to a confiscatory level will not work (I hear talk on this board all the way up to 99% marginal tax rate). On the flip side I hope the IRS is very aggressive about pricing his portfolio - is he going to have to liquidate prior to the IPO? He was a U.S. citizen during the run up. According to Forbes the taxes will become due if he tries to move the dollars off shore. I wonder if there is a look back period (tries to move it in a few years). As I understand it for normal people, if you try this tactic (drop citizenship and move to another country), your portfolio is immediately treated as liquidated and all taxes are owed. I guess you can delay this by not bringing the money out with you? I never knew that.

The U.S. is unusual in one way. As a U.S. citizen you are taxed on income received in any country even if the income has nothing to do with the U.S. (lets say you are living and working abroad). We are the only major economy that does this.

I feel much better. Good riddance to someone who wants to have it all without ever giving back.

Edit to ask: Would the tax rate be ordinary income or capital gains?

As he gets paid for his shares on the IPO. I guess it drops into limbo as he no longer becomes a U.S. citizen? Normally the tax bill would come due when he liquidates his portfolio. He becomes like a foreign national who invests in the U.S. going forward. I guess most normal people who might try this have their money in a IRA/401(k) (like me). That I know gets immediately treated as a withdrawal for tax purposes, and is taxed as ordinary income.

Once you're a US citizen, you will ALWAYS be a US citizen no matter where you go.

and now he cannot leagally give money to GOP Politicians.

So the IRS will value based on that time. He has been living in Singapore for a while.