I think they defer as much as they can until they die and their heirs get to inherit with a stepped up cost basis and they never pay tax. Borrow, buy, die.

If they’re really crafty, the heirs will overvalue assets when stepping up the cost basis so they can actually claim losses in the future.

From Wikipedia:

“The tax code of the United States holds that when a person (the beneficiary) receives an asset from a giver (the benefactor) after the benefactor dies, the asset receives a stepped-up basis, which is its market value at the time the benefactor dies (Internal Revenue Code § 1014(a)).”