IT: Welcome to Derry's fifth episode confirmed the deaths of four major characters. The horror show on HBO Max is a prequel to It and It: Chapter Two, set during Pennywise's active cycle in 1962. In a shocking twist in the first episode of the series, several of the presumed main characters were violently killed by Pennywise. However, the hallucinatory nature of the entity's powers left it unclear whether they were truly gone.
After Lilly (Clara Stack) witnessed Teddy (Mikkal Karim-Fidler), Phil (Jack Molloy Legault), and Susie (Matilda Legault) being ripped apart by Pennywise's demon baby form, it was assumed that the characters were dead. Then, Episode 5 of Welcome to Derry reintroduced Matty Clements (Miles Ekhardt), the first victim in the show, revealing he had escaped the sewers where the creature had been keeping him, providing hope that he and the others had survived Pennywise's attacks.
It: Welcome to Derry Confirms 4 Characters Are Truly Gone
As established in previous It chapters, Pennywise's lair in the sewers serves as the entity's feeding ground, where it takes its victims and devours them, creating a horrifying area filled with piles of bodies and bones. Matty tells Lilly and her friends in Episode 5 that "it kept some of us alive," suggesting that the clown needed children alive to feed on their fear.
Matty then confirms Teddy's fate, saying, "Teddy was dead when it dragged him in, his skull was ripped open, and it... ate his brains out right in front of me."
A similar fate is confirmed for Susie, with Matty revealing the creature left her to bleed out in the sewer: "Susie, one of her arms was gone, it just left her there, all night bleeding out, and crying. Until she stopped."
However, Matty gives the group hope that Phil is still alive. He tells them, "Phil, he's still down there. He can't talk or move, but he's alive, somehow." This leads the group of children to enact a plan to enter the sewers and save their friend from Pennywise's clutches.
Matty leads the group back into the sewers, where they come across the rotting corpses of Teddy and Susie in the water, confirming Matty's reports. However, a third body appears in the water, and this time it's Phil's, revealing he is, in fact, long dead. It's at this point that Matty starts to chant a rhyme, and the children discover a fourth body in the water: Matty's. The fake Matty then transforms, revealing Pennywise in his full clown form for the first time in IT: Welcome to Derry.
As it turns out, Pennywise pulled out a familiar, cruel trick, impersonating Matty to lure the children into the sewers, on the hope that their friend could be saved, when in reality, the entity had killed Matty, Phil, Susie, and Teddy a long time ago.
That being said, the children's hope that their friends might be alive isn't entirely unfounded. In It (2017), Pennywise chooses to abduct Beverly Marsh rather than kill her, which leads the other Loser's Club members to enter the sewers and find her. When they arrive in Pennywise's lair, they find Beverly catatonic and floating in the sky, having succumbed to the deadlights (the creature's proper form, which paralyzes and tortures victims). However, through their efforts, they can revive her and save her from her fate.
It's possible that the same could've happened to Matty, Phil, Teddy, or Susie in Welcome to Derry, with the creature keeping them alive but unresponsive as a trap to lure the others in. However, Pennywise didn't even need this to convince the children to enter the sewers, and instead went one step further by impersonating Matty and using him to lie to them, preying on the group's trusting nature and good intentions.
While the children managed to escape Pennywise's clutches in Episode 5, the entity is far from done with them.
Previews for the final few episodes of IT: Welcome to Derry Season 1 have hinted at the children digging more into Pennywise's lore (even uncovering his human form), and the entity's success with cracking Dick Hallorann's mental lock box spells bad news for the town of Derry, suggesting that Pennywise will have plenty more victims before the season is done.