2005 Winner: Ashley Massaro
Ashley Massaro won the 2005 Diva Search and was given quite a major push shortly thereafter. She was thrust into prominent feuds with several top women on the roster at the time, including Torrie Wilson, Trish Stratus, Victoria and Candice Michelle.
Once that feud ended, she began feuding with Mickie James but ended up on the losing end due to James’ superior wrestling skills. After this, she spent most of her time as a valet and as ‘eye candy’, as WWE tried to sell her based on her punk looks. This included some notable segments in which she took her clothes off, much to the delight of the audience at the time.
However, due to a lack of a creative direction by 2008, she wasn’t showcased as much and was released in July of that year. She hasn’t done anything related to pro wrestling since then but has been in wrestling-related news nevertheless.
Not only is she one of many people named in the class-action lawsuit against WWE over their policies towards concussions and other bodily damage, but she has also made headlines for alleging that WWE asked her not to go public over an alleged sexual assault in 2006.
