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Donating stocks to charity can be a profitable way to save on taxes. When you give property to a charity, you get a deduction equal to its fair market value on the date of the gift. The cost you acquired the property at is irrelevant to this value. It is possible to contribute stock to a charity, then purchase it back for its full value, thus retaining your share of the company and pocketing the money that you would have been taxed from the capital gains on the interest. To ensure the legality of the procedure and to avoid falling under the Alternative Minimum Tax category, get a competent professional to set up and review the transaction.