If I were to pay a friend’s delinquent real estate taxes of $10,000
to the county with my personal check, would I be able to legally apply
that deduction on my 1040?
It would be a gift, yes, but who would get the deduction?
(Thank you very much.)
I’m pretty sure your friend would get the deduction.
According to the IRS http://www.irs.gov/publications/p17/ch22.html#en_US_publink100033952
Since the tax was not imposed on you it is not deductible for you. If you pay the tax directly, rather than giving the money to him and letting him pay it, then it appears that it is not deductible by him either.
It’s a wrap then. Asked and answered.
Thank you both very much.