35. He thinks only “little people” should pay taxes

DT has made a profession of posing as one of the financial elite. Why that should endear him to so many unwealthy Americans is debatable, but it probably has something to do with people’s unhealthy obsession with money. Sadly, to many Americans, wealth is synonymous with success, and DT has always worn his wealth on his sleeve. Another tax cheat and con artist, Leona Helmsley, infamously proclaimed that “only little people pay taxes.” She and the 45th president clearly were cut from the same cloth.

This week’s revelations about DT’s tax liability confirm beyond any reasonable doubt what many have suspected all along: the legend is a fraud. What legend? Why, the legend about his being a fabulously wealthy, immensely successful businessman, of course. It’s a legend he has cultivated over decades. Considering the number of creditors he’s stiffed, it’s a wonder he wasn’t publicly exposed as a confidence trickster long ago. It would appear that the natural reticence of bankers combined with the shame and fear of those he swindled to create a wall of silence that shielded him. The wall wasn’t absolute, but it certainly kept the most damaging information from filtering down to most of the gullible masses who voted for him. The million dollar question now—or perhaps it would be better to call it the $750 question—is whether it will matter to more than a few of them.

It is not entirely clear why DT has gone to the trouble of faking his credentials as a member of the ultra-wealthy. Some clues can probably be found in his upbringing: the Tr-mp family was all about new money, not old, and their primary business—owning and managing apartment buildings in the outer boroughs—didn’t exactly give them entrée into the ranks of the social elite. No matter how much money DT’s father made, the New York aristocracy never considered him one of their own. As DT took on an increasingly prominent role in the family business, he engineered a number of audacious deals that put him, and by extension his family, into the limelight.

The fact that those deals weren’t entirely lucrative for the family seems to have been lost amid the glitter of his newfound celebrity. He hung out with famous models and A-list celebrities and brought them to his ribbon-cutting ceremonies, and this soon made him a celebrity in his own right. Who cared that he was playing with daddy’s money—and frequently squandering it? Evidently not daddy, who mistook celebrity for respectability and basked in the reflected glow of his son’s fame. Certainly not the New York press, who were more concerned about getting a juicy quote and a striking picture than interviewing the players behind the scenes and learning what was really going down. Some of those players, especially the bankers, realized the truth all too soon, but if they started balking, they had colleagues who were only too happy to take over the role of enabler. Remember, this was the 1980s, a time when glitzy deals were de riguere and it was bad form to ask inconvenient questions. The savings and loan crisis hadn’t happened yet. The Great Recession was decades away.

Okay, but why is DT still maintaining the pretense? Wouldn’t it have been better at some point to divest himself of his money-pit properties and turn over the running of the business to people who actually know how to turn a profit? He could have still been a celebrity, he’d have gotten to keep more money than most of us can even dream of, and those pesky Internal Revenue agents wouldn’t have kept dogging his every step. He even could have avoided entangling himself with the Russians, who after all are a bit scary. Hell, he could even have been out there on the golf cart every day.

There is no easy answer to this. My guess is that he’s been behaving this way for so long that he doesn’t know how to stop. As long as he can afford more cards, he’ll keep building his precarious house higher and higher. Trouble is, the dealer is longer just some schmuck on Wall Street. He’s got dealers in all the red states and on Capitol Hill and the federal courts.

Buy time or cut losses?

We can see now with blinding clarity that DT’s increasingly desperate efforts at reelection aren’t merely about massaging his ego (although that’s surely a part of it). He faces personal financial ruin and severe legal trouble when his presidency comes to an end, and with it his (alleged) legal immunity. So he’s buying time. Especially with the Supreme Court in his corner, another four years might afford him the opportunity to make certain changes to tax laws that would save him from the IRS and various prosecutors who’d otherwise want a piece of him. Without both houses of Congress backing him, it would be a tall order, but he could always issue executive orders and go on a firing spree at the IRS, cross his fingers and hope for the best. That the nation likely would be in open revolt by that time might make things a little more difficult for him, but he isn’t prone to thinking that far ahead.

If I were DT—and to say that those four words give me a terrible shudder is an understatement—I would try to cut a deal at this point. He thinks he’s good at deals, after all, so why not try? It would go something like this: I’ll announce that I am no longer running for a second term; I’ll resign by year’s end; Mike Pence will pardon me; and I’ll spend the rest of my dotage being an increasingly irrelevant talking head on Fox News, and they’ll pay me tens of millions for it. My core supporters will think I’m the victim of the “deep state” and will still buy my merchandise and revere me, but they’ll find someone else to adulate come 2024. That person will be one of my children. Maybe two of them. Maybe it will be a dynasty and they’ll build statues of us all. Mine will be the biggest.