Given the obvious lack of intent to avoid a CTR on Thursday, I lean towards some sort of legitimate need for two separate transactions on Monday and Tuesday. We've got someone who took out $40,000, then put it back in within 24 hours, three or four times in a single month, but he mentioned to employees that he was shopping for some type of large purchase. He actually requested a blank cashier's check, and when that was refused, he decided to bring cash since he thought he would for some reason get a better deal if he was able to show cash at the auction. They tried to make other arrangements with him, but he wanted cash. How about calling him? "Mr. Smith, in a review of accounts, your account was flagged with an alert, and I wanted to mention these three transactions to you, to make sure you were aware of them..." then see what Mr. Smith might volunteer, if anything, to help inform your decision.
_________________________
"It is natural to give a clear view of the world after accepting the idea that it must be clear." - Albert Camus