In 2016 I invested in a Private Placement. I subsequently converted some of the stock to a Roth IRA, paying all the appropriate taxes at $4.50 per share. The stock has now nearly bellied up at 33 cents per share and I'm looking for a way to recoup the money I paid in taxes. There is still a small amount in the Roth account. If I reassign all of the Roth stock to the issuer as an exchange for no remuneration, can I show a loss. There will be no forms from the issuer so unclear if or how I would recoup the taxes already paid and report that on 2021 filings. Thanks so much.
