Growing up in Long Island, New York, with a father, brother and uncle who competed in amateur wresting, Ashley Massaro was well-prepared to make it in the World Wresting Entertainment. A former gymnast, she competed in Miss Hawaiian Tropic pageants and was crowned Miss Hawaiian Tropic USA in 2002 and Miss Hawaiian Tropic Canada in 2005. She currently works as a model and a professional wrestler with the WWE. She came to the WWE as a contestant in the 2005 RAW Diva Search. After beating out seven other finalists, she received a one-year contract with the World Wrestling Entertainment.
Massaro tours around the world and appears in front of thousands of people at arena shows approximately four times a week. She appears on "WWE Raw," "Smackdown" and Pay-Per-View Weekly. She has done a tour of Iraq, Afghanistan and Kuwait, where she visited the troops with the WWE for the United Service Organizations (USO). She was on the cover of the April 2007, issue of Playboy. She has also appeared in FHM, Stuff, Maxim and the covers of Femme Fatale and FLEX magazines. She hosted several E! "Wild On" episodes and appeared on "Breaking Bonaduce" as his personal trainer. She has also guest-starred on CW's "Smallville" and "Extreme Makeover: Home Edition," and she brought her love of music to Fuse TV when she took part in a special edition of "The Sauce." MTV's "Celebrity Death Match" has also featured her in the claymation series. In her spare time, she visits numerous hospitals to boost morale, including the Bethesda War Veteran Hospital in Washington, DC.
Massaro received her Bachelor of Science degree in Communication with a minor in Business from State University of New York. She describes herself as spunky, quirky, optimistic, happy, resourceful, creative, adaptable and relentless. She is obsessed with all things music.
Massaro currently resides in East Northport, New York. Her birth date is May 26, 1979.
Ashley was placed on the Zhan Hu tribe. At camp, Ashley quickly became sick and couldn't help much in constructing the shelter. Despite her illness, Ashley was determined to stay in the game. Zhan Hu lost the inaugural Immunity Challenge and Ashley was targeted by Dave Cruser and Chicken Morris for her health that wasn't improving. At Tribal Council, when Jeff Probst asked who wanted to be the leader of the tribe, both Dave and Peih-Gee Law raised their hands. This caused Ashley to vote against Peih-Gee because she viewed Dave as the leader. Chicken and Dave voted against Ashley, but the rest of the tribe voted out Chicken due to his hesitance to take up leadership.
After returning to camp, Ashley still felt lethargic. Like several others, Ashley lost faith in Dave as a leader when he built a fire pit as opposed to an actual fire. This led to the first of many arguments between the two. Ashley participated in the second round of the Reward Challenge. Despite her best efforts, she was unable to help the Zhan Hu tribe win the fishing gear. After the challenge, Ashley and Dave continued bickering. Zhan Hu lost the next Immunity Challenge, largely due to Dave constantly tiring out. Ashley knew that Dave was voting against her. In an attempt to swerve the vote to Dave, Ashley tried to convince the tribe that he was crazy. Despite her efforts, Ashley was unanimously voted off.
Ashley originally returned to WWE in January 2008. But in July that year, she requested her release two months after an article from Rolling Stone magazine published a story about a high paid escort service that mentioned Ashley as a former client prior to competing in the Raw Diva Search. She later denied the story on her former MySpace.
On January 9, 2010, Ashley attended Survivor's 10-year anniversary party.
Ashley died of suicide by hanging at the age of 39 on May 16, 2019.
Ashley is the second castaway to receive votes from all of their original tribemates but not be voted out at their first Tribal Council, following Shii Ann Huang.