Pennywise's impact on the young residents of Welcome to Derry shapes them throughout their adult lives, transforming them into the exact individuals who keep the town's cycle of animosity alive. The creature finds easy targets on children from fractured homes — youngsters who frequently mature to repeat the identical behaviors as their guardians. But, the Hanlon family stands apart as one of the few households that remains intact, which may explain why Mike Hanlon, even after choosing to stay in the town, persists as the only Loser who never fully falls under the clown's influence.
In episode 4 of Welcome to Derry, Leroy at last grows increasingly conscious of the paranormal entities surrounding the neighborhood, particularly when It begins tormenting his child, Will, during their angling excursion. The Hanlon clan consists of some of the few grown-ups who are aware that things are not right with the town, notably the father, who was revealed to be receptive to the Shining when he was capable of sensing Dick Hallorann's use of it in the third episode. Later, Leroy sees one of Pennywise's signature balloons outside his house. This gift, coupled with his inability to feel fear, along with the base of his family, may be why he's able to see Pennywise's hauntings. But what if that psychic sensitivity is hereditary, and a key factor Mike Hanlon is among the few adults in the town who resisted succumbing to its cruelty?
Will is a member of the group of children at his school being terrorized by the clown. His classmates hail from broken homes, with parents who refuse to accept they're being haunted. The cause Will is being pursued is because of the cruelty of the community, combined with his potential sensitivity to psychic abilities, which renders him vulnerable. This family are ultimately outsiders in the town during 1962, which lends itself towards the family sensing anomalies exist about the locality from the beginning. Additionally, they possess a good foundation that remains unbroken, in contrast to the folks who come from the area, with bonds that have decayed internally.
Based on the original book, we know the juvenile Will will end up at the Black Spot, where the psychic will rescue him from a blaze that the local KKK members of the community will ignite. In the 2017 film, we observe that he has a son named Mike and that Will ultimately dies in a fire, with Leroy surviving his own child and adopting his grandchild. The official story in the film is that the parents were on substances, but now that we see him in the series, that's hard to believe. Maybe the timid youth, once he grew up, leaned into drink to free himself of the hauntings, or maybe the rotten town got to him first, with the hate group eventually finishing the task it started years ago. Whether through the fear of Pennywise or through the malice of the town, instigated by Pennywise, It eventually gets the final victory on Will.
These occurrences would clarify how Leroy transforms so drastically from what we see in It: Chapter 1 and the prequel. In his later years, he appears bitter and much stricter with his discipline. Since he outlived his own offspring, it's understandable to see such a profound shift. However, his words hold greater significance now that we know he's seen Pennywise's hauntings and the impacts they wrought upon his child. In the opening scene of the movie, we observe the boy pause to use a bolt gun on a animal at the family property. His grandfather chastises him for delaying and offers an analogy that results in a kill-or-be-killed situation.
“There are two places you can be in this existence. You can be in the open like us, or you can be in there,” he says as he points to the sheep. “You waste time indecisive, and someone is going to decide for you. Except you will be unaware it until you experience that bolt between your eyes.”
In hindsight, this could represent a bit of prediction, a lesson he wishes he had told his own child. Maybe he desires he had done something in his youth, but for certain factors, he was unable to avoid the repellent attraction of Derry.
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