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Cannabis licenses often require experience in the industry - but that is a Catch-22 because many operators in the industry have been in the black market for decades, and some have been arrested for their involvement - does that bar them from working in Cannabis?

Maybe.  But maybe not because not all criminal backgrounds are treated alike, at least not in Illinois, check your state for its own laws:

https://www.cannabisindustrylawyer.com/can-you-work-at-or-own-a-dispensary-or-grow-with-a-felony/

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