As many other promising-yet-underexposed AWA stars had before him (including Hulk Hogan, Rick Martel, and Bobby Heenan), Hennig left the AWA for the World Wrestling Federation in the fall of 1988, weeks after his AWA Title reign ended. Badd Company and Madusa faced the team of the Top Guns (Ricky Rice and Derrick Dukes) and Wendi Richter at the only AWA pay-per-viewSuperClash III on December 13, 1988.[8] Both Badd Company's Tag-Team Title and Wendi Richter's AWA World Women's Championship were on the line, but since Richter pinned Miceli, Badd Company remained the champions.[9] In 1988, Madusa was also the first woman to be awarded Pro Wrestling Illustrated's Rookie of the Year.[10]
Badd Company held the AWA Tag Team titles for a year before losing the titles on March 25, 1989, to “the Olympians" (Brad Rheingans and Ken Patera).[2] Shortly after their loss, they split from Page and had a short feud against each other before wrestling in singles competition until early 1990. At the time, DDP also worked as a color commentator in Florida Championship Wrestling (FCW) where he worked alongside Gordon Solie, before finally debuting as a professional wrestler. In 1990, Page received a tryout with the WWF as an announcer, but never got the job.[1] When FCW went down, Page was still involved in the club business until Dusty Rhodes returned to World Championship Wrestling. Dusty Rhodes started booking and brought Page in on a small contract in early 1991.[5]
With rumors that WCW wanted to take the Diamond Studd away from him,[1] DDP decided to take the advice of Magnum T. A. and begin to wrestle himself. He headed to the WCW Power Plant where Buddy Lee Parker, The Assassin, and Dusty Rhodes trained the 35-year-old rookie. He debuted as a wrestler in a tag team match later that year. With the Diamond Studd, he faced Kevin Sullivan and his partner. He was relegated to the "jobber" list. He made his wrestling pay-per-view debut at Starrcade in 1991, teaming with Mike Graham in a losing effort to Jushin Thunder Liger and Bill Kazmaier.[5] Page continued wrestling and brought other wrestlers into his stable, such as Scotty Flamingo (who later became better known as Raven) and Vinnie Vegas (Kevin Nash) in 1992.[20][21] The relationships between DDP, Flamingo, and Vegas were used in many angles over the following months. Page went in the corner of Scotty Flamingo, at Clash of the Champions XXI on November 18, 1992, when Flamingo fought Johnny B. Badd in a workedboxing match. Flamingo won this bout with a little help from Page and Vinnie Vegas who filled Flamingo's glove with water. Studd formed short-lived tag teams with Vinnie Vegas and Scotty Flamingo, while also teaming with members of Paul E. Dangerously's Dangerous Alliance,[14] a stable that also included Madusa. The idea of adding him to the Dangerous Alliance fell through, however, and he left WCW shortly after.[14]
The following year, after Scotty Flamingo also left the stable, Page teamed with Vinnie Vegas as the Vegas Connection.[20] The Vegas Connection never returned to WCW until 2001 under the name "The Insiders", because Page was fired from WCW shortly after the team's debut due to his torn rotator cuff.[1] The injury occurred in late 1992 in a tag match with Tex Slazenger and Shanghai Pierce (later known as The Godwinns).[6]
The Diamond Dolls were the professional wrestlingvalets that accompanied Diamond Dallas Page to the ring in the American Wrestling Association and World Championship Wrestling. When DDP was signed to appear as a manager in the AWA in 1987, he wanted to be over the top. So Page decided to bring along some "Diamond Dolls", pretty women who accompanied him to the ring. They would clean his rings and brush dirt off his coat and strut around the ring to distract his wrestlers' opponents. They were basically there to look good and give his wrestlers an edge.
Page's Diamond Dolls in the AWA were waitresses from Norma Jean's, his bar in Ft. Myers, Florida. They were Tonya G. (real name Tanya), Lee Ann and Wendy. Page claimed to have dated all of them and he says he did date Lee Ann in his biography, Positively Page. Tonya G. was the one that was always there. Page rarely had them all there at one time.
When Page arrived in WCW as the manager of The Diamond Studd and The Fabulous Freebirds, he brought a different Diamond Doll each week. Page's wife, Kimberly Page, made her debut on April 6, 1991, on TBS as one of his Diamond Dolls. When Page started wrestling, he did away with the Diamond Dolls. He brought them back in 1994, when Kimberly became his regular Diamond Doll. She first played a ditzy bimbo, but quickly changed character to innocent and disapproving of his cheating ways. In 1995, she left Page (kayfabe) when Johnny B. Badd freed her from Page in a match. The Diamond Doll name was not used after that as Kimberly went by her first name until leaving the sport in 2000.