happened, though he had many a man’s word that it wasn’t going to happen at all.
Trusting associates he’d had for ages despite an overriding eery feeling leading into the match, his longtime employer and arch-rival had lied to his face, pulled strings behind his back, and embarrassed him in front of the fans that worshipped him.
“I got the moves, that really move them.”
Beat by Michaels for the WWF Heavyweight Championship belt, the San Antonio stud forced Hart into an unscripted “submission” by using his own leg lock, The Sharpshooter, in The Hitman’s native land.
In an essence, it was as if Allen Iverson got his ankles broken by Luka Doncic in Philly, losing Game 7 of the NBA Finals by way of a killer crossover.
“I send chills, up and down their spines!”
Rolling out of the ring, Michaels made his exit while his theme song “Sexy Boy” — sung of course, by him — continued to play over the PA. Spoiling Hart’s homecoming and WWF curtain call, the infamous “Montreal Screwjob” seen at Survivor Series on Nov. 9, 1997, still stands as one of the most scandalous subjects in sports entertainment history.
Twenty-five years later, Boardroom breaks down the inside baseball that turned professional wrestling absolutely upside down.
The Spirit of Competition
On the surface, Bret “The Hitman” Hart and Shawn “The Heartbreak Kid” were natural rivals.
Occupying a similar territory with an opposite approach, both title toters emitted a gravitational pull where fanfare was concerned, packaged in a rock star sheen. Hart was big, brash, and tough while Michaels was bold, arrogant, and athletic.
Fighting for space like Shaq and Kobe, their dissimilar upbringings and over-the-top workspace made them opposing figures in the ring and locker room.
Deep behind the scenes, there was an even bigger rivalry going down.
Pro wrestling kingpin Vince McMahon was atop of the family business, having held the helm at the Worldwide Wrestling Federation since 1980.
Over the course of the ’80s, he helped break box office favorites like Hulk Hogan and”Macho Man” Randy Savage, making them larger-than-life characters idolized through VHS tapes and action figures.
For years, McMahon was competing with pro sports, TV sitcoms, and movies for fanfare. By the mid-90s, he was competing with Eric Bischoff.
Ascending in the ’80s at the American Wrestling Association, Bischoff broke through the ranks of wrestling from a humble salesman to an on-air personality. By 1991, he was working at the newly formed World Championship Wrestling, tasked with shaping storylines and stealing WWF talent.
Quickly, he proved good at both. In a matter of years, Hogan, Savage, and Ramon were all on WCW payroll, making more than they did for McMahon and rebranded in edgier fashion for a new generation. Bischoff was playing with McMahon’s pride and his pockets.
Over the course of 1996, WWF and WCW were at war for ratings. Trust meant more and less all at once as top talent took meetings with Bischoff for a taste of more money and energized writing. By that spring, the tides were turning.
At March’s Wrestlemania, Shawn Michaels took the WWF heavyweight title from Bret Hart as a means for the elder Canadian to take a much-needed break. As Sex, Lies, and Headlocks recounts, Hart wanted to pivot into acting but struggled to get parts.
By October 1996, Hart returned to the ring rather than the movies. The catalyst? A massive 20-year deal with WWF.
McMahon and Hart had agreed on a new contract that would pay him $10.5 million over the course of two decades. Already in his 30s, the partnership promised to transition Hart into a scriptwriting role as he aged out of the action. He was set for life, and McMahon had kept another top talent from jumping ship.
Months in, however, McMahon was having second thoughts.
Hoping Hart’s return would put an end to the WCW rise, fans were no longer flocking to TV just to watch the “Hitman” in action. At the same time, a Manhattan-based investment house was courting McMahon, advising him to take WWF public. To do so, he’d have to rid his business of any long-term burdens, the biggest being Hart’s contract.
Less than a year into the life-changing contract, McMahon told Hart he couldn’t afford to keep him. He advised Hart to take the money at WCW. To no surprise, he did.
Backed by Turner, WCW and Bischoff were able to offer Hart a reported $2.5 million a year. Though the money wouldn’t be as long as the two-decade deal McMahon muffed, it was still much more annually for a short stint and better than nothing.
Heading into Survivor Series, Hart had an easy exit set up, starring in the biggest match of the night for his last day on the job for McMahon.
Or so he thought.
Every so often in culture, generational talents make movements that absolutely wash away a former guard.
In music, Nirvana’s grunge rock sound nullified the massively popular hair metal movement, rendering arena acts as corny and commercialized almost overnight. In basketball, both the scoring point guard and the stretch big made conventional 1s and 5s suddenly extinct.
Entering the fall of 1997, wrestling was about to see the same shift.
Since the beginning of time, pro wrestling stars were built off stereotypes seen in culture as a means to ignite fans. From tropes of race to workplace dynamics, all walks of life were characterized in cartoonish fashion with superhero pageantry. Funny enough, it all proved profitable and family-friendly until it suddenly wasn’t.
At WCW, Bischoff built a brand of brash defiance embodied by the New World Order — a legion of ex-pats plucked from WWF made to appear and act like a motorcycle gang. This edgy appearance proliferated around the company, turning up the dial on attitude in a manner that felt less like a fairytale and more like an action movie.
It was a smart weapon of choice for Bischoff, but ultimately a weapon formed against him.
