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She later joins Sergeant Hank Voight's Intelligence Unit and is partnered with Detective Jay Halstead. She was meritoriously promoted to detective after her work on an undercover case. This event, combined with the childhood abuse, inspired Hailey to become a cop, where she eventually became a member of that same Robbery-Homicide unit. When the diner was robbed in 2003, by which time she was 10, she stayed by the desk of Sergeant Trudy Platt, who was part of a Robbery-Homicide unit at the time, until it was solved, all the while worrying for the health of her father. Despite the abuse, her mother remained at the house with her father even long after she and her siblings moved away. Upton was very abusive, as he would regularly beat her mother, brothers, and herself.

As a child, her family ran a diner in Greektown.