‘Chicago P.D.’ Season 9: Jay Halstead Actor Says Hailey Upton’s Motivations for Proposing Were ‘Murky’

Chicago P.D. Season 9 Episode 9 marks the fall season finale, and tensions are high for Jay Halstead, Hailey Upton, and Hank Voight. All season long, Upton’s had to deal with the consequences of shooting and killing Roy Walton. Later in the season, Halstead learned of Upton’s actions, jeopardizing their romance. And we can’t forget about the odd proposal Upton introduced into their relationship at the end of season 8. Here’s what Jay Halstead actor Jesse Lee Soffer said about Upton’s “murky” motivations.

Did Jay Halstead say ‘yes’ to Hailey Upton’s proposal at the start of ‘Chicago P.D.’ Season 9?

Tracy Spiridakos as Hailey Upton in 'Chicago P.D.' Season 9
Tracy Spiridakos as Hailey Upton in ‘Chicago P.D.’ Season 9 | Lori Allen/NBC

Jay Halstead and Hailey Upton developed a close relationship working together in the Intelligence Unit — and their relationship progressed heavily by the time Chicago P.D. Season 9 began. After Hailey Upton shot Roy Walton, she came home and proposed to Jay Halstead, catching him off guard. In season 9 episode 1, Halstead answered the proposal. He tentatively said yes, and he got down on one knee to properly propose to Upton. But he knew something was up with her strange actions.

Later in the season, Halstead tracked down Hank Voight to ask questions about Upton. Upton stopped eating and sleeping, but she refused to tell Halstead the truth about Walton. Finally, Voight told Halstead that Upton shot and killed Walton. This threw Halstead into a rage, and he confronted Upton about the truth.

By Chicago P.D. Season 9 Episode 8, the FBI knew something happened to Walton. They threatened Halstead to either rat out Voight for having something to do with Walton’s disappearance, or he and Upton would go down together. The Chicago P.D. Season 9 fall finale will address what Halstead decides to do.

Jay Halstead actor Jesse Lee Soffer said Hailey Upton’s motivations for proposing were ‘murky’

Hailey Upton and Jay Halstead certainly love each other. And Halstead feels loyal to Upton, or else he would’ve told the FBI what happened to Roy Walton. But Halstead actor Jesse Lee Soffer admitted Upton’s motivations for proposing were “murky,” though he thought the proposal was important and necessary to their relationship.

“It’s important to have that moment because even though the motivation on Hailey’s side is murky because she’s obviously going through such an emotional moment, and the guilt, and all this stuff,” Soffer told TVLine. “But it’s a real love between these two characters. I think for Jay to take the reins and say, ‘OK, yeah, this is how I feel, let’s do this,’ that’s important to see — that he’s not just along for the ride. That this is something that he wants.”

Their relationship could be in trouble in the ‘Chicago P.D.’ Season 9 fall finale

Jay Halstead, Hailey Upton, and Hank Voight in 'Chicago P.D.' Season 9
Jay Halstead, Hailey Upton, and Hank Voight | Lori Allen/NBC

The Chicago P.D. Season 9 finale will certainly test Jay Halstead and Hailey Upton. So far, Halstead hasn’t betrayed either Upton or Hank Voight — though FBI Agent North will certainly test Halstead’s loyalties. With so much internal conflict in the unit, Upton and Halstead’s relationship may crumble.

Given the synopsis for Chicago P.D. Season 9 Episode 9, though, it seems like Halstead is ready to fight for Voight and Upton. NBC describes the upcoming fall season finale with this synopsis, according to One Chicago Center: “With the FBI closing in on the Roy Walton investigation, Voight and Halstead strategize on a way out.” With this in mind, it seems like Voight, Halstead, and Upton will regain each other’s trust and work together to get themselves out of their current situation.

Chicago P.D. Season 9 Episode 9, the fall finale, airs Dec. 8, 2021, at 10 p.m. EST.

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