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Pennywise's impact on the children of Welcome to Derry molds them throughout their adult lives, transforming them into the very adults who keep the town's cycle of hatred alive. It preys most easily on children from broken homes — youngsters who frequently grow up to replicate the same patterns as their guardians. However, the Hanlon household distinguishes itself as a rare example of a households that never splinters, which may explain why Mike, even after choosing to stay in Derry, persists as the sole member who doesn't completely succumb under Pennywise's sway.

Hanlon Household's Distinctive Resilience

In episode 4 of the series, Leroy at last grows more aware of the supernatural forces enveloping the community, particularly when the entity begins tormenting his child, Will Hanlon, during their angling excursion. The Hanlon family comprises some of the few adults who are aware that something is amiss with the municipality, especially the father, 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. Later, Leroy sees one of the clown's trademark inflated orbs outside his residence. The ability, coupled with his inability to experience terror, combined with the base of his family, may be why he's capable of perceiving Pennywise's hauntings. But what if that shining is generational, and a key factor Mike is among the few adults in the town who resisted succumbing to the town's malevolence?

Will is a member of the collective of children at his educational institution being tormented by Pennywise. His classmates hail from dysfunctional families, with caregivers who don't believe they're being haunted. The cause Will is being haunted is due to the viciousness of the town, combined with his potential sensitivity to psychic abilities, which renders him vulnerable. This family are ultimately outsiders in Derry during 1962, which lends itself towards the household feeling anomalies exist about the locality from the beginning. Additionally, they possess a good foundation that isn't fractured, unlike the residents who come from the area, with bonds that have decayed within.

Historical Context

Drawing from the It novel, we know the juvenile Will Hanlon will end up at the Black Spot, where the psychic will rescue him from a blaze that the local KKK members of Derry will cause. In the 2017 movie, we observe that he has a boy named Mike and that Will ultimately dies in a configration, with his father outliving his own son and adopting his grandchild. The official story in the motion picture is that the parents were on substances, but now that we see him in the series, that's hard to believe. Maybe the shy boy, once he grew up, turned to alcohol to rid himself of the torments, or perhaps the rotten environment affected him first, with the hate group ultimately completing the job it began years ago. Whether through the fear of Pennywise or through the cruelty of the community, instigated by It, It eventually achieves the final victory on Will.

Leroy's Transformation

This chain of events would explain how the elder Hanlon transforms so drastically from what we witness in the first film and the prequel. In his later years, he seems bitter and much stricter with his parenting. Since he survived his own offspring, it's comprehensible to see such a profound shift. Nonetheless, his words carry more weight since we are aware he's seen Pennywise's hauntings and the impacts they wrought upon his child. In the initial sequence of the movie, we see the boy pause to use a stunning device on a sheep at Leroy's farm. His grandfather reprimands him for hesitating and offers an metaphor that results in a kill-or-be-killed scenario.

“There are two places you can be in this world. You can be out here like we are, or you can be in there,” he says as he points to the sheep. “You waste time hemming and hawing, and another is going to make that choice. But you won't know it until you experience that projectile in your head.”

In hindsight, this could be a bit of prediction, a lesson he regrets not imparting to his own son. Perhaps he wishes he had done something in his youth, but for some reason, he was unable to avoid the sickening attraction of Derry.