ANSWERS: 3
  • Its the IRS you probably can not resolve it.
  • Losses are not deductible; they are an entertainment expense. Winnings are income. Life is unfair.
  • You certainly can claim your losses against the win! You simply claim the amount from the 1099 as personal income and file long form. You will have to use a schedule A and itemize your deductions. You will only be able to claim losses up to the amount of the win. This is the truth!

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