The most serious political problem facing the Trump administration and the Trump White House is the Trump Organization, and the question is whether Donald Trump really knows this yet deep in his bones. He’s getting there, I think. In the eye-opening New York Times group interview, the president-elect does something very striking you almost never see leaders do: He muses aloud about the issue. He knows it’s trouble and he doesn’t really know what to do about it. He can’t help thinking aloud even in front of people he deems hostile to him because it’s haunting him. After all, he never truly thought he was going to win this thing—and he believed it was bad luck even to plan for it—and so he’s two months away from the swearing-in with a government to build from the ground up and the issue of what to do about a complex business he built over many decades that he did not expect he was going to have to move away from.

While my friend David Frum and others believe he pursued the presidency precisely for the purpose of winning and using it to enhance his business, I believe Trump completely when he says “I don’t care about my company. It doesn’t matter… The only thing that matters to me is running our country.” Why would he feel otherwise? Why on earth would he give two figs for the unsightliness of a wind farm near his Scotland golf course? Or the bookings at the hotel five blocks away from the White House? Thinking about those matters is nothing but a vestigial impulse. The likelihood that he didn’t really think he was going to make it this far (he told the Washington Post earlier this year that he put his chances of winning the GOP primary at 20 percent before he ran) means he has to shift, as they say these days, into an entirely different headspace from the one he’s occupied most of his life. He gives a hint of what that previous headspace was in the Times interview when he begins an anecdote by saying, “I went to a big event about two years ago. Just after I started thinking about politics.” In his mind, he only started thinking about politics within the past two years.

Most everyone who’s run for president has thought obsessively about it since he or she was 12 years old. Not so for Trump. Now he will be where only 44 people before him in history have been. All of a sudden he’s not in competition with Steve Roth of Vornado, or with the Marriott Corporation. His competition is the shade of Lincoln, or the ghost of FDR, or the specter of Truman, or the example of Reagan. Imagine the vertiginous quality of this. You think you’re finding Trump being president surreal? How about Trump himself?

And so, in my view, he’s winging it.

He begins defensively with whether he needs to divest himself of the Trump Organization as a legal matter: “As far as the, you know, potential conflict of interests, though, I mean I know that from the standpoint, the law is totally on my side, meaning, the president can’t have a conflict of interest… because everything a president does in some ways is like a conflict of interest.”

However inarticulately he might state it, Trump’s right here, and it goes to one of the more complicated aspects of the division of powers in the Constitution: Unlike the other elected and appointed offices in the United States, the presidency is a thing in itself. The powers of the executive branch do not exist independently of the person who holds it, and so, as Trump says, there’s not a thing he does outside the realm of pure governance that couldn’t be seen as a conflict of interest. Every royalty Barack Obama collected from the sale of The Audacity of Hope during his tenure could be viewed as a kind of emolument from his publishing firm, for example.

The harsh truth is that the only check and balance on a president’s misuse of his authority isn’t the FBI, which would in effect be the president arresting himself, but Congress—specifically, Congress’s power to impeach “for Treason, Bribery, or other high Crimes and Misdemeanors.” After a successful impeachment and removal from office, the ex-president can then be subject to “Indictment, Trial, Judgment, and Punishment, according to Law,” but not before.

James Madison’s notes on the discussions of the matter during the debates over the Constitution suggested this was considered a practical remedy, not the extreme sanction it seems now—and that its prospect was designed to temper any president’s temptation to use his office for personal enrichment or bad behavior. Maybe it’s worked, in fact; only two presidents out of 44 have ever been impeached, with neither successfully removed from office, and the one who would almost certainly have been tried and thrown out chose to resign before Congress acted.

Trump finds himself in an unprecedented situation: “There’s never been a case like this where somebody’s had, like, if you look at other people of wealth, they didn’t have this kind of asset and this kind of wealth, frankly.” The problem for him is that his business is tied up in real estate, so that it’s not really one unitary thing but rather a collection of a hundred different deals, each with their own deal points. Unwinding such a business isn’t, as he told the Times, “like selling stock.” He doesn’t know how to sell it off.

So as he wings it, he’s trying to figure out where the lines might be. As of yesterday, he was figuring it might be OK if Ivanka and Eric and Donald brought in an investor or two to take pictures with him in the White House: “The partners come in, they’re very, very successful people. They come in, they’d say, they said, ‘Would it be possible to have a picture?’ … They want to take a picture and come into my office, and my kids come in and, I originally made the deal with these people, I mean what am I going to say? I’m not going to talk to you, I’m not going to take pictures? You have to, you know, on a human basis, you take pictures.”

And let’s face it, in a world in which Bill Clinton literally sold overnight stays in the Lincoln Bedroom for campaign contributions, what would be so wrong with him taking pictures with these people?

In theory, nothing.

But in practical terms, everything.

If, unlike Frum, you take Trump at his word that he no longer really cares about the business and really does want to focus his attention on governing the country, then why would he take the risk that one of these people wouldn’t go around claiming the president promised him something in exchange for a new deal? Or what happens when he takes one of those pictures and it turns out the Trump Organization gets an insane sweetheart deal somewhere from a semi-state-run business somewhere that brags about its closeness to the president?

Such a thing would literally trip the very wire the impeachment clause is intended to trip. And precisely because there is no way to discipline the president other than impeachment, in such a circumstance the Republican-led Congress would be put in an impossible position. Trump went around promising to drain the swamp, but if the evidence suggests he and his family are bathing in it, will Republican politicians really hold the line for him? We’ve already seen how dramatically American politics can swing in just two years. Barack Obama had a huge majority in the House that evaporated between 2008 and 2010 when his own behavior gave rise to a protest movement, which swung 63 seats the other way and brought his entire program to a crashing halt.

The unprecedented nature of his run and his victory and his circumstances also poses an unprecedented danger for him. Trump’s presidency will not be safe from the ultimate sanction, and his historical reputation will be at constant risk if he does not find a way to silo off the Trump Organization or even just figure out a way to sell it for scrap. I take the Times interview as evidence he is coming to understand this; he’s fighting against it, but if he does so unreasonably he could end up, alone and raging and storm-tossed and undone, like Lear upon the heath.

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