Investors & landlords

Granny11,

 

From my understanding of your post, some good news and some not so good news:

 

First, the 2014  sale of stock held within your IRA was not supposed to be reported as a capital gain or loss on your 2014 tax return.  It was just a lowering of your IRA value.  However, as the 3 year lookback statute of limitations has passed, you won't need to file an amended return.

 

For the same reasons, the 2020 litigation recovery is technically a distribution from your IRA unless you deposited those funds into any current IRA within the 60 day rollover period.  Either way, you would enter the amount under the 1099-R section of income in TurboTax rather than as a capital gain under Schedule D.  If you redeposited it, then you would so indicate and no tax would be due.  If not, you would pay ordinary income tax rates on the amount and, if you were less than 59 1/2 last year, you would also pay an additional 10% early distributions penalty.