10 heartbreaking moments in WWE history

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Everyone knows that pro wrestling is staged. But there are some moments that really touch the audience and strike a chord with them. Be it an emotional onscreen portrayal of an underdog overcoming the odds or a real-life tragedy, WWE has always managed to keep its viewers emotionally invested This list looks at the 10 most heartbreaking moments in WWE history.


#10 Christian loses the World Title just five days after winning it

Christian would win and lose the World title in a space of five days in 2011
Christian would win and lose the World title in a space of five days in 2011

Ever since making his WWE debut in 1998, Christian consistently won championships. But as the year 2011 came about, Christian still hadn’t won the World Heavyweight title.

His real-life best friend Edge’s retirement as World Champion that year left the title vacated, and Christian would battle Alberto Del Rio to lay claim on the title at Extreme Rules in a ladder match. Captain Charisma would capture the title after some help from Edge, and the WWE fans blew the roof off the arena, delighted that Christian had finally got his chance to reach the top of the mountain.

Christian came into SmackDown that week and thanked the fans for sticking with him, and proceeded to describe how incredible he felt to finally win the big one in the WWE. However, he was booked to defend his title that very night – against Randy Orton. Despite Christian’s best efforts, Orton beat Christian to become the new champion.

The crestfallen look on Christian’s face as he came to terms with losing the title in his first title defence was legendary, and the fans (despite Orton being a fan favourite) felt his pain as well.

Christian would go on to beat Orton at Money in the Bank to reclaim the title, only to lose it back to Orton at the next PPV.

#9 Jeff Hardy almost beats the Undertaker in 2002

The Undertaker and Jeff Hardy had an amazing ladder match on Raw in 2002
The Undertaker and Jeff Hardy had an amazing ladder match on Raw in 2002

2002 was a unique year in WWE.

With the return of major WCW stars like Hogan, Nash and Hall to WWE TV, the roster was the most star-studded in the history of the company. The WWE Champion at that time was the American Badass, The Undertaker.

Meanwhile, Jeff Hardy was searching for an identity following the split of Hardy Boyz. The charismatic high-risk taker found himself without an angle in the WWE, and was floundering. But all that changed when he was put into a feud with the Deadman.

The Undertaker destroyed Hardy in his initial encounters, but Hardy refused to give up – intent on breaking out as a singles superstar. The WWE fans were definitely in the corner of the underdog when Hardy challenged the Undertaker once again for the WWE title, this time in a ladder match.

The match turned out to be a classic that is still talked about. Hardy matched Taker move for move, and a chair shot to the champion’s head gave the young pretender a great chance to climb the ladder and take the championship.

However, despite the WWE fans chanting for Hardy, Taker would recover and deliver a devastating chokeslam from the top of the ladder to end the match.

Taker beat up Hardy after the match got over, but Hardy grabbed the microphone and challenged a leaving Deadman to finish the job. A surprised Taker stormed the ring once again, but raised the hand of Hardy instead – signalling his respect for the young gun.

The WWE fans went home with a lump in their throats, after seeing how close their beloved Jeff had come to winning the title.

#8 The Montreal Screwjob

Bret Hart found himself on the wrong end of the Montreal Screwjob
Bret Hart found himself on the wrong end of the Montreal Screwjob

Bret Hart was the face of the WWE for much of the mid-1990s. However, he was getting increasingly frustrated with WWE’s attempt to introduce ‘attitude’ into their storylines and project Shawn Michaels as the brash new face of the company.

Hart decided to jump ship to WCW while he was still the WWE Champion, but he did not want to drop the title to real-life nemesis Michaels at the 1997 Survivor Series in Montreal. His understanding with Vince McMahon was that he would hold on to his title at Survivor Series and then vacate the title before moving to WCW.

However, McMahon broke his word and signalled the bell to be rung while Michaels had Hart trapped in Bret’s signature Sharpshooter. A visibly upset Hart spat in the face of McMahon after the match and air-wrote the words WCW to end the show, before proceeding to strike McMahon in the back, according to Mick Foley’s autobiography.

WWE fans were devastated at the treatment handed out to their beloved ‘Hitman’, who had given his heart and soul to the company.

#7 Shawn Michaels ends Ric Flair's career

Shawn Michaels would end Ric Flair’s career at Wrestlemania 24
Shawn Michaels would end Ric Flair’s career at Wrestlemania 24

Ric Flair might have been wrestling up to the age of 60, but nobody wanted to see the old dog hang up his boots.

In the months leading up to WrestleMania, Flair was placed in an angle where he would be forced to retire if he lost another singles match. The WWE fans were firmly behind the Nature Boy as they willed him on in his ensuing matches against various WWE superstars.

But when WrestleMania 24 came about, and Flair was booked in a match with Shawn Michaels, everyone knew what the outcome was going to be. The fact that Flair was added to the Hall of Fame the night before the match was a dead giveaway that his career was going to end the next night.

As expected, Michaels and Flair put out a classic match and told a fascinating tale inside the ring. And when Michaels mouthed ‘I’m sorry...I love you’ before delivering the decisive Sweet Chin Music to a hardly standing Flair to end the match and the veteran’s career, the fans in the arena and the thousands watching on TV found it hard not to shed a tear.

#6 Shawn Michaels loses his smile

The day the fans lost their smile for a moment
The day the fans lost their smile for a moment

Very few wrestlers have connected with the audience as well as Shawn Michaels has over his career.

Never was this more evident than on the February 13th, 1997 episode of Raw where Michaels gave his famous ‘I have lost my smile’ speech. The then WWE Champion informed the fans that he was seriously injured and that he might never wrestle again.

