So here is a wishful scenario that I’ve conjectured up in the shower and I am hoping people can poke holes in it —
- I currently own stocks or stock options in a private company in the US. I am an employee of the company, working in a directorial/managerial capacity.
- I am currently legally residing in the US, but not a citizen of the US.
- I’ve gotten my GV and my NHR at year 0.
- I’ve been living in the US for the past 12 years but after I got my GV, I decided to pack up all my stuff and move to Portugal at year 0.
- Subsequently, I continue to work for my existing company remotely in PT as an independent contractor, earning regular “wages” or payment to my invoices whatever you want to call it.
- I carefully plan my visit to the US so that I will FAIL the Substantial Presence Test during the NHR window.
- In year 6, I dispose of my stock holdings and/or exercise my options, yielding 100 million dollars in net proceeds.
Is my 100 million dollars tax-free as far as cap gain is concerned from both Uncle Sam and PT government?
Thanks for your help in advance.
P.S. I am also consulting with tax lawyers but starting with some crowd-sourced intel and open questions.