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>[...]put things like "your share of the cashout," "for atm skimming," and "for the cocaine," into the memo field (where you'd put "Rent" on a check)

The memo field is not terribly relevant. I've jokingly written things very similar to these examples on real bank checks and never had a problem with someone else cashing or depositing them.

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I went to the DPRK (North Korea) past summer. Beforehand we met with a guy who went there a year before. In the payment memo field for his trip he wrote something akin to 'Payment for North Korea'. The bank cancelled his wire transfer and nearly cancelled his account. In the end they only barred him from making other payments to that bank account number.

My guess is everything is monitored but red flags only go off when suspicious activity is frequent or serious enough.

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