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Apologies if this has already been asked but I haven't read the book so I'm unsure of something that happens in It: Chapter Two.

We learn that The Losers Club has to perform a ritual to destroy the entity It, and Mike tells them they have to:

find items from their summer to sacrifice to the ritual

Bill then comes across a storm drain and hears Georgie again.

he is then pulled in and when he manages to free himself he is holding the S. S. Georgie, presumably taken from It.

My question is, if It knew what the Losers were up to, why would he willingly allow Bill to have the item back?

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    I was confused by this as well. Thought the whole thing with the tokens was kind of weak and poorly executed. It was really just a plot device to throw in some flashbacks. Concept was solid but not super execution.
    – sanpaco
    Sep 23, 2019 at 4:09

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IT knew that mike lied about the death of the native americans and the loosers don't really believe in the ritual, so it may have thought that it could easily kill the loosers just like it killed the native americans. So I thought it like, it give back the boat is to let them get to their death.

After collecting each of their individual tokens needed to perform the Ritual of Chüd that will ostensibly defeat It, the six Losers - Mike, Bill (James McAvoy), Beverly (Jessica Chastain), Ben (Jay Ryan), Eddie (James Ransone), and Richie (Bill Hader) - head back into the old house on Neibolt Street to kill the clown for good. They go down into the sewers and begin to perform the ritual, which involves chanting and burning the tokens, but it doesn't work. Mike lied about the Ritual of Chüd, not revealing that the Native Americans who attempted it were killed by Pennywise, but he insists the key is to have belief that it'll work.

screenrant

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    This sounds like a great, thought out answer. The token was bait to trap Bill but through his personal battle with Pennywise. Since he was able to assert his personal will and survive the encounter, he got to keep his token. Kinda like getting a special weapon after defeating a level boss, before fighting the big bad at the end of the game :)
    – m1gp0z
    Sep 23, 2019 at 20:11

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