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Pennywise's influence on the children of Welcome to Derry molds them throughout their adult lives, twisting them into the exact individuals who keep the community's pattern of hatred alive. It preys most easily on kids from fractured homes — children who frequently mature to repeat the same patterns as their guardians. However, the Hanlon family distinguishes itself as one of the few households that never splinters, which could clarify why Mike, even after electing to remain in the town, remains the sole member who doesn't completely succumb under Pennywise's sway.

The Hanlon Family's Distinctive Resilience

In the fourth installment of Welcome to Derry, Leroy finally becomes more aware of the supernatural forces surrounding the community, particularly when It begins tormenting his son, Will Hanlon, during their fishing trip. The Hanlon family comprises some of the few grown-ups who are aware that something is amiss with the town, especially Leroy, who was shown to be sensitive to the Shining when he was able to detect a fellow psychic's employment of it in episode 3. Subsequently, Leroy spots one of Pennywise's signature balloons outside his house. The ability, alongside his failure to feel fear, along with the base of his household, could be why he's able to see the entity's manifestations. But what if that psychic sensitivity is hereditary, and one of the reasons Mike Hanlon is one of the only adults in the town 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. His classmates come from broken homes, with caregivers who refuse to accept they're being haunted. The reason Will is being pursued is because of the cruelty of the community, combined with his likely receptiveness to psychic abilities, which makes him susceptible. This family are fundamentally strangers in Derry during 1962, which lends itself 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 folks who come from the town, with bonds that have decayed internally.

Historical Context

Drawing from the It novel, we understand the juvenile Will will find himself at the infamous nightclub, where Hallorann will save him from a blaze that the local KKK members of the community will cause. In the 2017 film, we see that Will has a boy named Mike and that the father ultimately dies in a configration, with Leroy surviving his own child and adopting his grandchild. The official story in the motion picture is that the parents were on substances, but now that we see Will in Welcome to Derry, that's hard to believe. Perhaps the shy boy, once he became an adult, leaned into drink to free himself of the torments, or maybe the rotten town affected him initially, with the KKK eventually completing the task it began long before. Whether through the fear of Pennywise or via the cruelty of the community, instigated by It, the creature in the end gets the final victory on him.

Leroy's Transformation

These occurrences would explain how Leroy changes so drastically from what we witness in It: Chapter 1 and the prequel. In his older age, he appears bitter and much harsher with his discipline. Since he outlived his own offspring, it's comprehensible to observe such a profound shift. However, his statements hold greater significance since we are aware he's witnessed the clown's activities and the effects they had on his child. In the opening scene 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 offers an analogy that leads to a survival-of-the-fittest situation.

“There are two places you can be in this existence. You can be in the open like us, or you can be in there,” Leroy states as he gestures to the creature. “You dawdle indecisive, and someone is going to decide for you. But you won't know it until you feel that bolt in your head.”

Looking back, this could represent a piece of foreshadowing, something he regrets not imparting to his own child. Perhaps he wishes he had done something in his youth, but for some reason, he was unable to avoid the sickening allure of Derry.