Ivory started out in the World Wrestling Federation as a valet for D'Lo Brown and Mark Henry before becoming an in-ring competitor in early 1999. After defeating Debra to win her first Women's Championship, Ivory became a villainess and feuded with Tori for months, including defeating her in the first women's Hardcore Match in WWF/E history. Ivory lost the title to The Fabulous Moolah, who was 76 years of age at the time, but she would regain the title over a week later.
Ivory later joined the villainous Right To Censor faction, due to her more conservative views, and began dressing in more conservative gear. Ivory won her third Women's Championship as a member of RTC, but after losing the title, the faction disbanded. In 2001, the evil Ivory defected to the WCW/ECW Alliance during the Invasion angle, and her plan was to build a women's division to rival the WWF's; with Stacy Keibler and Torrie Wilson serving as Ivory's evil proteges. In her role, Ivory also served as the valet for Alliance star Lance Storm.
After the Alliance angle ended, Ivory appeared as a villainous trainer on Tough Enough in 2002. She would call out the show's co-winners, Linda Miles and Jackie Gayda, which led to a match between Ivory and Linda on Velocity. Ivory went on to defeat Linda after Jackie shockingly became a villainess and shoved Linda off the top rope. Ivory aligned with the evil Jackie a week later, but they were defeated by Linda and Trish Stratus. Ivory continued to feud with Trish sporadically for the rest of that year.