Ashley Massaro: Her Life Around Wrestling, and WWE’s Ethical Failures

Ashley Massaro

Content Warning: This article contains discussions of sexual assault and suicide as well as other anecdotes from Ashley Massaro, please proceed with care.

Introducing Ashley Massaro

As the winner of World Wrestling Entertainment’s (WWE) Diva Search Contest, Ashley Massaro’s future in the company was expected to be bright, but was instead cut staggeringly short. After three years with the company, she put in a surprising request to be released, but it would later be revealed just how badly the wrestling promotion wronged her. WWE repeatedly protected their reputation over anything else, and they continued to do so even in the glaring light of her passing.

Ashley was handpicked by WWE more than once, but choosing her wasn’t the only way they should have shown her they cared. She deserved a lot from the company she poured herself into, but in the end, was saddled with more than any person should endure. She suffered internal and external, acute and chronic injuries. Massaro remains important in the eyes of fans, but was looked at as disposable to the company that she chose to dedicate herself to. Even though they thought her dispensable, they often chose her right back.

Ashley Massaro was born on May 26, 1979, in Babylon, New York, and had one younger brother Ronnie. A foreshadowing of her career to come, her father, brother, and uncle were all amateur wrestlers. Massaro grew up in East Northport, Long Island, and was a tomboy from a young age.

A lifelong friend of hers later said Ashley loved skateboarding and listening to the Doors. When she was only fourteen she started modeling, the job that would eventually summon her to the wrestling ring. After graduating from John Glenn High School, she went on to college, and got a communications degree from SUNY Albany. When Massaro was twenty years old in 1999, she got pregnant and gave birth to her daughter Alexa, whom many have referred to as the center of her universe.

Pageantry to WWE

Ashley’s journey to wrestling really began in the Miss Hawaiian Tropic pageant circuit. Known for sun care and swimsuit pageants, the contest first started in 1984, the heyday of pageant maximalism. In 2002, Ashley won Miss Hawaiian Tropic USA and just two years later was also crowned Miss Hawaiian Tropic Canada, the latter of which sounds like an oxymoron.

At this time, Ashley was modeling in various magazines and was featured in Maxim, FHM, and Playboy. After winning one of the pageants, Ashley was approached by an unnamed executive from World Wrestling Entertainment (WWE). He was casting for the upcoming Diva Search Contest and wanted her to try out.

To set the scene that Ashley was entering from stage left, WWE’s women’s division had been suffering from a lack of attention. The effects of its malnutrition were clear in storylines, character development, and poor training. To put it in numbers, in 2005 there were 283 matches at live events, give or take a few. Only twenty of them were women’s matches, and three were a variation of bra and panties matches. Women’s opportunities in the company were slim. And in 2005, if someone wanted to be a WWE Diva, the search contest was the only way in. Throughout the six years of the competition, many big names were discovered through it; the Bella Twins, Michelle McCool, Maryse, Eva Marie, Layla and more.

Diva Search Contest Begins

In June 2005, the second annual Diva Search competition aired as a weekly segment on Raw, the same episode that featured the notorious wedding between Edge and Lita featuring Kane. Out of the thousands who auditioned, only eight contestants made it to the finals. When Ashley heard her name announced as a finalist, her beaming smile penetrated through the screen.

At the direction of the WWE, that year’s contest was full of debauchery and the incidents summed up their sentiments about women. The first contest introduced the finalists as they stripped down to their bras and panties. A talent contest followed, and Ashley stood out when she demonstrated a wrestling move she learned, and launched the previous year’s winner Christy Hemme off the corner. The next week’s competition featured a hot dog eating contest that would have put Joey Chestnut in therapy. Ironically, at the end of the segment the camera quickly panned over a sign from the audience that read, “Degrading towards women.” The following round was a “Queen of the Mountain” challenge, the objective of which was to knock one’s opponent off of a platform with a giant stick. During that segment, comedian Rob Schneider came out to take photos of the contestants on a disposable camera. He was there to promote the critically panned Duece Bigalow: European Gigolo, a movie Roger Ebert referred to as “aggressively bad, as if it wants to cause suffering to its audience.”

Massaro made it through all of the trials and landed in the top four, all the while thinking of ways she could stand out from her competitors. In a last-ditch effort, the finalists were given thirty seconds to plead with fans for their vote and Ashley devised a plan. In a prelude to parasocial relationships, she gave out her real cellphone number saying she personally wanted to thank everyone for helping her get as far as she did. She later said that out of the thousands of calls she took, there wasn’t one that was ill-intended or disrespectful, it was mostly people proposing marriage to her. Ashley was popular, and it was not just because of her transparency with the fans, she had a unique presence that shined every time she held the microphone.

