Especially given the LLM does not trust the user. An LLM can be jailbroken into lowering it's guardrails, but no amount of rapport building allows you to directly talk about material details of banned topics. Might as well never trust it.

No vigilant insider is making a series of "single market predictions with high accuracy" on the same account. They would make unlinkable bets on fresh accounts.

You can't be sure that they are an insider or lucky, just from onchain data.