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Pennywise's impact on the young residents of Welcome to Derry molds them long into adulthood, transforming them into the exact individuals who keep the town's pattern of animosity ongoing. The creature preys most easily on kids from broken households — children who frequently mature to repeat the same patterns as their guardians. But, the Hanlon household distinguishes itself as a rare example of a family unit that remains intact, which may explain why Mike, even after electing to remain in Derry, remains the only Loser who never fully falls under Pennywise's sway.

The Hanlon Family's Unique Resilience

In the fourth installment of Welcome to Derry, Leroy Hanlon at last grows more aware of the paranormal entities surrounding the community, particularly when the entity begins tormenting his son, Will Hanlon, during their angling excursion. The Hanlon family comprises a small number of grown-ups who are aware that things are not right 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, Leroy sees one of the clown's trademark balloons outside his house. The ability, alongside 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 shining is generational, and a key factor Mike is among the few individuals in the town who resisted succumbing to its cruelty?

Will is a member of the group of children at his school being terrorized by Pennywise. All his school friends come from broken homes, with parents who refuse to accept they're being haunted. The cause he is being pursued is due to the viciousness of the town, combined with his potential sensitivity to psychic abilities, which makes him susceptible. This family are fundamentally outsiders in the town during the early sixties, which lends itself towards the family feeling something is off about the locality from the onset. Additionally, they possess a solid base that isn't fractured, in contrast to the residents who come from the town, with relationships that have decayed internally.

Historical Context

Drawing from the original book, we know the young Will will end up at the infamous nightclub, where Hallorann will rescue him from a blaze that the town bigots of the community will ignite. In the recent movie, we observe that he has a son named Mike and that Will eventually perishes in a configration, with his father surviving his own son and adopting his grandchild. The official story in the film is that the parents were on substances, but now that we see him in Welcome to Derry, that's hard to believe. Perhaps the timid boy, once he grew up, leaned into drink to rid himself of the hauntings, or maybe the rotten environment affected him first, with the hate group eventually completing the job it started long before. Be it via the terror of Pennywise or via the cruelty of the community, instigated by Pennywise, the creature in the end achieves the final victory on Will.

Leroy's Transformation

These occurrences would explain how the elder Hanlon changes so drastically from what we witness in the first film and the prequel. In his older age, he appears resentful and much stricter with his parenting. Because he survived his own son, it's understandable to see such a profound shift. However, his words carry more weight since we are aware he's witnessed Pennywise's hauntings and the effects they wrought upon his son. In the opening scene of the movie, we see the boy pause to use a bolt gun on a sheep at the family property. His grandfather chastises him for hesitating and offers an metaphor that results in a survival-of-the-fittest scenario.

“You have two options you can be in this world. You can be out here like us, or you can be in there,” he says as he gestures to the creature. “You waste time hemming and hawing, and another is going to decide for you. Except you won't know it until you experience that projectile between your eyes.”

In hindsight, this could be a piece of foreshadowing, a lesson he wishes he had told his own son. Perhaps he wishes he had acted differently in his youth, but for certain factors, he couldn't resist the sickening attraction of Derry.