The series It: Welcome to Derry is packed with connections to Stephen King's vast collection of tales. Apart from the obvious ties to It, the show showcases a direct connection to The Shining via the appearance of a young Dick Hallorann. Now, as the story unfolds, Welcome to Derry is weaving in one more beloved tale from King which merits a revisit.
Although The Shawshank Redemption may not be considered horror, particularly compared to a lot of King's other work, it is a haunting tale about an wrongfully convicted man sentenced to live his remaining years in a infamous penitentiary. It is that very penitentiary that becomes central in this context, since the Shawshank facility holds significant lore throughout King's fictional world — a pattern that continues within It: Welcome to Derry.
Some of the tales which mention the prison are Dolores Claiborne, Needful Things, Apt Pupil, 11/22/63, and It. Via these narratives, we learn about the terrible conditions at the state penitentiary plus several of the inmates within, including the boyfriend of a of Pennywise's early targets, who was convicted of armed robbery.
Thus far, however, the most we have discovered concerning Shawshank was via the perspective of the protagonist from Shawshank Redemption, played by the actor Tim Robbins in the 1994 film. Andy ends up in Shawshank following being wrongly convicted, then experiences assaulted and abused by other prisoners, and taken advantage of by the authority figures for his expertise in finance. It takes nearly three decades to tunnel his way out of the prison, prior to making his way "through sewage" to reclaim his freedom.
Regarding It: Welcome to Derry, viewers initially discovered about the prison's involvement from an initial preview for the show, where a correctional transport was seen bearing the title displayed on its side. During the second episode, it is revealed which character is probably headed to the prison.
Though it is known he was not responsible for the child deaths initially, the character Hank Grogan (played by Stephen Rider), dad to Ronnie (Amanda Christine), is arrested for those offenses. A teaser for episode 3, "the upcoming installment," shows an officer telling a jailed Hank, "Do you know what they do to child murderers at that prison?"
Considering that the actual murderer in Derry is an ancient power from another world preying on and killing kids, Hank's prospects of clearing his name do not look good. And even if he does go to Shawshank and the audience don't follow him there, understanding what is known about that prison makes it clear that his experience would not be pleasant.
More importantly, however, this development would endanger Ronnie. He acts as her guardian. Horrible things are occurring in the town that nobody, young or old, understands and Ronnie just has her new group of friends to rely on. She's going to need her father as the story progresses, but if Shawshank has any say, she may be out of luck.
A single fact is apparent: Hank lacks 28 years to dig to freedom.
Welcome to Derry the first two episodes are currently available on HBO Max. Additional installments are released each week each Sunday.