Ashley was born in Liberty City and knew several of the members of the Lost Alderney Chapter since childhood, including Johnny Klebitz. After joining the Lost, she became Johnny's girlfriend and also became a drug addict, using cocaine and crystal meth. Her addictions, coupled with her infidelity (which was many times induced by her desire to obtain cheap drugs), eventually led to Johnny breaking up with her, which had a devastating effect on Ashley's life, severely increasing her drug problem.
The Lost and Damned
Eventually, her addictions later led to her being held-up in a crackhouse by some drug dealers when she couldn't pay them, although Johnny managed to save her. At some point, Ashley begun a relationship with Ray Boccino, a capo of the Pegorino Family. Ray used this to his advantage, convincing her to use The Lost to steal several diamonds which originally belonged to Ray Bulgarin. Despite this, he is shown to have genuine concern towards her and her addiction. She also borrowed money from the Russian Mafia to pay for her habit. This led to her becoming in debt to Dimitri Rascalov, and Johnny and Malc are forced to kidnap Roman Bellic to settle it.
Later, Ray orders Johnny to take part in a deal exchanging the diamonds which were stolen previously for money. However, the deal is ambushed by Luis Lopez, and among the confusion, Johnny decides to take the money for himself and the Lost. He then gives it to Jim Fitzgerald for safekeeping. Ashley unwittingly informs Ray of this and he has Jim kidnapped and tied up in his basement to be tortured, in hopes that he will reveal what happened to the money. Johnny is lured to Ray's but the two escape before parting ways. Ashley then calls Johnny to warn him that he is in pursuit by some of Ray's goons. Although he manages to escape successfully, Ashley informs him that Jim was killed and that Billy Grey is planning on turning states while in prison, pinning a drug ring on The Lost.
After completion of The Lost and Damned's storyline, she is not seen again. However, if Johnny calls Ashley, she'll ask for forty dollars. Johnny declines, saying that she can kill herself on her own. She also e-mails Johnny, saying that she checked into rehab, and is doing well. Johnny wishes her good luck but also tells her to stay away from him. A few days later, she sends Johnny another email reluctantly confessing that she was booted out of the rehab facility and asking Johnny for yet more money, to which Johnny reinforces his wishes for her to stop contacting him.
Grand Theft Auto V
At some point between 2008 and 2013, Johnny, Terry, Clay, Ashley and several other members of the Lost MC relocated to Blaine County, where they set up a new base of operations. The gang would then become heavily involved in drugs and arms trading. Ashley and Johnny got back together, and Johnny himself also got addicted to meth like Ashley. The gang also became affiliated with Trevor Philips, but the relationship seemed shaky as Trevor would often have sex with Ashley, much to Johnny's dismay. Ashley's appearance during this time also radically changed; her hair color changed from black to red, and she became thinner and more haggard (likely a result of meth use).
In early 2013, Trevor met and allied with an unknown hitman. Trevor would frequently send this Hitman on missions to meddle with The Lost with the intention of furthering his affair with Ashley.
Sometime in 2013, Johnny confronted Trevor again for having sex with Ashley. Trevor, who has just found out about Michael De Santa's survival, finally snapped after Johnny's smack talking, and retaliated by beating him to death. Ashley, along with Ron Jakowski and Wade Hebert, watched in horror as Trevor repeatedly stomped the glass pieces on Johnny's head. He then left with Ron and Wade, leaving Ashley to mourn over Johnny's body. The rest of the Lost MC, including Terry Thorpe and Clay Simons, would soon be wiped out by Trevor as well.
Should the player decide it, Ashley can be killed as well and dialogue between Trevor and Wade will acknowledge this during the ride over to the Lost compound. However, regardless of the player's decision, a Weazel News report and an internet news article will later reveal that Ashley died after participating in a heroin orgy in a Paleto Baycondo, along with four local males in their 50s and 80s. According to the article, police broke down the doors to the apartment after neighbors complained about an unpleasant smell and found five naked corpses.
Ashley's appearance changes significantly between games. During The Lost and Damned, her hair is black and her skin is noticeably more pale. In GTA V, her hair is red, and she looks much older, possibly due to her meth use. She appears to have a tattoo reading "TLAD" near her left breast.
LCPD Database Record
Place of Birth:
Linked to the Lost MC and the Alderney based Pegorino Crime Syndicate.
2001 - Possession Controlled Substance: Cocaine
"Old Lady" of Billy Grey, head of the Alderney Chapter of the Lost Outlaw Motorcycle Gang.
Seen with Ray Boccino, a Capo in the Alderney-based Pegorino Crime Syndicate.
Believed to be a condult between those two organizations.
Her name is a combination of Ashley Wilkes and Rhett Butler, two major male characters in the novel Gone with the Wind. Ashley is both a male and female name.
The player can also occasionally call her after certain missions to hear her input on what's going on in the game's storyline, like Roman Bellic in GTA IV.
Though possibly a taunt, Ray will tell Johnny in "Was It Worth It?", "I fucked Ashley my friend, and now I'm gonna fuck you!" meaning Ray may have had a sexual affair with her (which is rather likely due to her drug addictions).
Ashley is still very much in love with Johnny Klebitz, as shown in Coming Down, when she tries to advance on Johnny, who declines the advances. She also states in this mission that "Johnny is her habit" when he brings up her ice addiction. She is visibly touched when Johnny admits to Trevor that he still loves her and even mourns Johnny after he is killed by Trevor.
In the mission Coming Down, Ashley will say, "Hit me, teach me a lesson!". If the player hits her, she will say "That's enough now".
Ashley owns a private Lifeinvader account. After "Mr. Philips," regardless of whether the player killed her or not, Ashley will leave a threat on Ron Jakowski's account, telling him that they all will pay for Johnny's death. This is presumably an oversight.
In her description on the Rockstar website in People & Places, her description is "Party girl who has partied too much".
Nearly every notable event in The Lost and Damned storyline is due to Ashley's actions and dishonesty. Her cheating with Billy Grey strained his and Johnny Klebitz' friendship, which eventually led the gang to civil war. Her debt with the Russians made Johnny kidnap Roman Bellic. Her affair with Ray Boccino sucked Johnny into the diamonds story arc. Finally, her cheating with Trevor Philips led to Johnny's death and several Lost members of the Stab City chapter.
It is very likely that one or more of the protagonists could call or receive calls/texts from Ashley in the early versions of GTA V as there's a contact picture for her in the game files.