Would it be the end of the world for this guy to sign over checks to individual family members, them have them give him cash and maybe give them a piece for their troubles? Or then he'd be dragging others into it, which could open up a whole new can of worms.
Ace described a SAR perfectly. If you're at a casino and engage in cash transactions of over $10k in a 24-hr period, they are supposed to print up a currency transaction report. So if I'm at the Venetian and cash in $7k of chips at one cage and then they see me walk to another cage to cash in another $5k, you can bet your ass they'll file an SAR since it's obvious I'm trying to avoid reaching the $10 mark. Will anything come of it? Probably not...the IRS gets tons of them, and most go overlooked. If you try dicking around with them regularly, though...the'll probably start taking a closer look at where your cash is coming from.
The small amounts won't be of any help, unless your bud plans to open several checking accounts at different banks. And even though they are in $3k increments, depositing all of them at the same bank won't help you fly under the CTR radar. Banks obviously have software that runs algorithms which check for unusual account activity...so even if I went to 10 separate Wells Fargo branches and deposited a $3k check at each one, that kind of unusual activity will stand out if my balance is suddenly 5x what it normally is after a given day.
Btw, to the poster who suggested flying internationally and getting cash...that's a far worse option. Lots of luck trying to explain to US customs why you're flying back into the country with 40 grand in pure cash...think that won't raise a few red flags? You'd be insane to put it into your checked bag, and it would show up on the scanner at the airport if you tried to carry it on.
The nice part about using a local is you don't have to deal with any of this. I've collected 5 figures at once before, but using cash has become a pain in the ass in recent years.