First you have to define the tax, is it income or is it capital gains. Two very different taxes. Warren Buffet pays no income tax, Mitt Romney pays no income tax among other wealthy folks. Cashing stock at 15%-20% CGTax is better than paying 35%+ on ITax. Of course most are stupid as tax is always thought to be ITax. Of course there are 1,000s of ways to zero out you ITax bill if you control multitudes of businesses and real estate. Wasn’t it the left who fought the flat tax eliminating the tax shenanigans. Leave it to the NYSlimes to feed the low IQs