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Monster Ann led Crystal Security, a UNSC business that was actually the front for a crime syndicate. One of her underlings, Thin Kinkle, had kidnapped James James' daughter, Janissary James, after Jan messed up a rape Kinkle had set up as a gang initiation test.
When Jan's father tried to rescue her, Kinkle killed him in front of Jan. Jan, with her mother Gilly, launched a revenge assault on the Crystal Security building to hunt down Kinkle. There they were able to corner Kinkle and Monster Ann. In an attempt to be motherly and spare her daughter from having to kill, Gilly shot her.
From the Janissary story showing how Monster Ann Dies.
Thin: Hey, this must be your mom, babysitter. Thin: I knew you didn't get your looks from your dad! Jan: You bastard. (loads guns) Monster Ann: Take him... He'll pay the price for what he done. Thin: You trying to sell me out to save your skin, Ann?! Jan: Gladys? Gladys: We're here, kiddo. Jan: ...I don't know what to do. Monster Ann: Kill Thin... let Monster Ann go... I'll make it worth your while... Jan: I just... don't know. Gilly: Jan, this isn't who you are. Jan: (painfully) He...shot...him... He shot him like a dog! Gilly: Jim didn't want this for you. Thin: You're still not pulling the trigger, babysitter... Thin: A lot I could still teach you. You know it! Jan: What kind of daughter am I?! Gilly: The best, Jan. (crying) Thin: Heh. Gilly: Your father was so proud of you. Gilly: And he would never want you to turn into... one of us. Thin: Hey, hey, hey they're talking truth, babysitter. Jan: Shut up! Gilly: I've never been much of a mother for you, Jan. Gilly: I never got to bandage up a scraped knee, Gilly: never had to read you a story at bed time, Gilly: never had to brush your hair... (loads gun) but I can do this... Thin: No...! (gunshot) Monster Ann: Agh! (gunshot, both fall to the floor)