Webber's early career largely centered around the upper Midwest region of the United States where he managed and teamed with Lenny Lane. In 1996, Webber had his television debut appearing on American Wrestling Federation programming. His gimmick was that of a nephew of Lord Alfred Hayes called Aloysius Hayes.
In 1997, Webber tried out for WCW, but was ejected from the locker room by then-President Eric Bischoff after a misunderstanding. Webber nearly retired, but instead focused his energy as a manager in Steel Domain Wrestling. He managed was known as the "Chicago Group" (Ace Steele, Danny Dominion, and Brad Bradley).
Total Nonstop Action (2002)
Webber appeared on the first NWA-TNA Weekly PPV as Mortimer Plumtree, a weaselly nerd who managed the masked Johnson Brothers (Richard & Rod) who notoriously resembled a pair of penises. The Johnsons soon after broke with Plumtree and left TNA.
Webber appeared infrequently on-screen as Plumtree for a few months. Instead he concentrated on being a backstage staff member. In October, he started managing Ace Steele but that ended after only a few shows after Steele was released.
In January 2003, TNA booker Vince Russo allegedly wrote the Plumtree character out of all future TNA programming due to his feeling that Webber was aligned with Jerry Jarrett in office politics. He remained on staff full-time until June, when he moved back to Minnesota. He would appear only a handful of times after that, both for the failed Force 1 Wrestling promotion he assisted with booking and with another short-lived group, the American Wrestling League.
- Wrestlers Managed