10 Most Heartbreaking Major WWE Defeats
1. Ric Flair Vs. Shawn Michaels (WrestleMania XXIV)
Ric Flair may have been a millionaire playboy who was past his prime by 2008, but he had become one of those rare legends who defied typical heel/babyface characteristics. By '08, wrestling fans dearly loved seeing the 'Nature Boy', so imagine how emotional it was at WrestleMania XXIV when Shawn Michaels retired him.
Shawn's whisper of, "I'm sorry, I love you" shortly before delivering his match-winning Sweet Chin Music has become one of WWE's most-replayed highlights. There was magic in the air between both; carried by Michaels, who still had several more years ahead of him, Ric turned back the clock and entered a performance befitting of the occasion.
The tears shed by Ric, Shawn and the fans inside Orlando's Citrus Bowl were very much real. Whether he was ready to stop wrestling or not (he wasn't), Flair knew this was WWE's way of putting him out to pasture. He can't complain, because they let him live one of wrestling's most touching moments.
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Which WWE losses broke your heart? Let us know about your most tear-jerking WWE defeats down in the comments section below!