Ashley Massaro was a former WWE superstar who appeared on the reality TV series, “Survivor: China,”, as well as appear on the cover of Playboy magazine.
However, the story of Massaro’s career and her legacy within WWE and beyond is so much more than a few highlights.
On May 16th 2019, the world received the news that at the age of just 39, Ashley Marie Massaro had passed away after being taken to the hospital from her home in Long Island, New York. Many have since spoken on the life and love they have for her, including the likes of Torrie Wilson, Cody Rhodes, Melina, Trish Stratus, Mick Foley, Taz and WWE themselves.
Upon receiving the news at TWM News, all of us were shocked and saddened. As of with the rest of the world that knew her, we all had our own memories of her, so with this in mind, this article is our insight into the life and legacy that Ashley Marie Massaro left behind.
Ashley Massaro was born on May 26, 1979 in New York City, and grew up within a family of wrestlers – her brother and father both performed at amateur level, which seemed to solidify Ashley’s fate. This wasn’t something that was to happen immediately, however. She studied and received a Bachelor of Science degree in Communication with a minor in Business from the State University of New York at Albany. A few years after this in the year 2000, she gave birth to her daughter Alexa, her only child – someone she made sure to keep out of the public limelight, and someone who she prioritised over everyone and everything in her life.
Before her career in wrestling took off, Ashley competed in various paegents. In 2002, she competed in and was crowned Miss Hawaiian Tropic. She also competed in 2004 and was crowned Miss Hawaiian Tropic Canada. On top of this, she also appeared in Playboy in 2003 and 2004.
Her wrestling career took off in 2005, after being found by a WWE Casting Director whilst she was involved in an unrelated swimsuit photoshoot. She competed in the WWE Raw Divas Search, competing alongside talent such as Kristal Marshall (also known as Kristal Lashley on TNA), and Leyla Milani. Ashley won this contest, winning $250,000 in August of that year, and this is when she began training properly to compete on the WWE roster.
Her run on WWE was certainly a memorable one, being involved in many storylines in her run between 2005 and 2008. From being Paul London and Brian Kendrick’s valet, to her Playboy Cover announcement, to competing in two Wrestlemania matches, it’s safe to say that Ashley cemented her legacy in WWE history.
A week after winning the WWE Divas Search contest, she was briefly involved in a feud with Vince’s Devils, particularly with Candice Michelle and Torrie Wilson. Ashley made her in-ring debut on the August 29 episode of Raw, losing to the leader of this faction Victoria. This escalated over the coming months, and when Ashley was aided by a face Trish Stratus, it began a tag team feud which resulted in Massaro and Stratus beating them both at Unforgiven and WWE Homecoming. After this feud, Ashley continued to wrestle in typically single matches through the rest of 2005. She was offered her first title shot for the WWE Women’s Championship, at Fulfil Your Fantasy Diva Battle Royal – where she was eliminated by Victoria.
Going into 2016, Ashley started off in style winning the first ever Bra and Panties Gauntlet match, and then immediately began a feud with Mickie James. This resulted in a loss at Royal Rumble 2006, but then a win on the following week of Raw. During the edition of February 20, 2006 Massaro suffered a fractured left fibula resulting in her feud with James to be cut short.
During her recovery, Ashley still appeared on Raw as part of the Stratus/James feud, however in a non-active role. She was then moved to Smackdown a few months after this on June 2nd, appearing to still be in a non-competitor role. She won her debut match on Smackdown on July 21st, teaming up with Jillian Hall to defeat Michelle McCool and Kristal. Unfortunately, she sustained another injury when she broke her knuckle in a match against Kristal in August.
Soon after this, Massaro became the valet for Paul London and Brian Kendrick for the majority of 2016, accompanying them to the ring. On the October 27 episode of SmackDown! Ashley participated in a “Trick or Treat Battle Royal” which was won by Kristal. She then began a feud with Jillian Hall, towards the end of 2006, which ultimately resulted in Ashley beating her.
Kicking off 2007, Ashley teamed up with London and Kendrick in a losing effort to the MNM (Mercury & Nitro & Melina) in a six-person mixed-tag-team match, which became their feud until February, when Ashley 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. Alongside this, Ashley began a feud with the Women’s Champion Melina, who was also angry over the publicity. This resulted in Ashley once again teaming up with London and Kendrick in a losing effort to MNM.
This escalated Ashley and Melina’s feud – which eventually landed Ashley’s first Wrestlemania match against her at Wrestlemania 23 for the WWE Women’s Championship in a LumberJill match. Although Ashley lost this match, this was arguably one of Ashley’s best matches in her career, and it showed her to be a top dog on the roster. She continued valeting for Paul London and Brian Kendrick but sustained another injury which agitated her previous fracture in her fibula.
She returned back to Smackdown in June 2007, but this was short lived as Ashley was written off TV to participate on the show Survivor: China. She was the second to be eliminated off this after being on the show for six days. This was one of many mainstream platforms she was involved in in 2007, as she also featured in several music videos, including Timbaland’s ‘Throw it on Me’, and later Rev Theory’s ‘Hell Yeah’.
Massaro returned on January 7, 2008 to the Raw brand and began a feud with Maria and Santino Marella surrounding Marella’s unhappiness of Ashley’s suggestion for Maria to pose for Playboy. This segment had several highlights – including funny back and forths with Marella, and during the No Way Out pay-per-view, Ashley appeared with Maria at the Playboy Mansion. This feud ended at the end of March, at Wrestlemania XXIV, as she replaced Candice Michelle to compete at the Playboy Bunnymania Lumberjack match, teaming up with Maria against Beth Phoenix and Melina. Marella interfered in the match, which resulted with Beth and Melina getting the upper hand and defeating Maria and Ashley.
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. In July 2008, Ashley was released from her contract with WWE after her daughter fell ill.
After her release, Ashley Massaro kept a relatively low profile, primarily focusing on family life – although she would make appearances at indy events, as well as attend wrestling conventions and meet ups. Right until her last days, she was regularly communicating and interacting with fans – sending fan letters, accepting photo requests, and replying to fan responses via social media platforms.
Reflecting at her achievements both in and out of the ring, it’s no surprise that the outpour of love, reminiscing and support has been coming from fans across the world to the family and friends of Ashley. As someone who grew up watching WWE in the 2000’s, Ashley was someone who exulted personality, talent, and wasn’t afraid to be less conventional than some of the other women on the roster. She showed herself to be, at the time, a brilliant face character on the roster – and worthy of being a future WWE Hall of Famer.
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