The long, rocky relationship between Hailey Upton and Jay Halstead has been an emotional roller coaster for One Chicago fans. Hailey and Jay met during Season 4 of “Chicago P.D.” They don’t get on at first — after they team up as partners, she is wholly involved in getting the job done, while Jay copes poorly with losing his former partner on the force, Erin Lindsay (Sophia Bush). Over the course of Seasons 5 and 6, they get closer and closer together. It all culminates in a marriage during Season 9. Unfortunately, during Season 10, Jay stabs a perp in self-defense and his guilt (and Hailey’s attempt at helping to cover up his crime) leads to him turning in his badge. The incident strains his new marriage to Hailey as well.
Jay is ultimately unable to cope with his PTSD and leaves Chicago for a job in Bolivia. There, he’ll be hunting down drug cartel members while working with the Army. He tells Hailey that morality there isn’t grey but black and white. Their marriage is left on pause while he vacates Chicago for eight months. While she continues to take care of her very dangerous job, she hasn’t referred to Jay since his departure. It’s quite possible they divorced off-screen. But Season 10 left the door wide open for him to return and reunite with Hailey. It’s currently a waiting game to see if that actually occurs, but hopefully, Hailey’s exit will be a joyful, and not a tragic one.
