Ashley is a former gymnast who has experience in front of the camera. She has hosted a number of “Wild On” shows on the E! Channel, and has also posed for Stuff, FHM and multiple swimsuit calendars. Ashley is a big fan of rock & roll, fishing, boating and motorcycles. She also grew up in a wrestling family as her brother, dad and uncle all competed in the sport.

Ashley Massaro came to the WWE in June 2005 as a contestant in the 2005 RAW Diva Search. After beating the seven other chosen finalists, Massaro was declared the winner on the August 15, 2005 edition of RAW which stood in Montreal, Quebec. She won $250,000 and a one year contract with World Wrestling Entertainment.

Massaro made her first WWE appearance as an official Diva on the August 21, 2005 pre-SummerSlam edition of HEAT. This featured Ashley conducting interviews with the fans, including WWE Legends The Fabulous Moolah and Mae Young. Later that night, Massaro made her first appearance at a pay-per-view event when she joined the other bikini-clad divas in washing Mr. McMahon's presidential limo backstage.

The following night on RAW, WWE Divas Candice Michelle and Torrie Wilson called out Massaro, claiming they wanted to welcome her to RAW. After Massaro came out, Michelle and Wilson turned heel and beat down Ashley. Massaro continued to feud with the two divas who were soon joined by Victoria, Victoria would defeat Massaro in Massaro's first match.

Massaro was later joined by the returning Trish Stratus who helped Massaro fend off attacks from the three divas. The pair would defeat the three divas who became known as the Ladies in Pink (and later Vince's Devils) on several occasions including WWE's 2005 Unforgiven pay-per-view, and at the WWE Homecoming in a 3-on-2 Bra and Panties match.

Massaro would continue to wrestle matches through the rest of 2005 and was involved in the annual Fulfill Your Fantasy Battle Royal at Taboo Tuesday for her first shot at the WWE Women's Championship. Ashley was able to eliminate Candice Michelle before being eliminated by Victoria.

One of Ashley Massaro's biggest wins to date came at New Year's Revolution when Massaro was able to win the first ever Bra and Panties Gauntlet match by being the final Diva left still wearing her clothes. Following WWE tradition, to please the fans, she removed them herself before making her exit.

Through the early part of 2006 Massaro would get in the midst of an ongoing feud between Trish Stratus and Mickie James. Siding with Stratus, Massaro became the victim of a series of vicious attacks from a jealous Mickie James. At the Royal Rumble, Mickie defeated Ashley with Stratus as the special guest referee. However, Massaro would get her revenge by pinning James in the rematch on RAW.

During the February 20, 2006 edition of RAW Ashley Massaro would suffer a fractured left fibula while being eliminated from the women's Battle Royal. Upon further medical consultation, it was announced on WWE.com that because of the spiral crack in her left fibula Massaro would need surgery. She underwent the procedure to have a plate positioned in her leg in March 2006.

During her recovery Massaro would still occasionally appear on RAW as part of the Stratus/James feud, albeit in a non-active role. On March 22, 2006, Ashley Massaro announced on her MySpace blog that she signed a three year contract extension with WWE.

WWE.com announced on June 1, 2006 that Ashley would be the newest SmackDown! diva, thus she made her debut on the June 2, 2006 edition of SmackDown! as Ashley Massaro during the Kristal Marshall vs Jillian Hall match as a special guest commentator. The next week on Smackdown, Ashley defeated Jillian Hall, Kristal Marshall, and Michelle McCool in a "Summer Kick-Off Bikini Contest".

On the February 16, 2007 edition of SmackDown!, Ashley unveiled her Playboy cover. Surrounding the release of the magazine, Ashley engaged in a feud with Jillian Hall over who was the most talented Diva on SmackDown! and Halls' jealousy over Ashley's Playboy cover. At No Way Out, Ashley won the first ever Diva Invitational by removing her top to reveal her breasts which were covered with Playboy bunny pasties. Ashley continued to feud with Jillian, but also began a feud with then WWE Women's Champion, Raw's Melina. Melina was angry over the publicity Ashley had been receiving because of the cover and believed that she deserved more publicity than Ashley for being the Women's Champion.

For much of 2007 Ashley was out of competition while she competed on CBS' "Survivor: China" television program.

In January 2008 Ashley returned to WWE broadcasts but on the Raw brand. She competed for the first few months in tag team matches, usually with Mickie James, against some combination of Beth Phoenix, Jillian Hall or Melina.

In May a story broke in Rolling Stone magazine, that Ashley had worked for a New York escort service that the FBI was investigating. Although she denied that the story was true there were some controversy over the matter and Rolling Stone's editor stated that he stood by his story.

On July 2nd Ashley announced on her MySpace page that her daughter was having medical problems and that she had decided to ask the WWE for her release.