She also had a distinct style from the others, the only contestant who embraced the pop-punk fashion trends of the mid-aughts. Massaro would usually wear a variation of white, pink, or black, featuring a crop top, and pleated skirt or cargo pants. Ashley rocked fingerless elbow-length gloves, a backward trucker hat on her head, and opted for Demonia boots rather than wrestling shoes. Her long bleach blonde hair with accents of dark brown fell to her back, and her Monroe piercing above her lip glittered from the lights around her. In the crowd, dozens of signs with Ashley’s name on them stood out, demonstrating just how much fans resonated with her.

When Ashley was announced as the winner, she started crying as her knees gave out from under her. In a later interview with her hometown newspaper she said, “I was just so overwhelmed with feeling, I just fell.” She was visibly shaking, but bore the biggest smile. She was awarded a $250,000 check and a contract with WWE and could not stop screaming in joy.

A Rocky Start

Ashley alleged that there were precarious goings on right from the beginning of her career. She stated that after she won, Vince McMahon, WWE’s head honcho, immediately began encouraging Massaro to hire a representative, a man he referred to as “Rich.” He said that hiring him would be advantageous, and he would only take twenty percent of her winnings as payment. That was not the original agreement and Massaro was not willing to budge. The whole debacle almost resulted in her losing the contract altogether.

It is clear that the Diva Search Contest did not include any in-ring training. The WWE, at this time, was more known to use femininity as a tool for sexual satisfaction than as a weapon to be wielded. Historically, many women who were discovered in the contest were dancers, models, or generally athletic people who would either be trained to wrestle or assigned valet or manager work. Ashley immediately requested to be trained, but was repeatedly denied by Stephanie McMahon, who told her training was unnecessary because she would not be wrestling. Left with no option, she conceded.

Yet after only one week in WWE, Ashley was slowly integrated into storylines, and then was placed in matches…with no experience whatsoever. Ashley alleged that this lack of training put her and others in danger, and many accidents occurred. Massaro suffered numerous concussions, a broken leg, herniated discs, and a fracture in her spine to name only a few. In September of 2005, when Massaro and Torrie Wilson were preparing for a bout, Wilson gave Massaro a neck breaker and she was knocked unconscious for five minutes. When she came to she was not given any medical attention.

Ashley even alleged McMahon, himself, once ordered a crew member to saw off the cast of her broken hand moments before throwing her into a match. She and other wrestlers have, repeatedly, alleged the immense pressures that were put on talent to work through many injuries. Once, when she broke her leg in multiple places, she was still placed in a storyline in which her injury was significantly exacerbated, afterward needing several corrective surgeries.

Some Ashley Massaro Highlights

As her time went by in the company, Ashley was given the full WWE Diva treatment. In 2007, she was on the cover of Playboy, with a full spread. The same year, Ashley competed on Survivor’s season in China. On the first night she got sick with a fever and chills, but looked right at the camera stating it would not hold her back because she once had to wrestle with a 104-degree temperature.

Ashley was all over the television sphere, where she hosted E! gigs, had a cameo in the show Smallville, and was on an episode of Extreme Makeover: Home Edition with Bautista and John Cena.

Life was a whirlwind as that same year, Massaro was in her first WrestleMania match against Melina for the WWE Women’s Championship. Even though she was unsuccessful in the bout, Ashley’s opportunities kept coming. The year after, she was given another match at WrestleMania, this time teamed with Maria Kanellis against Melina and Beth Pheonix. Later, Ashley would say her entrance at that WrestleMania match was one of her favorite moments in her career. It remained a surreal, mind-blowing experience that she cherished.

In 2008 Ashley, relatively abruptly, asked to be released from her WWE contract. She stated her daughter Alexa was sick, and she needed the time to care for her. All of her friends would later say Ashley talked about her daughter nonstop, how much she loved her, and that she was everything to her.

WWE Concussion Lawsuit & Ashley Massaro Testament

In 2016, years after leaving the company, Ashley became part of a class action lawsuit that was known as the WWE Concussion Lawsuit. There were sixty other wrestlers alongside her telling their stories. McMahon’s company had and still have a long history of mistreating their wrestlers, and not providing them with the aftercare a career in sports often requires. WWE is known to offer one-time sponsorships to rehab or pay for a former wrestler’s surgery, but overall they seem to specialize in short-term fixes, and refuse to adopt the philosophy of prevention.

They also continuously fight to classify their wrestlers as independent contractors, so medical insurance is not provided. The lawsuit focused on these areas of issue and stated many plaintiffs were cheated out of proper care leaving them to suffer from long term issues. This level of exploitation cannot help but come across as regressive. Vince McMahon became, in the eyes of the public, a resurrected Louis B. Mayer-type, his wrestlers being the teenage talent whose lives he controlled.

