Welcome to Derry Could Have Solved a Lingering Pennywise Enigma
Pennywise's influence on the young residents of Welcome to Derry shapes them long into adulthood, twisting them into the exact individuals who perpetuate the community's pattern of animosity alive. It finds easy targets on children from broken households — children who frequently mature to repeat the same patterns as their parents. However, the Hanlon household distinguishes itself as a rare example of a households that remains intact, which may explain why Mike, even after electing to remain in Derry, persists as the sole member who never fully falls under Pennywise's sway.
The Hanlon Family's Unique Resilience
In the fourth installment of the series, Leroy at last grows increasingly conscious of the supernatural forces enveloping the neighborhood, especially when It starts haunting his son, Will, during their fishing trip. The Hanlon clan comprises a small number of grown-ups who are cognizant that something is amiss with the town, especially the father, who was shown to be receptive to the Shining when he was able to detect a fellow psychic's employment of it in episode 3. Later, he sees one of the clown's trademark balloons outside his residence. The ability, alongside his failure to feel fear, along 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 a key factor Mike is among the few adults in Derry who resisted succumbing to the town's malevolence?
Will is part of the collective of kids at his school being terrorized by the clown. His classmates come from broken homes, with caregivers who refuse to accept 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 renders him vulnerable. This family are fundamentally strangers in the town during 1962, which lends itself towards the household sensing something is off about the town from the beginning. They also have a good foundation that remains unbroken, in contrast to the residents who come from the town, with relationships that have deteriorated internally.
Backstory Connections
Drawing from the original book, we understand the juvenile Will will find himself at the infamous nightclub, where Hallorann will rescue him from a blaze that the local KKK members of the community will cause. In the recent movie, we see that Will has a boy named Mike and that the father eventually perishes in a fire, with his father outliving his own son and taking his grandson in. The official story in the motion picture is that Mike's parents were on drugs, but given our current view of Will in the series, that's difficult to accept. Maybe the timid boy, once he grew up, turned to drink to rid himself of the hauntings, or maybe the rotten town affected him initially, with the KKK eventually finishing the job it began long before. Be it via the terror of Pennywise or through the malice of the community, instigated by It, It eventually achieves the last laugh on him.
Leroy's Transformation
These occurrences would clarify how Leroy changes so radically from what we see in It: Chapter 1 and Welcome to Derry. In his later years, Leroy appears resentful and much stricter with his discipline. Because he outlived his own offspring, it's understandable to see such a drastic change. Nonetheless, his words carry more weight now that we know he's seen the clown's activities and the effects they had on his son. In the opening scene of It, we see Mike hesitate to use a bolt gun on a animal at the family property. His grandfather reprimands him for delaying and offers an analogy that results in a kill-or-be-killed scenario.
“You have two options you can be in this existence. You can be out here like we are, or you can be trapped inside,” Leroy says as he points to the sheep. “You dawdle hemming and hawing, and someone is going to make that choice. Except you will be unaware it until you feel that bolt in your head.”
In hindsight, this could represent a bit of foreshadowing, a lesson he wishes he had told his own son. Maybe he desires he had done something in his youth, but for some reason, he was unable to avoid the repellent attraction of the town.