#4 Vince McMahon and Nailz
Kevin ‘Nailz’ Wacholz was another big man whom WWE gave a ridiculous gimmick during the early 1990s. In his case, Nailz was a former prison inmate, and his reason for entering the WWE was to get revenge on his former guard, The Big Boss Man. But it wasn’t Boss Man that became Nailz’s target; instead, it was Vince McMahon.
In December 1992, Nailz confronted McMahon in his office, upset over an alleged financial dispute. This dispute turned physical, as Nailz proceeded to turn over furniture and tried to ‘choke Vince out’. Nailz was released from WWE instantaneously, but the problems between these two men continued for over a year.
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Nailz and WWE filed lawsuits against one another, with Nailz going so far as to claim that Vince sexually assaulted him. In 1994, Nailz also testified against McMahon in the latter’s steroid trial, but his testimony was so contradictory and full of fallacies that it led to an acquittal against Vince.
In hindsight, perhaps Vince should be thankful to Nailz that his failure in court led to Vince no longer having to worry about the steroid scandal.