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Massaro had one daughter named Alexa. When her daughter became sick in mid-2008, Massaro asked for an early release from WWE to care for her. On May 22, 2019, after Massaro's death, several former WWE female wrestlers who were Massaro's coworkers, grouped as "The Squared Circle Sisters", opened a crowdfunding campaign on GoFundMe in order to create a college fund for Massaro's daughter, setting a goal of $100,000.

On May 15, 2019, Massaro, after finishing replying to fanmail, did not show up at 94.3 The Shark for work which caused one of the DJs who was working that night to fill in for her. Hours later, paramedics responded to a rescue call made at 5:23 am when authorities discovered Massaro unresponsive inside her Long Island home. By the time they arrived at the hospital, she was pronounced dead on May 16, 2019, ten days before her 40th birthday.

On May 21, she was buried at the Saint James Episcopal Church Cemetery in St. James, New York. Also on May 21, TMZ reported that Massaro's cause of death was due to an apparent suicide by hanging. As of June 2019, the Suffolk County medical examiner's office had yet to release an official cause of death due to a New York law concerning privacy issues.

On June 30, 2018, Massaro began working as a radio DJ for Long Island station 94.3 The Shark where she originally worked the Saturday portion from 10 am to 3 pm. A couple weeks prior to her death in May 2019, she just got promoted to hosting the station's afterdark program on Wednesday nights.

In September 2017, Massaro made a brief return to professional wrestling by competing in Zero1 Professional Wrestling USA with former WWE Diva Jillian Hall.

In November 2016, Massaro joined a class action lawsuit against WWE, litigated by Konstantine Kyros, who has been involved in a number of other lawsuits against them, alleging that the company concealed risks of injury that caused them neurological damage. Massaro also alleged that she was sexually assaulted at a US military base during a WWE tour of Kuwait and that WWE apologized but persuaded her to not report it to the appropriate authorities. The lawsuit was dismissed in late 2018. After her death, WWE said they received an email from Massaro in October 2018 in which she expressed regret for having taken part in the lawsuit. An affidavit by Massaro describing the sexual abuse allegations in detail was released by the law firm that represented her after her death. WWE would later answer to the allegations described in the affidavit by saying they were not informed about anything of this.

She left WWE in mid-2008. During her tenure in the company, she had appeared on the covers of several magazines, including the April 2007 issue of Playboy, and has also made an appearance on television and in music videos. In addition, Massaro spent the last two years of her life working as a radio DJ for 94.3 The Shark.

Massaro returned on January 7, 2008 to the Raw brand, winning a Lingerie Pillow Fight against Maria, Jillian Hall, Melina, and Mickie James. On the January 14 episode of Raw, Massaro teamed up with Mickie James and Maria in a losing effort to the team of Beth Phoenix, Jillian Hall, and Melina in a 6 person-tag-team match. Massaro began a storyline with Maria and Santino Marella on the January 21, 2008 episode of Raw, attempting to convince Maria to pose for Playboy but was interrupted by Marella. At the Royal Rumble pay-per-view, Massaro again attempted to convince Maria by telling her that Hugh Hefner wanted her to pose for Playboy before Maria could answer Marella interrupted and objected to the proposal. Massaro would then beat down Marella's surprise Big Dick Johnson when he attempted to perform a striptease. At the No Way Out pay-per-view, Massaro would appear with Maria in a segment at the Playboy Mansion. On the March 24, 2008, episode of Raw, Massaro interfered in the match between Maria and Melina. After the match, Santino Marella came down to the ring, so Jerry "The King" Lawler (who was tired of Marella's actions over previous weeks) knocked Santino out of the ring. Which set up the six-person mixed-tag-team match, in which they lost to Marella, Melina and Phoenix. On March 30, 2008, Massaro replaced Candice Michelle, who was out with an injury, in the Playboy Bunnymania Lumberjack match at WrestleMania XXIV teaming up with Maria, losing to Beth Phoenix and Melina after the interference from Marella.

