Hmmm.
The two tragedies that I'm familiar with, are the Ford family and the heirs of Henry Kaiser.
Ford, of course, was a crank, touched in the head before he became senile. He hated banks, from the time he founded his first two Ford companies (both went bust but one of them became the Cadillac Motor Car Company, and bought by GM). He hated investors and partners, from the time Henry Leland tried to get Henry to take the rising Ford Motor Company in a different direction.
He hated accountants and bookkeepers. He kept no records of his expenditures - he estimated bills due by WEIGHING STACKS OF BILLS. Some of his clerks figured the monthly outlays to pounds of mail, and he used THAT to figure his monthly costs.
So Henry died, with his shares of FMC stock in the Ford Foundation - a "charitable foundation" without a stated purpose. An obvious, crude tax dodge.
The Ford family almost had to sell to pay the Estate Taxes. Actually they did - they went public in 1956, but constructed a stock-class scheme that gave the Ford Family total voting control. It would not be legal today; but back then, after 7 years of bribery and pettifoggery, the tax bill was settled.
Henry Kaiser was less lucky. He made his money with government road-paving contracts; then became the principal contractor to the Boulder Dam (Hoover Dam) and then, bought a shipyard and then built a few more, to mass-produce Liberty Ships.
He wanted to build cars, and after a convoluted dance with bankruptcy, he wound up owning Willys-Overland - which had a new product, the civilianized Jeep.
With time, that operation grew. It was a small, profitable moneymaker - and Henry was branching out into large real-estate development in Hawaii; into broadcasting (Kaiser Broadcasting had UHF channels in a number of American cities). He had Kaiser Steel, Kaiser Aluminum, Kaiser Permanente hospitals.
He died, 1967. Without proper estate planning.
The Tax Man cometh.
EVERYTHING had to be sold, to pay the 40-per-cent estate taxes. Kaiser Jeep, sold to American Motors. The television stations, sold to other investors or closed down and the facilities sold. Likewise his industrial operations. Kaiser Hospital Corporation, converted to a non-profit.
These, the two Henrys, were not foolish or insubstantial people. Henry Ford was cracked, but he wasn't stupid. What Kaiser did, has yet to be duplicated by others. Today's entrepreneurs don't build; they immerse themselves in the gusher of seigniorage, becoming rentiers.
Taxes could have been reduced somewhat, but even if Kaiser had given his estate away before death, he'd have been hit with Gift Taxes. Henry Ford DID create a charitable foundation, and it wasn't enough for the tax collectors.