Welcome to Derry Could Have Solved a Lingering It Mystery
The clown's influence on the children of Welcome to Derry molds them long into adulthood, transforming them into the exact individuals who perpetuate the community's cycle of hatred alive. It finds easy targets on children from fractured homes — children who often mature to repeat the identical behaviors as their guardians. But, the Hanlon household stands apart as a rare example of a households that never splinters, which may explain why Mike Hanlon, even after electing to remain in the town, remains the only Loser who never fully falls under Pennywise's sway.
The Hanlon Family's Unique Resistance
In episode 4 of Welcome to Derry, Leroy at last grows increasingly conscious of the supernatural forces enveloping the neighborhood, particularly when the entity starts haunting his child, Will, during their angling excursion. The Hanlon family consists of a small number of grown-ups who are aware that something is amiss with the municipality, especially Leroy, who was shown to be sensitive to the Shining when he was capable of sensing Dick Hallorann's use of it in episode 3. Subsequently, he spots one of the clown's trademark inflated orbs outside his residence. The ability, alongside his failure to experience terror, combined with the base of his household, may be why he's able to see Pennywise's hauntings. However, consider if that shining is hereditary, and one of the reasons Mike is one of the only adults in Derry who didn't lose themselves to the town's malevolence?
Will is a member of the collective of children at his educational institution being tormented by the clown. All his school friends hail from dysfunctional families, with caregivers who don't believe they're being targeted. The cause Will is being pursued is due to the cruelty of the town, combined with his potential sensitivity to psychic abilities, which makes him susceptible. This family are fundamentally outsiders in Derry during the early sixties, which lends itself towards the family feeling anomalies exist about the town from the onset. They also have a solid base that isn't fractured, in contrast to the residents who originate in the area, with bonds that have decayed internally.
Backstory Connections
Drawing from the It novel, we know the juvenile Will will find himself at the Black Spot, where the psychic will save him from a fire that the local KKK members of the community will cause. In the 2017 film, we see that he has a boy named Mike and that Will ultimately dies in a configration, with his father surviving his own child and taking his grandson in. The public account in the film is that Mike's parents were on substances, but given our current view of Will in the series, that's difficult to accept. Perhaps the timid boy, once he became an adult, turned to alcohol to rid himself of the torments, or perhaps the corrupt environment affected him first, with the hate group ultimately completing the job it started years ago. Whether through the terror of the entity or via the cruelty of the town, instigated by Pennywise, the creature eventually gets the last laugh on him.
Leroy's Transformation
These occurrences would explain how Leroy changes so radically from what we see in the first film and Welcome to Derry. In his later years, Leroy appears resentful and much stricter with his parenting. Since he survived his own son, it's comprehensible to see such a profound shift. Nonetheless, his words carry more weight now that we know he's witnessed Pennywise's hauntings and the effects they wrought upon his son. In the initial sequence of the movie, we observe Mike pause to use a stunning device on a sheep at Leroy's farm. His grandfather chastises him for hesitating and provides an analogy that leads to a kill-or-be-killed scenario.
“You have two options you can be in this existence. You can be in the open like us, or you can be trapped inside,” Leroy states as he points to the sheep. “You dawdle indecisive, and someone is going to decide for you. Except you won't know it until you feel that projectile in your head.”
In hindsight, this could represent a piece of prediction, a lesson he regrets not imparting to his own child. Maybe he desires he had acted differently in his past, but for some reason, he was unable to avoid the sickening allure of the town.