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While I suspect that the answer to my question is "no," I want to be sure . . . the only scenario treated is one in which a salary-earner contributes cash from earned income into the IRA . . . So is it a non-starter?Yup, even if you bought the stock just now. It's a cash-only deal.Your plan has a big hole in it, regardless. Why would you want to put the stock into an IRA, using your scheme, and convert a capital gains tax of 20% to an income tax of 28% or more?A few ways for you to take advantage of the capital gains is to:1) Donate some stock to a charity for an immediate full deduction2) Donate it to a charitable remainder trust3) If you and/or your wife can contribute to a 401k and have not maxed it out, sell the stock and use the proceeds to replace lost income from maxing out your 401k. In the short term, the 28+% value of the deduction will make for the 20% tax.
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