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Ashley Marie Massaro (May 26, 1979 – May 16, 2019) was an American retired professional wrestler, actress and model best known for her time in WWE as Ashley from 2005-2008 after winning the 2005 WWE Diva Search. Starting off as a member of Vince's Devils with Candice Michelle, Torrie Wilson, and Victoria, she eventually became a valet for Paul London and Brian Kendrick before transitioning into a full-time competitor until retiring in mid-2008 to tend to her sick daughter.

Massaro was never trained properly by WWE before getting into the ring, which led to her botching a lot, becoming injury prone and her being considered one of WWE's worst in-ring performers. Regardless, she still had a lot of fans due to her sex appeal, and has posed for Playboy multiple times. She was also a contestant on Survivor: China in 2007.

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After a decade away from wrestling, she was planning on a return to a ring but unfortunately she passed away on May 16, 2019 at the age of 39.

"You'd better hold on tight, 'cause I'm gonna trope you nice!"

  • Action Mom: Had a daughter, believe it or not.
  • Arch-Enemy: Melina would be the biggest. They actually faced each other at two WrestleManias
  • Barely-There Swimwear: At No Way Out 2007, she showed up in a bikini with two tiny Playboy bunny pasties on her breasts.
  • Big Applesauce: From Long Island.
  • Bound and Gagged: What Mickie James did to her to psych Trish Stratus out.
  • Buxom Is Better: Had very large implants.
  • Canon Name: She only wrestled as Ashley, but is almost always called by her full name in retrospect.
  • Cassandra Truth: Ashley was the first to recognize something was not quite right with Mickie James but no one paid her much attention until Mickie was tying her up and beating the piss out of her.
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  • The Cavalry: Downplayed in Victory Pro Wrestling, as she didn't interfere in Payton Banks and Jillian Hall's match when Jillian started cheating, despite the "We Want Ashley" chants, but she did convince the referee to reverse his decision.
  • Dark Is Not Evil: Dressed up as a gothic angel and fairy for two Halloweens, was a face at the time.
  • Downer Ending: Her unexpected passing at 39.
  • Expository Hairstyle Change: She cut her hair in 2008, shortly before retiring.
  • Faux Action Girl: Was actually given two WrestleMania matches and pushed for the Women's title at one point, despite her wrestling ability being... well... nonexistent. She revealed years later that WWE had never actually trained her properly and she had only ever been trained on a per-match basis.
  • Finishing Move: A spear and the Starstruck (a diving-from-the-second-rope elbow drop).
  • Glass Cannon: Was only in WWE for three years and probably suffered as many injuries as someone who had been wrestling for ten years due to her lack of training.
  • Hair of Gold, Heart of Gold: She was a face during her entire WWE tenure and had blonde hair.
  • Ill Girl: Was sick the entire time she was on Survivor: China.
  • Jerkass: She was shown as pretty unpleasant on Survivor: China, quickly beginning to quarrel with fellow contestant Dave Cruser.
  • The Load: Her illness on Survivor turned her into this, resulting in her being voted off in the second episode after six days with a 6–1 vote.
  • Marshmallow Hell: Was a victim of this on one occasion when Jillian Hall tried to smother her out of jealousy for her appearance in Playboy.
  • Minidress of Power: Or skirt if you will.
  • Ms. Fanservice: Posed for Playboy three times (though the first two were before she joined WWE). And was frequently showing as much skin as possible on TV.
  • The Mentor: On screen, it was Trish Stratus. Off screen, Matt Hardy helped when he could.
  • Multicolored Hair: Black, blonde and pink.
  • Older Than She Looks: She actually looked better than she did in her twenties while she was in her thirties.
  • Perky Goth: While having Goth looks (complete with several tattoos and piercings), she loved to party, and to find the party in people who claim they don't.
  • Shout-Out: On Survivor, she mocked fellow contestant Dave's past as a model by voting for "Derek Zoolander" — I mean, Dave" at her last Tribal Council.
  • Sitcom Arch-Nemesis: To Dave on Survivor: China.
  • Stocking Filler: Fishnets were usually a big part of her look.
  • Tomboyish Baseball Cap: She wore a backwards black cap in her debut in 2005 (she also won the 2005 Diva Search). She stopped wearing it in around her return in 2008.
  • You Gotta Have Blue Hair: Had the occasional coloured streak in her hair, usually pink or blue.
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