The central story of HBO’s Welcome to Derry escalated dramatically in its fifth episode, titled “Neibolt Street.” The episode, which aired on November 23, 2025, finally brought the show’s characters face-to-face with Bill Skarsgård’s Pennywise in the dreaded sewers, leading to a major character death and a game-changing psychological defeat for one hero.
The Descent into the Sewers
The episode saw both the group of kids and the military operation descending into the labyrinth of tunnels beneath Derry, all paths converging on the evil lurking at 29 Neibolt Street. The children, seeking their lost friend Phil, took a handful of Lilly’s mother’s prescription pills in an attempt to numb their fear, leaving them heavily sedated and vulnerable in the depths. Meanwhile, Major Leroy Hanlon and his team, guided by Dick Hallorann and Taniel, were in the same sewers searching for the ancient pillars that can control the creature.
The horror unfolded quickly as Pennywise tormented them with visions. Leroy saw his wife, Charlotte, morph into a long-fanged monster, forcing him to open fire. The kids were confronted with the floating bodies of their dead friends. The tension peaked when the missing boy, Matty, began singing and transformed into Pennywise, revealing the clown’s monstrous set of teeth and sending the children fleeing.
A Heroic Sacrifice and a Narrow Escape
In the ensuing chaos, Leroy’s son, Will, ran toward the armed soldiers. Leroy, believing his son to be another one of Pennywise’s illusions, raised his gun to shoot. Seeing the real danger, Captain Pauly Russo pulled the weapon toward himself, taking the fatal bullet to save Will. Pauly died in Leroy’s arms as he apologized to his friend.
Another child, Lilly, was also cornered by Pennywise. The clown taunted her with a drawn-out “Tooo baaad, sooo saaaad” before closing its mouth and disappearing. Lilly was spared when she discovered one of the glowing, powerful pillars in the water at her feet.
Dick Hallorann’s Psychological Defeat
While Dick Hallorann physically survived the ordeal, he suffered a critical psychological loss. Pennywise attacked him by infiltrating his mind, transporting him to a vision of his childhood bathroom. There, the clown took the form of Dick’s abusive grandfather, who forced open a mysterious “lockbox.”
This box is a psychic construct Dick’s grandmother taught him to use, a place to trap all the terrifying memories and entities he has encountered. Chris Chalk, the actor who plays Dick, explained the concept: “All the terror that he has ever seen, he just slipped it in the box… These are not entities that want to be trapped. And so when they can break free, they do and it changes Dick forever.”
The episode ended with a shellshocked Dick emerging from the sewers, now able to see the dead, glassy-eyed spirit of Pauly. With his lockbox forced open, the dark contents of his mind are now free, taking Dick to what executive producer Jason Fuchs described as “some extremely dark places.”
The Aftermath and Looking Ahead
The discovery of the pillar by Lilly and the opening of Dick’s lockbox set the stage for the final three episodes of the season. The characters now have a potential weapon against the evil, but they have also lost a key ally in Pauly, and one of their most powerful psychic defenders has been profoundly compromised.
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