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Pennywise's influence on the children of the Derry series shapes them throughout their adult lives, transforming them into the exact individuals who perpetuate the community's cycle of animosity ongoing. It finds easy targets on kids from fractured homes — children who frequently mature to replicate the same patterns as their parents. However, the Hanlon household stands apart as a rare example of a households that never splinters, which could clarify why Mike Hanlon, even after electing to remain in the town, remains the sole member who doesn't completely succumb under Pennywise's sway.

Hanlon Household's Distinctive Resilience

In the fourth installment of Welcome to Derry, Leroy finally becomes increasingly conscious of the paranormal entities surrounding the community, especially when It starts haunting his son, Will, during their fishing trip. The Hanlon family consists of some of the few adults who are cognizant that something is amiss with the town, notably Leroy, who was revealed to be receptive to the Shining when he was capable of sensing a fellow psychic's employment of it in the third episode. Later, Leroy sees one of Pennywise's signature balloons outside his residence. The ability, alongside his failure to experience terror, combined with the foundation of his household, could be why he's able to see Pennywise's hauntings. But what if that shining is hereditary, and one of the reasons Mike is among the few individuals in the town who didn't lose themselves to its cruelty?

Will is part of the group of children at his school being tormented by Pennywise. His classmates hail from dysfunctional families, with parents who don't believe they're being haunted. The reason he is being pursued is because of the viciousness of the community, combined with his likely receptiveness to shine, which renders him vulnerable. This family are fundamentally outsiders in the town during 1962, which contributes towards the family feeling anomalies exist about the locality from the beginning. They also have a good foundation that remains unbroken, unlike the residents who originate in the area, with relationships that have decayed within.

Historical Context

Based on the It novel, we know the juvenile Will Hanlon will find himself at the Black Spot, 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 he has a son named Mike and that Will ultimately dies in a fire, with Leroy surviving his own child and adopting his grandchild. The public account in the film is that the parents were on drugs, but now that we see Will in the series, that's difficult to accept. Perhaps the timid boy, once he grew up, turned to drink to rid himself of the torments, or perhaps the corrupt town affected him initially, with the KKK eventually finishing the task it started years ago. Whether through the fear of the entity or via the cruelty of the town, seeded by Pennywise, It eventually gets the final victory on Will.

Leroy's Transformation

This chain of events would explain how Leroy changes so radically from what we witness in It: Chapter 1 and the prequel. In his older age, he appears resentful and much stricter with his parenting. Because he survived his own son, it's comprehensible to see such a drastic change. Nonetheless, his words carry more weight now that we know he's seen Pennywise's hauntings and the impacts they had on his son. In the initial sequence of the movie, we observe Mike hesitate to use a bolt gun on a animal at Leroy's farm. His grandfather chastises him for hesitating and provides an analogy that leads to a survival-of-the-fittest scenario.

“There are two places you can be in this existence. You can be out here like us, or you can be in there,” Leroy says as he points to the creature. “You dawdle hemming and hawing, and someone is going to make that choice. Except you will be unaware it until you experience that projectile between your eyes.”

Looking back, this could represent a piece of prediction, a lesson he regrets not imparting to his own child. Maybe he desires he had done something in his past, but for certain factors, he couldn't resist the repellent attraction of Derry.