Welcome to Derry May Have Unraveled a Longstanding It Enigma
Pennywise's influence on the young residents of the Derry series molds them long into adulthood, transforming them into the very adults who keep the community's cycle of animosity ongoing. The creature finds easy targets on children from fractured homes — children who often grow up to replicate the same patterns as their guardians. But, the Hanlon family distinguishes itself as one of the few family unit that remains intact, which may explain why Mike Hanlon, even after electing to remain in Derry, persists as the sole member who doesn't completely succumb under Pennywise's sway.
Hanlon Household's Distinctive Resistance
In episode 4 of the series, Leroy at last grows increasingly conscious of the paranormal entities enveloping the neighborhood, particularly when It starts haunting his child, Will Hanlon, during their angling excursion. The Hanlon clan comprises a small number of 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 a fellow psychic's employment of it in the third episode. Subsequently, he spots one of Pennywise's signature balloons outside his residence. This gift, coupled with his failure to experience terror, combined with the foundation of his household, may be why he's able to see Pennywise's hauntings. But what if that shining is generational, and a key factor Mike Hanlon 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 educational institution being terrorized by the clown. All his school friends come from dysfunctional families, with parents who don't believe they're being targeted. The reason Will is being pursued is because of the viciousness of the town, combined with his likely receptiveness to shine, which makes him susceptible. The Hanlons are fundamentally outsiders in Derry during the early sixties, which contributes towards the household feeling something is off about the town from the onset. They also have a solid base that remains unbroken, unlike the residents who originate in the area, with bonds that have deteriorated internally.
Backstory Connections
Based on the It novel, we know the young Will will end up at the infamous nightclub, where Hallorann will save him from a fire that the town bigots of Derry will ignite. In the 2017 movie, we observe that Will has a son named Mike and that Will eventually perishes in a configration, with Leroy surviving 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 difficult to accept. Perhaps the timid boy, once he became an adult, leaned into drink to rid himself of the torments, or perhaps the corrupt town affected him first, with the hate group ultimately completing the job it began years ago. Whether through the fear of Pennywise or via the cruelty of the town, seeded by It, the creature in the end gets the final victory on Will.
Leroy's Transformation
This chain of events would explain how Leroy transforms so radically from what we see in It: Chapter 1 and Welcome to Derry. In his later years, he seems bitter and much stricter with his parenting. Because he outlived his own offspring, it's understandable to see such a profound shift. However, his words carry more weight now that we know he's seen the clown's activities and the impacts they had on his child. In the initial sequence of the movie, we see Mike hesitate to use a bolt gun on a sheep at Leroy's farm. Leroy chastises him for delaying and provides an analogy that leads to a kill-or-be-killed situation.
“You have two options you can be in this world. You can be in the open like us, or you can be in there,” Leroy states as he gestures to the sheep. “You waste time hemming and hawing, and someone is going to decide for you. Except you won't know it until you experience that projectile in your head.”
Looking back, this could represent a bit of prediction, a lesson he regrets not imparting to his own child. Perhaps he desires he had acted differently in his past, but for certain factors, he couldn't resist the sickening attraction of Derry.