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Deducting massive gambling losses may raise pink flags at the IRS. The IRS is always looking for supposed “business” activities that might be just hobbies. If you’re eager about these online casino gaming occasions, you need to keep on the lookout for the schedule often. Remember, casual gamblers can only declare losses as itemized deductions on Schedule A as much as the number of their winnings. It is a slam dunk for IRS auditors if you happen to claim extra losses than winnings. So, the IRS is expecting you to say these winnings on your tax return. If you look carefully at Type W-2G, you may notice that there are containers for reporting state and native winnings and withholding. The state of the place you live typically taxes all of your earnings together with gambling winnings.