Do I have to declare online poker winnings on my taxes?

A. The safest way in life is to declare all income on your income taxes, and may we recommend this. Any money that hits your bank account should be declared in full. If you begin to play seriously, you should keep detailed, and really specific records of your play, session by session. These records will allow you to file a proper tax return. For Americans, the IRS has a guide for this, guide 529, available at the IRS.gov website.