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Private: ‘IT: Welcome to Derry’s Final Mystery Centers on the Tragic Fate of Will Hanlon: “Why Would Will Have Gone Back into the Cage?”

ZamPointBy ZamPointDecember 15, 2025No Comments4 Mins Read
‘IT: Welcome to Derry’s Final Mystery Centers on the Tragic Fate of Will Hanlon: “Why Would Will Have Gone Back into the Cage?”
Photo: HBO

IT: Welcome to Derry Episode 8 “Winter Fire” theoretically wraps the first season of the HBO show up with a happily ever after. However, multiple moments in the Welcome to Derry season finale hit differently if you remember the first time we met Jovan Adepo‘s Leroy Hanlon as an old man (Steven Williams) in Andy Muschietti‘s 2017 film, It.

**Spoilers for IT: Welcome to Derry Episode 8 “Winter Fire,” now streaming on HBO Max**

In Muschietti’s original adaptation of Stephen King’s It, Leroy is dead set on toughening his orphaned grandson Mike (Chosen Jacobs) up. He wants Mike to be able to kill livestock in the farm’s abattoir without flinching, comparing him unflatteringly to his deceased father, Will (Blake Cameron James).

Considering the fact that the Leroy of IT: Welcome to Derry takes a gentler approach with young Will — letting him know at a pivotal moment he doesn’t have to be brave like him — what are we to make of Grandpa Leroy’s harsh life lesson? One in which he tells Mike that in life, you can either be outside the killing pen pulling the trigger or inside with the sheep about to be slaughtered?

Couple this with the fact that in Muschietti’s version of events, Will and his eventual wife (who might or might not be Amanda Christine‘s Ronnie Grogan?) are killed in an arson, and we have to wonder… What exactly happened to Leroy and Will’s relationship between IT: Welcome to Derry and It?

“I think that’s a great mystery,” IT: Welcome to Derry co-showrunner Jason Fuchs said. “We don’t know, because Leroy ends, obviously, this season outside the cage of Derry. He’s made the choice to stay behind to help tend to the cage, essentially.”

“The question is, why would Will have gone back into the cage?” he continued. “Did Will forget? Which is sort of possible, right? There’s a lot of ambiguity in terms of the rules relating to memory.”

Leroy Hanlon (Jovan Adepo) telling Will (Blake Cameron James) he loves him in 'IT: Welcome to Derry' Episode 8 Photo: HBO

IT: Welcome to Derry ends with Will writing to Ronnie that he doesn’t know what they will or won’t remember. Is it possible that Will totally forgot that Derry once spelled danger for him and his friends?

“So, I don’t know why Will went back in. I don’t know if it’s because he forgot, the memories went away. I don’t know if it’s because he had something so important that required him to go back inside Derry,” Fuchs said. “We just don’t know the answer to those things, but it certainly casts that scene that you’re referring to at the beginning of Chapter One in a very different light when you think about what Leroy says to Mike.”

Fuchs points out that Leroy’s lesson about the sheep and the pen may very well be a metaphor for Derry. “Well, is he talking about the cage? Is he trying to tell Mike something? Does Leroy remember the truth of all this at that point? I don’t know.”

Lest you think that Fuchs is teasing that future seasons might tackle this mystery, think again.

“Those are mysteries that part of me never wants to know the answer to, because I think part of what makes It so special is that there are these enduring mysteries that we don’t have the answers to,” Fuchs said.

“We’ve certainly done our fair share of demystifying a lot of those things in the context of this show so it feels like we have to pay it forward a bit in terms of leaving some mysteries for people to chew on.”

Do you think something happened while Pennywise was “dormant” to draw Will and his bride back into Derry’s cage?

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