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Dhruv Sharma
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It: Welcome to Derry's episode 5 reveals a chilling Pennywise twist before ending on an ambiguous note where it seemingly draws a connection to Doctor Sleep.
The young characters in It: Welcome to Derry struggle to understand what they should do next to save themselves from Pennywise. However, to their surprise, this is when Matty suddenly appears and claims that Phil might still be alive. Determined to save Phil from Pennywise before it is too late, Lilly convinces her friends to head to the sewers. In the meantime, even the military prepares to cage Pennywise to be able to eventually use it as a weapon.
In the episode's final arc, almost all the main characters in the Stephen King TV show find themselves in the murky depths of the sewer where Pennywise lives. All of them face the dire consequences of daring to cross paths with the cosmic being, and Leroy even makes a grave mistake. Hallorann seems to be affected the most because his encounter with the monster unleashes something he had "boxed" for a very long time.
Dick Hallorann's "Box" & Its Connection To Doctor Sleep's Dan Torrance Explained
Pennywise forces its victims to face their deepest fears before it tries to consume them. Owing to this, it exposes Dick Hallorann to a terrifying vision that combines his childhood trauma and his darkest fears surrounding his "shining" powers. In the vision, he finds himself in a confrontation with his grandfather who threatens to open his "box." When his grandmother asks him to resist, his grandfather tries to teach him a lesson by opening the box himself.
The episode does not explicitly reveal what the box contains but hints it has something evil inside it. It is hard not to see the box more as a visual representation of the "lockbox" ability possessed by the ones with the "shining" powers. Stephen King's Doctor Sleep also introduces the same ability through Dan Torrance, revealing that he has the power to construct mental boxes that trap evil forces. Hallorann has seemingly been using the same ability to trap many evil forces since his childhood.
However, after Pennywise takes control of his mind, the monster manipulates him into opening the box and unleashing all the evil it contains. This not only seems to make Pennywise a lot stronger but also releases other long-buried ghosts and spirits that were never meant to lurk in the human world.
Why Hallorann Grows Concerned After Seeing Pauly's Ghost
Dick Hallorann (Chris Chalk) looking alarmed in IT: Welcome to Derry episode 4
Leroy's closest friend in the military, Pauly, ends up dead before the It: Welcome to Derry episode ends. Surprisingly, however, Hallorann sees his ghost towards the end of the episode and notices how the pupils in his eyes have turned white and shallow. This seems to make him realize that Pauly is dead, and his ghost is aimlessly lurking in the human world.
Hallorann's grows increasingly concerned and confused after seeing Pauly because he seemingly realizes that Pennywise might have opened the portal between the living and the dead that he had seemingly kept sealed through the lockbox. The open gate between the living and the dead will now likely allow many evil forces from the Netherworld to lurk into the human world in future episodes.
This, in turn, will help Pennywise spread its terror across Derry even though it cannot physically escape its cage.
Pennywise's Plan To Lure Lilly & Her Friends Explained
Bill Skarsgard's Pennywise smiles under sinister lighting in It Welcome to Derry
Moments before Phil and his friends became Pennywise's victims in It: Welcome to Derry's episode 1, they saw an evil vision of Matty. Believing that Matty was still alive, they fell into Pennywise's trap and walked right into its lair. Pennywise seemingly uses the same trick in episode 5 by making Lilly and her friends believe that Matty is still alive. Realizing that Lilly would set out to save Phil if Matty told her he was possibly alive, Pennywise manipulates her with a vision of the young boy.
When the kids finally walk into the sewers, Matty suddenly morphs into Pennywise's clown form, revealing he was a mere projection of the clown all this while. The kids also find the bodies of Pennywise's previous victims, confirming that neither Phil nor Matty made it out alive. Fortunately, for Lilly and her friends, they manage to leave the sewers before it is too late.
How Taniel Unknowingly Saves Lilly From Pennywise
It: Welcome to Derry's episode 4 harkened back to Pennywise's origins, revealing how it arrived on Earth before humans through a fallen star. The episode also revealed that its only kryptonite is the fallen star and its shards, which were used by Rose and her people to keep the monster trapped in the woods. Before Taniel heads to the sewers with the military, Rose gives him one shard from the star to ensure he can protect himself and the others.
Taniel, however, accidentally drops the shard in the sewer while attempting to escape the men from the military. Moments later, Lilly almost becomes Pennywise's victim when she gets left behind by her friends. Luckily, for her, she ends up right next to the shard, which drives Pennywise away as soon as it tries to come close to her. With this, Lilly acquires the powerful weapon, which she will likely use in the show's future episodes to confront the monster.
Why Leroy Shoots Pauly
Jovan Adepo looking serious in It: Welcome to Derry©HBO / Courtesy Everett Collection
General Shaw recruited Leroy for Operation Precept in Derry because he knew about his previous acts of bravery. Leroy proves to be the ideal candidate to confront and contain Pennywise because of his inability to feel fear, which is the only thing Pennywise feasts on. Even in It: Welcome to Derry's episode 5, Shaw stands tall against the monster's manipulations when it tries to haunt him with a vision of his wife.
However, Shaw's fear nearly becomes his own undoing when he almost shoots his son, believing he is another projection of Pennywise's visions. Before he can harm his son, though, Pauly steps forward and takes the bullet.
Pennywise's "I Want You" Uncle Sam Form Explained
Pennywise smiling in It Welcome to Derry
In a brief sequence in It: Welcome to Derry's episode 5, two military men encounter Pennywise in the sewer. Interestingly, Pennywise takes the terrifying form of Uncle Sam from the "I Want You" recruitment posters. The posters first gained wide recognition in the United States during the American Civil War when they used to call for enlistment in the military. In more ways than one, the posters even became symbols of duty, sacrifice, and the pressure to be brave and unbreakable.
The two military men in the episode already struggle to keep themselves together as they walk deeper into the sewer. However, their responsibility as military men holds them back from heading out. By taking the form of Uncle Sam, Pennywise riffs on their deepest fear of authority and not being able to respect the chain of command. Unfortunately, they, too, fall for Pennywise trap and become its victims in the It: Welcome to Derry's episode.
It: Welcome to Derry
TV-MA
Horror
Mystery
Drama
7/10
48
9.1/10
Release Date
October 26, 2025
Network
HBO
Cast
Taylour Paige, Jovan Adepo, James Remar, Stephen Rider, Matilda Lawler, Amanda Christine, Clara Stack, Arian S. Cartaya, Peter Outerbridge, Chris Chalk, Rudy Mancuso, Alixandra von Renner, Dmitry Chepovetsky, Eli Katz, Mark MacRae, Lochlan Ray Miller, Maya McNair, Maya Misaljevic, Hannah Storey, Thomas Mitchell, Chad Rook, Michael Koras, Robert Clarke, Brittany Spiteri, Sean Sansom
Directors
Andy Muschietti
Writers
Jason Fuchs, Stephen King, Austin Guzman
Franchise(s)
IT
Main Genre
Horror
Genres
Horror, Mystery, Drama
Creator(s)
Andy Muschietti, Barbara Muschietti, Jason Fuchs
Executive Producer(s)
Andy Muschietti, Bárbara Muschietti, Bill Skarsgård, Brad Kane, Dan Lin, Jason Fuchs, Roy Lee, David Coatsworth, Shelley Meals
Producers
Anna Beben, Cherie Dimaline, Sarah Rath
Seasons
1
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