If he's doing it that way, he's doing it wrong. The right way is to donate the stock to the foundation directly -- this avoids realizing the capital gain and still earns the deduction; possibly a slightly higher deduction because you can claim it at fair market value without selling and selling that much stock will likely reduce the price.
I would have to check the SEC filings here, because Jeff may be already selling it through his foundations and the media itself may be aggregating the ownership back to Jeff
The feds would get lots of extra revenue from closing these loopholes, too. But lobbying really is effective so nothing gets done, I guess.
I think its a shame that people don't understand the tax code and express their disdain by getting their favorite politician to "tax the rich" by raising "income" taxes, because thats all their gullible constituents know about from their personal experience, and this outcome only affects wage-workers like them.
There is almost zero benefit in accurately explaining this because it might actually change.
The suggestion I responded to about borrowing instead of selling would further reduce the fed's revenue. I don't consider that a loophole either.
A loophole for me would be using inadvertent outcomes of unclear regulatory guidance in a way that people didn't expect. Or passing a law yourself and then using it.
Unlike income, the raw tax footprint would be at long term capital gains tax rate of 20% + 3.8% and Washington State has no tax on this kind of transactions.
He can get a further 50% deduction on that moving half the money to a foundation he owns and controls completely. If he had any carryover foundation donations in the past then it applies here too.
Any prior substantial long term capital losses offset this as well
and his other non-amazon projects likely pass through Net Operating Losses directly to him (if structured as a partnership)
He probably pays 8% tax on this if that, doesn't have to worry about margin calls, its totally free and clear.