Good posters such as yourself disappeared and that message board went downhill, so after awhile, I dropped AOL and began posting my thoughts on blogs instead.

The radio station owner pled guilty to structuring, was fined and spent a couple of years on probation.

Implied into the system is that the defendant did need to withdraw at least $10k+, though.  And he's aware, at least vaguely, of 31 C.F.R. § 103.22, which makes it mandatory to report currency transactions of $10k+.

Okay, assume for purposes of argument that Spitzer, a nice button-downed rich kid whose family has always had tax accountants go over their records to get every deduction, routinely puts almost everything he spends on debt or credit cards. He doesn't ordinarily deal in much cash, not even for walking-around money in NYC (he takes limos instead of taxis, he doesn't eat at Mickey D's and pay cash).

But a few times each year, he wants to pay for play.  He doesn't want to leave an Amex or wire transfer paper trail, so he wants to pay in cash.

Maybe sometimes he structures two play-dates for consecutive nights on an out-of-town weekend, or maybe he is into the occasional three-way, or maybe he's just trying to avoid trips to the bank. But for whatever reason, he wants to have on-hand within a relative short period of time more than $10k in cash.  And he knows -- being a former organized crime prosecutor for Manhattan DA Morgenthal -- that if he goes to Citibank and takes out $12k in cash, it will trigger a Suspicious Activity Report.

So Tuesday he goes to Citibank and withdraws $6k. Thursday he goes back to Citibank and withdraws another $6k.  He thinks he's in the clear.

Rinse and repeat that scenario somewhat irregularly -- say, 15 times in a year, with an average periodicity of less than a month, maybe one (a long week when the wifey and daughters were in Europe) bumping up into the $20k within a week range.

What he doesn't realize is that Citibank (or whoever), post-9/11, is really touchy about all big and irregular cash transactions.  And he doesn't know about 31 C.F.R. § 103.18. But Citibank -- taking seriously all that "had reason to suspect" language, confirming that there are individual transactions of more than $5k (even if they're not more than $10k), and finally noting that, "Hey, we can't think of any good reasonable explanation for the Governor of New York to be filling briefcases with cash this way," decides to be safe rather than sorry, punt, and file a report.

IRS/Treasury says, Holy cow, a politican with suitcases of cash, yada yada. They're ultimately disappointed that it's not bribery, it's just prostitution. On the other hand, it's expensive prostitution, and it's interstate prostitution. And by then they've got a great paper trail of withdrawals that can't be explained in any other way than by his splitting up, into closely spaced chunks, the more than $10k+ sums he needs.  With the wire taps they have him dead-to-rights on the underlying conduct.

I haven't studied the regs exhaustively, and I'd agree that this may not fit the particular definition of "structuring" you quoted from 31 C.F.R. § 103.11(gg).

But the scenario I've just described does fit the literal language of the statute, 31 U.S.C. § 5324(a), with or without a reg to specifically further define what "structuring" is: "[F]or the purpose of evading the reporting requirements of section 5313 (a) ... or any regulation prescribed under any such section [specifically, 31 C.F.R. § 103.22]," Spitzer "(1) ... attempt[ed] to cause a domestic financial institution to fail to file a report required under section 5313(a) ... or any regulation prescribed under any such section [again, specifically, 31 C.F.R. § 103.22]."