HBO’s official renewal of the “IT” prequel series has brought new narrative weight to the production. On August 17, 2026, the network confirmed a second season for Welcome to Derry, shifting the horror saga’s timeline further into the past while maintaining a specific connection to the future Losers’ Club.
The upcoming season is set to move the clock back to 1935, placing the story in the heart of the Great Depression. This era focuses on a notorious piece of Derry folklore: the Bradley Gang massacre. While Stephen King’s original novel places this violent event in 1929, the television adaptation has confirmed a shift to the mid-1930s for its second outing. This move places the narrative decades before the events of the 2017 and 2019 films.
The Non-Linear Connection
The primary hurdle for an appearance by the adult version of Bill Denbrough—played by James McAvoy in IT Chapter Two—is the chronological gap. However, the first season of the series, which premiered in October 2025, introduced a pivotal mechanic regarding Pennywise’s perception of reality. The Season 1 finale established that the entity, played by Bill Skarsgård, experiences time in a non-linear fashion.
In those final moments, it was revealed that Pennywise is plagued or motivated by visions of the children who will eventually defeat him. By framing the Losers’ Club as a future threat that the entity can “see” through the decades, the series provides a narrative loophole for the character of Bill Denbrough to appear in a dream, a vision, or a psychological haunting, even during the 1935 setting. This connection suggests that Pennywise’s obsession with the Losers’ Club did not begin in the 1950s or 80s, but has been a lingering shadow across his entire history in Derry.
Production Shifts for Season 2
As the series prepares for its next chapter, there have been significant changes behind the scenes. Brad Caleb Kane is now serving as the sole showrunner for Season 2, steering the production toward the darker, historical focus of the Bradley Gang era. Bill Skarsgård is expected to continue his role as the titular shape-shifting entity, providing the connective tissue between the various timelines.
As of September 2026, McAvoy has been heavily involved in his directorial debut, California Schemin’. While no official casting announcement has linked him to a specific episode of Welcome to Derry, the show’s strategy focuses on bridging the gap between the prequel’s historical horror and the modern-day conclusion of the “IT” duology.
By centering on the Bradley Gang massacre, Season 2 is expected to explore how the town’s cycles of violence feed the entity. With Pennywise’s ability to see into his own future now a confirmed part of the television canon, the presence of Bill Denbrough serves as a reminder of the monster’s eventual downfall, even at the height of its power in the 1930s.