The lawsuit documents still remain online, but unfortunately, only serve as a relic of what could have been. The judge dismissed the case due to differing elements. The lawyer spearheading the suit may have been in over his head as judges had thrown out similar cases before due to ineptitude.

Ashley’s affidavit, where she speaks for herself, remains online. Part of what she divulges are her injuries, both acute and chronic. She described how the multiple concussions she endured led to her experiencing short-term memory loss at only 37 years old. Additionally, she was suffering from depression and anxiety, which the injuries exacerbated. She stated that chronic pain from the aforementioned injuries had led her, and many of her compatriots, to drug misuse. So many in fact that in 2014, WWE tried to implement a drug and alcohol resistance program for former talent who needed it. Ashley had been battling addiction and went to rehab herself in 2010. She deemed it funny that WWE created a whole rehabilitation program before acknowledging that head trauma leads to drug dependency in the first place.

Devastating Information Comes to Light

In her affidavit, Ashley disclosed further information on how severely the WWE failed her. She revealed that while on a military base on tour with the company, she was sexually assaulted by a soldier. In 2007, Massaro went to the Middle East with the WWE to visit the American troops stationed in Kuwait. On the tour with her was Gary Hart, Maria Kanellis, Ron Simmons and the mouth of the south, Jimmy Hart. While on base, Ashley said she was struggling with menstrual cramps, and requested to sit in the shade, out of the hot sun. The escorts told her she must be dehydrated and insisted she get an IV. Even though she repeated it was just menstrual cramps, she said she was put in a car and taken to a medical tent. After sitting with an IV in for what felt like hours, Jimmy Hart came to check on her. She was relieved, and told him the medical personnel, despite her requests, wouldn’t release her. He told her he was going to lunch, but he would help her after.

Ashley felt like something was off, and her intuition was unfortunately right. After hours of just sitting there, a man wearing, what she remembered to be, an orange shirt and cargo shorts came through her door. At first he claimed he was a military doctor, and with him was another soldier, a woman in full fatigues. He suddenly approached her, and Ashley alleged he injected her with a substance that rendered her unable to move.

She reported that he moved her into another room and raped her for what she said felt like an eternity. The camouflaged woman kept guard from the inside of the door and watched. Like she wasn’t there at all. Massaro goes into further detail in her affidavit. While it was happening, Gary or Jimmy Hart came to see her, and when he was told she was moved into another room, he went there and started banging on the door. Ashley said the two scrambled, and threw a blanket over her body. When they walked out of the room, Ashley heard someone ask what was happening. She then remembered being picked up by Gary Hart, carried to a car, and taken to her hotel room, where she was left to sleep.

On a blog Jimmy Hart had at the time, he talked about his time in Kuwait with Ron Simmons, Maria Kanellis, Gary Hart and Ashley. He specifically mentioned picking her up from a medical tent, as well, but goes into no further detail.

When back in the States, a WWE doctor, Dr. Rios, approached her, knowing there was something wrong. He implored her to tell him what happened, and when she conceded it was with the caveat of keeping it between the two. He did not follow through. Later that week, Massaro was called into a surprise meeting with Dr. Rios, John Laurinaitis, WWE’s vice president of talent relations at the time, several other executives she had never met, and of course, Vince McMahon.

After being forced to repeat the details, McMahon apologized to Massaro for what she had gone through but encouraged her not to report it to the police. He could not risk the WWE having a sour relationship with the U.S. military because of, what he referred to as, “One bad experience.” In her affidavit Ashley quotes:

“Vince went on to say that I would not be required to travel to the Middle East ever again and…WWE would institute a new policy where any time a female WWE performer went to the Middle East, she would have a female WWE escort with her 24/7…This did not make me feel better about the situation. It had already happened to me and the damage was already done. But again, I felt so defeated at that point that it seemed pointless to protest. I also admittedly was uncomfortable with the thought of all the wrestlers finding out so I asked Vince and those in the room to keep the incident quiet and they agreed. “

Massaro’s attorney wrote of the ethical impact of the WWE’s treatment of Ashley and their workers as a whole stating:

“This incredible situation derives from the WWE’s employment misclassification scheme wherein the WWE (deems itself) neither responsible for Massaro’s safety (despite being on a WWE tour in the Middle East) nor does the WWE deem itself responsible to report or collect data about incidents such as this. The WWE in order to protect its public image and insulate itself from paying for its injured workers prefers to remain silent.”

