She was first corporated into the Raw brand, where she had her first wrestling feud against Vince's Devils (a villainous female stable) while aligning herself with Trish Stratus to defeat the team.

[1] Massaro evened the score on the September 12 episode of Raw when she brought out the returning Trish Stratus (who then turned face), and the duo proceeded to attack them.

[1] The feud continued into WWE Homecoming, where Stratus and Massaro defeated Wilson, Candice, and Victoria in the first ever three on two Bra and Panties match by stripping all three of their opponents.

[16] Massaro 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.

[17] On January 8, 2006, at New Year's Revolution, Massaro won the first ever Bra and Panties Gauntlet match by being the final wrestler left still wearing her clothes.

[19] At Royal Rumble on January 29, James defeated Massaro with then Women's Champion, Trish Stratus, as the special guest referee.

[21] On the February 20 episode of Raw, however, Massaro suffered a fractured left fibula while being eliminated from the Women's Battle Royal,[22] and her feud with James was cut short.

[1] Three months later after being once again absent, she returned to television on June 2, this time on SmackDown!, as a special guest commentator during a match between Kristal Marshall and Jillian Hall.

[25] Two days later at The Great American Bash event, Massaro won a fatal four-way bra and panties match in which she defeated Hall, McCool and Marshall.

[30] On the December 22 episode of SmackDown!, Massaro teamed up with Layla in a winning effort defeating Jillian Hall and Kristal in a tag-team match.

[1] On the January 26 episode of SmackDown!, Massaro teamed up with London and Kendrick in a losing effort to the MNM (Mercury & Nitro & Melina) in a six-person mixed-tag-team match.

[9][33] At No Way Out, Massaro won the first ever Diva Invitational by removing her top to reveal her breasts which were covered with Playboy bunny pasties.

[35] On the March 16 episode of SmackDown!, Ashley teamed up with London and Kendrick in a losing effort to MNM in a six-person mixed-tag-team match.

[1] On the March 23 episode of SmackDown!, Massaro would get a catfight after Melina attempted to make an interference during Kendrick and Paul's match with MNM.

[1] On the March 26 episode of Raw, Massaro teamed up with Torrie Wilson and Candice Michelle in a winning effort defeating Melina, Hall and Victoria.

[1] At WrestleMania 23, Massaro unsuccessfully challenged Melina for the WWE Women's Championship in a LumberJill match to retain her title.

[19][36] After WrestleMania, Massaro continued as a valet for WWE Tag Team Champions Paul London and Brian Kendrick.

[37] In reality, Massaro had loosened a screw in her ankle, which had been inserted the previous year after she legitimately fractured her tibia and fibula while in a battle royal.

[1] This return was short-lived when on the edition of June 8 of SmackDown!, Massaro was suspended indefinitely after accidentally spilling Vince McMahon's coffee on him.

[19] Massaro returned on January 7, 2008 to the Raw brand, winning a Lingerie Pillow Fight against Maria, Jillian Hall, Melina, and Mickie James.

[1] On March 30, 2008, Massaro replaced Candice Michelle, who was out with an injury, in the Playboy Bunnymania Lumberjack match at WrestleMania XXIV teaming up with Maria, losing to Beth Phoenix and Melina after the interference from Marella.

[47] She was assigned to the Zhan Hu tribe in the first episode and quickly began quarreling with fellow contestant Dave Cruser.

[7][19] Massaro guest starred on an episode of Extreme Makeover: Home Edition alongside WWE wrestlers John Cena and Batista.

[67] An affidavit by Massaro describing the sexual abuse allegations in detail was subsequently released by the law firm that represented her after her death.

[72] On May 15, 2019, Massaro finished replying to fan mail,[73] but did not show up for work at WWSK-FM later that night, prompting another DJ to fill in for her.

[74] On May 19 at the Money in the Bank pay-per-view event, WWE acknowledged Massaro's death by projecting a graphic of her at the start of the show.

[82] Massaro had taken part in a suicide prevention music video by her WWSK co-worker Brian Orlando, who had recorded a song with Brandon B.