Welcome to Derry May Have Unraveled a Lingering Pennywise Mystery

The clown's impact on the young residents of the Derry series shapes them long into adulthood, twisting them into the very adults who keep the community's cycle of hatred ongoing. The creature finds easy targets on children from broken households — youngsters who often mature to repeat the same patterns as their parents. However, the Hanlon household distinguishes itself as a rare example of a family unit that remains intact, which could clarify why Mike, even after electing to remain in Derry, persists as the only Loser who never fully falls under the clown's influence.

Hanlon Household's Unique Resilience

In episode 4 of Welcome to Derry, Leroy Hanlon finally becomes more aware of the supernatural forces surrounding the neighborhood, particularly when the entity starts haunting his son, Will, during their fishing trip. The Hanlon family consists of a small number of grown-ups who are aware that things are not right with the municipality, notably the father, who was shown to be receptive to the Shining when he was capable of sensing a fellow psychic's use of it in the third episode. Subsequently, Leroy spots one of Pennywise's signature balloons outside his residence. The ability, coupled with his failure to feel fear, combined with the base of his family, may be why he's able to see Pennywise's hauntings. However, consider if that shining is hereditary, and a key factor Mike Hanlon is one of the only adults in the town who didn't lose themselves to the town's malevolence?

Will is a member of the collective of kids at his educational institution being terrorized by the clown. All his school friends come from broken homes, with caregivers who refuse to accept they're being targeted. The cause he is being haunted is because of the viciousness of the town, paired with his likely receptiveness to psychic abilities, which renders him vulnerable. The Hanlons are ultimately outsiders in the town during the early sixties, which lends itself towards the family feeling something is off about the locality from the beginning. They also have a good foundation that remains unbroken, unlike the folks who come from the area, with bonds that have decayed within.

Historical Context

Drawing from the original book, we understand the juvenile Will will find himself at the infamous nightclub, where Hallorann will rescue him from a fire that the local KKK members of Derry will ignite. In the recent film, we see that he has a son named Mike and that Will eventually perishes in a fire, with his father outliving his own child and adopting his grandchild. The official story in the motion picture is that the parents were on substances, but given our current view of Will in the series, that's hard to believe. Maybe the shy boy, once he became an adult, leaned into drink to free himself of the hauntings, or maybe the corrupt environment got to him initially, with the hate group eventually completing the job it started years ago. Whether through the terror of Pennywise or through the malice of the community, instigated by Pennywise, It in the end achieves the final victory on Will.

Leroy's Transformation

This chain of events would clarify how Leroy changes so drastically from what we see in It: Chapter 1 and the prequel. In his later years, Leroy seems resentful and much stricter with his discipline. Since he survived his own offspring, it's comprehensible to see such a profound shift. Nonetheless, his words carry more weight now that we know he's witnessed the clown's activities and the impacts they wrought upon his son. In the opening scene of It, we see the boy pause to use a bolt gun on a animal at the family property. Leroy chastises him for hesitating and offers an metaphor that leads to a kill-or-be-killed situation.

“You have two options you can be in this existence. You can be in the open like us, or you can be trapped inside,” he says 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, something he wishes he had told his own child. Perhaps he desires he had done something in his past, but for certain factors, he couldn't resist the sickening attraction of Derry.