Jay Halstead's (Jesse Lee Soffer) and Hailey Upton’s (Tracy Spiridakos) breakup was similar to another couple in the Chicago PD universe. Halstead and Upton had a slow-burn romance after Erin Lindsay left and ended the relationship with her and Halstead. While Halstead and Upton didn’t kiss until season 8, there was evident chemistry between them, and the wait was worth it when they did kiss. It was an intimate wedding in season 9, episode 9, “Way Out,” and a beautiful moment for them.
In season 4, Sophia Bush left Chicago PD, and the writers had to end the on-again-off-again relationship between Erin Lindsay and Jay Halstead. It can be tricky for writers when actors ask to leave the show. The writers wrote Chicago Fire, another actor left, and the writers wrote her ending and the end of the relationship similarly to Halstead and Upton.
Dawson Left With No Warning On Chicago Fire
Gabby Dawson (Monica Raymund) abruptly left Chicago Fire. She went to Puerto Rico to help with the recovery effort. This is similar to how Jay Halstead left Chicago PD. He chose to leave to the Narcotics operations. They were both leaving to avoid the messes they had created themselves. Both Dawson and Halstead also extend their trips.
Dawson had a habit of cutting Matt Casey (Jesse Spencer) out of decisions, especially regarding kids. Casey and Dawson found out it could be dangerous for Dawson to get pregnant. Casey, of course, wanted to explore other options, but Dawson doubled down on wanting to get pregnant. While her stubbornness was something Casey loved in her, it constantly tore them apart too. Dawson wasn’t going to change her mind, so it left Casey and Dawson at a stalemate. She took the Puerto Rico opportunity to get a break from the relationship.
Dawson Said Goodbye While Halstead Disappeared On Chicago PD
Unlike Halstead, Dawson appeared in Chicago Fire season 7, episode 1, to say her final goodbye to Matt Casey. At first, they had a video call, and then she came home to tell him she had made the job permanent. Casey said her experience as a pandemic and firefighter prepared her for this job. It was a nice moment between the two. Unfortunately, Chicago PD had a heartbreaking scene between Halstead and Upton that didn’t bring closure.
While Dawson and Casey were in when she left, Halstead doesn’t appear to have answered Upton’s calls. She had to call someone above him to find out if Halstead was alive. He didn’t even tell her he extended his tour. It’s a much more heartbreaking ending for Upton and Halstead than for Dawson and Casey. There could be more heartbreak coming for Halstead and Upton because their marriage is most likely coming to an end.
Dawson Returning To Chicago Fire Briefly Helped Soften Her Exit
If Gabby Dawson’s last scene were her asking Chief Hatcher (Sam Porretta) more about the unit being sent to Puerto Rico, that would have been an awful ending for her character. It would have given no closure to fans. But Monica Raymund returned for the season 7 premiere to bring closure to Dawson and Casey’s relationship. As Casey had said, this was the accumulation of everything she had done on Chicago Fire, so it was a great ending for her character but also bittersweet.
Halstead deserved a better ending to wrap up his character and to give closure to the Halstead and Upton relationship. It’s unclear how Chicago PD will bring this relationship to a close, but the writers must let Hailey move on, so her character can move on to her next chapter. The best way to do this would be to bring Jesse Lee Soffer back for a similar moment that Casey and Dawson had. However the writers decide to bring it to a close, it’s important Chicago PD fixes the messy ending for a fan-favorite relationship and character.