While Wall Street aimed at taking WWF public, McMahon publicly made his family-friendly brand more and more like its competitor, pushing the limits so far that WCW started to look like PBS. Atop the early transition was going all in on Shawn Michaels, the baby-face favorite who was now the leader of McMahon’s answer to nWo: D-Generation X.
Rebranding Hunter Hearst Helmsley — a smug equestrian strongman — as Triple H, the buff blondes formed forces with an amazon named Chyna. Representing rebellious youth, the defiant trio took sticking it to opponents of all walks to new heights. Wearing black leather jackets and telling authority to “suck it,” fans of all ages publicly chopped their hands towards their private parts as a pledge of allegiance toward the Michaels mantra.
Suddenly, Shawn had the whole world wrapped around his waistline.
Prior to Hart’s botched WWF deal, Michaels was said to be the highest-paid pro at his company. After Hart’s sabbatical and a new contract, his money more than doubled that of the “Sexy Boy” breadwinner. At Survivor Series, all wrongs were set to be righted with Hart having a 13-year run come to an end at home in Canada, offering a kosher curtain call as he left for WCW to pursue money McMahon had gone back on.
However, Hart didn’t want to lose to Michaels in front of his home country.
The plan was for Hart to walk out a winner and then relinquish the title belt. The problem was that tension between Hart and Michaels had been mounting for months behind the scenes and in the press. If Hart walked away a winner and made his WCW debut the following week with the WWF title in tow, it would be humiliating for McMahon.
So, the boss called in a fix.
In what was later described as “high-level espionage” by Triple H in an hour-long A&E documentary spotlighting the infamous event, the plan was made by McMahon to have referee Earl Hebner call the match as a tap-out with no knowledge passed on to The Hitman.
For Hart, it was assumed that his own crew, The Hart Foundation, would run in mid-match to cause a ruckus as would D-Generation X. The result would be a forfeit with no true loser and the belt changing hands after Hart left the WWF.
Obviously, that’s not what happened.
In a mid-match sequence where Michaels put Hart in his own Sharpshooter leg lock as a way to rise the tension, McMahon screamed from the sideline for Ebner to ring the bell. He did, to the shock of a speculative Hart and chagrin of WWF forces in fear of a WCW embarrassment.
Hart was stunned and disgusted in the moment, with McMahon making out like the biggest bad guy in sports entertainment. Michaels had his title and a new era of Jerry Springer dialogue and parental advisory warnings at WWF was in full swing.
The Attitude Era had begun.
When the wrestlers returned to the locker room in Molson Centre and “Sexy Boy” had stopped playing in the speakers, anger spread amongst the WWF veterans.
Around the company, friends of Hart felt betrayed. How could a loyal company man and superstar be screwed by both his boss and a colleague in front of his own country? Even if all were about to get paid, was there any way to properly right this wrong? In the world of pro wrestling, such matters were not up for litigation by a lawyer or the court of public opinion.
To settle things for the moment, Hart had to punch his former boss in the face.
Accepting a fist to the jaw in private after giving a corporate kick in the pants in public, McMahon let Hart hit him square in the mouth as he fell to the ground. A longtime commentator turned head of the business, now Vince himself was in on the actual action even if the fans couldn’t see.
Quickly that would change.
As the Attitude Era unfolded, the biggest bad guy in WWF would not be mountainous men like Kane or The Undertaker. Rather it would be Vince McMahon: the animated boss set to screw his employees. Playing foil to “Stone Cold” Steve Austin, Dwayne “The Rock” Johnson, and even Shawn Michaels, the real-life narrative of McMahon’s shrewd business move would play out in animated scripted form night after night.
Fans loved to hate Vince, and Vince loved the drama it created. Whether you rode with D-Generation X or The Nation of Domination, everyone had a common enemy in the man that wrote the checks and screwed Bret Hart.
Funny enough, it was that man and all his existing employees that were getting richer off of it all.
By April 1998, WWF was back on top. Over at WCW, Hart had more money coming in annually, enjoying the perks of a raise and more creative control. Sadly, a string of injuries and what some considered lackluster storylines kept things from ever hitting the commercial heights hit in younger years.
On Oct. 19, 1999, the WWF launched an IPO on the heels of the Attitude Era. At the time of typing, the company trades for $75.77 a share though the entire enterprise was valued at $172.5 million when it first went public.
Heading into the 2000s, WWF continued to climb, rebranding to WWE and eventually returning to its original niche of family-friendly content. In that decade, both Bischoff and Hart would work with McMahon after years of bad blood. Both are members of the WWE Hall of Fame and are revered by fans in their own right.
On Dec. 28, 2009, Hart and Michaels made up in the ring on live television, calling for a truce and exchanging hugs. For months of programming, the Montreal Screwjob was used as a storyline to build drama on-screen between McMahon and Hart.
Though the two were never friends in the same fashion ever again, they are said to be on speaking terms.
In 2022, 25 years after the Montreal Screwjob, the biggest brand in pro wrestling is once again at a turning point. Vince McMahon has been removed from the company while new leadership looks to rekindle the magic it once had.
Perhaps it will come in the form of the recently relaunched XFL. Or maybe another Attitude Era is on the way.
Controversy has proved a powerful pivot for the company before but after all these years, even those inside wonder at what cost.
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