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I own stocks that were given to me as a gift from my former employer that was privately held. The company was then bought by a public company and the stocks were converted to that companies stock. I sold the unrestricted stock last year after holding on to it for over a year. My question is will I be able to claim the loss on the stock I sold base on the price on the date it was issued or will I have to claim it as a gain because it was a gift?

For a gift, you take the giver's basis and holding period, which will be that of the original privately held stock because that held over to the new stock it was exchanged for..

I have a second question. The rest of the stock that was issued was restricted. A third of it has vested, if I sold this stock would it be tax based on the date the restricted stock was issued or the date it vested?

I'm not shure what you're talking about. Stock options "vest" and which time, I think, the holding period begins. Restricted stock becomes "unrestricted." The holding period being unchanged.

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