Random Thoughts

Sometimes I think about weird stuff. No, not how many licks to the center of a Tootsie Pop stuff. Here are some questions and general thoughts:

When you win a large sum of money (5 figures or more) on online poker and want to cash out, how do you claim it on taxes if it is not legal in the U.S.? Does the website give you a 1099 (or European equivalent) and it's treated like you were overseas when you won it?

If you win your seat to an event ($10,000), either live or online, are you responsible for taxes on the 10 grand. That would suck to win a satellite for entry, get knocked out before the money and still have to pay taxes on the entry fee. I guess best case is you got in on a discount.

What a pain in the ass it must be to keep track of your finances if you are a pro gambler! Loans gone bad, paying out shares, losing big pots, winning big televised pots, airfare, hotels, buy-ins. I'm surprised we have not heard any stories come out yet about some pro that is being charged with tax evasion. They would seem to be a likely target with the money involved and the highly televised profiles of the players now.

Congrats to all of those that "invested" in Ryan at the Main Event, and of course congratulations to Ryan as well. I wanted to buy a piece, but by the time I had decided to do it, he had sold all his shares. For some reason, it never really seemed like a gamble because of his experience and talent. Oh well, maybe I'll try to race that horse next year.