Every investor at some point has kicked himself for holding an asset too long. Perhaps none, however, has made such a monumental miscalculation. By refusing to divest his portfolio upon taking office, Trump bogged down his presidency with ethics issues for years, while also missing a chance to cash in on a market boom he helped propel.
If he had sold everything on Day 1, paid the maximum capital-gains taxes on the sales, then put the proceeds into a conflict-free fund tracking the S&P 500, Trump would have ended his presidency an estimated $1.6 billion richer than he is today.
As is, he is worth an estimated $2.4 billion, enough to qualify for No. 1,299 on the Forbes billionaires list, down from No. 1,001 last year. Trump is actually richer than he was a year ago, when we knocked valuations down at the start of the pandemic, but he couldn’t keep up with the other billionaires on the list, whose fortunes soared.
Below are the four Trump properties that gained the most and the two that lost the most while he was in office.
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