5 Questions That Need Answers in IT: Welcome to Derry Season 2

The first season of HBO’s horror hit IT: Welcome to Derry just finished. The show looks at what happened in Derry, Maine, before the movies we know. Season one ended with Pennywise forced back into hibernation. But the story is far from over.

Co-creator Andy Muschietti planned the show to have three seasons from the start. Season one was set in 1962. If the show continues, season two would jump back to 1935. This would explore an earlier time Pennywise terrorized the town. The final scene of season one and comments from the creators set up major questions for the next chapter. Here are the five biggest ones that need answers.

How Will the Show Handle Time Travel?

The season one finale introduced a big new idea: Pennywise might not experience time the way people do. During a confrontation on a frozen lake, Pennywise told a young girl named Marge that he knows her future son, Richie Tozier, will help defeat him. Marge is left wondering if Pennywise can move through time.

“What if he tries to go back and kill someone from the time before we were born, like our parents?” Marge asks her friend Lilly.

This line feels like a direct setup for season two. If Pennywise can go back to 1935, he could try to change the future by targeting the ancestors of the heroes from 1962 or even the famous Losers’ Club from the movies. However, some fans question if making Pennywise a time traveler gives him too much power. It could make him seem unbeatable. The show will need to explain the rules of this ability clearly.

Who Will Be the New Main Characters?

A jump to 1935 means a mostly new cast. The kids from 1962—Lilly, Will, Ronnie, and Marge—will likely not return as main characters. Their story in that time period seems finished.

The one actor sure to return is Bill Skarsgård as Pennywise. Other characters who could appear are those with long lifespans in Derry. This includes Ingrid Kersh, who has been in Derry since at least 1908. We saw younger actors play her in flashbacks, so they could return for a 1935 story. Rose, the Native American woman who understands the town’s history, is another character who could bridge the timelines.

The show will probably introduce a whole new group of children and adults facing Pennywise. Their connection to the characters we already know will be a key part of the story.

What Will Happen in the Bradley Gang Massacre?

Creators have said season two would focus on a famous tragic event from Derry’s past: The Bradley Gang Massacre of 1935.

In Stephen King’s novel, this event is part of the town’s hidden history. A gang of bank robbers was ambushed and killed by Derry citizens at a three-way intersection. In the show, the skeletons of the gang were already discovered in their car during season one. Season two would show the massacre itself and how Pennywise influenced the violence.

This event would serve the same purpose as the Black Spot fire in season one. It is the major tragedy that marks the end of Pennywise’s active cycle in that time period. Showing this brutal piece of history will let the series dive deeper into how Pennywise corrupts the entire town of Derry, not just its children.

How Will the Story Connect to the First Season?

Even with a new setting and characters, the story needs to feel connected. The time travel idea is one clear link. If Pennywise is going back to 1935 to attack ancestors, we could see the grandparents or parents of characters like Will Hanlon or Marge.

Another link could be through objects or places. The thirteen pillars that cage Pennywise are ancient. Characters in 1935 might also be trying to protect them or might accidentally weaken them. The show might also feature younger versions of familiar adult characters. We already saw a flashback of General Shaw as a child in 1908. Similar glimpses of other characters’ pasts could help tie the story together.

What Does Pennywise Want with Ingrid Kersh?

The character of Ingrid Kersh had a major twist in season one. She is the daughter of the original human Bob Gray, the circus performer whose identity Pennywise stole. In the finale, Pennywise did not kill her but showed her something terrifying in the “Deadlights”. She was taken away catatonic but showed a sly, knowing look.

The final scene of the season jumped to 1988. It showed an elderly Kersh in the Juniper Hill asylum talking to a young Beverly Marsh. This directly connects to a scene in the movie IT: Chapter Two. This confirms Kersh lives a long, twisted life in Derry. Her story is clearly not over.

Season two set in 1935 could show what happens to her next. Is she trapped with her father’s spirit? Is she becoming a monster herself? Her unique connection to Pennywise makes her a wild card for future seasons.

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