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Pennywise's influence on the children of the Derry series shapes them long into adulthood, transforming them into the exact individuals who perpetuate the community's cycle of animosity alive. The creature preys most easily on children from fractured homes — children who frequently mature to repeat the same patterns as their parents. However, the Hanlon household distinguishes itself as a rare example of a households that remains intact, which could clarify why Mike Hanlon, even after electing to remain in the town, remains the only Loser who doesn't completely succumb under Pennywise's sway.

The Hanlon Family's Unique Resilience

In the fourth installment of Welcome to Derry, Leroy at last grows increasingly conscious of the supernatural forces surrounding the community, particularly when the entity starts haunting his child, Will Hanlon, during their fishing trip. The Hanlon clan comprises some of the few adults who are cognizant that things are not right with the municipality, especially the father, who was revealed to be receptive to psychic abilities when he was capable of sensing Dick Hallorann's use of it in the third episode. Subsequently, he spots one of Pennywise's signature inflated orbs outside his house. This gift, coupled with his failure to feel fear, along with the base of his household, may be why he's able to see Pennywise's hauntings. But what if that psychic sensitivity is hereditary, and one of the reasons Mike is one of the only individuals in Derry who didn't lose themselves to its cruelty?

Will is part of the collective of kids at his educational institution being tormented by the clown. All his school friends come from broken homes, with parents who refuse to accept they're being targeted. The reason Will is being haunted is due to the cruelty of the town, combined with his likely receptiveness to shine, which makes him susceptible. This family are ultimately strangers in the town during 1962, which contributes towards the family sensing anomalies exist about the town from the onset. They also have a solid base that remains unbroken, in contrast to the residents who originate in the area, with bonds that have deteriorated within.

Historical Context

Based on the It novel, we know the juvenile Will will find himself at the infamous nightclub, where Hallorann will rescue him from a fire that the town bigots of the community will ignite. In the 2017 film, we see that he has a boy named Mike and that Will ultimately dies in a configration, with his father outliving his own child and adopting his grandchild. The public account in the film is that Mike's parents were on substances, but now that we see him in the series, that's difficult to accept. Perhaps the shy boy, once he grew up, turned to alcohol to free himself of the torments, or perhaps the rotten environment got to him first, with the KKK eventually completing the task it began long before. Whether through the fear of the entity or through the malice of the town, instigated by Pennywise, the creature eventually gets the last laugh on him.

Leroy's Transformation

These occurrences would explain how Leroy transforms so radically from what we witness in the first film and the prequel. In his older age, he seems resentful and much harsher with his parenting. Because he survived his own son, it's understandable to see such a drastic change. However, his words hold greater significance since we are aware he's witnessed Pennywise's hauntings and the effects they had on his child. In the opening scene of It, we see Mike hesitate to use a bolt gun on a animal at Leroy's farm. Leroy reprimands him for hesitating and provides an metaphor that results in a survival-of-the-fittest situation.

“You have two options you can be in this world. You can be out here like us, or you can be in there,” he states as he points to the sheep. “You waste time indecisive, and another is going to decide for you. But you won't know it until you feel that bolt between your eyes.”

Looking back, this could represent a bit of foreshadowing, something he wishes he had told his own son. Maybe he desires he had acted differently in his past, but for some reason, he couldn't resist the repellent attraction of Derry.