On the April 14 episode of Raw, Massaro teamed up with Maria in a losing effort to the team of Melina and Hall in a tag-team match. Massaro also participated in a 12 wrestler Tag Team match at Backlash, where Phoenix pinned her to get the win for her team. On the April 28 episode of Raw, Massaro competed in her last match by teaming up with Michelle McCool, Cherry, Kelly Kelly, Maria and James in a winning effort defeating Layla, Melina, Phoenix, Natalya, Hall and Victoria. Massaro was released from her WWE contract on July 9, 2008. A week prior to her release, she announced that she had asked to be let go from her contract due to her daughter being sick.

Massaro appeared in two WWE video games. She made her in-game debut in WWE SmackDown vs. Raw 2008 and in WWE SmackDown vs. Raw 2009.

Massaro, Paul London, and Brian Kendrick defeated Idol Stevens, KC James and Michelle McCool in a Six-Person Mixed Tag Team match. Following the victory, Massaro became the valet for London and Kendrick, accompanying them to the ring for their matches on SmackDown! and pay-per-views. On the October 27 episode of SmackDown!, Massaro participated in a "Trick or Treat Battle Royal" which was won by Kristal. On the edition of December 19 of SmackDown!, Massaro teamed up with Layla in a winning effort defeating Jillian Hall and Kristal in a tag-team match. On the edition of January 2 of SmackDown!, Massaro competed against Hall in a winning effort. On the January 26 episode of SmackDown!, Massaro teamed up with London and Kendrick in a losing effort to the MNM (Mercury & Nitro & Melina) in a six-person mixed-tag-team match. During the edition of February 16, 2007 of SmackDown!, Massaro unveiled her Playboy cover. Surrounding the release of the magazine, Massaro engaged in a feud with Jillian Hall, who was envious of the attention Massaro received due to the Playboy cover. At No Way Out, Massaro won the first ever Diva Invitational by removing her top to reveal her breasts which were covered with Playboy bunny pasties.

After WrestleMania, Massaro continued as a valet for WWE Tag Team Champions Paul London and Brian Kendrick. In storyline, on the April 13 episode of SmackDown!, Massaro was attacked by Jillian Hall. In reality, Massaro had loosened a screw in her ankle, which had been inserted the previous year after she legitimately fractured her tibia and fibula while in a battle royal. Massaro returned on the June 1, 2007, episode of SmackDown!, helping McCool defeat Hall after she distracted her. This return was short lived when on the edition of June 8 of SmackDown!, Massaro was suspended indefinitely after accidentally spilling Vince McMahon's coffee on him. In reality, Massaro was taking time off to participate on the show Survivor.

Massaro was a contestant on CBS's Survivor: China, which was the fifteenth season of the show, in 2007. Massaro approached the WWE with the idea of doing the show, and after going through the casting process, she found out she made the show ten days before she had to leave for China to film. Prior to the experience, Massaro had never been camping before, so to train for the show she had to get used to being out in nature. She was assigned to the Zhan Hu tribe in the first episode and quickly began quarreling with fellow contestant Dave Cruser. In the second episode, Massaro was voted off after six days with a 6–1 vote.

In February 2007, Massaro and Glenn "Kane" Jacobs filmed an episode of the CW's Smallville that aired on March 22, 2007. In April 2007, Massaro also appeared as a guest on Fuse TV's show The Sauce. On April 20, 2007, Massaro and several other wrestlers filmed Timbaland's video, "Throw It on Me" featuring the Hives. In 2008, she appeared in Rev Theory's video for "Hell Yeah."

On January 8, 2006, at New Year's Revolution, Massaro won the first ever Bra and Panties Gauntlet match by being the final wrestler 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 this year, Massaro became the victim of a series of attacks from Mickie James. At Royal Rumble on January 29, James defeated Massaro with then Women's Champion, Trish Stratus, as the special guest referee. Massaro got her revenge one week later by pinning James in the rematch on Raw. On the February 20 episode of Raw, however, Massaro suffered a fractured left fibula while being eliminated from the Women's Battle Royal, and her feud with James was cut short. She underwent surgery to insert a five-inch metal plate and eight screws into her leg. During her recovery, Massaro still occasionally appeared on Raw as part of the Stratus/James feud, albeit in a non-active role. Massaro returned on the March 20 episode of Raw, being kidnapped by James to lure Stratus in to saving her but James was successful and attacked Stratus.

