Massaro made her debut in WWE after winning the WWE Diva Search in 2005. Following an initial rivalry with Vince's Devils – an alliance of female villains – she became the valet for the WWE Tag Team Champions Paul London and Brian Kendrick. Her most high profile matches were a WWE Womens Championship match against Melina at WWE WrestleMania 23 and a Playboy Bunnymania Lumberjill match at WWE WrestleMania 24. She left WWE in mid-2008. During her tenure in the company, she appeared on the covers of several magazines, including the April 2007 issue of Playboy. She has also made guest appearances on several television shows and performed in music videos.