Editor’s Note: The following contains spoilers for 2026’s One Chicago crossover event “Reckoning”.Over the course of 13 seasons, Chicago P.D. has captivated fans with hard-hitting storylines and characters that have been embraced, flaws and all. It doesn’t mean there haven’t been any missteps along the way. The appearance and subsequent unexplained departure of Vanessa Rojas (Lisseth Chavez) in Season 7, the way it handled the long-awaited Burzek wedding, or Hank Voight’s (Jason Beghe) repeated lack of consequences for his many sins are all black marks on the police procedural. Yet its most egregious mistake has to be the departure of Jay Halstead (Jesse Lee Soffer) and the baffling fallout from it, ending the fan-favorite union of Halstead and Hailey Upton (Tracy Spiridakos), “Upstead,” on a quiet and dour note. But, contrary to the adage that reads “you can’t fix what’s already broken,” the latest One Chicago crossover event, “Reckoning,” has fixed Chicago P.D.‘s biggest mistake with one scene that’s been a long time coming.
Upstead Comes to a Halting Crash in ‘Chicago P.D.’
Upton was introduced in the Season 4 episode “Fagin,” and would be partnered with Halstead at the onset of Season 5. The pair became a cohesive unit, developing a deep friendship that had them looking out for one another even outside the work environment, with Upton pushing Halstead to find help for his PTSD, and, in turn, Halstead helping Upton confront the abuses of her childhood at the hands of her father. The relationship grew more intimate, resulting in their first kiss in Season 8’s “Tender Age,” and Upton proposing to Halstead in the season finale. An agonizing summer later, Halstead accepted her proposal before turning around and asking her to marry him, saying he’s known for years that he wanted it to be him and her, always. And in the ninth episode of the season, the pair got married in a secret courthouse wedding, a moment five years in the making.
‘Chicago P.D.’s Most Gut-Wrenching Episode in 13 Seasons Reveals a Side to This Character We Never See
No one saw it coming.
This just highlights just how epic Chicago P.D.‘s biggest mistake is. In Season 10’s third episode, Halstead, growing increasingly anxious about the lack of a moral code in the unit, signed up for a job with the Army for an eight-month deployment, hunting down Bolivian drug cartels, without warning Upton of his plans. At the end of the episode, he left, a move that is completely out of character. Only that’s not the worst of it. Halstead ended up ghosting her completely, and when Upton reached out to his boss overseas in Episode 10, she learns that he had extended the length of his assignment without telling her. It’s a raw, heartbreaking moment, a cruel end with no reasonable explanation. It instantly shattered Halstead’s well-earned reputation as an honorable man and left Upton shattered, eventually playing a part in her leaving Chicago.
The One Chicago Crossover Event “Reckoning” Rights ‘Chicago P.D.’s Biggest Wrong
Then comes “Reckoning,” another stellar crossover event, with all three shows under the One Chicago banner working together in the face of a deadly chemical attack that is unleashed on board a plane, killing everyone inside (the most eerie scene you will ever see this year) and threatening to do the same to anyone exposed, however briefly. FBI Special Agent Upton comes in because the case is first classified as a terrorist event. There are ties to a drug cartel investigation led by, you guessed it, Halstead, who arrives in time to come to Upton’s aid right when she’s taken down by a suspect. It’s not as surprising as you’d expect, with both Upton and Halstead aware that each would be in Chicago.
But when the crisis is over, Chicago P.D. gives fans the scene that rights its biggest wrong. Halstead finds Upton in the locker room, packing up, and asks when her flight is. He admits that he stayed to work on the case simply because she was there, while Upton admits she came because he was there too. Far less frosty than anticipated, but she turns around to leave after wishing him good luck.
Before she walks through the door, however, Halstead does what he should have done from the start: apologize. He apologizes for everything, for losing himself, leaving her, and how he didn’t find his way back to her. He’s sorry for all the wrong he did. She pauses and then apologizes back, and with a slight smile, before asking what time his flight is. Practically beaming, Halstead replies he doesn’t care, and Upton invites him to get a drink. Just like that, years of frustration and disappointment that fans had with the series because of its greatest sin melt away. Is it the reunion we hoped for? Perhaps not, but it is, at the very least, a suggestion that all is not lost. And if we never see them again, at least Upstead, at long last, gets a proper goodbye on a hopeful note.
