Question of the Day - 15 December 2025

Yep.

Jean Scott had to write four editions of a book about this topic to expiate all the grief and hassle she endured over the years from lots and lots of W-2Gs and 1099s, extensive gambling diaries, letter audits, and special situations -- oh, as well as helping gamblers with their own tax returns.  

And Bob Dancer has written extensively about playing high-limit video poker, so high that hitting three-of-a-kind triggered tax paperwork. 

There are any number of associated issues for slot influencers beyond just keeping track of wins and losses. For example, many participate in group pulls, so the division of any winnings have to be accounted for. If they claim professional-gambling status, there are all the travel expenses to track. And in Brian Christopher's case, when he was living in his home country of Canada, there was all the cross-border tax reporting. We remember a blog years ago, in which Christopher wrote something to the effect of telling U.S. casinos to withhold taxes on his jackpots, so he'd have a nice surprise at tax time, but that the U.S. Treasury took 18 months to refund the withholdings. (Christopher is now a naturalized U.S. citizen.)

The best advice for these kinds of tax nightmares is to hire an accountant, of course, but even that has its own pitfalls. CPAs and Enrolled Agents who understand all the ins and outs of gambling taxes are few and far between. They're becoming more common as gambling, especially sports betting, spreads, but even then, influencers and gambling pros have to prepare all the documentation and check the returns thoroughly. It's never easy.