In May of 1992, Wacholz debuted in the WWF under the persona of Nailz, which would become his most remembered gimmick. As Nailz, he portrayed a former convict who claimed he was innocent of the crime for which he had been imprisoned. He alleged that while incarcerated, he suffered immense brutality and dehumanization at the hands of the penitentiary's guard, the Big Boss Man. Nailz's storyline revolved around his quest for revenge against the Big Boss Man.

Over the next six months, Nailz decimated a series of low-tier wrestlers while causing chaos in the WWF as he pursued a match with the Big Boss Man. At Survivor Series 1992, the two finally collided in a nightstick-on-a-pole match. Big Boss Man won the match, and Nailz departed the WWF shortly thereafter.

While the 1992 feud portrayed Nailz as the villain and Big Boss Man as the hero, later events led many to reevaluate the storyline. In 1998, after a brief hiatus, Big Boss Man returned to the WWF as an enforcer for the villainous Vince McMahon. As a rough and vicious thug, he brutally attacked McMahon's enemies with his nightstick, akin to what Nailz had claimed. Big Boss Man's actions during this period, including his heinous attacks on Shawn Michaels, his disturbing antics with Al Snow which involved kidnapping Snow's dog and then feeding it to him, and his relentless mockery of the Big Show's father's cancer diagnosis which culminated in the Boss Man crashing the father's funereal and stealing his coffin and corpse, suggested that Nailz's allegations of mistreatment might have had some truth to them. This reinterpretation of the feud cast Nailz in a more sympathetic light, as perhaps he was an innocent man who fell victim to the cruelty of the Boss Man behaving badly.

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