[caladri]

It's a common financial strategy among the fabulously-wealthy. Selling shares would incur all kinds of taxes, but he can get a line of credit with a reasonable interest rate quite easily, pay no income taxes, and actually deduct the interest he pays from his taxes. So he carries a lot of debt but it's all backed by assets and paying the interest is tolerable.

Yes, if that's what he's doing, then in the event that his assets utterly evaporate he'll be in a spot of bother. But it's a pretty well-trod path, and probably some non-trivial portion of his assets are quite stable and reliable and not terribly volatile. I won't pretend to know the precise details of his situation, but living off a line of credit isn't at all uncommon and perhaps isn't even unreasonable (from the perspective of financial self-interest alone) for a person in his position.

[damoncali]

Funny, though - Were I in his position, I'd just sell the stock, pay the taxes and own whatever it was I wanted to own. Perhaps that says something about why I am not in his position.