A non-customer comes in with a check for $14,000 drawn on a customer at our bank. He buys one check for $9,500 and another check for $2,500 made payable to himself and takes the rest in cash. He also pays for the check fees in cash. It looks to me like he structured his transaction to avoid CTR reporting. Would you file a SAR?

I don't see anything SARable happening yet, but that doesn't mean it won't.

It's quite possible that the payee simply intends to deposit those checks in different accounts and wanted to save himself a step later.

It's also quite possible that he is structuring intends to cash those checks elsewhere.

My suggestion is to watch for the cashiers checks to clear, get copies of them, and determine at that point when and how they were used. Once you have a complete picture of the whole series of transactions, then determine if it's a SARworthy event.