Massaro made her debut in WWE after winning the WWE Diva Search in 2005. She was first incorporated 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. With Stratus, she was involved in another feud with the then-debuting Mickie James, who was obsessed with Stratus and jealous of Massaro's friendship with her, attacking and causing her to lose matches. Massaro 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.