Chicago Med Keeps Dropping Clues About Will And Natalie, So Is Manstead Payoff Coming In The Finale?

Nick Gehlfuss as Will Halstead in Chicago Med Season 8
(Image credit: NBC)

Warning: spoilers ahead for Episode 21 of Chicago Med Season 8, called “Might Feel Like It’s Time for a Change.”

Chicago Med is just one episode away from summer hiatus and the long wait for the doctors and nurses of NBC’s hit medical drama to return, with the potential complication of the WGA writers strike. Before the break, however, the show has what looks like an action-packed finale, and a moment from the penultimate episode leads me to wonder if we’re on the verge of a surprise Manstead development. 

Manstead was arguably the biggest relationship of Chicago Med up until Torrey DeVitto’s departure as a series regular at the end of Season 6, and Will (Nick Gehlfuss) and Natalie parted on good terms when she made a cameo in the Season 7 premiere, which is available streaming via Peacock Premium subscription. Will hasn’t really dwelled on her too much since she left, but after “Might Feel Like It’s Time for a Change” dropped a touching reference, I can’t help but feel that the show is building to a payoff, for better or worse. 

Following a big throwback in March with Will talking about Natalie to Hannah (Jessy Schram) of all people, the latest episode delivered a scene early on with him smiling at a drawing from Owen, who should be around 7 years old at this point. It’s hard to blame him for smiling, since it was a drawing of Will himself, and he explained to Grace (TV Carpio) that he got it from his “friend Owen” and that he and Natalie keep in touch. He went on to tell Grace that he doesn’t think their attempt at a relationship will work. 

So, in one short scene, Will established that he and Natalie still talk, revealed that Owen remembers him well enough to draw a picture that’s as accurate as one could hope from a 7-year-old, and shut down a romantic future with Grace. Throw in that the promo for the Season 8 finale says that “SOMEONE WILL GO” and Med has managed to sneakily include Torrey DeVitto without spoiling it before, and I’m entertaining the idea that the show is bringing back Natalie to write Will out. 

Now, is this partly informed by the fact that I was at an impressionable age when I saw how ER reunited George Clooney’s Doug and Julianna MarguliesCarol back in the day? Almost certainly, but it’s worth noting that Chicago Med brought back Yaya DaCosta as April to reunite her with Ethan and say goodbye to Brian Tee. As much as I’d hate to lose Nick Gehlfuss and Will Halstead, I would applaud the show for keeping a tight lid on the spoiler. I’m hoping that Manstead at least gets another mention!

I don't think a goodbye to Will is entirely out of the question, even if it is partly rooted in me watching ER reruns as a kid. I’m certainly excited to see what happens! Plus, the promo previews that all the conflict about OR 2.0 is going to come to a head with Jack Dayton (Sasha Roiz), Crockett (Dominic Rains), and Will, with Goodwin (S. Epatha Merkerson) in a difficult position and Dean (Steven Weber) in need of a kidney. Check out the promo:

Tune in to NBC on Wednesday, May 24 at 8 p.m. ET for the Season 8 finale of Chicago Med, followed by the Season 11 finale of Chicago Fire (with the return of Jesse Spencer as Matt Casey) at 9 p.m. and the Season 10 finale of Chicago P.D. in the wake of a shocking episode for Torres (Benjamin Levy Aguilar) at 10 p.m. All the shows have been renewed for the 2023-2024 TV season, so Med will absolutely be back, with or without Manstead payoff in the Season 8 finale. 

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).