At the time of her statement, Ashley said the incident haunted her daily. The fact that no one was there to protect her before, during, or after is heartbreaking. Especially because her experience does not exist alone. Sexual assaults on military bases have been ignored for decades. The statistics reflect rates of sexual assault on civilians, but researchers fear stigma refrains survivors from coming forward. The military-industrial complex has inserted itself into several forms of American media throughout the last 100 years, including the old Hollywood system, Marvel movies, and of course, a multi-million dollar relationship with the country’s biggest professional wrestling company.

Massaro was more than devastated by how the sexual assault was handled. Dr. Rios, who Ashley claimed was more sympathetic than the others, even requested for her to have extra time off because of injuries and trauma, but his request was denied.

“Vince approached my rape in the same manner he approached all wrestler injuries. He did not want to damage the reputation of the WWE by making them public knowledge, so he exerted extreme pressure on us to stay silent, to perform whether or not it was safe to do so, and had almost no regard for our well-being. We were treated as replaceable commodities. WWE’s top priorities seemed to be generating profits and avoiding liabilities, regardless of how this affected its workers.”

Remaining in the Hearts of Fans

In light of these events, looking back to Ashley’s “abrupt” resignation in 2008, only a year after the assault, her leaving does not remain a surprise. Even though these were unforgivable instances, Ashley still had incredible moments in the business, and years after her career, often took to social media to discuss them. She remained in touch with some of the women she spent time with on the road, saying they all had something unique in common and were a part of this entity that had a life of its own. That life force is fortified by the fandom behind it, and Ashley remained fossilized in their hearts. Fans would regularly see her at conventions and said she remained the same Ashley that was introduced in 2005.

Her admiration, not limited to her peers or fans, was also expressed towards the women who wrestled in WWE after her. She was encouraging of their success and hoped they could experience a better company than she had. Unfortunately, though some women’s careers have been exceptions, the overarching rule still pertains. There are still many who feel like they have been failed.

In 2017, after the lawsuit was halted, Ashley returned to the ring in Zero1 Professional Wrestling for a brief time. She also started DJing for a local Long Island station, *radio voice* WWSK-FM 94.3 The Shark, where she worked every Saturday. Throughout the next year, she would also model with a Paul Heyman-led modeling agency, called the Heyman Hustle, a name that should have been workshopped more…it sounds like a 1980s dance move or a grifters guide to grifting.

In April 2019, Ashley posted to her Instagram how she planned to start training again, and although she was scared of ring rust, she was excited to get back in there and oil those joints up.

About a month later on May 15th, 2019, Ashley tweeted a photo of bundles of fan mail she had responded to, exhibiting her loving relationship with her fans. That same week though, she did not show up to her job at the radio station on Saturday. At 5am the next morning, Ashley was found unresponsive in her home in Smithtown, Long Island. She had taken her life. It was only a few weeks shy of her 40th birthday.

After her passing, WWE alumni Trish Stratus, Lilian Garcia and Lisa Marie Varon (Victoria) sought out Mick Foley for help. At Ashley’s funeral service, Foley approached her family asking permission to start a college fund for her daughter, Alexa which he opened up to fans. They raised over $100,000. The same women wrestlers made a video for Alexa affirming how much her mom loved her, and what an incredible person she was.

Sadly, only a year and a half after her death, Ashley’s younger brother Ronnie Massaro was stabbed and killed in a seemingly random attack. His assailant was arrested the day after when it was caught on CCTV. Loved ones told the Daily News that the year after Ashley’s death had been filled with grief, and Alexa sadly relayed, “They were very close…[and] spent a lot of time together, so it was really hard-hitting.” They both died at the age of 39.

After her death, WWE released a statement expressing condolences to Massaro’s family. Unfortunately, they made sure to include that Ashley had apologized for participating in the concussion lawsuit. Manipulating her narrative even after her passing. Their statement falls on deaf ears though, because the entirety of Massaro’s affidavit is full of assertions that multiple people persuaded her to cover-up, not discuss, or seek justice for the wrongdoings inflicted upon her. The affidavit still lives online as a testament of her true feelings toward the company.

To this day, no significant news sites have reported how WWE covered up her sexual assault. The fight for medical insurance still persists and as of April 2021, another WWE Concussion Lawsuit was stopped in its tracks by the Supreme Court.

Ashley’s growing legacy has left an unforgettable and lasting mark on us all. To read the words Ashley testified to is to see through World Wrestling Entertainments veil, but just taking in her words isn’t enough. Having discussions around the subject, and fighting for change in WWE and all other industries, this is how we embrace the power that was always hers but had been taken away so many times.

Stay tuned to the Last Word on Pro Wrestling for more on this and other stories from around the world of wrestling, as they develop. You can always count on LWOPW to be on top of the major news in the wrestling world, as well as to provide you with analysis, previews, videos, interviews, and editorials on the wrestling world.