In 2005, Ashley Massaro beat the likes of Leyla Milani (better known as the woman who held case #13 on NBC's Deal or No Deal) and Kristal Marshall (the former flame of Bobby Lashley) to win the Raw Diva's Search competition. Massaro came from a family of wrestlers as both
her father and brother competed in amateur wrestling. As a result, you'd think Massaro would be hellbent on making her family proud in the wrestling business. Instead, her three year run with the company is rather unmemorable. Having been involved in lackluster feuds such as those with Vince's Devils and Michelle McCool, the WWE landscape at the time didn't do Massaro many favors. However, this isn't to say that she was polished in the ring or on the mic and her feud with Mickie James is a perfect example of this. Not to forget, she's likely remembered by most for her Playboy cover as opposed to anything wrestling related.