Hypothetical Taxpayer Information

George Conway, a client of your firm Tide & Tusk, LLP, is a single 34 year-old attorney with no children.In addition to the salary he has earned as an attorney, has two sources of income that are new to him in 2020. George went to Harrah’s casino in February, and won $5,000 in an amateur poker tournament.The win left him so confident that he enrolled in a poker tournament for professional players in July.George spent $8,000 in the tournament before he was eliminated.In August, George’s bank forgave half of his $20,000 business loan, leaving him with a balance of $10,000.George was solvent both before and after the loan was forgiven.


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George Conway has reached out to you to learn more about his tax situation in 2020.Prepare a brief research memo, complete with citations and analysis of primary authority, to support your conclusions.Remember that George is not a professional tax preparer, so it is important that you explain your position in a clear and concise manner that is not overly technical (i.e., you will need to do considerably more than simply copy and paste excerpts from primary authorities).


Specifically, answer the following questions in your research memo.Your answers must be supported by statutory law (internal revenue code), case law, and/or regulations.


  • What is George’s filing status?
  • Are George’s gambling winnings taxable?Are his gambling losses deductible?
  • Is the forgiveness of George’s business loan taxable income?

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