Welcome to Derry May Have Unraveled a Longstanding Pennywise Enigma
The clown's impact on the children of the Derry series molds them long into adulthood, transforming them into the exact individuals who keep the town's cycle of hatred alive. The creature finds easy targets on children from fractured households — youngsters who often mature to repeat the same patterns as their guardians. But, the Hanlon household stands apart as one of the few family unit that never splinters, which may explain why Mike, even after electing to remain in Derry, persists as the sole member who doesn't completely succumb under Pennywise's sway.
The Hanlon Family's Unique Resistance
In the fourth installment of Welcome to Derry, Leroy finally becomes more aware of the paranormal entities surrounding the neighborhood, particularly when the entity starts haunting his child, Will Hanlon, during their angling excursion. The Hanlon family comprises a small number of grown-ups who are aware that something is amiss with the municipality, especially the father, who was revealed to be sensitive to psychic abilities when he was able to detect Dick Hallorann's use of it in episode 3. Later, Leroy sees one of the clown's trademark inflated orbs outside his house. The ability, coupled with his inability to experience terror, combined with the base of his family, could be why he's able to see Pennywise's hauntings. However, consider if that shining is hereditary, and one of the reasons Mike is one of the only adults in Derry who didn't lose themselves to its cruelty?
Will is part of the collective of children at his school being tormented by the clown. All his school friends come from broken homes, with parents who refuse to accept they're being haunted. The reason he is being pursued is because of the viciousness of the community, paired with his likely receptiveness to shine, which renders him vulnerable. The Hanlons are fundamentally 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 solid base that remains unbroken, in contrast to the residents who originate in the area, with bonds that have decayed within.
Historical Context
Drawing from the It novel, we know the juvenile Will Hanlon will find himself at the Black Spot, where the psychic will rescue him from a blaze that the town bigots of the community will ignite. In the recent movie, we see that he has a boy named Mike and that Will ultimately dies in a fire, with Leroy surviving his own son and adopting his grandchild. The official story in the film is that the parents were on drugs, but given our current view of him in Welcome to Derry, that's hard to believe. Perhaps the shy youth, once he became an adult, leaned into drink to free himself of the torments, or perhaps the corrupt environment got to him initially, with the KKK eventually finishing the task it began years ago. Be it via the fear of the entity or through the malice of the community, instigated by Pennywise, the creature in the end gets the final victory on him.
Leroy's Transformation
These occurrences would explain how the elder Hanlon transforms so drastically from what we see in the first film and Welcome to Derry. In his later years, he seems resentful and much harsher with his parenting. Since he outlived his own offspring, it's comprehensible to see such a drastic change. Nonetheless, his words carry more weight since we are aware he's witnessed the clown's activities and the effects they had on his child. In the opening scene of the movie, we observe Mike pause to use a stunning device on a animal at Leroy's farm. His grandfather reprimands him for delaying and offers an analogy that leads to a survival-of-the-fittest scenario.
“You have two options you can be in this existence. You can be out here like us, or you can be in there,” Leroy says as he gestures to the creature. “You waste time indecisive, and someone is going to make that choice. Except you will be unaware it until you experience that bolt in your head.”
Looking back, this could be a bit of foreshadowing, something he regrets not imparting to his own child. Perhaps he wishes he had done something in his past, but for some reason, he was unable to avoid the repellent allure of Derry.