Just like Pennywise changes form to surprise and shock, IT: Welcome To Derry also surprises with each twist becoming bolder than the last. One twist, in particular, will break your heart in ways you never expected, even if you had guessed the connection beforehand. Fans have long suspected that Marge Truman (Matilda Lawler) may have a direct connection to The Loser's Club, the kids who ultimately defeat Pennywise 27 years later in It: Chapters One and Two. The speculation is that Marge might be the future mother of Richie Tozier, the witty kid portrayed by Finn Wolfhard. Similar to Richie, Marge is also a glasses-wearing class clown at times. Furthermore, fans of Stephen King's original IT novel may remember that Richie's mother is named Maggie, which is a nickname for Margaret or Marge. The biggest clue came when Marge found herself trapped in the Black Spot during a racist attack. Despite Rich Santos (Arian S Cartaya) sacrificing himself to save her, Marge felt a deep connection to him. It is hinted that Marge might name her future son after Rich to honor his sacrifice. Confirmation of this connection comes in an unexpected way in the final chapter of season one. Episode 8 sees Pennywise going on a murderous spree, kidnapping children from a school, including Will. Lilly, Ronnie, and Marge attempt to save their friend using a special dagger. However, Pennywise captures Marge, revealing a sinister interest in her. Pennywise taunts Marge, hinting at her future son Richie and his role in Pennywise's demise or birth. This revelation hints at Pennywise's unique perception of time. Pennywise even shows Marge a missing poster with Finn Wolfhard's face, hinting at her future child. This revelation takes fans by surprise, showcasing Pennywise's complex consciousness. Despite the horror implications, the reveal also highlights the genuine love and warmth in Marge's connection to Richie. Rich's death is portrayed as the most emotional part of IT: Welcome To Derry, with his spirit living on in Marge's son, Richie Tozier.