Payment of Settlement Agreement

[Citysitter]

Looking for assistance for a question that nobody that I have talked to can answer related to payment of a settlement agreement being tax deductible. iRS has no answers and neither does my tax professional.

I sold a home in 2022, paid the capital gain on the real estate in 2022,  got sued in 2023 by the buyer, and settlement agreement was reached in 2024. I was self represented and used the resources available online, but none offer any advice after the settlement is reached so I don’t have an attorney to ask this question ti.

i also completed and sent a 1099-MISC form for the payment that was made to the plaintiff. 
the payment was not specifically for any reason and it was paid as a no fault meaning I was not found to be in violation of any government law, did not pay for injuries or any specific reason. I’m mentioning this because some of the information I read in the IRS bulletin refers back to

the settlement agreement but there’s nothing specific that would answer this. Has anyone else been I. This position? 
IRS also does not offer an individual why filed a 1099-MISC form any assistance or training for staff. I’m in a quandary and hope one of you can provide me with some advice or information.

Thank you for your time.

[jtax]

That's a good question. I don't have a definite answer for you but here are two things to look at.

this thread says you should report it as a sale of real estate in the year you paid the settlement with zero basis, thereby creating a capital loss.

https://ttlc.intuit.com/community/tax-credits-deductions/discussion/how-do-i-deduct-legal-settlement...

That thread does not explain WHY you can do that. Perhaps it is because of I.R.C. 1341 relating to prior year income that you thought you had a right to ("claim of right") but later found out was challenged and you returned/repaid some of it. I am not sure it applies in your case but you might research it. I think (but am not certain) that you might even be able to get around the $3k capital loss limitation with a 1341 deduction.

See as a starting point

• https://www.thetaxadviser.com/issues/2019/jul/sec-1341-claim-of-right-doctrine.html
• https://www.law.cornell.edu/uscode/text/26/1341
• https://www.law.cornell.edu/cfr/text/26/1.1341-1
• https://www.irs.gov/irm/part21/irm_21-006-006r

[Citysitter]

Thank you for your response. I will definitely research the links you suggested and hopefully it becomes clear how to handle this situation.