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Pennywise's impact on the children of Welcome to Derry shapes them long into adulthood, transforming them into the exact individuals who keep the town's cycle of hatred alive. It preys most easily on children from broken households — children who often mature to replicate the identical behaviors as their parents. But, the Hanlon household distinguishes itself 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 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 supernatural forces enveloping the neighborhood, especially when It begins tormenting his son, Will, during their angling excursion. The Hanlon family consists of some of the few grown-ups who are aware that things are not right with the municipality, especially the father, 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. Subsequently, Leroy sees one of Pennywise's signature balloons outside his house. This gift, alongside his failure to experience terror, combined with the base of his family, could be why he's able to see the entity's manifestations. But what if that shining is generational, and a key factor Mike is one of the only individuals in the town who resisted succumbing to its cruelty?

The boy is part of the group of children at his school being tormented by Pennywise. His classmates hail from dysfunctional families, with parents who refuse to accept they're being targeted. The reason he is being haunted is because of the cruelty of the community, combined with his potential sensitivity to psychic abilities, which makes him susceptible. The Hanlons are fundamentally strangers in the town during 1962, which contributes towards the household sensing anomalies exist about the locality from the beginning. They also have a solid base that isn't fractured, unlike the folks who originate in the area, with relationships that have decayed within.

Historical Context

Drawing from the It novel, we know the juvenile Will will end up at the Black Spot, where Hallorann will rescue him from a blaze that the town bigots of Derry will cause. In the recent film, we see that Will has a boy named Mike and that the father ultimately dies in a fire, with Leroy surviving his own son and taking his grandson in. The public account in the motion picture is that the parents were on substances, but given our current view of Will in Welcome to Derry, that's hard to believe. Maybe the shy youth, once he grew up, turned to alcohol to rid himself of the torments, or perhaps the rotten environment got to him first, with the KKK eventually finishing the job it started long before. Be it via the fear of Pennywise or through the malice of the town, instigated by It, the creature eventually gets the last laugh on him.

Leroy's Transformation

This chain of events would explain how Leroy transforms so radically from what we see in It: Chapter 1 and Welcome to Derry. In his later years, Leroy appears bitter and much harsher with his discipline. Since he outlived his own offspring, it's comprehensible to observe such a profound shift. Nonetheless, his words carry more weight since we are aware he's witnessed Pennywise's hauntings and the effects they wrought upon his child. 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 delaying and offers an analogy that leads to a survival-of-the-fittest situation.

“There are two places you can be in this existence. You can be out here like us, or you can be trapped inside,” Leroy states as he points to the creature. “You waste time indecisive, and another is going to make that choice. Except you won't know it until you feel that bolt in your head.”

Looking back, this could be a bit of foreshadowing, something he wishes he had told his own son. Maybe he desires he had done something in his past, but for some reason, he was unable to avoid the repellent attraction of the town.