Question from a reader:”I won some money on an online poker site and they are not sending me a 1099 for my winnings like I asked. Instead they are sending me a listing of my gross winnings, less entry fees, net winnings and then more net entry fees that make a negative amount. This sounds like a scam to me.”
It sounds like a scam to me as well. The online site is not doing itself a favor by promoting tax fraud. Gaming commissions can’t touch some sites because they are offshore but there are some serious problems for honest citizens who win on gaming sites and don’t declare their winnings. Remember the business of income taxes – you are taxed on all worldwide income. So if you win off of a site in the Bahamas, you still need to pay taxes on it.
You are also taxed on all your winnings. They generally go on Line 21 of your 1040 form as Other Income as gambling winnings. You can offset your losses to the amount of winnings on your Schedule A but you better have darn good records if you are doing double digit or triple digit winnings. By the way, congrats if you did win big that way!
Entry fees would fall into the category of an expense if you are a professional poker player. Guess what? The IRS looks pretty closely at professional gamblers and you better not only have accurate records, you might run the risk that your entry fees will be overturned if you play too footloose and fancy free with your expenses. If you are classified as a hobby, no expenses for you. You also need to think twice about doing this because if you do say you are a professional gambler, you are on the hook for both sides of social security tax and self-employment tax no matter what your losses might be.
So, save yourself some aggrevation, avoid tax scams and declare your earnings honestly and take your legit deductions and/or expenses.

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Kim Isaac Greenblatt
Tax Scams Surface With Bad Advice on Reporting Income







