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Pennywise's impact on the children of Welcome to Derry shapes them throughout their adult lives, transforming them into the exact individuals who perpetuate the town's cycle of hatred ongoing. The creature preys most easily on children from fractured homes — children who often mature to repeat the same patterns as their guardians. However, the Hanlon household stands apart as one of the few family unit that never splinters, which may explain why Mike Hanlon, even after choosing to stay in the town, remains the only Loser who never fully falls under Pennywise's sway.

Hanlon Household's Distinctive Resilience

In the fourth installment of Welcome to Derry, Leroy Hanlon finally becomes more aware of the supernatural forces surrounding the community, particularly when the entity starts haunting his son, Will Hanlon, during their fishing trip. The Hanlon clan consists of a small number of adults who are aware that things are not right with the town, especially Leroy, who was shown to be sensitive to the Shining when he was capable of sensing a fellow psychic's employment of it in episode 3. Later, he sees one of Pennywise's signature inflated orbs outside his residence. The ability, coupled with his inability to feel fear, combined with the base of his family, may be why he's able to see Pennywise's hauntings. However, consider if that psychic sensitivity is generational, and one of the reasons Mike is one of the only adults in the town who didn't lose themselves to the town's malevolence?

The boy is part of the collective of children at his school being terrorized by the clown. All his school friends come from dysfunctional families, with parents who don't believe they're being haunted. The reason Will is being pursued is because of the cruelty of the community, combined with his likely receptiveness to shine, which makes him susceptible. This family are ultimately strangers in the town during 1962, which lends itself towards the family feeling something is off about the locality from the beginning. Additionally, they possess a solid base that isn't fractured, unlike the folks who originate in the town, with bonds that have deteriorated within.

Historical Context

Drawing from the original book, we know the young Will Hanlon will find himself at the Black Spot, where the psychic will rescue him from a blaze that the town bigots of the community will ignite. In the recent film, we see that he has a son named Mike and that the father eventually perishes in a fire, with his father 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 him in the series, that's hard to believe. Maybe the timid youth, once he became an adult, turned to alcohol to free himself of the hauntings, or perhaps the corrupt environment affected him first, with the KKK ultimately finishing the task it started long before. Be it via the fear of Pennywise or through the malice of the community, instigated by Pennywise, It in the end achieves the last laugh on Will.

Leroy's Transformation

This chain of events would clarify how the elder Hanlon transforms so radically from what we see in the first film and Welcome to Derry. In his older age, Leroy appears resentful and much harsher with his discipline. Because he outlived his own offspring, it's comprehensible to observe such a profound shift. However, his words hold greater significance now that we know he's witnessed Pennywise's hauntings and the impacts they had on his son. In the initial sequence of It, we see the boy pause to use a stunning device on a sheep at the family property. Leroy chastises him for hesitating and offers an analogy that leads to a survival-of-the-fittest scenario.

“There are two places you can be in this existence. You can be in the open like us, or you can be trapped inside,” he says as he gestures to the sheep. “You waste time hemming and hawing, and someone is going to make that choice. But you will be unaware it until you experience that bolt in your head.”

In hindsight, this could be a bit of foreshadowing, something he regrets not imparting to his own son. Maybe he wishes he had acted differently in his past, but for certain factors, he couldn't resist the sickening allure of Derry.