Welcome to Derry Could Have Solved a Lingering Pennywise Enigma
Pennywise's impact on the young residents of Welcome to Derry molds them long into adulthood, transforming them into the very adults who perpetuate the town's cycle of animosity alive. It finds easy targets on children from broken households — youngsters who often mature to repeat the same patterns as their guardians. But, the Hanlon household distinguishes itself 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 doesn't completely succumb under Pennywise's sway.
Hanlon Household's Unique Resistance
In the fourth installment of Welcome to Derry, Leroy at last grows more aware of the supernatural forces enveloping the neighborhood, particularly when It begins tormenting his son, Will, during their angling excursion. The Hanlon clan comprises some of the few grown-ups who are cognizant that something is amiss with the town, especially Leroy, who was shown to be receptive to the Shining when he was capable of sensing Dick Hallorann's employment of it in episode 3. Later, he sees one of Pennywise's signature balloons outside his residence. The ability, coupled with his inability to feel fear, combined with the foundation of his household, may be why he's able to see Pennywise's hauntings. However, consider if that psychic sensitivity is generational, and one of the reasons Mike Hanlon is among the few individuals in Derry who resisted succumbing to the town's malevolence?
Will is part of the group of kids at his educational institution being terrorized by Pennywise. His classmates come from dysfunctional families, with parents who refuse to accept they're being targeted. The reason he is being pursued is because of the viciousness of the town, combined with his likely receptiveness to shine, which makes him susceptible. This family are ultimately strangers in the town during 1962, which lends itself towards the household feeling something is off about the locality from the beginning. Additionally, they possess a good foundation that isn't fractured, in contrast to the folks who originate in the town, with relationships that have decayed within.
Backstory Connections
Based on the It novel, we know the juvenile Will will find himself at the infamous nightclub, where Hallorann will rescue him from a blaze that the town bigots of the community will ignite. In the recent movie, we see that Will has a boy named Mike and that Will eventually perishes in a fire, with his father surviving his own child and adopting his grandchild. The official story in the motion picture is that Mike's parents were on drugs, but now that we see him in Welcome to Derry, that's difficult to accept. Perhaps the shy youth, once he became an adult, leaned into drink to free himself of the hauntings, or perhaps the rotten environment got to him initially, with the hate group eventually completing the job it started long before. Whether through the fear of the entity or via the malice of the community, seeded by It, It in the end gets the final victory on him.
The Father's Evolution
This chain of events would explain how Leroy transforms so radically from what we witness in the first film and the prequel. In his older age, Leroy appears resentful and much harsher with his parenting. Since he survived his own son, it's understandable to observe 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 It, we see Mike hesitate to use a stunning device on a animal at the family property. Leroy reprimands him for delaying and offers an metaphor that results in a survival-of-the-fittest scenario.
“There are two places you can be in this existence. You can be in the open like us, or you can be in there,” Leroy states as he points to the sheep. “You waste time indecisive, and another is going to decide for you. But you won't know it until you experience that projectile between your eyes.”
Looking back, this could represent a piece of foreshadowing, a lesson he regrets not imparting to his own son. Perhaps he wishes he had acted differently in his youth, but for some reason, he couldn't resist the repellent attraction of the town.