Early feuds (1996–1999)

By 1996, Flynn had worked as a jobber for the WWF, performing in a few house shows before making his way into WCW with help from Brian Blair, a friend of road agent Paul Orndorff, and Mark Starr, who helped gain Flynn a tryout at Universal Studios Florida for a WCW WorldWide taping. He began performing regularly on WCW's secondary TV program, WCW Saturday Night, in 1997 and by the following year was gaining numerous wins over low-card performers.^[5]

In 1998, Flynn began to elevate his status, wrestling on Monday Nitro, the company's flagship program. He had a series of matches with Bill Goldberg, which saw Flynn come close to beating Goldberg, but ended up losing, adding several notches in Goldberg's streak, until his defeat by Kevin Nash at Starrcade. In 1999, he had a short-lived feud with Ernest "The Cat" Miller and his manager Sonny Onoo after Miller and Onoo attacked Flynn backstage during an interview with Gene Okerlund and cut off his hair.^[5] The feud ended when Flynn gained revenge by defeating Miller and Onoo in a handicap match at the Uncensored pay-per-view.^[5] Later that year, he unsuccessfully participated in the Junkyard Invitational at Bash at the Beach.^[5]

First Family and departure (1999–2000)

He then became a member of The First Family, a heel stable managed by Jimmy Hart.^[5] However, an injury Flynn sustained led to the eventual disestablishment of the group.^[2] In November 1999, Flynn and Juventud Guerrera were arrested for DUI. He then began a feud with mixed martial arts fighter Tank Abbott which Flynn later expressed enthusiasm for.^[5] During this time, Flynn's persona emphasized his shootfighting skills including a "shootfight rules" match against The Wall on Thunder.^[6] His feud with Abbott culminated at the 2000 Souled Out where Abbott defeated him via knock-out in a mere 1:39.^[5] He was released in April of that year.