'Chicago P.D.' Season 9: Jay Halstead's Military Past Will Come Back to Haunt Him, Jesse Lee Soffer Says

Chicago P.D. Season 9 Episode 1 finally answered one of the many burning questions fans wanted to know. During the Chicago P.D. Season 8 finale, Hailey Upton proposed to Jay Halstead suddenly and without warning — and Halstead had yet to respond. He finally accepted her proposal in the season 9 premiere. But it looks like Jay Halstead and Hailey Upton’s relationship may be past impacted by Halstead’s past. Here’s what actor Jesse Lee Soffer explained.

[Spoiler alert: Chicago P.D. Season 9 Episode 1 spoilers ahead regarding Halstead and Upton’s relationship.]

‘Chicago P.D.’ Season 9 Episode 1 featured Jay Halstead and Hailey Upton’s engagement

Chicago P.D. Season 9 Episode 1 started off with a big moment for Jay Halstead and Hailey Upton. During the Chicago P.D. Season 8 finale, Upton proposed to Halstead — and he was shocked by the proposal. This, of course, came after Upton killed Roy, the perpetrator who shot Kim Burgess. Upton and Hank Voight didn’t tell anyone about Roy’s death. Instead, Voight did away with the body, and Upton was left to sweat about the future consequences.

Finally, in episode 1 of the new season of the show, Halstead answered Upton. But he first asked if she was just asking him to marry her because of what happened to Burgess.

“Maybe,” she answered, “but why does that matter? I love you. … Maybe it took Kim getting shot to give me the courage to tell you that.”

In the end, Halstead got down on one knee and gave Upton a proper proposal. They ended the premiere engaged.

Jesse Lee Soffer said the show will delve deeper into Jay Halstead’s military past

Jay Halstead and Hailey Upton ended Chicago P.D. Season 9 Episode 1 happier than ever. But we imagine they’ll have a number of setbacks. While Upton has to fight her own demons, Halstead has to as well. And Halstead actor Jesse Lee Soffer spoke to TVLine about what’s coming next for Halstead.

“There’s a clearer picture as to why Jay doesn’t want to talk about his time in the Army,” Soffer tells TV Line. He also hinted fans will see exactly what he means in Chicago P.D. Season 9 Episode 3.

Additionally, Soffer told One Chicago Center fans will see “someone from Jay’s past” this season. “We haven’t done a lot about his military background in a while, but, in the beginning of the season, there’s a great episode where someone from Jay’s past who he served with in Afghanistan comes back,” the actor adds.

Jay Halstead and Hailey Upton’s relationship might be in trouble

We’re not sure exactly what’s in store for Jay Halstead and Hailey Upton in Chicago P.D. Season 9. But given Upton’s recent circumstances with Roy and Halstead’s military past, we imagine their relationship is about to get very complicated.

Despite it all, Soffer guarantees there’s true love between the characters — and perhaps love will conquer all. But executive producer Rick Eid said “consequences” may come for Upton and Voight after their cover-up. This could deeply affect Upton and Halstead’s engagement.

“They are both complicit in the cover-up, and consequences could fall down hard on them both,” executive Eid told TV Insider.

Chicago P.D. Season 9’s air date is every Wednesday at 10 p.m. EST on NBC.

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