Let's read the GoPro example closely: - $500m of GoPro stock was donated at about $95 per share, but actually sold by the fund at $18 per share (or so the arti

Let's read the GoPro example closely: - $500m of GoPro stock was donated at about $95 per share, but actually sold by the fund at $18 per share (or so the article implies). - Assuming the highest marginal tax rate (39.6%), the $500m tax-deductible donation would produce a net gain of $198m from reduced income taxes over the next 5 years. - Selling all the stock at $18 per share would have produced a net gain of $76m ($94m minus $19m in 20% capital gains taxes). So by 'donating' the large block of stock at its highest price point, the donor profited an extra $122m over what the stock was ever actually worth, in addition to the positive publicity associated with generously donating $500m (that was actually only worth $94m). My reading of this is that the 'loophole' in this example has less to do with the particular recipient of the donation, and more to do with the supposed misrepresentation of the 'fair market value' of the stock donation, which the article implies was closer to $94m than $500m. However, there appears to be a law specifically prohibiting this kind of inflated misrepresentation of stock value based on current selling price, 26 CFR 1.170A-1(c)(3) [1]: > (3) If a donor makes a charitable contribution of property, such as stock in trade, at a time when he could not reasonably have been expected to realize its usual selling price, the value of the gift is not the usual selling price but is the amount for which the quantity of property contributed would have been sold by the donor at the time of the contribution. So the so-called 'loophole' implied by the $500 million example doesn't actually exist. Assuming the full $500 million was actually deducted at its full value seems to be either fuzzy speculation on the part of the author, or something that will undoubtedly be heavily scrutinized/challenged in a future IRS audit based on the legal definition of 'value' of a charitable contribution. [1] https://www.law.cornell.edu/cfr/text/26/1.170A-1 https://www.law.cornell.edu/cfr/text/26/1.170A-1