Why Chicago PD’s Halstead and Upton could still end up together
By Kari Highman
2. Their thing that works
Another defining moment between Halstead and Upton came later in Chicago PD season 5, in the episode “Ghosts” when Hailey resumed an old undercover identity to catch Ron Booth (guest star Titus Welliver), a career criminal she had history with. This worried Jay, who thought she might be too close to the case to see things clearly.
In something of a role reversal, Halstead was the levelheaded one as he tried to help Upton sort through her feelings about her own partner turned love interest, whom Booth had killed. At the end of the episode, fans got their first glance at what would soon become a regular occurrence between the two: deep conversations, usually with some form of alcohol.
This theme of their being able to open up to one another continued on into Chicago PD season 6, when Jay helped Hailey deal with her guilty conscience in “True or False” and when Hailey helped Halstead cope without closure to a case in “Outrage.”
One of the most telling moments between them happened in the season 6 finale “Reckoning” when Upton let Halstead talk regarding Hank Voight’s (Jason Beghe) ominous last words about Jay someday running the unit. Upton saw the concern in his eyes, and hers showed a saddening thought: maybe this really was it for them.
With Brian Kelton (John C. McGinley) ready to disband Intelligence at the time, Halstead and Upton were left uncertain about their future together. But Upton reassured Halstead that Kelton would get what was coming to him, and he tried to reassure her that no matter what, he wouldn’t forget about her. As has been said on the show before, they have a thing that works between them, and it’s not just in the big moments.