Welcome to Derry May Have Solved a Longstanding Pennywise Enigma
The clown's influence on the children of the Derry series molds them long into adulthood, transforming them into the exact individuals who perpetuate the town's cycle of hatred alive. The creature finds easy targets on kids from broken homes — youngsters who often grow up to replicate the same patterns as their parents. 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 Derry, persists as the sole member who doesn't completely succumb under Pennywise's sway.
The Hanlon Family's Unique Resilience
In episode 4 of Welcome to Derry, Leroy at last grows more aware of the supernatural forces enveloping the community, especially when the entity starts haunting his child, Will, during their angling excursion. The Hanlon clan comprises a small number of adults who are aware that something is amiss with the town, notably Leroy, who was shown to be sensitive to psychic abilities when he was able to detect Dick Hallorann's use of it in episode 3. Subsequently, Leroy sees one of the clown's trademark balloons outside his residence. This gift, coupled with his failure to feel fear, combined with the base of his household, may be why he's capable of perceiving Pennywise's hauntings. But what if that psychic sensitivity is generational, and a key factor Mike is one of the only adults in Derry who resisted succumbing to the town's malevolence?
The boy is a member of the group of kids at his school being tormented by the clown. All his school friends come from broken homes, with caregivers who don't believe they're being targeted. The cause Will is being haunted is due to the viciousness of the community, combined with his likely receptiveness to psychic abilities, which renders him vulnerable. This family are fundamentally strangers in the town during 1962, which lends itself towards the family sensing anomalies exist about the town from the beginning. Additionally, they possess a good foundation that isn't fractured, in contrast to the residents who originate in the area, with relationships that have deteriorated internally.
Historical Context
Based on the It novel, we understand the young Will Hanlon will find himself at the infamous nightclub, where Hallorann will save him from a blaze that the town bigots of Derry will ignite. In the 2017 movie, we see that Will has a boy named Mike and that Will eventually perishes in a fire, with his father surviving his own son and adopting his grandchild. The public account in the film is that the parents were on substances, but now that we see Will in Welcome to Derry, that's hard to believe. Maybe the shy youth, once he grew up, turned to alcohol to rid himself of the hauntings, or maybe the corrupt town affected him initially, with the KKK eventually completing the task it started long before. Whether through the fear of Pennywise or via the cruelty of the community, instigated by Pennywise, It eventually achieves the final victory on him.
Leroy's Transformation
This chain of events would clarify how the elder Hanlon transforms so radically from what we see in the first film and Welcome to Derry. In his later years, Leroy seems bitter and much stricter with his discipline. Since he outlived his own offspring, it's understandable to observe such a drastic change. Nonetheless, his words carry more weight since we are aware he's seen Pennywise's hauntings and the effects they wrought upon his child. In the opening scene of It, we observe the boy pause to use a bolt gun on a animal at Leroy's farm. Leroy chastises him for delaying and provides an metaphor that leads to a kill-or-be-killed scenario.
“There are two places you can be in this existence. You can be out here like us, or you can be in there,” he says as he points to the sheep. “You waste time indecisive, and another is going to make that choice. But you will be unaware it until you feel that projectile in your head.”
Looking back, this could be a piece of foreshadowing, a lesson he regrets not imparting to his own son. Maybe he wishes he had done something in his past, but for some reason, he was unable to avoid the repellent allure of Derry.