The horror prequel IT: Welcome to Derry is set to go even deeper into the past for its second season, and creators confirm its story will focus on the show’s most heartbreaking characters. After a first season set in 1962, the plan is for the story to jump back 27 years to 1935. This backward leap will allow the series to expand on the tragic tale of Bob Gray, the man who became Pennywise, and his devoted daughter, Ingrid Kersh.
Co-creator Andy Muschietti has stated the show was designed as a multi-season story that moves in reverse through time. While HBO has not yet made an official announcement about a second season, the creators have a clear plan. They intend to explore earlier, infamous events from Derry’s history, with season two centered on the 1935 Bradley Gang Massacre.
The Tragic Story of Bob Gray and Ingrid Kersh
The first season of Welcome to Derry introduced the human origins of the clown that terrifies Derry. Before the entity known as It took his form, Bob Gray was a real person. He was a struggling circus performer trying to support his daughter, Ingrid. His story is not one of inherent evil, but of a hopeful father whose life ended in tragedy when he was lured into the woods and consumed by the ancient entity.
His daughter, Ingrid, witnessed this horror but arrived at a devastating conclusion. She became convinced that her father’s soul was still trapped inside the monster that wore his face. This belief twisted her grief into a dangerous mission. In the 1962 timeline, an older Ingrid, played by Madeleine Stowe, appears as an antagonist. Dressed as a clown herself, she helps orchestrate tragedies around Derry, believing that creating fear and pain will summon Pennywise and give her a chance to free her father.
Her story ends in season one with a moment of terrible clarity. She finally realizes her father is truly gone and that Pennywise is merely using his appearance. The entity then shows her the Deadlights—a glimpse of its true form that shatters her mind, leaving her institutionalized at Juniper Hill Asylum.
What Season 2 Will Reveal About the Father-Daughter Duo
Because the show moves backward in time, season two will not continue from this ending. Instead, it will show an earlier chapter in Ingrid’s life. The season is set in 1935, a period when Ingrid was still deeply under Pennywise’s influence and actively working to see her father again.
Andy Muschietti has confirmed that the upcoming season will devote significant time to this storyline. He describes Ingrid as a uniquely tragic figure.
“I think it’s a pretty tragic character. She’s a very specific, very unique character, because she’s a victim, but she’s a perpetrator too. She’s tricked into thinking that her dad is still there somewhere in the shadows of that monster, and she wants to liberate him, but the only way to see him and try to liberate him is by creating all these baits [and] all this pain, because she knows that he will show up.”
This exploration promises to add emotional depth to the horror. It will show how love and loss can be corrupted into something monstrous, making Ingrid both a figure of sympathy and a source of terror. The season will also likely show more of Bob Gray’s life before his transformation, fleshing out the man behind the clown’s smile.
The 1935 Setting and the Bradley Gang Massacre
The historical backdrop for season two will be the Great Depression, a time of widespread poverty and fear that provides a perfect breeding ground for Pennywise’s influence. The central historical event will be the Bradley Gang Massacre.
In Stephen King’s novel, the Bradley Gang was a group of bank robbers who hid in Derry. After they kidnapped and killed a local banker, the townspeople took justice into their own hands, violently killing the entire gang. Pennywise was reportedly present during the chaos, even participating in the violence.
The first season of Welcome to Derry already hinted at this event. In an early episode, the U.S. military unearthed a car buried beneath Derry containing the skeletal remains of the gang. Season two is expected to dramatize the events leading up to and including this brutal massacre, showing how Pennywise feeds on the town’s collective fear and rage.
How Pennywise’s View of Time Changes Everything
The first season finale introduced a game-changing element that will shape future stories. During a confrontation, Pennywise revealed to a young woman named Marge Truman that he experiences time in a non-linear way. Past, present, and future all exist at once for him. He knew that Marge would grow up to become Margaret Tozier, the mother of Richie Tozier—a member of the Losers Club who helps defeat him in 2016.
This revelation suggests Pennywise could potentially target the ancestors of his future enemies to change his fate. In the finale, Marge voiced a theory that Pennywise might try to go back in time to kill the parents of her friends, which directly sets up the premise of the show moving to earlier eras. This time-twisting logic allows the prequel to have stakes that connect directly to the events of the original IT films.
Connections to the Wider IT Story and Future Plans
The show continues to build bridges to the familiar story of the Losers Club. The season one finale featured a cameo from Sophia Lillis as a young Beverly Marsh. In a post-credits scene set in 1988, an elderly Ingrid Kersh comforts Beverly after her mother’s death at Juniper Hill Asylum. This moment recontextualizes a scene from IT Chapter Two, showing that Pennywise’s influence and Ingrid’s tragic story stretched across decades.
Looking ahead, if the series continues as planned, a potential third season would jump back another 27 years to 1908. That season would likely explore another tragic event from Derry’s past mentioned in Mike Hanlon’s research: the Kitchener Ironworks explosion.
IT: Welcome to Derry is streaming on HBO Max.
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