Say I won a good amount of money playing online poker.

How do I report this on taxes and is there a way around it? I figure if I deposit that kind of amount into my checking account, it would throw up a red flag.

 

You report it on line 21 of your form 1040, "other income".
Sure there is a way around it. Don't report it. We have a voluntary tax system and you may never get caught. But then if you do, you could face penalties, and even jail if it was big enough. However, as an owner of an S2000, we all know what an honest, upright person you must be, that would always do the right thing.

 

have a link at where to play?

 

I agree with Morris.

Are you sure the site isn't going to report the winnings? (Or is it an off-shore site?) Any winnings over $600 and you should be getting a W-2G. Winnings over 5K and some inocme tax should have been withheld before you got any money.

I have a friend who did a lot of gambling and he reported (almost) all of his winnings. He also deducted his gambling losses because he itemized. It was generally a wash for him.

 

http://www.bankrate.com/brm/itax/tips/20010131a.asp

Hit the big one? Here's how to report the winnings and deduct the losses
By Kay Bell