4: Undertaker destroys Vince’s teddy bear
Before you guys say that it was just a teddy bear, its what Vince’s teddy bear symbolized that got that incident on this list.
It was February 1999 and The Undertaker was just at the beginning of his Ministry of Darkness phase. Taker was in the midst of a feud with Vince McMahon, and he was trying to intimidate Vince by threatening his daughter’s safety.
This led Vince to put Undertaker in an inferno match with kayfabe brother Kane. Following the match, Taker took the teddy bear, which used to belong to Stephanie when she was young and set it on fire in front of a mentally broken down Vince McMahon. The bear represented Stephanie’s safety which Vince sadly, could no longer guarantee.
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