Welcome to Derry May Have Solved a Lingering Pennywise Mystery
Pennywise's influence on the young residents of the Derry series shapes them long into adulthood, twisting them into the very adults who perpetuate the community's pattern of hatred alive. It finds easy targets on children from broken households — children who frequently grow up to repeat the identical behaviors as their guardians. But, the Hanlon household distinguishes itself as a rare example of a households that remains intact, which may explain why Mike Hanlon, even after electing to remain in the town, remains the only Loser who never fully falls under the clown's influence.
The Hanlon Family's Unique Resistance
In the fourth installment of the series, Leroy finally becomes increasingly conscious of the paranormal entities enveloping the community, particularly when It starts haunting his child, Will Hanlon, during their fishing trip. The Hanlon clan comprises some of the few grown-ups who are aware that something is amiss with the town, especially the father, who was shown to be sensitive to psychic abilities when he was capable of sensing Dick Hallorann's employment of it in episode 3. Subsequently, Leroy spots one of the clown's trademark inflated orbs outside his residence. The ability, coupled with his inability to feel fear, along with the base of his family, could be why he's able to see the entity's manifestations. However, consider if that shining is hereditary, and one of the reasons Mike is one of the only individuals in Derry 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 come from dysfunctional families, with parents who don't believe they're being haunted. The reason Will is being haunted is because of the cruelty of the community, paired with his potential sensitivity to shine, which makes him susceptible. This family are fundamentally outsiders in Derry during 1962, which lends itself towards the household feeling anomalies exist about the locality from the onset. Additionally, they possess a good foundation that remains unbroken, unlike the residents who originate in the town, with relationships that have deteriorated internally.
Backstory Connections
Based on the It novel, we know the young Will Hanlon will find himself at the Black Spot, where Hallorann will save him from a fire that the town bigots of Derry will cause. In the 2017 film, we see that Will has a boy named Mike and that the father ultimately dies in a fire, with his father outliving his own son and taking his grandson in. The official story in the motion picture is that Mike's parents were on substances, but given our current view of Will in Welcome to Derry, that's difficult to accept. Maybe the timid boy, once he grew up, leaned into alcohol to free himself of the hauntings, or maybe the corrupt environment got to him initially, with the KKK ultimately completing the job it began years ago. Be it via the fear of Pennywise or through the malice of the community, instigated by It, It in the end achieves the final victory on him.
Leroy's Transformation
This chain of events would clarify how the elder Hanlon changes so drastically from what we see in It: Chapter 1 and the prequel. In his older age, he appears bitter and much harsher with his discipline. Since he survived his own son, it's understandable to see such a drastic change. However, his words carry more weight since we are aware he's witnessed the clown's activities and the effects they wrought upon his son. In the opening scene of the movie, we see the boy pause to use a bolt gun on a animal at the family property. His grandfather chastises him for hesitating and provides an metaphor that leads to a survival-of-the-fittest scenario.
“There are two places you can be in this world. You can be in the open like us, or you can be trapped inside,” he says as he gestures to the sheep. “You waste time indecisive, and another is going to decide for you. Except you will be unaware it until you experience that bolt between your eyes.”
In hindsight, this could be a piece of foreshadowing, something he wishes he had told his own son. Maybe he wishes he had done something in his past, but for certain factors, he couldn't resist the sickening allure of Derry.