I discovered this interesting article by ProPublica on tax strategies of the ultrarich.
It boils down the strategy to Buy Borrow Die.
The idea is you have tons of stock you don't sell. You borrow against it and use that money to fund your lifestyle. Then you set up a complex trust to avoid the estate tax.
I don't understand how borrowing does anything. We assume the ultrarich need money to fund their lifestyle. They borrow it, but they need to pay borrowed money back. So where does the money to settle the debt come from? We are back to square 1.