7 Saddest Moments in Pro-Wrestling History
For many, WWE is pure fantasy—heroes, villains, twists, and epic matches in front of roaring crowds. But not everything in this world is glitz and glory.
Behind the curtain, away from the cameras and the cheers, there are stories filled with pain, irreparable losses, and silences that scream louder than any grand entrance.
So if you think you’ve seen it all in wrestling… think again.
Ric Flair’s Last Match
WrestleMania 24 was the stage for Ric Flair’s farewell after more than four decades in the ring. He faced Shawn Michaels in an emotionally charged match.
And the peak of it all was when Michaels knelt down, looked at Flair, and said: “I’m sorry. I love you.” before delivering the final blow.
It was impossible to hold back the emotion. That moment wasn’t just acting — it was real. And that’s what made it hurt so much.
Eddie Guerrero Leaves Without Warning
It’s a fact: Eddie Guerrero’s sudden death in 2005 caught everyone by surprise.
And on the following night’s Raw, WWE held one of the most emotional tributes in its history. Friends and fellow wrestlers like John Cena, Rey Mysterio, Chris Benoit, and Chavo Guerrero paid tribute with tears in their eyes. The belt in the ring, the video packages, the memories… everything was filled with emotion.
Sadly, Eddie didn’t get a farewell in life, but he was remembered as the legend he truly was.
Connor “The Crusher”
Connor Michalek was just a little boy, but he became a giant in WWE history.
Battling brain cancer, he fulfilled his dream of meeting Daniel Bryan.
He got a special entrance, an honorary title, and the genuine affection of the entire WWE roster. When he passed away shortly after WrestleMania 30, the void was massive. His Hall of Fame tribute, with the Warrior Award, was a testament to his strength and the real connection he built with the wrestling world.
The Undertaker’s Final Farewell
Three damn decades. That’s how long The Undertaker walked among us — and beyond — in WWE rings.
In 2020, at Survivor Series, it was time to say goodbye. And even without a live audience, due to the pandemic, all eyes were on him, and the ceremony gave chills. The presence of legends, Vince McMahon’s speech, the hologram of Paul Bearer… Everything pointed to the end of an era. And it was impossible not to feel the weight of that.
Ultimate Warrior
In 2014, the Ultimate Warrior returned to WWE with a symbolic, intense speech, as if he was saying goodbye. The next day… he passed away.
It was a shock. But at the same time, it felt like he knew. His words, his gestures — everything hinted at a farewell. And that’s why the moment became even more powerful and painful.
The Night of Brodie Lee
AEW also showed how to deliver a true tribute with the special dedicated to Brodie Lee in December 2020.
Brodie’s son stepped into the ring, Amanda Huber, his wife, was there, his friends cried, fought for him, and with him in their hearts. Tony Khan made Brodie the “Forever TNT Champion.”
It was more than respect — it was love. In that moment, wrestling proved that, above all, they’re a family.
Bobby Heenan and the Absence That Hurt the Most
During his 2004 Hall of Fame speech, Bobby “The Brain” Heenan reflected on his brilliant career. But one phrase stuck with everyone:
“I wish Monsoon were here.”
Gorilla Monsoon, his inseparable commentary partner, had passed away, and the pain in Heenan’s voice said it all. Losing a friend like that goes beyond the job — it’s like losing part of yourself. And even though it was a simple moment, it was brutally human.
And you — which moment broke you? Drop a comment on the video and send it to that friend who never misses a Raw.