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Warning: The following contains spoilers for this Wednesday’s One Chicago crossover.
Amidst One Chicago’s latest epic crossover on Wednesday, there was also a very important and highly anticipated reunion: For the first time since 2022, former Chicago P.D. Intelligence unit team members Jay Halstead (played Jesse Lee Soffer) and his ex-wife Hailey Upton (Tracy Spiridakos) came face-to-face back in the Windy City.
As you may recall, Upton and Halstead’s marriage broke up after he left Chicago in Season 10 to join the Army in Bolivia, where he was going to be tracking drug cartel targets. Then Upton left in Season 11 after Halstead, essentially, ghosted her, and they officially divorced. Cut to the present day, and the pair’s new career paths have put them on a collision course during the crossover. Upton resurfaced in their old stomping grounds first, when a passenger airplane tied to her narco trafficking case brought her to Chicago. Now an FBI agent in the Detroit field office, Upton looped in CFD and the CPD after the flight went radio silent in the air and all those on board were later found dead due to a chemical agent. But Upton also had another motive for returning to Chicago: She found out that Halstead’s cover had been blown, and she was trying to protect him. Still, she was surprised when she ran into him while chasing a lead, and he saved her life.
As showrunner Gwen Sigan pointed out, there’s much still unresolved at this point between Halstead and Upton, who haven’t had a real conversation in a very long time. “They haven’t seen each other in years. They probably haven’t spoken in years. The last time was definitely through letters and voicemails and texts,” Sigan reminds Soaps.com. “So this is the first time we’re really getting to see them back together. There’s just so much unsaid.”
And yet, Upton wasn’t eager to talk after Halstead admitted that there were so many times he wanted to reach out after their split. “The past is the past, Jay. Let’s leave it there,” she said.
As the crossover unfolded and the investigation wrapped up, the vibe between the exes started to shift, and they finally had a very overdue conversation. Halstead confessed he stayed to work this case because she was here, to which Upton replied that she came here because he was here. At long last, Halstead apologized for the way he left and for the dissolution of their relationship.
“I lost myself here, in this team, in this city, and I’m sorry I couldn’t find my way back. Sorry for all the wrong I did. All of it. I’m sorry that I lost you,” Halstead said.
“I’m sorry, too,” Upton responded, before handing him an olive branch. “What time’s your flight?”
“I don’t care,” Halstead bluntly answered. Upton then asked if he wanted to get a drink, and the two of them left together.
“I think it’s a nice moment of sort of catharsis for the two of them,” Sigan says. “They’re finally talking about things. They’re being very open with each other, vulnerable in a way that they haven’t, and sort of both taking responsibility for their side of things and what went wrong.”
So can this exchange be considered the first step in a romantic reconciliation for the pair? “It’s an open door, right?” Sigan says. “I think the fact that Upton’s even offering it, and then that he accepts it so readily, means that there’s going to be more conversations and just more hope for the two of them moving forward. I think possibility is what I take out of it.”
And that is something positive fans can hold on to after the sad and unfinished note on which Upton and Halstead’s marriage ended. Giving much-needed closure to their relationship was something that was “baked in pretty early on, pretty much from when we started breaking this [crossover],” Sigan shares. “When we came up with the title [“Reckoning”] and sort of the themes of reckoning, it did feel like the perfect place for the two of them to come back and have this story of getting to sort of have a different ending together.”