Wacholz debut in the American Wrestling Association (AWA) as Kevin Kelly in 1984, as a babyface midcarder.

This led to a feud with Tommy Rich, who answered one of his challenges on an edition of AWA Championship Wrestling on ESPN.

Wacholz, still performing under the name Kevin Kelly, received a tryout match on June 6, 1989, at a WWF Superstars taping in Madison, WI, defeating Tim Horner.

After the AWA folded, Wacholz received another tryout match, this time at a WWF Superstars taping on May 6, 1991, defeating Brian Costello.

[5] In early 1992, Wacholz returned to the WWF as Nailz, an ex-convict who, in a series of promos, alleged he was abused by former prison guard Big Boss Man during his incarceration.

Following Big Boss Man's squash of Dave Roulette on the May 30 episode of WWF Superstars of Wrestling, Nailz (dressed in an orange prison jumpsuit) attacked Boss Man, handcuffing him to the top rope before repeatedly hitting and choking him with his own nightstick.

The feud came to its climax when Big Boss Man defeated Nailz in a nightstick match at Survivor Series.

The two had a stare down on the October 24 episode of Superstars, a photo of which was used as the cover of the January 1993 issue of WWF Magazine.

Wacholz was released from his WWF contract in December 1992, after he attacked Vince McMahon in his office over a financial dispute,[6][10] while John Nord watched the door.

Bret Hart recalled in his autobiography that Wacholz "cornered Vince in his office and screamed at him for fifteen minutes".

Hart claims he was just down the hall from the office when he heard a loud crash, which was Wacholz "knocking Vince over in his chair, choking him violently".

[13] However, his testimony was later ruled to be inadmissible after Wacholz openly stated that he had a personal hatred for McMahon while on the stand.

After getting fired from the WWF, Wacholz appeared at World Championship Wrestling's (WCW) Slamboree event in 1993 as "The Prisoner" (looking identical to his Nailz persona), losing to Sting.