Chicago P.D.'s Best Upstead Moments That Already Make Me Miss Jesse Lee Soffer's Jay Halstead

Chicago P.D. is gearing up to make one of the biggest changes in its ten-season history by saying goodbye to Jesse Lee Soffer as Detective Jay Halstead. He has been part of the One Chicago universe for more than 200 episodes between the three shows, and even appeared on Chicago Fire before P.D. even premiered. While there are too many standout moments for him as a character to count and list, his relationship with Hailey Upton has created some of the most emotionally poignant stories in this procedural TV show over the last several years.

So, in light of his exit in Season 10, I was ready to look back at my favorite Upstead moments that are already making me miss Jesse Lee Soffer and what he brought to the show. Let’s start with a blast to the past, of Tracy Spiridakos’ first full season as a series regular playing Halstead’s partner!

Jesse Lee Soffer as Halstead in Chicago PD Season 5

(Image credit: NBC)

Halstead Invites Himself In – Season 5 - “Ghosts”

While “Ghosts” was primarily an Upton episode, it was also an episode that bonded them as friends and partners beyond their work in the Intelligence Unit. She went rogue, he pushed back to try and help her, and the episode ended with him deciding to crash her evening so she wouldn’t be alone with her ghosts after physically and emotionally going through the wringer. He got her to open up for one of the first times on Chicago P.D. He knew she wasn’t fine, so he stayed. 

Jesse Lee Soffer in Chicago PD Season 6 as Jay Halstead

(Image credit: NBC)

Nothing Good Comes Of A Workplace Romance - Season 6's "True or False"

The era of Upton and Ruzek’s secret relationship actually was pretty solid for Upstead as a duo, including when Halstead came over to Upton’s for a drink and a heart-to-heart during a rough case. Ruzek made things awkward when he showed up and then promptly left, leading Halstead to wonder if Ruzek got the wrong impression. She responded that she doesn’t date people she works with, which Halstead deemed a “good policy” because “nothing good comes out of a workplace romance.” And surprisingly, neither of their pants caught on fire from how much they were lying!

Halstead and Upton in Chicago P.D. Season 6 episode "Trigger"

(Image credit: NBC)

The Thing That Works - Season 6's "Trigger"

Halstead’s continued struggles with PTSD resurfaced in “Triggers” after a series of bombings, not helped by the reveal that it was another veteran who was ultimately responsible. He wasn’t exactly feeling his best and tried to tell Upton that he wanted to be alone, leading her to explain the “thing that works” between them: even when one doesn’t want the other around, the other stays anyway, they talk, and they feel better. The pep talk worked – he opened up, she listened, and he felt better. 

Tracy Spiridakos as Upton in Chicago PD Season 6

(Image credit: NBC)

Upton Would Follow Him Blind - Season 6's "Good Men"

In the Chicago P.D. half of a Season 6 crossover with Chicago Fire, Halstead made a judgment call that seemed like a pretty terrible idea, but Upton followed his lead after he looked at her and she “got it.” She told him that she trusted him from the day they met, and if she was going to follow someone blind, it would be him. He returned the sentiment in Season 7, telling her that he’d follow her anywhere. Who doesn’t love a good parallel in a mostly procedural TV show?

Upton and Halstead walking in hospital in Chicago PD Season 7

(Image credit: NBC)

Reunited, And It Felt So Good - Season 7's "Intimate Violence"

Upton and Halstead were actually split as partners for a lot of Season 7, but were officially put back together in “Intimate Violence.” Both clearly felt good to be partnered up again. There was a lighthearted moment – yes, in Chicago P.D.! – in the middle when he ended up having to buy a bouquet of roses to protect his cover and gave them to his partner, and then a much more serious moment when they did their “thing that works” after he attacked a domestic abuser and she opened up more about her past.

Halstead on the phone with Upton in Chicago PD Season 7

(Image credit: NBC)

Absence Makes The Flirting Go Harder - Season 7's "Silence of the Night"

Toward the end of Season 7, Upton was sent off to FBI for a crossover. Unlike the last time Halstead had a partner leave to work with the feds in New York, Upton kept in close contact with him, and was evidently homesick enough to open up about missing pizza, the wind, and him. This gets a spot on this list just because I love the idea that they were only comfortable actually flirting when it was over the phone with several hundred miles between them. Running into gunfire? Sure. Light flirtation? Save it for the safety of a phone call!

Chicago P.D.'s Upton and Halstead about to kiss in Season 8

(Image credit: NBC)

They Pass The Point Of No Return - Season 8's "Tender Age"

“Tender Age” delivered the game-changer that featured Upton confessing her feelings and Halstead kissing her. While I give the episode credit for shocking the hell out of me when he went for a kiss instead of a hug, my favorite part was actually Halstead trying and failing to seem happy about her FBI offer throughout the episode. It’s worth a laugh looking back, but he was still supportive of her if she wanted to take the job in New York, which just proved why he was the kind of partner she wouldn’t want to leave. Plus, they kissed! (And I can’t emphasize enough that I 100% thought he was going for a hug.)

