Massaro made her debut in WWE after winning the WWE Diva Search in 2005. She was firstly incorporated into the Raw brand where she had her first wrestling feud against Vince's Devils (a villainous female stable) while she also aligned herself with Trish Stratus in the process to defeat the team. With Stratus, she was involved in another feud with the then debuting Mickie James who was obsessed with Stratus and was jealous of Ashley's friendship with her, attacking and causing her to lose matches. She was later drafted to SmackDown! and became the valet for the WWE Tag Team Champions Paul London and Brian Kendrick. Her most high-profile matches were a WWE Women's Championship match against Melina at WrestleMania 23 and a Playboy Bunnymania Lumberjill match at WrestleMania XXIV. She left WWE in mid-2008. During her tenure in the company, she had appeared on the covers of several magazines, including the April 2007 issue of Playboy. She also made guest appearances on several television shows and performed in music videos.
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