Five years ago, he had a golden opportunity to diversify his fortune. Fresh off the 2016 election, federal ethics officials were pushing Trump to divest his real estate assets. That would have allowed him to reinvest the proceeds into broad-based index funds and assume office free of conflicts of interest.
Trump decided to hang onto his assets. At the time, they were worth an estimated $3.5 billion, after subtracting debt. If he had instead chosen to sell off everything, there is a chance that he would have had to pay significant capital gains taxes. Trump acquired his five most valuable holdings long ago, so he likely has huge untaxed gains locked in each of them. If he paid the maximum possible capital gains tax—23.8% to the federal government, plus 8.8% to the New York State authorities on every penny he owned—that would have shaved about $1.1 billion off his fortune, leaving him with $2.4 billion on the first day of his presidency. But what would have appeared to be a huge sacrifice at first could have turned into a lucrative realignment. By plowing that $2.4 billion in an index fund tracking the S&P 500, for example, Trump’s fortune would have ballooned to $4.5 billion by now, leaving him 80% richer than he is today. His refusal to divest, in other words, cost him $2 billion.
Well, isn’t that something?
Yeah, you and me both, Mr. Obama.
Of course, it’s fitting that Trump’s predictable sleaziness eventually led to his defenestration from Forbes’ exclusive penthouse since he lied his way onto it in the first place. As Jonathan Greenberg recounted for The Washington Post in April 2018, Trump originally conned his way onto the rich people list with the help of his alter ego, John Barron, who is distinct from Trump only by dint of a slightly altered speech pattern that’s conspicuously lacking in McNugget-sauce-gurgling sounds.
In May 1984, an official from the Trump Organization called to tell me how rich Donald J. Trump was. I was reporting for the Forbes 400, the magazine’s annual ranking of America’s richest people, for the third year. In the previous edition, we’d valued Trump’s holdings at $200 million, only one-fifth of what he claimed to own in our interviews. This time, his aide urged me on the phone, I needed to understand just how loaded Trump really was.
The official was John Barron — a name we now know as an alter ego of Trump himself. When I recently rediscovered and listened, for first time since that year, to the tapes I made of this and other phone calls, I was amazed that I didn’t see through the ruse: Although Trump altered some cadences and affected a slightly stronger New York accent, it was clearly him. “Barron” told me that Trump had taken possession of the business he ran with his father, Fred. “Most of the assets have been consolidated to Mr. Trump,” he said. “You have down Fred Trump [as half owner] . . . but I think you can really use Donald Trump now.” Trump, through this sockpuppet, was telling me he owned “in excess of 90 percent” of his family’s business. With all the home runs Trump was hitting in real estate, Barron told me, he should be called a billionaire.
We’ll see if Trump, who appears beset on all sides by legal troubles, can scare up enough low-rent, crackpot lawyers to sue Forbes for hurting his fee-fees. He once sued author Timothy L. O’Brien for claiming Trump wasn’t worth what he wanted to be worth—and it didn’t work out very well for Trump or his lavish claims of outsized wealth. He lost the suit and was outed as an unusually prolific liar.
And, of course, The New York Times’ explosive September 2020 story on Trump’s tax returns revealed that he paid a paltry $750 in income tax—when he paid taxes at all—and hemorrhaged money like a gutted hog. Oh, and he was also a chronic tax dodger who owed his father every bit of his success.
I would have loved to have been a fly on Mike Pence’s head when those stories broke, just as I’d like to be one of the bedbugs at Trump’s Doral resort when he explodes over this news. Because you know he will.
The only question? Will he attempt to do anything about it other than sputter and spritz like the colossal fucking loser he is?
It made comedian Sarah Silverman say, “THIS IS FUCKING BRILLIANT,” and prompted author Stephen King to shout “Pulitzer Prize!!!” (on Twitter, that is). What is it? The viral letter that launched four hilarious Trump-trolling books. Get them all, including the finale, Goodbye, Asshat: 101 Farewell Letters to Donald Trump, at this link. Or, if you prefer a test drive, you can download the epilogue to Goodbye, Asshat for the low, low price of FREE.