2005-2006


Ashley made her first WWE appearance as an official WWE Diva on the August 21, 2005 pre-SummerSlam edition of HEAT where she conducted interviews with the fans, The Fabulous Moolah, and Mae Young. Later that night, Massaro made her first appearance at a pay-per-view event when she joined the other bikini-clad divas in washing Mr. McMahon's presidential limo backstage. The following night on Raw, WWE Divas Candice Michelle and Torrie Wilson called out Massaro, claiming they wanted to welcome her to Raw. After Ashley came out, Candice and Wilson turned heel and started attacking Ashley. Ashley continued to feud with the two divas who were soon joined by Victoria. Victoria later defeated Ashley in her in-ring debut match. Ashley was later joined by the returning Trish Stratus, who helped Ashley fend off attacks from the three divas. The pair defeated the trio, who became known as the Ladies in Pink (and later Vince's Devils) on several occasions including at Unforgiven and at WWE Homecoming in a 3-on-2 Bra and Panties match. Ashley continued to wrestle matches through the rest of 2005 and was involved in the annual Fulfill Your Fantasy Diva Battle Royal at Taboo Tuesday for her first shot at the WWE Women's Championship. Ashley eliminated Candice Michelle before being eliminated by Victoria. One of her biggest wins was at New Year's Revolution when Ashley won the first ever Bra and Panties Gauntlet match by being the final Diva left still wearing her clothes.[9] Following WWE tradition, to please the fans, she removed them herself before making her exit. Through the early part of 2006, Ashley became the victim of a series of attacks from a jealous Mickie James. At the Royal Rumble, Mickie defeated Ashley with then Women's Champion, Trish Stratus, as the special guest referee. Ashley got her revenge one week later by pinning James in the rematch on Raw. During the February 20, 2006 edition of Raw, however, Ashley suffered a fractured left fibula while being eliminated from the Women's Battle Royal, and her feud with James was cut short. She underwent the procedure to have a plate positioned in her leg in March 2006. During her recovery, Ashley still occasionally appeared on Raw as part of the Stratus/James feud, albeit in a non-active role. She returned to television on June 2, now on SmackDown!, as a special guest commentator during the Kristal Marshall vs. Jillian Hall match. Ashley immediately aligned herself with Hall as they feuded with Michelle McCool and Kristal Marshall. She won her debut match on the July 21 edition of SmackDown!, where she teamed up with Hall and defeated McCool and Marshall. At The Great American Bash, Massaro won the Fatal Four-Way Bra and Panties match. On the August 4 edition of SmackDown!, Ashley broke her knuckle in a match against Kristal Marshall. Ashley returned to the ring on the September 8, 2006 edition of SmackDown! where she, Paul London, and Brian Kendrick defeated Idol Stevens, K.C. James and Michelle McCool in a Six-Person Mixed Tag Team match. Following the victory, Ashley became the valet for London and Kendrick, accompanying them to the ring for their matches on SmackDown! and pay-per-views.