Quote:
Originally Posted by encapsulated
Not joking - I've seen people in tournament final tables restructuring the payout to avoid having to pay taxes on them. I've cashed out 6k in chips from blackjack and no questions as asked - they simply asked to see my ID to verify I'm 21+. I've also seen high rollers ask multiple people to go cash their chips for them separately to avoid being issue a CTR. I know professional gamblers must keep a ledger of all wins and losses for the end of the year - as a recreational player - I am just asking because the rules aren't posted except for the poker room's cage where it states winning if 10K+ must be reported.
You are skirting dangerously close to discussion of illegal activities. Please avoid going over the line so we don't need to moderate anything.
1- No amount of structuring your cashouts will let you (legally or illegally) avoid "having to pay taxes". You are responsible for paying taxes on any gambling winnings (even $1) according to your local jurisdiction, regardless of how you take the cashout.
1a- You probably can't even avoid withholding (W-2G) in most cases, since most casinos have a formula they use for tourney wins, and will never issue W-2Gs for cash game wins (since they don't track how much you bought in for and have no idea whether a cashout even corresponds to a win or a loss).
2- The only thing you might accomplish is avoiding a CTR or SAR. These are not IRS/tax documents, they are FinCEN/Homeland Security ones. They don't give or remove tax liability, they allow DHS to track and prosecute money laundering. (Though there are some who believe that they may also find their way to the IRS and make audits more likely, I don't know if there is evidence to support this one way or another.)
3- Structuring your cashout to avoid CTRs is actually illegal, so if you do this you may take a completely legal activity (cashing out your money) and turn it into an illegal one (structuring). Don't do this.
4- If you structure and the casino finds out or even suspects (which they probably will, eventually... surveillance is very good at this), instead of a CTR you will get an SAR (suspicious activity report) filed against you instead, and you'll continue to generate them every time you cash out from that point forward. If you think having a CTR filed is bad, imagine what having hundreds of SARs will do for you.
5- The "rules" aren't posted because the casino is forbidden from discussing them by DHS. You will never get a straight answer about their reporting cutoffs, at least not formally/publicly. You can do all the research you want on the FinCEN anti-money-laundering laws, though. Or just listen to us here.
6- Bottom line, don't worry about CTRs. Cash out however you would normally, and just don't worry about it. You should also pay your taxes on your winnings, but whether you do or not has nothing to do with the issuance of CTRs.
Last edited by dinesh; 07-19-2018 at 01:55 PM.