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Pennywise's influence on the young residents of Welcome to Derry shapes them long into adulthood, transforming them into the exact individuals who keep the town's pattern of hatred alive. The creature preys most easily on kids from broken homes — children who frequently mature to replicate the same patterns as their guardians. However, the Hanlon family distinguishes itself as one of the few households that remains intact, which may explain why Mike Hanlon, even after choosing to stay in the town, persists as the only Loser who doesn't completely succumb under the clown's influence.

Hanlon Household's Unique Resilience

In the fourth installment of the series, Leroy Hanlon at last grows more aware of the paranormal entities surrounding the community, particularly when It begins tormenting his son, Will Hanlon, during their fishing trip. The Hanlon family consists of a small number of adults who are cognizant that things are not right with the municipality, notably the father, who was shown to be sensitive to psychic abilities when he was capable of sensing Dick Hallorann's use of it in the third episode. Subsequently, Leroy sees one of the clown's trademark inflated orbs outside his house. This gift, coupled with his inability to experience terror, along with the foundation of his household, could be why he's capable of perceiving Pennywise's hauntings. However, consider if that shining is generational, and a key factor Mike Hanlon is among the few adults in the town who didn't lose themselves to the town's malevolence?

Will is a member of the collective of children at his school being terrorized by Pennywise. His classmates hail from broken homes, with parents who don't believe they're being haunted. The reason he is being haunted is because of the cruelty of the community, paired with his likely receptiveness to shine, which makes him susceptible. The Hanlons are fundamentally outsiders in the town during the early sixties, which lends itself towards the family feeling anomalies exist about the town from the onset. They also have a good foundation that remains unbroken, in contrast to the residents who originate in the town, with bonds that have decayed within.

Historical Context

Based on the original book, we know the young Will will find himself at the Black Spot, where the psychic will save him from a blaze that the local KKK members of Derry will ignite. In the recent film, we see that he has a boy named Mike and that Will ultimately dies in a fire, with Leroy outliving his own son and taking his grandson in. The official story in the film is that Mike's parents were on substances, 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 drink to rid himself of the hauntings, or perhaps the corrupt environment affected him first, with the KKK ultimately completing the job it started long before. Be it via the fear of the entity or via the malice of the town, instigated by Pennywise, the creature eventually achieves the last laugh on Will.

Leroy's Transformation

This chain of events would clarify how Leroy transforms so drastically from what we witness in the first film and the prequel. In his later years, he appears bitter and much stricter with his discipline. Since he survived his own son, it's understandable to see such a drastic change. Nonetheless, his statements hold greater significance since we are aware he's witnessed Pennywise's hauntings and the effects they had on his son. In the opening scene of It, we observe Mike pause to use a bolt gun on a animal at the family property. His grandfather reprimands him for hesitating and provides an analogy that results in 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 in there,” he states as he gestures to the sheep. “You dawdle indecisive, and someone is going to decide for you. But you won't know it until you feel that bolt between your eyes.”

In hindsight, this could represent a bit of foreshadowing, a lesson he regrets not imparting to his own son. Maybe he wishes he had done something in his past, but for some reason, he couldn't resist the sickening allure of Derry.