[KGIII]

It is also possible that he never realized the gain. An example would be to gift the shares directly to a trust which sells and then 'loans' BO the money. Tada! You made a billion dollars disappear. That is, I believe, lawful. Consult a qualified legal representative, however.

[loeg]

One problem with this plan is that the debtor is obligated to repay the principal with interest.

If billionaires could do this, they would be doing it all the time. And the IRS would be screaming about it. Instead, they're stuck with higher risk options like illegal tax evasion or just paying the tax they owe.

[KGIII]

The above should count as tax avoidance and interest rates can be decided by the parties involved. Tax evasion is illegal. Tax avoidance is legal.

Consult a qualified tax professional and legal council.

[loeg]

I believe I was very explicit about illegal tax evasion being a separate, a higher risk option. I am careful with my terminology.

[dingaling]

But the interest rate between two private parties is entirely arbitrary. 0.01% over 25 years, say.

[loeg]

As a creditor, you're obligated to pay taxes as if you charged a fair market rate, regardless of what you actually charge the debtor. So the actual floor rate at which the creditor isn't losing money is more like 33% (presuming business tax rate, or higher for individuals) of 3-4% (for 25 year loans), or about 1-1.3%.

Also, 100% + 0.01%^25 is still more than the sum loaned. And realistically, the interest rate must be higher than 0.01% annually. Sure, you could invest it over 25 years and theoretically beat the interest floor, but this adds a lot of unnecessary risk. When you've already won the game, I think paying the 25% in tax for a guaranteed cash return is worth it over dabbling in high risk, gray area legality tax avoidance.