Welcome to Derry May Have Solved a Longstanding Pennywise Mystery
The clown's influence on the children of the Derry series shapes them throughout their adult lives, twisting them into the very adults who perpetuate the community's cycle of hatred ongoing. The creature preys most easily on children from fractured homes — youngsters who often grow up to repeat the same patterns as their parents. But, the Hanlon family stands apart as a rare example of a households that never splinters, which may explain why Mike, even after choosing to stay in the town, persists as the only Loser who doesn't completely succumb under the clown's influence.
Hanlon Household's Unique Resistance
In episode 4 of the series, Leroy finally becomes increasingly conscious of the supernatural forces surrounding the neighborhood, particularly when the entity begins tormenting his child, Will Hanlon, during their fishing trip. The Hanlon family consists of a small number of grown-ups who are cognizant that things are not right with the town, notably the father, who was shown to be receptive to psychic abilities when he was capable of sensing a fellow psychic's employment of it in episode 3. Subsequently, he spots one of the clown's trademark balloons outside his residence. This gift, alongside his inability to feel fear, combined with the base of his household, may be why he's capable of perceiving Pennywise's hauntings. But what if that shining is generational, and a key factor Mike Hanlon is one of the only individuals in the town who resisted succumbing to the town's malevolence?
The boy is a member of the collective of children at his school being tormented by Pennywise. His classmates hail from dysfunctional families, with caregivers who refuse to accept they're being haunted. The reason he is being haunted is due to the cruelty of the community, paired with his potential sensitivity to shine, which renders him vulnerable. This family are ultimately outsiders in the town during 1962, which lends itself towards the family feeling anomalies exist about the town from the beginning. Additionally, they possess a good foundation that isn't fractured, in contrast to the folks who come from the area, with bonds that have deteriorated internally.
Backstory Connections
Based on the original book, we understand the juvenile Will will end up at the infamous nightclub, where Hallorann will rescue him from a fire that the local KKK members of Derry will cause. In the 2017 film, we see that Will has a boy named Mike and that the father eventually perishes in a configration, with his father surviving his own son and taking his grandson in. The official story in the motion picture is that Mike's parents were on drugs, but given our current view of Will in Welcome to Derry, that's hard to believe. Maybe the shy youth, once he grew up, leaned into drink to free himself of the hauntings, or maybe the rotten town got to him initially, with the hate group eventually completing the task it started long before. Be it via the fear of Pennywise or through the malice of the community, seeded by It, It in the end achieves the final victory on him.
The Father's Evolution
These occurrences would explain how Leroy changes so drastically from what we see in the first film and Welcome to Derry. In his later years, Leroy appears resentful and much stricter with his parenting. Because he survived 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 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 animal at Leroy's farm. His grandfather reprimands him for hesitating and provides an metaphor that leads to a kill-or-be-killed situation.
“You have two options you can be in this existence. You can be out here like us, or you can be trapped inside,” he states as he points to the sheep. “You waste time indecisive, and another is going to decide for you. Except you won't know it until you experience that projectile in your head.”
In hindsight, this could be a piece of prediction, something he wishes he had told his own child. Maybe he desires he had done something in his past, but for certain factors, he couldn't resist the repellent attraction of the town.