[lordnacho]

The point is by borrowing the money you avoid paying the same amount of tax, because the income tax on whatever you're servicing the loan with is not the same amount as what you'd pay if you sold the shares?

Depends on the numbers of course.

[thaumasiotes]

In a general debt-vs-immediate-payment question that could work, I guess, because you can e.g. pay the debt off over such a long period that the total income you need divided by the number of years you take falls into a lower tax bracket than otherwise.

I have trouble seeing how it would work in the example under discussion, where we know that the person is extremely wealthy -- and thus should hit the maximum income tax bracket no matter what -- and that capital gains taxes are likely to be the least heavily taxed income source available, so that it would be difficult to beat selling stock.

[lordnacho]

Depends a lot on what country we mean. Also, the debt never had to be repaid. You can keep rolling it as an interest-only loan, so long as the collateral is enough to satisfy the lender.