#5 Bearer does the unthinkable
For fans of WWE in the 1990s, The Undertaker and Paul Bearer were so closely aligned, it is almost difficult to remember that they actually split in 1996 after Bearer turned heel on the Deadman at that year's SummerSlam.
Undertaker had first been introduced to WWE by Ted DiBiase, who quickly moved him to the tutelage and guidance of Brother Love. Love then in turn decided he was just a little too busy to steer the career of the Undertaker, who'd go on to become arguably WWE's greatest ever character. Instead, he introduced us to Paul Bearer, the pale faced, high-pitched mortician as the man who'd lead 'Taker going forward. And lead he did. He oversaw The Undertaker's WWE Championship victory in 1991 over Hulk Hogan, as well as memorable feuds against Jake Roberts and Yokozuna and others. Bearer was by his side as he went from a feared and despised character in the eyes of the WWE Universe, to a beloved fan favouritie.
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Imagine the shock, then, when the above pictured scene played out at SummerSlam. Undertaker was against Mankind in the infamous Boiler Room Brawl. Mankind had become a real thorn in the side of the man from the darkside, so Undertaker undoubtedly needed to keep his closest ally, Bearer, close. It was a real shock when, at the climax of the bout, Bearer stunningly turned on his charge and friend, aiding Mankind to victory before going on to manage him and Vader among others
Paul Bearer and The Undertaker would reunite years later, but this act from 1996 was probably the betrayal of the decade.