I know of no business that traded tokens for casino's and sold the obsoletes. It would be illegal under gaming regs in NV.
That said, there was employees that would put the $ in and sell obsolete chips and tokens out the back door.
In the days you are talking about machines would take most tokens. No one cared if you got a couple obsolete $1 tokens in the machine. They would have cared about $100 tokens.
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