It's long term capital gains and does not get taxed at ordinary income rates. If you are in a state with income tax, they will usually tax your capital gains at your ordinary state income tax bracket.

Provided the security/asset is held for a year or more, it is taxed as Long-Term Capital Gains, and given quite the tax break.

It is even possible to pay 0% federal rate on sale of stock, I did it on my 2016 return.

> It is even possible to pay 0% federal rate on sale of stock, I did it on my 2016 return.

Up to the top of the 15% bracket, yes, or $37,950 in total income for single earners in 2017 ($75,900 joint). It's easy to pay little in long-term cap. gains taxes if you are retired (or unemployed) with a cheap-to-moderate lifestyle.

But not possible for ~$1 billion in gains, like Bezos' sale :-).

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.

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.

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.

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

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

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.

>> But not possible for ~$1 billion in gains

Quite possible given enough trust lawyers and accountants. Mitt Romney managed to own a lot of his stock in his Roth IRA. The PayPal gang is famous for paying almost zero taxes though the same tricks. Yes, you dont get to spend it until retirement, but he isnt spending the billion, he is just reinvesting it.

No, the Romney move is still not possible in Bezos' shoes. Bezos couldn't have invested in Amazon in his IRA when it was worth nothing:

https://en.wikipedia.org/wiki/Self-directed_IRA#Permitted_in...

> IRA funds are allowed to be invested in private companies. ... The IRS puts restrictions on private equity investments that can be made by an IRA. It cannot purchase stock that the IRA holder already owns. ... In most cases, neither the IRA holder nor any disqualified persons to the plan can be employed by the company while the IRA has an equity position in that company.

Bezos founded Amazon, so he's definitely had them for over a year :)

> I assume that plus whatever regular income tax for his bracket is

No. Capital gains aren't income.

Yes they are.

Ordinary income = salary/wages, bonuses, commissions, etc.

Capital gains are income, but short-term (within a year) are taxed at ordinary income rates, while long-term (greater than a year) are charged at special capital gains tax rate.