The Derry Chronicles May Have Solved a Lingering Pennywise Enigma
The clown's influence on the children of the Derry series molds them throughout their adult lives, twisting them into the very adults who keep the community's cycle of hatred alive. The creature preys most easily on children from broken households — children who often grow up to repeat the same patterns as their guardians. But, the Hanlon family stands apart as one of the few family unit that remains intact, which could clarify why Mike, even after electing to remain in the town, remains the sole member who never fully falls under the clown's influence.
Hanlon Household's Distinctive Resilience
In the fourth installment of Welcome to Derry, Leroy Hanlon at last grows more aware of the supernatural forces enveloping the community, particularly when It starts haunting his child, Will, during their angling excursion. The Hanlon family comprises some of the few adults who are cognizant that something is amiss with the town, especially Leroy, who was shown to be sensitive to the Shining when he was capable of sensing a fellow psychic's use of it in the third episode. Later, he spots one of the clown's trademark inflated orbs outside his house. This gift, coupled with his inability to feel fear, along with the foundation of his family, may be why he's capable of perceiving the entity's manifestations. However, consider if that psychic sensitivity is generational, and one of the reasons Mike Hanlon is among the few adults in the town who didn't lose themselves to its cruelty?
Will is a member of the group of children at his school being tormented by the clown. His classmates hail from broken homes, with parents who don't believe they're being haunted. The reason Will is being haunted is because of the viciousness of the town, combined with his potential sensitivity to shine, which renders him vulnerable. This family are fundamentally strangers in Derry during the early sixties, which lends itself towards the family feeling something is off about the town from the onset. Additionally, they possess a good foundation that isn't fractured, unlike the residents who originate in the town, with relationships that have deteriorated internally.
Historical Context
Based on the original book, we understand the juvenile Will Hanlon will find himself at the infamous nightclub, where Hallorann will rescue him from a blaze that the town bigots of Derry will ignite. In the recent film, we observe that Will has a son named Mike and that the father eventually perishes in a fire, with his father outliving his own son and taking his grandson in. The public account in the motion picture is that the parents were on drugs, but given our current view of Will in Welcome to Derry, that's hard to believe. Maybe the timid boy, once he grew up, leaned into alcohol to free himself of the hauntings, or maybe the rotten town got to him initially, with the hate group eventually completing the job it started years ago. Whether through the terror of the entity or via the cruelty of the town, seeded by Pennywise, It in the end 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 the first film and Welcome to Derry. In his later years, he appears bitter and much harsher with his parenting. Since he outlived his own offspring, it's understandable to observe such a profound shift. However, his words hold greater significance since we are aware he's witnessed Pennywise's hauntings and the impacts they wrought upon his son. In the initial sequence of It, we observe Mike pause to use a bolt gun on a animal at the family property. His grandfather reprimands him for hesitating and provides an analogy that leads to a kill-or-be-killed scenario.
“There are two places you can be in this world. You can be in the open like us, or you can be in there,” he says as he gestures to the creature. “You dawdle indecisive, and another is going to make that choice. But you won't know it until you experience that bolt between your eyes.”
In hindsight, this could represent a bit of foreshadowing, something he wishes he had told his own son. Perhaps he desires he had acted differently in his youth, but for certain factors, he was unable to avoid the repellent allure of Derry.