Upton and Halstead in Chicago PD Season 8

(Image credit: NBC)

The Morning (And Day) After - Season 8's "Unforgiven"

As “Unforgiven” proved when it picked up the morning after Upton’s confession, Halstead definitely wasn’t just going for a hug after the previous episode’s cut to black! While it’s not exactly a fun or lighthearted episode other than the opening moments of the two in bed, I get a laugh in hindsight out of how Halstead immediately went into serious relationship mode after they spent one night together, expecting to go meet her family in the hospital as soon as she got bad news about her dad. With Chicago P.D., get your laughs and enjoy heartwarming moments where you can!

Upton looking at Halstead in Chicago PD Season 8

(Image credit: NBC)

The First "I Love You" - Season 8's "Signs of Violence"

“Signs of Violence” in Season 8 got off to such a happy and romantic note that fans probably should have realized immediately that something would spoil it. Halstead accidentally spooked Upton by triggering some of her childhood trauma when he told her he loved her, and the case of the week was an ugly one as she spiraled. But he came over when she asked him to and promised that he wasn’t going anywhere, and she was able to say it back

Chicago P.D. Halstead proposes to Upton in Season 9

(Image credit: NBC)

Halstead Proposes - Season 9's "Closure"

I wasn’t a fan of Upton’s proposal to Halstead in the Season 8 finale since it was more or less a product of her panic after shooting Roy, and it was very fast after less than a full season of dating with no sign that they’d discussed marriage. Halstead fixed the situation for me by the end of the Season 9 premiere, when he needed to know if she only wanted to get married as a reaction to what happened to Burgess. Once she clarified, they were on the same page. He had a little speech of his own and dropped down on one knee to propose. Romance: Chicago P.D.-style!

Chicago PD Upton having a panic attack in Season 9

(Image credit: NBC)

Halstead Figures Out Why Upton Is Spiraling - Season 9's

I’ll be honest: even though it’s not the most romantic, “In the Dark” in Season 8 is my favorite Upstead episode, partly because Jay finally got to be proactive instead of just concerned. He clocked that something was very wrong with Upton when she was scratching herself bloody and unable to sleep from guilt, and she seemed on the verge of finally ‘fessing up about killing Roy. Tracy Spiridakos and Jesse Lee Soffer were at their best as Halstead helped Upton through her panic attack, and then brushed off his detective skills when he saw Voight stare her down until she forced herself to calm down.  

And he figured it out and forced a confrontation with Voight! Even when Voight revealed that Upton was the one who pulled the trigger, Halstead maintained the responsibility was solely Voight’s because of what he'd done to her. The sergeant – in a spectacular failure to read the detective’s mood – said he didn’t think Halstead knew who he was sleeping next to, and Halstead punched him in the face. He was justifiably upset about the secret, but he went to bat for her 100%. I’d un-watch and rewatch this episode again for the first time if I could!

Halstead and Upton get married in Chicago PD Season 9

(Image credit: NBC)

The Courthouse Wedding - Season 9's "A Way Out"

After taking some time, Halstead decided that he was still all-in on their relationship, even telling her that he didn't want her to turn herself in for killing Roy because he’d rather not start their marriage with the woman he loves in prison. So, after he managed to bring the FBI investigation to an end in the midseason finale, Halstead decided that he wanted to marry her ASAP. In a very smart decision considering what has happened to weddings on both Chicago Med and Chicago Fire, they eloped at the courthouse in a wedding scene intercut with their much less restrained wedding night. All in all, it was a cathartic way to head into hiatus. 

Upton and Halstead in Chicago PD Season 10 premiere

(Image credit: NBC)

They Avoid A Fight - Season 10's "Let It Bleed"

Season 10 hasn’t exactly delivered an abundance of Upstead moments, but one that stood out to me in the Season 10 premiere was when Upton was trying to bring Halstead around to the idea that it’s not his job to help Voight through his messy situation. He responded “I know,” not altogether convincingly, so she tried to make the point again. Instead of snapping, he just responded with “I said I know.” It could have become a fight, they remained on the same page. And it was better than the tension and secrets in the next episode!

Just as there are too many impactful Halstead moments to count, there were too many memorable Upstead moments to list here, but these are the ones that stand out to me at the end of an era. No matter how Chicago P.D. ultimately says goodbye to Jesse Lee Soffer’s character after ten seasons, fans can always reflect on (and rewatch streaming with a Peacock subscription) their favorite parts of Halstead’s long story. New episodes of Chicago P.D. will continue airing on Wednesdays at 10 p.m. ET on NBC even after Halstead is gone.

Laura Hurley
Senior Content Producer

Laura turned a lifelong love of television into a valid reason to write and think about TV on a daily basis. She's not a doctor, lawyer, or detective, but watches a lot of them in primetime. CinemaBlend's resident expert and interviewer for One Chicago, the galaxy far, far away, and a variety of other primetime television. Will not time travel and can cite multiple TV shows to explain why. She does, however, want to believe that she can sneak references to The X-Files into daily conversation (and author bios).