It may surprise "frustrated immigrant", but there will no doubt be plenty of businesses here in the US to replace the one he takes off-shore. For that matter, if he has enough to personally pay millions of dollars in taxes, why doesn't he apply for an investor's visa? Business executives are a dime a dozen in the US, and we really don't need to import them. For truly exceptional ones, well, "frustrated immigrant's" company could and should have brought him on a green card (or an L-1) if they valued him that highly. They apparently didn't, or preferred to delay applying for a green card to try him out. Or possibly he took his chances changing companies and found himself out of time. He knew, or should have known, going in that getting an H1-B is no guarantee of getting a green card.
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