The Derry Chronicles Could Have Solved a Longstanding Pennywise Mystery
Pennywise's influence on the children of Welcome to Derry molds them long into adulthood, twisting them into the very adults who perpetuate the town's cycle of hatred alive. The creature finds easy targets on kids from broken households — youngsters who frequently mature to repeat the identical behaviors as their parents. But, the Hanlon household distinguishes itself as one of the few family unit that remains intact, which may explain why Mike, even after choosing to stay in Derry, persists as the only Loser who never fully falls under the clown's influence.
Hanlon Household's Unique Resistance
In the fourth installment of Welcome to Derry, Leroy finally becomes increasingly conscious of the supernatural forces surrounding the community, especially when It starts haunting his child, Will Hanlon, during their fishing trip. The Hanlon family comprises some of the few adults who are aware that things are not right with the town, notably Leroy, who was shown to be receptive to psychic abilities when he was capable of sensing Dick Hallorann's employment of it in the third episode. Subsequently, Leroy sees one of Pennywise's signature inflated orbs outside his residence. This gift, coupled with his inability to feel fear, along with the foundation of his household, could be why he's able to see the entity's manifestations. But what if that psychic sensitivity is generational, and a key factor Mike Hanlon is one of the only adults in the town who didn't lose themselves to its cruelty?
The boy is a member of the group of children at his educational institution being terrorized by the clown. His classmates hail from broken homes, with parents who refuse to accept they're being haunted. The cause he is being pursued is due to the viciousness of the town, paired 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 anomalies exist about the locality from the beginning. They also have a good foundation that isn't fractured, unlike the folks who originate in the area, with bonds that have deteriorated within.
Backstory Connections
Based on the It novel, we know the juvenile Will will find himself at the Black Spot, where Hallorann will rescue him from a fire that the local KKK members of Derry will ignite. In the 2017 movie, we observe that he has a son named Mike and that the father ultimately dies in a configration, with Leroy outliving his own son and taking his grandson in. The public account in the motion picture is that the parents were on substances, but now that we see Will in the series, that's hard to believe. Maybe the timid youth, once he became an adult, leaned into alcohol to rid himself of the hauntings, or maybe the rotten environment affected him first, with the hate group eventually completing the job it started long before. Whether through the fear of Pennywise or through the malice of the community, instigated by Pennywise, It eventually gets the last laugh on Will.
The Father's Evolution
These occurrences would explain how the elder Hanlon transforms so drastically from what we see in It: Chapter 1 and Welcome to Derry. In his older age, Leroy seems resentful and much stricter with his discipline. Because he outlived his own offspring, it's comprehensible to observe such a profound shift. However, his words carry more weight since we are aware he's seen Pennywise's hauntings and the effects they had on his child. In the initial sequence of the movie, we see the boy pause to use a bolt gun on a animal at Leroy's farm. His grandfather chastises him for hesitating and offers an metaphor that leads to a survival-of-the-fittest situation.
“There are two places you can be in this existence. You can be out here like us, or you can be in there,” Leroy states as he points to the sheep. “You waste time indecisive, and another is going to make that choice. But you won't know it until you feel that projectile between your eyes.”
In hindsight, this could be a piece of foreshadowing, a lesson he wishes he had told his own child. Perhaps he desires he had acted differently in his past, but for certain factors, he was unable to avoid the sickening allure of Derry.