Massaro made her debut in WWE after winning the WWE Diva Search in 2005. She was firstly incorporated into the Raw brand where she had her first wrestling feud against Vince's Devils (a villainous female stable) while she also aligned herself with Trish Stratus in the process to defeat the team. With Stratus, she was involved in another feud with the then debuting Mickie James who was obsessed with Stratus and was jealous of Ashley's friendship with her, attacking and causing her to lose matches. She was later drafted to SmackDown! and became the valet for the WWE Tag Team Champions Paul London and Brian Kendrick. Her most high-profile matches were a WWE Women's Championship match against Melina at WrestleMania 23 and a Playboy Bunnymania Lumberjill match at WrestleMania XXIV.

Massaro initially found out about World Wrestling Entertainment's (WWE) 2005 Raw Diva Search when she met a WWE casting director during a swimsuit pageant. After beating the seven other chosen finalists, Massaro was declared the winner on the episode of Raw which aired on Monday, August 15, 2005. Her winnings included $250,000 and a one-year contract with WWE.

A week later on the August 22, 2005, episode of Raw, Candice Michelle and Torrie Wilson attacked Massaro after pretending to welcome her to the brand. Massaro's storyline feud with Wilson and Michelle continued over the next couple weeks, as the duo, along with their enforcer Victoria (dubbed as the "Skankateers" by commentator Jim Ross), made things difficult for Massaro. Massaro made her in-ring debut on the August 29 episode of Raw, in a losing effort to Victoria. On the September 5 episode of Raw, Massaro was defeated by Wilson due to interference from Victoria and Candice. Massaro evened the score on the September 12 episode of Raw when she brought out the returning Trish Stratus (who then turned face), and the duo proceeded to attack them. On the September 18 episode of Raw, The pair defeated the trio—who became known as the Ladies in Pink (and later Vince's Devils). This led to a tag team match at Unforgiven, where the team of Stratus and Massaro defeated Wilson and Victoria. The following night on Raw, Massaro accompanied Trish where she defeated Wilson. After the match, The duo were attacked by The Vince Devils. The feud continued into WWE Homecoming, where Stratus and Massaro defeated Wilson, Candice, and Victoria in the first ever three on two Bra and Panties match by stripping all three of their opponents. Massaro continued to wrestle matches through the rest of 2005 and was involved in the annual Fulfill Your Fantasy Diva Battle Royal at Taboo Tuesday for her first shot at the WWE Women's Championship. Massaro eliminated Candice Michelle before being eliminated by Victoria.

Massaro competed in Miss Hawaiian Tropic pageants and was crowned Miss Hawaiian Tropic USA in 2002 and Miss Hawaiian Tropic Canada in August 2004. Massaro appeared in FHM, Stuff, Maxim, and on the cover of Playboy after joining WWE, though she had previously posed for Playboy in 2003 and 2004. Massaro tried out for Playboy scouts when they were searching for models for the 50th Anniversary Playmate Hunt. She appeared in the accompanying pictorial in the December 2003. In addition, she appeared in both Femme Fatales and Flex magazines. Massaro also hosted several E! channel Wild On! episodes and appeared on Breaking Bonaduce as Danny Bonaduce's personal trainer. Massaro guest starred on an episode of Extreme Makeover: Home Edition alongside WWE wrestlers John Cena and Batista. In addition, she appeared in campaign ads for both Hawaiian Tropic and Yamaha.

Ashley Marie Massaro (May 26, 1979 – May 16, 2019) was an American professional wrestler, reality television contestant, television host, model, and radio personality. She was best known for her time with World Wrestling Entertainment (WWE) and for her appearance on Survivor: China.