“That would have cost Stew several hundred million dollars in unnecessary taxes— as his tax basis is just a few bucks per share. And he would have missed out on several hundred million dollars in still-tax-deferred additional gains.” If you are overweight an asset that isn’t liquid and is selling 20 percent below Nav, if you sell at a 5 percent discount to NAV , the true tax is 5-7 percent at what might be lower low tax rates rather than after the 2028 elections. He would have reinvested the proceeds in liquid assets, he loves Jpm, how would that have worked out? Who knows what he might have done with the proceeds 3-5 years ago? What if he passed what are his estate plans, who knows if his heirs would sell brkb down weekly for years? May they change the stepped up basis at death? Would team Mamdani, Aoc, Sanders, etc try to change those tax regs? If I were in his shoes I sell into team trumps tax laws in case I have to leave the country. :)