The Derry Chronicles Could Have Unraveled a Lingering Pennywise Mystery
The clown's impact on the children of Welcome to Derry molds them long into adulthood, twisting them into the exact individuals who keep the town's pattern of animosity alive. It preys most easily on children from fractured homes — children who often mature to repeat the identical behaviors as their parents. However, the Hanlon household distinguishes itself as one of the few households that remains intact, which may explain why Mike Hanlon, even after choosing to stay in Derry, remains the sole member who never fully falls under Pennywise's sway.
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, especially when It begins tormenting his child, Will Hanlon, during their angling excursion. The Hanlon family consists of some of the few grown-ups who are cognizant that something is amiss with the town, notably the father, who was shown to be receptive to the Shining when he was able to detect Dick Hallorann's employment of it in the third episode. Later, he sees one of the clown's trademark balloons outside his house. This gift, alongside his failure to experience terror, along with the base of his household, could be why he's capable of perceiving the entity's manifestations. But what if that shining is generational, and one of the reasons Mike is among the few adults in the town who didn't lose themselves to the town's malevolence?
Will is a member of the collective of kids at his school being terrorized by Pennywise. His classmates hail from dysfunctional families, with parents who refuse to accept they're being targeted. The cause Will is being haunted is because of the cruelty of the town, paired with his likely receptiveness to shine, which renders him vulnerable. This family are fundamentally strangers in Derry during 1962, which lends itself towards the household feeling something is off about the town from the onset. Additionally, they possess a solid base that remains unbroken, unlike the folks who come from the area, with relationships that have decayed internally.
Historical Context
Drawing from the It novel, we understand the juvenile Will will find himself at the Black Spot, where Hallorann will save him from a blaze that the local KKK members of Derry will cause. In the recent movie, we see that Will 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 film is that Mike's parents were on drugs, but now that we see him in the series, that's hard to believe. Maybe the timid boy, once he became an adult, turned to drink to rid himself of the hauntings, or perhaps the corrupt environment got to him first, with the hate group ultimately completing the job it began long before. Be it via the fear of the entity or via the cruelty of the community, seeded by Pennywise, the creature eventually gets the final victory on Will.
Leroy's Transformation
This chain of events would clarify how the elder Hanlon transforms so drastically from what we see in the first film and Welcome to Derry. In his later years, he seems resentful and much harsher with his parenting. Because he outlived his own son, it's understandable to see such a profound shift. Nonetheless, his statements hold greater significance since we are aware he's witnessed Pennywise's hauntings and the effects they wrought upon his child. In the initial sequence of It, we see the boy pause to use a bolt gun on a sheep at the family property. Leroy chastises him for hesitating and provides an analogy that results in a survival-of-the-fittest situation.
“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 states as he gestures to the sheep. “You dawdle hemming and hawing, and another is going to decide for you. But you won't know it until you feel that projectile in your head.”
In hindsight, this could be a bit of foreshadowing, something he wishes he had told his own child. Perhaps he wishes he had done something in his youth, but for certain factors, he was unable to avoid the sickening attraction of Derry.