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Pennywise's impact on the young residents of the Derry series molds them throughout their adult lives, twisting them into the very adults who keep the community's pattern of animosity alive. It preys most easily on kids from fractured households — youngsters who frequently grow up to replicate the same patterns as their guardians. But, the Hanlon family stands apart as a rare example of a family unit that remains intact, which may explain why Mike Hanlon, even after electing to remain in Derry, persists as the only Loser who doesn't completely succumb under the clown's influence.

Hanlon Household's Unique Resilience

In the fourth installment of Welcome to Derry, Leroy finally becomes increasingly conscious of the paranormal entities enveloping the community, especially when It starts haunting his child, Will, during their angling excursion. The Hanlon clan consists of some of the few adults who are cognizant that things are not right with the municipality, especially the father, who was shown to be receptive to the Shining when he was capable of sensing Dick Hallorann's use of it in episode 3. Subsequently, he spots one of Pennywise's signature inflated orbs outside his residence. The ability, alongside his inability to experience terror, combined with the foundation of his family, may be why he's capable of perceiving 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 its cruelty?

The boy is a member of the collective of children at his school being terrorized by the clown. His classmates come from broken homes, with caregivers who don't believe they're being haunted. The reason he is being pursued is because of the cruelty of the community, paired with his potential sensitivity to shine, which makes him susceptible. This family are ultimately strangers in the town during the early sixties, which lends itself towards the household feeling something is off about the locality from the beginning. Additionally, they possess a good foundation that remains unbroken, in contrast to the residents who come from the town, with relationships that have decayed within.

Historical Context

Drawing from the It novel, we know the juvenile Will Hanlon will end up at the infamous nightclub, where Hallorann will rescue him from a fire that the local KKK members of the community will cause. In the 2017 film, we observe that he has a son named Mike and that Will ultimately dies in a fire, with his father surviving his own son and taking his grandson in. The public account in the motion picture is that Mike's parents were on drugs, but now that we see Will in Welcome to Derry, that's difficult to accept. Perhaps the shy boy, once he grew up, leaned into drink to rid himself of the torments, or maybe the rotten town got to him initially, with the KKK ultimately finishing the task it began years ago. Be it via the fear of Pennywise or through the cruelty of the town, instigated by It, the creature eventually gets the final victory on Will.

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 Welcome to Derry. In his older age, Leroy seems resentful and much stricter with his parenting. Since he outlived his own son, it's understandable to observe such a profound shift. However, his words carry more weight since we are aware he's witnessed the clown's activities and the impacts they had on his son. In the opening scene of It, we see the boy hesitate to use a bolt gun on a sheep at Leroy's farm. Leroy chastises him for delaying and provides an metaphor that leads to a kill-or-be-killed scenario.

“You have two options you can be in this world. You can be in the open like us, or you can be in there,” he says as he points to the sheep. “You dawdle hemming and hawing, and another is going to make that choice. Except you will be unaware it until you feel that projectile in your head.”

In hindsight, this could be a piece of foreshadowing, a lesson he wishes he had told his own son. Maybe he desires he had done something in his past, but for some reason, he couldn't resist the sickening allure of Derry.