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The losses you deduct cannot exceed your income from all forms of gambling, including but not limited to horse racing, casinos, and raffles. If you win the jackpot and take the annuity payout , the annual payments will be recorded individually in each tax year, and will count towards your gambling income for that year. Income reported on form 1099 such as Civil Service Retirement benefits, annuities, pensions, Social Security benefits, Veteran’s benefits, and military retired pay, withdrawals from 401 K plans, unemployment compensation, workers' compensation, interest and dividends from savings accounts, stocks, personal loans, or home mortgages held, insurance proceeds, gifts, inheritances, estates
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