Those are classified as “other” income but effectively taxed at the same rate as the taxes on your “regular” income.
And it's important to note that this is on top of Federal taxes on gambling winnings. Whether you bet at Caesars Sportsbook Massachusetts or any other sportsbook, this is a tax on your total gambling winnings, not on any particular win. Massachusetts taxes gambling income at 5%, the same rate they tax all ordinary income. What are the Tax Rates for Gambling in Massachusetts? If you’re lucky enough to win greater than $5000, you will have to provide the casino with your SSN or Tax ID number, plus two forms of ID, and they will issue you the Form. If you win above $5000, the casino or sportsbook must withhold 24% and is obligated to issue you Form W-2G, which will document their withholdings. If you win under $5000, there is no withholding, but it's still potentially subject to taxes. You will be required to pay taxes on gambling winnings with sports betting apps, sites and retail sportsbooks in Massachusetts. Reporting gambling winnings is the responsibility of every Massachusetts resident, however small the wins. Are My Gambling Winnings Taxed in Massachuestts? Gambling problem in Massachusetts? Call 1-80 to speak with a trained specialist free and confidentially 24/7. Massachusetts bettors must be 21+ and present to place wagers in the state.