The Derry Chronicles May Have Unraveled a Longstanding Pennywise Enigma
The clown's influence on the children of Welcome to Derry shapes them throughout their adult lives, twisting them into the very adults who keep the community's cycle of animosity alive. It preys most easily on children from fractured homes — children who frequently grow up to replicate the same patterns as their parents. But, the Hanlon family stands apart as one of the few family unit that remains intact, which could clarify why Mike, even after choosing to stay in the town, remains the only Loser who doesn't completely succumb under the clown's influence.
The Hanlon Family's Unique Resistance
In the fourth installment of Welcome to Derry, Leroy at last grows more aware of the supernatural forces surrounding the community, especially when the entity begins tormenting his son, Will, during their fishing trip. The Hanlon family consists of a small number of adults who are aware that things are not right with the municipality, notably Leroy, who was shown to be receptive to the Shining when he was able to detect a fellow psychic's employment of it in the third episode. Subsequently, Leroy sees one of Pennywise's signature balloons outside his residence. The ability, alongside his failure to experience terror, combined with the base of his family, could be why he's able to see Pennywise's hauntings. But what if that psychic sensitivity is generational, and a key factor Mike is one of the only individuals in the town who didn't lose themselves to the town's malevolence?
The boy is a member of the collective of children at his educational institution being tormented by Pennywise. His classmates come from broken homes, with caregivers who refuse to accept they're being haunted. The cause he is being haunted is because of the viciousness of the community, paired with his likely receptiveness to shine, which makes him susceptible. The Hanlons are ultimately outsiders in Derry during the early sixties, which lends itself towards the household sensing anomalies exist about the locality from the onset. Additionally, they possess a solid base that isn't fractured, unlike the residents who come from the area, with relationships that have decayed within.
Historical Context
Drawing from the original book, we understand the juvenile Will will end up at the Black Spot, where Hallorann will save him from a fire that the local KKK members of Derry will cause. In the recent movie, we see that he has a boy named Mike and that Will eventually perishes in a configration, with his father surviving his own child and adopting his grandchild. 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 shy youth, once he became an adult, leaned into drink to free himself of the hauntings, or maybe the corrupt environment affected him initially, with the KKK ultimately completing the task it started long before. Be it via the terror of Pennywise or through the malice of the community, instigated by It, the creature in the end gets the final victory on Will.
Leroy's Transformation
This chain of events would clarify how the elder Hanlon changes so radically from what we witness in It: Chapter 1 and the prequel. In his older age, he seems bitter and much stricter with his parenting. Since he outlived his own offspring, it's comprehensible to observe such a profound shift. However, his statements carry more weight now that we know he's seen the clown's activities and the impacts they had on his child. In the initial sequence of It, we see Mike pause to use a bolt gun on a animal at the family property. Leroy chastises him for hesitating and offers an analogy that results in a survival-of-the-fittest scenario.
“There are two places you can be in this world. You can be out here like us, or you can be trapped inside,” Leroy says as he points to the creature. “You dawdle indecisive, and someone is going to decide for you. But you will be unaware it until you experience that bolt in your head.”
In hindsight, this could represent a piece of prediction, a lesson he regrets not imparting to his own child. Maybe he wishes he had acted differently in his youth, but for some reason, he couldn't resist the repellent allure of the town.