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Jesse Lee Soffer’s First-Ever Line as Jay Halstead Was Surprisingly Hilarious

Soffer actually appeared on Chicago Fire as Halstead before Chicago P.D. 

By Chris Phelan
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They say you only have one chance to make a great first impression. And for Chicago P.D. alum Jesse Lee Soffer, his first impression as his character Detective Jay Halstead was surprisingly hilarious. In a One Chicago retrospective shared on social media in 2021, Soffer looked back on Halstead's first-ever line in the franchise. Do you remember it? 

How to Watch

Watch Chicago P.D. Wednesdays at 10/9c on NBC and next day on Peacock

Let's go back to, interestingly, Chicago Fire Season 2, Episode 1, where Jay made his first One Chicago appearance in a guest role. He was undercover at Molly's and he asked the bar, "Hey, can I please send a couple of Long Island iced teas to the ladies in the corner?"

Soffer remembered saying the line like it was yesterday. "I guess at the beginning of the show, Jay Halstead was undercover… and on the prowl," he said in the video, below. So cheeky and funny in hindsight. 

It was an instantly classic line that creatively introduced the character of Detective Jay Halstead to One Chicago fans. Of course, his quirky attempt to get the affection of a couple of strangers earned him the nickname of "Mr. Long Island Iced Tea" by Monica Raymond's Gabriela Dawson

Jesse Lee Soffer and Tracy Spiridakos met up in Portugal

Soffer's Halstead was part of an unforgettable on-screen relationship with Hailey Upton, memorably portrayed by Tracy Spiridakos, on P.D. The two, affectionately shipped as "Upstead," ultimately ended their relationship because of Halstead moving to Bolivia. In real life, Chi-Hards will be happy to know that Soffer and Spiridakos are still good friends; they even recently met up on vacation together in Portugal! 

It's great seeing the pals spending time together—especially on holiday. 

Your favorite One Chicago shows return this fall on NBC

Although viewers won't see fan favorites like Soffer and Spiridakos in the One Chicago world this year, fans have enough reasons to get excited for the new seasons of Chicago Med, Chicago Fire, and Chicago P.D.—the premieres are just around the corner. 

Watch the premieres of Chicago Med, Chicago Fire, and Chicago P.D. on Wednesday, September 25 starting at 8/7c on NBC. Med airs first, followed by Fire then P.D. 

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