Welcome to Derry Could Have Unraveled a Lingering Pennywise Mystery

Pennywise's impact on the young residents of Welcome to Derry molds them long into adulthood, twisting them into the very adults who perpetuate the community's cycle of animosity ongoing. The creature finds easy targets on kids from broken households — children who often mature to repeat the identical behaviors as their parents. However, the Hanlon household stands apart as a rare example of a family unit that never splinters, which could clarify why Mike, even after choosing to stay in the town, persists as the sole member who doesn't completely succumb under Pennywise's sway.

Hanlon Household's Unique Resilience

In episode 4 of the series, Leroy Hanlon finally becomes more aware of the supernatural forces surrounding the community, particularly when the entity starts haunting his child, Will Hanlon, during their angling excursion. The Hanlon family consists of a small number of adults who are cognizant that something is amiss with the town, especially Leroy, who was shown to be receptive to psychic abilities when he was able to detect Dick Hallorann's use of it in episode 3. Subsequently, he sees one of Pennywise's signature inflated orbs outside his residence. This gift, alongside his inability to experience terror, along with the foundation of his household, may be why he's able to see the entity's manifestations. However, consider if that shining is generational, and a key factor Mike is among the few individuals in the town who resisted succumbing to its cruelty?

Will is a member of the collective of kids at his school being terrorized by the clown. His classmates hail from broken homes, with caregivers who don't believe they're being targeted. The cause he is being haunted is because of the cruelty of the community, combined with his likely receptiveness to psychic abilities, which makes him susceptible. This family are ultimately strangers in Derry during 1962, which lends itself towards the family sensing something is off about the town from the beginning. They also have a solid base that remains unbroken, in contrast to the folks who originate in the town, with bonds that have deteriorated within.

Historical Context

Based on the original book, we understand the juvenile Will will find himself at the Black Spot, where the psychic will save him from a blaze that the local KKK members of Derry will ignite. In the recent film, we observe that Will has a boy named Mike and that Will ultimately dies in a fire, with Leroy surviving his own son and adopting his grandchild. The public account in the motion picture is that Mike's parents were on drugs, but now that we see Will in the series, that's hard to believe. Maybe the timid boy, once he grew up, leaned into drink to free himself of the torments, or maybe the corrupt town affected him first, with the KKK eventually completing the task it started years ago. Whether through the terror of the entity or through the malice of the town, seeded by Pennywise, It in the end achieves the final victory on Will.

Leroy's Transformation

These occurrences would explain how the elder Hanlon changes so drastically from what we see in the first film and the prequel. In his older age, Leroy appears resentful and much harsher with his discipline. Since he outlived his own offspring, it's comprehensible to see such a drastic change. Nonetheless, his statements hold greater significance now that we know he's witnessed Pennywise's hauntings and the effects they wrought upon his son. In the initial sequence of the movie, we observe the boy pause to use a bolt gun on a sheep at the family property. His grandfather chastises him for delaying and offers an analogy that results in a kill-or-be-killed 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,” he says as he gestures to the sheep. “You waste time hemming and hawing, and someone is going to decide for you. But you will be unaware it until you feel that projectile in your head.”

In hindsight, this could be a bit of foreshadowing, something he wishes he had told his own child. Perhaps he wishes he had acted differently in his past, but for certain factors, he was unable to avoid the repellent attraction of Derry.