I did miss the Medicare Tax part yes, however he takes a $1 salary which would put his regular tax bracket at 10% and long term capital gains would be 0% to start and work his way up to 15%. As long as he doesn't cash out $400k a year he never pays that 20%, and he shouldn't need to ever. You also need to subtract IPO price from current price. Which is about going to drop those estimates about 35%. It still a big chunk of change, no doubt, but I have no problem with getting around it by going to charities. Especially when he already paid ~$2Billion in taxes for the stock at IPO time. The top 400 tax payers only payed $16Billion in 2009 so, he has paid a huge amount.