Welcome to Derry Could Have Solved a Longstanding Pennywise Mystery
Pennywise's impact on the young residents of Welcome to Derry shapes them throughout their adult lives, transforming them into the very adults who perpetuate the town's pattern of animosity alive. It preys most easily on kids from broken homes — youngsters who often mature to repeat the same patterns as their guardians. However, the Hanlon household stands apart as one of the few family unit that remains intact, which could clarify why Mike, even after electing to remain in the town, remains the sole member who never fully falls under the clown's influence.
The Hanlon Family's Distinctive Resistance
In episode 4 of the series, Leroy finally becomes more aware of the supernatural forces surrounding the community, especially when the entity starts haunting his son, Will Hanlon, during their angling excursion. The Hanlon family consists of some of the few grown-ups who are cognizant that something is amiss with the municipality, notably Leroy, who was revealed to be sensitive to psychic abilities when he was able to detect a fellow psychic's use of it in the third episode. Subsequently, Leroy sees one of the clown's trademark inflated orbs outside his house. This gift, alongside his failure to feel fear, combined with the base of his household, could be why he's capable of perceiving Pennywise's hauntings. However, consider if that shining is generational, and a key factor Mike is one of the only individuals in Derry who resisted succumbing to its cruelty?
Will is part of the collective of kids at his educational institution being terrorized by the clown. His classmates hail from broken homes, with caregivers who refuse to accept they're being targeted. The reason he is being pursued is due to the viciousness of the town, paired with his likely receptiveness to shine, which renders him vulnerable. The Hanlons are ultimately outsiders in the town during 1962, which lends itself towards the household feeling something is off about the town from the beginning. Additionally, they possess a good foundation that isn't fractured, unlike the residents who come from the town, with bonds that have deteriorated within.
Historical Context
Drawing from the original book, we understand the juvenile Will will find himself at the infamous nightclub, where Hallorann will save him from a fire that the town bigots of Derry will cause. In the 2017 movie, we observe that he has a boy named Mike and that Will eventually perishes in a fire, with Leroy outliving his own child and taking his grandson in. The public account in the film is that Mike's 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 hauntings, or perhaps the corrupt town got to him initially, with the KKK ultimately finishing the job it started years ago. Whether through the terror of the entity or via the cruelty of the community, seeded by Pennywise, It in the end gets the last laugh on him.
Leroy's Transformation
This chain of events would clarify how Leroy transforms so radically from what we witness in the first film and Welcome to Derry. In his later years, Leroy seems bitter and much stricter with his discipline. Because he outlived his own offspring, it's understandable to see such a profound shift. Nonetheless, his statements carry more weight now that we know he's witnessed Pennywise's hauntings and the effects they wrought upon his child. In the initial sequence of It, we observe Mike pause to use a stunning device on a sheep at Leroy's farm. Leroy reprimands him for hesitating and provides an metaphor that results in a kill-or-be-killed scenario.
“There are two places you can be in this existence. You can be out here like we are, or you can be in there,” Leroy states as he gestures to the creature. “You waste time hemming and hawing, and someone is going to make that choice. Except you will be unaware it until you experience that bolt in your head.”
In hindsight, this could represent a piece of prediction, something he wishes he had told 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 the town.