Welcome to Derry Could Have Unraveled a Longstanding It Enigma
Pennywise's impact on the young residents of Welcome to Derry molds them throughout their adult lives, twisting them into the very adults who keep the community's pattern of hatred alive. The creature preys most easily on kids from broken homes — youngsters who often grow up to repeat the identical behaviors as their parents. However, the Hanlon family stands apart as a rare example of a households that never splinters, which may explain why Mike, even after choosing to stay in Derry, persists as the sole member who doesn't completely succumb under Pennywise's sway.
Hanlon Household's Unique Resistance
In the fourth installment of Welcome to Derry, Leroy Hanlon at last grows more aware of the paranormal entities surrounding the neighborhood, particularly when the entity starts haunting his son, Will Hanlon, during their angling excursion. The Hanlon family consists of a small number of grown-ups who are aware that things are not right with the town, especially the father, who was shown to be sensitive to the Shining when he was capable of sensing Dick Hallorann's employment of it in episode 3. Subsequently, Leroy spots one of the clown's trademark balloons outside his house. This gift, coupled with his inability to feel fear, combined with the base of his family, may be why he's able to see the entity's manifestations. However, consider if that shining is hereditary, and one of the reasons Mike Hanlon is one of the only individuals in Derry who didn't lose themselves to the town's malevolence?
The boy is part of the collective of kids at his school being terrorized by Pennywise. All his school friends hail from broken homes, with parents who don't believe they're being targeted. The reason Will is being haunted is because of the cruelty of the community, combined with his likely receptiveness to psychic abilities, which makes him susceptible. This family are fundamentally strangers in the town during the early sixties, which lends itself towards the household sensing something is off about the locality from the onset. They also have a solid base that remains unbroken, in contrast to the residents who come from the area, with relationships that have decayed internally.
Historical Context
Based on the It novel, we understand the juvenile Will Hanlon will end up at the infamous nightclub, where the psychic will save him from a blaze that the local KKK members of the community will cause. In the recent film, we see that Will has a son named Mike and that Will eventually perishes in a configration, with Leroy surviving his own child and adopting his grandchild. The public account in the motion picture is that the parents were on drugs, but now that we see Will in Welcome to Derry, that's hard to believe. Perhaps the timid boy, once he became an adult, leaned into alcohol to rid himself of the torments, or maybe the corrupt town affected him first, with the KKK eventually completing the job it began long before. Be it via the terror of Pennywise or via the malice of the town, seeded by It, It in the end gets the final victory on him.
Leroy's Transformation
This chain of events would explain how Leroy transforms so drastically from what we see in It: Chapter 1 and the prequel. In his later years, Leroy seems bitter and much harsher with his discipline. Since he outlived his own offspring, it's understandable to observe such a drastic change. However, his statements carry more weight now that we know he's witnessed Pennywise's hauntings and the effects they wrought upon his son. In the opening scene of the movie, we observe the boy pause to use a bolt gun on a sheep at Leroy's farm. His grandfather chastises him for hesitating and provides an metaphor that leads to a kill-or-be-killed scenario.
“You have two options you can be in this world. You can be in the open like us, or you can be trapped inside,” Leroy states as he points to the creature. “You waste time hemming and hawing, and another is going to decide for you. Except you will be unaware it until you feel that projectile between your eyes.”
Looking back, this could be a bit of foreshadowing, a lesson he wishes he had told his own child. Maybe he wishes he had done something in his youth, but for some reason, he couldn't resist the repellent attraction of Derry.