Gregory was questioned in regards to the murder of teenager Brian Haddick, who was found bludgeoned to death at his construction site, with a hammer covered in Brian's blood being found to belong to Gregory. It was also revealed that the piece of cloth found in Brian's hand was from a shirt worn by Ashley, who Gregory identified as his sister during his interrogation. When questioned by Sara Sidle, Ashley claimed she had been lured to the construction by Brian under the claim of looking for his lost cat, where he suddenly attacked and began trying to rape her before another person arrived and attacked him with the hammer, allowing Ashley to flee.
While Ashley claimed not to know who killed Brian, the team came to believe it was Gregory and that Ashley was lying to protect her brother. Later on, though, crime scene evidence indicated Brian was attacked and killed by four assailants, with the team's investigation finding three of those assailants were fellow McKinley High students: Benny Lizzio and brothers Aaron and Jared Gilbert. While the boys all refused to reveal what transpired or who the fourth assailant was, Sara came to a shocking discovery when it was determined that the reason behind Brian's assault was robbery: Ashley was the fourth assailant, as the items she bought at the mall after Brian's death totalled to $125; the exact amount of money Brian got from his under-the-table waiter job that was left unaccounted for given that Benny, Aaron, and Jared were each found to have gotten a combined total of $375 from Brian after killing him.
Sara confronted Ashley in interrogation, as her fingerprint in Brian's blood was found on a $20 bill Jared had in his possession and her lip gloss was discovered in Benny's bedroom. Ashley attempted to claim she had lied to protect her friends and stole from Brian posthumously for "pain and suffering", only for Sara to reveal that she had deduced that Ashley lied about being assaulted by Brian to cover up her actions. As revealed through flashbacks, Ashley had plotted to kill Brian with her three cohorts, having them smash watermelons in Benny's room in preparation for attacking Brian and cheering them on. Later on, Ashley lured Brian to the construction site under the pretense of wanting to have sex with him, where Brian was ultimately beaten to death by Ashley and her cohorts with hammers she stole from Gregory, with Ashley laughing during the attack and later collecting the weapons from the boys after Brian was dead.
When asked by Sara for a reason behind the attack, the evil Ashley stated that she and Brian were friends before he decided to leave behind his delinquent behavior, with the villainess believing Brian thought himself too good for her and their friends. Ashley was blasted by Sara for her actions and was assured by her that she would do everything in her power to make sure Ashley was tried as an adult, with the sociopathic teen boasting that she intended to manipulate the court into believing her innocent, even planning to use her late parents to garner sympathy. Ashley was then arrested (off-screen) for her role in Brian's murder.
- (Sara: "Why Brian?") Before he went straight, we were buds. But then he got too good for us. But he wasn't too good to wanna get with this." (Ashley revealing her reason for mastermining Brian's murder)
- (Sara: "You're not a victim; you're a lure. Do you know how many people don't report a rape because they're afraid no one will believe them?") Of course. It's what I was counting on. (Sara: "I'm gonna do everything in my power....to make sure that you're tried as an adult.") Good luck. I dress up real nice. Couple barrettes, little lace collar, two dead parents. I'll be the saddest little girl in the world." (Ashley's sinister boast before her off-screen arrest)