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Pennywise's impact on the children of Welcome to Derry molds them long into adulthood, transforming them into the exact individuals who perpetuate the community's pattern of animosity alive. The creature finds easy targets on kids from fractured households — youngsters who often mature to replicate the same patterns as their parents. But, the Hanlon family stands apart as one of the few family unit that remains intact, which could clarify why Mike Hanlon, even after electing to remain in the town, remains the sole member who doesn't completely succumb under the clown's influence.

Hanlon Household's Unique Resilience

In episode 4 of Welcome to Derry, Leroy finally becomes more aware of the paranormal entities enveloping the neighborhood, especially when the entity begins tormenting his son, Will, during their angling excursion. The Hanlon clan consists of a small number of grown-ups who are cognizant that things are not right with the town, especially Leroy, who was shown to be sensitive to psychic abilities when he was capable of sensing Dick Hallorann's employment of it in episode 3. Subsequently, Leroy sees one of Pennywise's signature balloons outside his residence. This gift, coupled with his inability to feel fear, along with the foundation of his family, may be why he's able to see the entity's manifestations. But what if that shining is generational, and a key factor Mike is one of the only individuals in the town who didn't lose themselves to its cruelty?

The boy is a member of the collective of kids at his educational institution being tormented by Pennywise. All his school friends hail from dysfunctional families, with caregivers who refuse to accept they're being haunted. The reason Will is being haunted is due to the cruelty of the town, paired with his likely receptiveness to psychic abilities, which renders him vulnerable. This family are ultimately outsiders in Derry during 1962, which lends itself towards the household feeling anomalies exist about the locality from the beginning. Additionally, they possess a solid base that remains unbroken, unlike the residents who come from the town, with bonds that have deteriorated internally.

Historical Context

Based on the original book, we know the juvenile Will will find himself at the Black Spot, where Hallorann will save him from a blaze that the local KKK members of the community will ignite. In the 2017 movie, we see that Will has a son named Mike and that Will ultimately dies in a configration, with his father outliving his own child and adopting his grandchild. The official story in the motion picture is that the parents were on drugs, but given our current view of him in Welcome to Derry, that's hard to believe. Maybe the timid boy, once he became an adult, turned to alcohol to free himself of the torments, or perhaps the rotten town affected him initially, with the hate group ultimately finishing the task it started years ago. Whether through the fear of Pennywise or through the malice of the town, instigated by It, It in the end achieves the last laugh on him.

Leroy's Transformation

This chain of events would clarify how Leroy transforms so radically from what we see in the first film and the prequel. In his later years, he appears bitter and much harsher with his parenting. Because he survived his own son, it's understandable to see such a profound shift. However, his words hold greater significance now that we know he's witnessed Pennywise's hauntings and the impacts they had on his son. In the opening scene of the movie, we observe Mike hesitate to use a bolt gun on a sheep at the family property. Leroy reprimands him for delaying and offers an analogy that leads to a kill-or-be-killed situation.

“You have two options you can be in this existence. You can be in the open like we are, or you can be trapped inside,” he says as he gestures to the creature. “You dawdle hemming and hawing, and another is going to make that choice. But you won't know it until you feel that bolt in your head.”

In hindsight, this could be a bit of foreshadowing, something he wishes he had told his own child. Maybe he wishes he had acted differently in his past, but for certain factors, he couldn't resist the repellent allure of Derry.