Welcome to Derry May Have Solved a Longstanding It Enigma
The clown's influence on the children of the Derry series molds them throughout their adult lives, transforming them into the exact individuals who keep the community's cycle of animosity ongoing. The creature preys most easily on children from broken homes — youngsters who often mature to replicate the identical behaviors as their guardians. But, the Hanlon household stands apart as one of the few households that remains intact, which could clarify why Mike Hanlon, even after choosing to stay in the town, persists as the sole member who doesn't completely succumb under the clown's influence.
The Hanlon Family's Distinctive Resistance
In episode 4 of Welcome to Derry, Leroy at last grows more aware of the paranormal entities enveloping the community, particularly when the entity starts haunting his child, Will Hanlon, during their angling excursion. The Hanlon clan consists of some of the few grown-ups who are aware that things are not right with the municipality, notably the father, who was shown to be sensitive to the Shining when he was able to detect Dick Hallorann's employment of it in the third episode. Subsequently, he sees one of Pennywise's signature inflated orbs outside his residence. The ability, alongside his inability to experience terror, combined with the base of his family, could 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 the town who resisted succumbing to its cruelty?
Will is part of the collective of children at his educational institution being tormented by the clown. All his school friends hail from dysfunctional families, with caregivers who don't believe they're being haunted. The cause he is being pursued is because of the viciousness of the town, paired with his likely receptiveness to psychic abilities, which makes him susceptible. 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 solid base that isn't fractured, unlike the residents who originate in the town, with bonds that have decayed internally.
Historical Context
Based on the original book, we understand the young Will Hanlon will find himself at the infamous nightclub, where Hallorann will save him from a blaze that the local KKK members of the community will cause. In the recent movie, we see that he has a son named Mike and that Will ultimately dies in a configration, with his father outliving his own son and adopting his grandchild. The public account in the film is that the parents were on substances, but given our current view of Will in the series, that's difficult to accept. Perhaps the timid youth, once he became an adult, turned to drink to free himself of the torments, or maybe the rotten environment got to him first, with the hate group ultimately completing the job it started long before. Be it via the fear of the entity or through the malice of the town, seeded by Pennywise, It in the end gets the final victory on him.
Leroy's Transformation
This chain of events would explain how the elder Hanlon changes so radically from what we see in It: Chapter 1 and the prequel. In his later years, Leroy appears bitter and much stricter with his discipline. Because he survived his own son, it's comprehensible to see such a drastic change. However, his words carry more weight since we are aware he's seen the clown's activities and the effects they had on his son. In the opening scene of It, we observe the boy pause to use a bolt gun on a sheep at the family property. Leroy chastises him for delaying and offers an analogy 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 we are, or you can be trapped inside,” Leroy says as he gestures to the creature. “You waste time indecisive, and another is going to decide for you. But you will be unaware it until you experience that bolt in your head.”
Looking back, this could be a piece of foreshadowing, a lesson he regrets not imparting to his own son. Perhaps he desires he had done something in his youth, but for some reason, he couldn't resist the repellent allure of the town.