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Pennywise's influence on the young residents of the Derry series shapes them throughout their adult lives, twisting them into the very adults who perpetuate the community's cycle of animosity ongoing. The creature preys most easily on kids from fractured households — children who often mature to replicate the same patterns as their parents. However, the Hanlon family stands apart as one of the few households that never splinters, which may explain why Mike, even after choosing to stay in the town, remains the only Loser who never fully falls under the clown's influence.

Hanlon Household's Distinctive Resistance

In the fourth installment of Welcome to Derry, Leroy finally becomes increasingly conscious of the paranormal entities enveloping the community, particularly when the entity begins tormenting his son, Will, during their fishing trip. The Hanlon family comprises a small number of adults who are aware that something is amiss with the municipality, notably Leroy, who was revealed to be sensitive to psychic abilities when he was capable of sensing Dick Hallorann's use of it in the third episode. Later, he spots one of Pennywise's signature inflated orbs outside his residence. The ability, alongside his failure to experience terror, along with the foundation of his family, could be why he's capable of perceiving Pennywise's hauntings. But what if that shining is generational, and a key factor Mike Hanlon is one of the only adults in the town who resisted succumbing to its cruelty?

The boy is part of the collective of children at his school being tormented by Pennywise. All his school friends come from broken homes, with parents who refuse to accept they're being haunted. The reason he is being pursued is due to the cruelty of the community, combined with his potential sensitivity to psychic abilities, which makes him susceptible. This family are fundamentally strangers in the town during the early sixties, which lends itself towards the household feeling something is off about the locality from the onset. They also have a solid base that isn't fractured, in contrast to the folks who originate in the area, with relationships that have deteriorated within.

Historical Context

Based on the original book, we understand the young Will Hanlon will find himself at the Black Spot, where Hallorann will save him from a fire that the town bigots of the community will ignite. In the 2017 movie, we see that he has a son named Mike and that Will eventually perishes in a fire, with his father surviving his own child and taking his grandson in. The official story in the motion picture is that Mike's parents were on drugs, but now that we see Will in Welcome to Derry, that's difficult to accept. Perhaps the timid boy, once he became an adult, turned to alcohol to rid himself of the hauntings, or maybe the corrupt town got to him first, with the KKK ultimately completing the job it started years ago. Whether through the terror of Pennywise or via the cruelty of the town, seeded by Pennywise, the creature eventually achieves the final victory on Will.

Leroy's Transformation

These occurrences would clarify how Leroy transforms so radically from what we witness in the first film and the prequel. In his later years, Leroy appears resentful and much stricter 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 Pennywise's hauntings and the impacts they had on his child. In the initial sequence of the movie, we observe Mike pause to use a bolt gun 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 in there,” he says as he points to the creature. “You dawdle hemming and hawing, and another is going to make that choice. Except you will be unaware it until you experience that projectile between your eyes.”

In hindsight, this could represent a piece of foreshadowing, a lesson he wishes he had told his own child. Maybe he desires he had acted differently in his youth, but for some reason, he couldn't resist the repellent allure of Derry.