I’ve gotten I’m sure a lot of CTRs issued against me from casinos but as long as reasonably speaking the output from the casino more or less equals the input I don’t think the government cares.
One of my banks it issues cashier’s checks with the next day’s date on them after 2pm PST so if I want to present such a payment to a casino that day it needs to be a cash payment. Where it gets tricky is the bank CTR when I withdraw from one of my companies will be in the EIN of the company and then the deposit CTR will be in my personal SSN (casinos don’t conduct business via EIN) but this hasn’t been an issue yet I assume because my entities are mostly 100% owned by me.
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