“Over the last few months, I’ve lost a lot of things and one of the things I’ve lost is my smile, and I know it doesn’t mean a lot to everyone else, but it means a lot to me and I have to go and fix myself and take care of myself and find my smile because somewhere along the line I lost it and I don't care if its unpopular and people want to make fun of me because I’m an emotional guy.”

Michaels would go on to vacate his WWE Championship and leave the ring in a segment that left many young fans openly crying.

In reality, Michaels did not want to drop the belt to real life rival Bret Hart at WrestleMania and had (allegedly) cooked up the entire angle. He would return a few months later and regain the WWE title.

Michaels would eventually retire after a defeat to the Undertaker in 2010, and he delivered another heartwarming speech before exiting the ring with the words ‘Shawn Michaels has left the building’.

#5 Edge announces his retirement

Edge announces his retirement on Raw
Edge announces his retirement on Raw

This was an announcement that caught most wrestling fans unawares.

On the April 11th, 2011 episode of Raw, the reigning World Champion Edge addressed the fans and revealed that he was going to retire from wrestling, effective immediately, due to cervical spinal stenosis.

The move came as a surprise as Edge had just retained his World title against Alberto Del Rio the previous night at WrestleMania 27.

Edge talked about the various injuries that he had encountered in the ring and confided to the fans that if he were to continue wrestling, there was a strong chance that he could end up paralysed.

He also reflected on his decades in the business – how he had started out as a wide-eyed Canadian teenager in awe of pro wrestling, and how he used to go on various North American indie tours with little or no money just to gain experience so as to one day make a mark in the WWE.

Later that week, Edge would relinquish his World title on SmackDown, and the entire arena stood up in respect of the Rated R Superstar.

#4 Droz's injury

Droz would become a quadriplegic after an in-ring accident
Droz would become a quadriplegic after an in-ring accident

Darren Drozdov may have had an in-ring career in the WWE for less than two years, but his name will forever be remembered by WWE fans as well as any wrestler entering the squared circle.

In 1999, Droz was in a match with D-Lo Brown on a SmackDown taping. D-Lo was trying to set up Droz for his trademark running powerbomb, but he could not get a proper grip on Droz and the latter could not jump properly in order to cushion the impact. This resulted in Droz hitting the mat squarely on his head.

Droz fractured two discs in his neck and underwent emergency surgery to save his life. Unfortunately, he ended up a quadriplegic. WWE, to their credit, continued to employ Droz in various capacities like a writer and a guest on WWE Byte This!.

Droz would regain most of the use of his upper body and arms in his later years.

#3 Eddie Guerrero's tribute shows

WWE roster giving a tribute to Eddie Guerrero
WWE roster giving a tribute to Eddie Guerrero

Eddie Guerrero was probably the most popular WWE superstar in 2004 and 2005. His ‘Lie, cheat and steal’ lifestyle had struck a chord with the fans and they used to cheer him at the top of their lungs irrespective of whether Guerrero was performing as a heel or a face.

But on November 13, 2005, the 38-year-old El Paso native died of heart failure in his Minneapolis hotel room.

Fans were shocked at the development, as were his WWE colleagues. That week’s Raw as well as SmackDown shows were aired as tribute shows to Guerrero, and all the wrestlers broke kayfabe to pay their respects to Eddie.

Various other wrestling organizations like ROH, TNA and OVW also paid tribute to Guerrero following his death.

#2 The Chris Benoit tragedy

Chris Benoit committed suicide in 2007
Chris Benoit committed suicide in 2007

Chris Benoit was one of those wrestlers who were loved by the fans and respected by their peers. His emotional journey to winning the World Heavyweight title at WrestleMania 20 had been the perfect way for WWE to market the Show of shows in 2004.

On June 25, 2007, the bodies of Benoit, his wife Nancy and 7-year-old son Daniel were found in his home. It emerged that Benoit had strangled his wife and son and had committed suicide.

The news came as a shock to WWE and despite having aired a tribute package to Benoit instead of that Monday's Raw, the company began to distance itself from Benoit once the nature of his family’s death came around.

Fans and fellow wrestlers were stupefied that a man as gentle as Benoit could resort to such actions. It was later brought to light that the multiple concussions Benoit had suffered during his wrestling career had made his brain resemble that of ‘an 85-year-old Alzheimer’s patient’, according to the doctor who examined his body.

He might have had an advanced form of dementia, leading to depression and tendency to cause bodily harm to himself and people around him. The incident also revealed that Benoit and several other wrestlers had been given steroids by the WWE.

#1 Owen Hart's death

The signature mentioning Owen Hart at the 1999 Over the Edge
The signature mentioning Owen Hart at
the 1999
Over the Edge

There is no other contender for the most heartbreaking moment in WWE history – nothing compares to what happened on 23 May 1999 at Over the Edge PPV, when Owen Hart fell to his death after an equipment malfunction during his entrance from the rafters.

Owen, who was wrestling as the Blue Blazer at that time, had a cartoonish Superhero gimmick. He was supposed to descend from the rafters and fall flat on his face from a safe distance for comedic relief. However, the harness gave way early and Owen fell chest first on to the top rope from a height of nearly 80 metres.

He succumbed to his injuries despite being rushed to the hospital.

WWE landed in a controversy after it allowed the event to go ahead despite Hart’s death, and was sued by his widow Martha, eventually settling for $18 million.

A special tribute show named ‘Raw is Owen’ was aired by the WWE where the entire roster broke kayfabe and praised the life and work of Owen.

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