Category Archives: Gambling

What happens when you make a few bets and win? Well, besides ending up with more money in your pocket, you have something else to put on your tax return; gambling winnings are taxable in the United States and go … Continue reading →

One of the most vexing things for the layman is the difference between a hobby loss and a business loss. Because the US taxes all income earned worldwide, it makes no difference whether you earn money in a hobby or … Continue reading →

The Tax Court today looked at whether a heretofore charitable organization (a 501(c)(3)) that has a gaming operation can retain its’ charitable (501(c)(3)) status. This case gives an excellent example of some of the drawbacks of “charitable” gambling from a … Continue reading →

If you’re lucky enough to win the lottery (tonight’s MegaMillions jackpot is somewhere around $225 Million), and you elect the annuity option (you’ll receive your winnings over an extended period of time, probably around 25 years), each of your payments … Continue reading →

You’re a successful business, with revenues over $1 million annually. Besides income taxes, your only regulatory fee is a $387 business license fee. The city you’re in proposes a 15% gross receipts tax (subject to voter approval on November 8th). … Continue reading →

Harrah’s Entertainment, the big casino conglomerate, apparently forgot to withhold from about 400 winners (mainly Canadians) at this year’s World Series of Poker®. Harrah’s is now “making up” for this by not allowing these players to play in another poker … Continue reading →

This final article in the series begins with a discussion of withholding. This leads into a discussion of poker tournaments (in cardrooms and casinos). Lastly, we’ll examine banking regulations and how they impact online gambling. The IRS is mandated with … Continue reading →

In this, the fourth of five parts of my series on taxes and online gambling, I’ll examine state income taxes, withholding requirements, and some legal issues, including the Silver Platter Doctrine. State Income Taxes Americans not only pay federal income … Continue reading →

In this article, part 3 of probably 5 parts, I examine recordkeeping and professional status for online gamblers. Unfortunately, a lot of this material is, frankly, boring. But it’s necessary. Some of the material in this article is based on … Continue reading →

I recently read a blog where a very successful online poker player wrote, There really aren’t IRS regulations on online gambling. It exists in a grey area. As fun160 pointed out “In the financial markets money earned off-shore is not … Continue reading →