The Derry Chronicles Could Have Unraveled a Longstanding Pennywise Enigma
Pennywise's influence on the young residents of the Derry series molds them throughout their adult lives, twisting them into the very adults who keep the town's cycle of animosity alive. The creature preys most easily on children from fractured households — youngsters who often grow up to replicate the same patterns as their parents. However, the Hanlon household distinguishes itself as one of the few households that never splinters, which may explain why Mike, even after electing to remain in the town, persists as the only Loser who doesn't completely succumb under Pennywise's sway.
Hanlon Household's Distinctive Resistance
In episode 4 of the series, Leroy Hanlon finally becomes more aware of the paranormal entities surrounding the community, particularly when It starts haunting his child, Will Hanlon, during their angling excursion. The Hanlon family comprises some of the few adults who are aware that things are not right with the municipality, especially Leroy, who was revealed to be receptive to the Shining when he was capable of sensing Dick Hallorann's employment of it in episode 3. Subsequently, he spots one of Pennywise's signature balloons outside his house. This gift, alongside his inability to experience terror, along with the foundation of his family, may be why he's capable of perceiving Pennywise's hauntings. But what if that psychic sensitivity is generational, and a key factor Mike is among the few individuals in the town who didn't lose themselves to its cruelty?
The boy is part of the collective of children at his school being terrorized by the clown. All his school friends come from broken homes, with caregivers who refuse to accept they're being haunted. The cause Will is being haunted is due to the cruelty of the community, combined with his potential sensitivity to shine, which makes him susceptible. This family are ultimately outsiders in the town during 1962, which contributes towards the family feeling something is off about the town from the onset. They also have a good foundation that isn't fractured, in contrast to the residents who come from the town, with relationships that have decayed within.
Historical Context
Based on the original book, we understand the young Will will find himself at the Black Spot, where Hallorann will rescue him from a blaze that the town bigots of the community will ignite. In the recent film, we observe that Will has a boy named Mike and that Will eventually perishes in a fire, with his father surviving his own child and taking his grandson in. The official story in the motion picture is that Mike's parents were on drugs, but given our current view of him in Welcome to Derry, that's hard to believe. Perhaps the shy boy, once he grew up, leaned into alcohol to rid himself of the torments, or maybe the rotten environment got to him first, with the KKK eventually finishing the task it started years ago. Be it via the terror of the entity or through the cruelty of the community, instigated by Pennywise, the creature eventually achieves the last laugh on Will.
The Father's Evolution
This chain of events would explain how the elder Hanlon changes so radically from what we see in the first film and the prequel. In his older age, Leroy appears resentful and much harsher with his parenting. Since he outlived his own son, it's understandable to observe such a drastic change. Nonetheless, his words hold greater significance since we are aware he's witnessed Pennywise's hauntings and the impacts they wrought upon his child. In the opening scene of the movie, we observe Mike hesitate to use a stunning device on a animal at the family property. Leroy reprimands him for delaying and provides an analogy that leads to a survival-of-the-fittest situation.
“You have two options you can be in this world. You can be out here like us, or you can be trapped inside,” Leroy states as he points to the sheep. “You dawdle hemming and hawing, and someone is going to decide for you. But you won't know it until you experience that bolt in your head.”
Looking back, this could be a piece of prediction, a lesson he wishes he had told his own son. Maybe he wishes he had done something in his youth, but for some reason, he couldn't resist the sickening allure of the town.