Originally Posted by
Alan Mendelson
This is why I am laughing about this entire "challenge." Who wouldn't try to offset modest wins with losses so there is no tax liability? It certainly can be done and the IRS probably wouldn't raise an eyebrow over it.
Even a hundred thousand dollar annual win could be considered "modest" for a frequent player and could be easily offset with losses. It's when someone wins a million dollars that you probably would face IRS scrutiny.
If Arc paid taxes on a gambling profit my hat's off to him! He deserves a medal.
But Rob, what makes you different is that you claimed you offset your average $100,000 per year wins not with losses, but with hokey pokey business deductions for having dinner with your wife, buying groceries, and hosting parties. So Rob tell us: why do something controversial when the simple way out would be just to report losses? A profit of $100,000 a year is not hard to hide for a high denomination player, and especially for one who played at multiple casinos and may not have had a players card tracking all play.
Honestly Rob, unless I see your tax returns showing something different, I can't possibly think or accept that you offset your wins with dinners, groceries and parties and I don't care who told you it was okay to pull off that kind of hokey pokey. I posted what the IRS guidelines are previously, and everyone can read them just as I did. I think your tax returns are going to show modest "business deductions" and routine losses just like every other gambler with a profit does. Maybe you did actually have a profit but I don't think the Rob Singer we all know would ever want to pay taxes. So my guess is -- drum roll please -- your tax returns will show both losses and business deductions wiping out your wins.
Just to reiterate -- I don't have any winning/profitable years so I didn't have to do any hokey pokey when I filed taxes for all the years I've been going to casinos. And here's some ammunition for you, Rob, so you can start your 2016 insults: even with my $100,000 royal in October of 2015, Rob, I didn't have profit for the full year. That $100,000 profit was too little, too late to offset the previous 9 months of gambling and what I lost playing after. And I'm not ashamed at all because while I don't have a profit I didn't go into a deep hole, nor will I have to file bankruptcy. I was a recreational player and that $100,000 royal gave me plenty of recreation following the win and offset the losses I had in the previous nine months or so.
So Rob, if you want to insult me, go ahead. I'm prepared. You always insult me when the going gets tough -- because you hope I will suspend you so that you have an excuse for not responding to everyone else on the forum. Well Rob, NO suspension is coming. This time we're going to see it through to "the end."
Now, with that said, at "the end" you might be due for a giant apology and a giant atta-boy for really having on average $100,000 per year of profits, and for really offsetting your entire tax liability with dinners, groceries and parties. And if that's what I see when/if I get your tax returns I will become your biggest cheerleader.
Remember Rob, I never doubted that you won the money you said you did. It makes perfect sense to me that a high denomination player like you who quits when ahead, could total up profits of $100,000 per year. What I doubt is your claim about offsetting the taxable gains with dinners, groceries, parties and other hokey pokey business deductions and getting an OK from the IRS in audits.
Prove me wrong, Rob, by showing me the returns.