The winner of the 2005 Diva Search, Ashley Massaro had a modeling past before she joined the WWE roster. She had been a Hawaiian Tropic girl in the past and won Miss Hawaiian Tropic USA in 2002. Massaro took that modeling a step further when she posed for Playboy magazine in both 2003 and 2004. After she won the Diva Search, WWE naturally thought Ashley could increase their mainstream attention. Massaro posed for Playboy a third time, gracing the April 2007 cover and receiving numerous title matches as a result. Massaro's previous photo shoots actually look nothing like her since she was a typical, bleached blonde Playboy girl for her first two pictorials. When she won the Diva Search, Ashley had transformed herself into a punk character with piercings and tattoos. As a result, her third shoot for Playboy stood out as something new and different.
