The right to resign Scowlee status

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Why is it that every time I get a few dollars ahead in blackjack, the pit boss stands over the game and watches my play? Jeff K. 

Fair enough, Fred; yes there are some pit bosses who stand guard over a blackjack table like the German Shepard in front of Col. Klink’s office. They sweat the money as if it were their own spoils. But pit bosses know, or at least ought to know, that the casino will suffer short term losing streaks, and that the players’ winnings more often than not will flow back the casino’s way over time, simply because the longer folks gamble with the house’s money, the more exposure they have to the casino’s edge.

When I pit bulled, if the game was on the up-and-up, I wasn’t on pins and needles when a player won decent chunk of money, even on a meager bankroll. It is not all that rare for a player to unleash a hundred dollar bill and run it up to four digits, or even higher. Plus, the house guards against financial ruin during your winning streak by setting table-betting limits. It is the “house limit” that protects the casino bankroll against your lucky assault.

Being that there are plenty of pit bosses who don’t sweat the money, I would suggest that you move to another table, pit or casino where they actually prefer a few winners, because winners, Jeff, tell the 90 plus percent who lose where they won. PR like that just can’t be bought.

I read a column of yours where you talked about offsetting gambling winnings with gambling losses. Can I also offset gambling winnings with stock losses if I sell them in the same year at a loss? Earlier this year, I won a slot jackpot of $18,000. I have collected a few hundred dollars worth of lotto tickets, but I could include some stocks that I can take a loss on. James B.

Reportable gambling winnings reported on the Other Income Line (1040) can come from lotteries, bingo, raffles, horse and dog racing, online poker, casino table games, and of course, your slot jackpot win. You can, though, offset the taxes on your winnings by reporting your gambling losses. Unfortunately, gathering up a couple hundred in lottery tickets or scratch-offs isn’t going to cut it, James, nor will your market losses.

As a loss-claimant, you must substantiate your loss claims with a flawlessly documented, descriptive gambling diary, but what you are not able to do is include your stock losses against your jackpot win. Only gambling losses can offset gambling wins. Uncle Sam won’t let you counterbalance a stock market loss against a gaming windfall.

And there’s more, James. Besides verifiable records necessary to support your losses pertaining to gambling, you can only deduct them if your deductions are itemized, and they must be deducted in the year of the loss or they are forever departed as deductions.

Oh, and if I haven’t ruined your day yet, James, be aware that now that you have won a jackpot and received a W2-G, don’t imagine that Uncle Sam doesn’t know of your tax liability. The IRS also receives a copy of your W2-G from the casino, and their computers are acquainted with your payday before, dare I say, you give it all back.

Gambling Wisdom of Week: “Next to the pleasure of winning is the pleasure of losing; only stagnation is unendurable.” –Hubert Howe Bancroft California Inter Pocula 1888 US historian

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