Welcome to Derry Could Have Solved a Lingering Pennywise Enigma
The clown's influence on the young residents of Welcome to Derry molds them long into adulthood, twisting them into the exact individuals who perpetuate the town's cycle of animosity alive. The creature preys most easily on kids from fractured homes — children who frequently mature to repeat the identical behaviors 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 Hanlon, even after electing to remain in Derry, remains the sole member who doesn't completely succumb under Pennywise's sway.
The Hanlon Family's Unique Resilience
In the fourth installment of Welcome to Derry, Leroy Hanlon at last grows increasingly conscious of the paranormal entities surrounding the neighborhood, particularly when the entity starts haunting his son, Will Hanlon, during their fishing trip. The Hanlon family comprises some of the few grown-ups who are cognizant that something is amiss with the municipality, notably the father, who was shown to be receptive to psychic abilities when he was able to detect Dick Hallorann's employment of it in episode 3. Later, he sees one of the clown's trademark balloons outside his house. The ability, coupled with his failure to experience terror, combined with the foundation of his household, could be why he's able to see the entity's manifestations. But what if that psychic sensitivity is generational, and a key factor Mike is among the few adults in Derry who resisted succumbing to the town's malevolence?
Will is a member of the group of kids at his educational institution being tormented by Pennywise. His classmates come from dysfunctional families, with caregivers who refuse to accept they're being targeted. The cause he is being haunted is due to the cruelty of the community, paired with his likely receptiveness to psychic abilities, which makes him susceptible. This family are ultimately outsiders in Derry during 1962, which contributes towards the household sensing something is off about the locality from the beginning. They also have a good foundation that isn't fractured, in contrast to the folks who come from the town, with relationships that have decayed within.
Backstory Connections
Based on the original book, we know the juvenile Will will find himself at the Black Spot, where the psychic will save him from a fire that the town bigots of the community will cause. In the recent movie, we observe that he has a son named Mike and that the father eventually perishes in a configration, with his father surviving his own child and taking his grandson in. The official story in the film is that Mike's parents were on drugs, but now that we see Will in Welcome to Derry, that's difficult to accept. Maybe the shy boy, once he grew up, leaned into alcohol to free himself of the torments, or perhaps the rotten town affected him initially, with the KKK ultimately completing the task it started long before. Whether through the terror of the entity or via the cruelty of the town, seeded by Pennywise, It eventually gets the last laugh on Will.
The Father's Evolution
This chain of events would clarify how the elder Hanlon transforms so radically from what we see in It: Chapter 1 and the prequel. In his later years, he appears resentful and much harsher with his parenting. Since he outlived his own son, it's understandable to see such a profound shift. However, his statements hold greater significance now that we know he's seen the clown's activities and the effects they had on his son. In the initial sequence of the movie, we see the boy hesitate to use a bolt gun on a sheep at Leroy's farm. Leroy reprimands him for hesitating and offers an analogy that results in a survival-of-the-fittest situation.
“There are two places you can be in this world. You can be in the open like us, or you can be trapped inside,” he states as he points to the creature. “You dawdle hemming and hawing, and someone is going to decide for you. Except you will be unaware it until you experience that projectile between your eyes.”
In hindsight, this could be a piece of prediction, a lesson he wishes he had told his own son. Maybe he desires he had acted differently in his youth, but for some reason, he was unable to avoid the sickening attraction of Derry.