Welcome to Derry Could Have Unraveled a Longstanding Pennywise Mystery
The clown's influence on the young residents of Welcome to Derry molds them throughout their adult lives, transforming them into the very adults who keep the town's cycle of hatred ongoing. It finds easy targets on kids from broken homes — youngsters who often grow up to repeat the same patterns as their guardians. But, the Hanlon household distinguishes itself as one of the few households that never splinters, which may explain why Mike, even after electing to remain in Derry, persists as the sole member who never fully falls under Pennywise's sway.
The Hanlon Family's Distinctive Resistance
In the fourth installment of Welcome to Derry, Leroy at last grows more aware of the paranormal entities surrounding the community, particularly when It begins tormenting his son, Will, during their fishing trip. The Hanlon clan comprises some of the few adults who are aware that things are not right with the town, notably the father, who was shown to be receptive to psychic abilities when he was able to detect a fellow psychic's use of it in the third episode. Subsequently, he spots one of the clown's trademark balloons outside his residence. The ability, alongside his failure to feel fear, combined with the foundation of his household, could be why he's able to see the entity's manifestations. However, consider if that shining is hereditary, and one of the reasons Mike Hanlon is one of the only adults in the town who didn't lose themselves to its cruelty?
The boy is part of the group of kids at his educational institution being terrorized by the clown. All his school friends come from broken homes, with parents who don't believe they're being targeted. The cause he is being haunted is due to the cruelty of the community, combined with his potential sensitivity to psychic abilities, which makes him susceptible. This family are fundamentally strangers in the town during 1962, which contributes towards the household sensing something is off about the town from the beginning. They also have a good foundation that remains unbroken, in contrast to the folks who come from the area, with bonds that have decayed internally.
Historical Context
Drawing from the It novel, we know the juvenile Will will find himself at the infamous nightclub, where the psychic will save him from a fire that the town bigots of Derry will ignite. In the 2017 movie, we observe that Will has a son named Mike and that Will ultimately dies in a fire, with Leroy surviving his own child and adopting his grandchild. The official story in the motion picture is that the parents were on drugs, but now that we see him in Welcome to Derry, that's difficult to accept. Maybe the shy youth, once he grew up, turned to alcohol to free himself of the torments, or maybe the rotten town got to him initially, with the KKK eventually completing the task it began years ago. Be it via the terror of Pennywise or via the cruelty of the community, seeded by Pennywise, It eventually gets the final victory on Will.
The Father's Evolution
These occurrences would explain how Leroy transforms so drastically from what we see in the first film and Welcome to Derry. In his later years, Leroy appears bitter and much harsher with his parenting. Because he survived his own son, it's comprehensible to observe such a drastic change. However, his words carry more weight since we are aware he's witnessed Pennywise's hauntings and the effects they wrought upon his son. In the opening scene of the movie, we observe the boy hesitate to use a bolt gun on a sheep at Leroy's farm. Leroy chastises him for hesitating and offers an analogy that results in a survival-of-the-fittest situation.
“You have two options you can be in this world. You can be out here like we are, or you can be in there,” Leroy says as he points to the creature. “You dawdle hemming and hawing, and another is going to decide for you. But you will be unaware it until you feel that projectile in your head.”
Looking back, this could represent a piece of foreshadowing, a lesson he regrets not imparting to his own child. Perhaps he wishes he had done something in his youth, but for some reason, he couldn't resist the sickening attraction of Derry.