Trump himself helpfully demonstrated the complexity of his returns for the world to see, when he tweeted this photo of himself:

This was apparently meant to show (in keeping with Trump’s well documented modesty and restraint) how rich he is, but it also illustrates why not releasing his returns could prove politically untenable over time. “It’s disconcerting that someone who acknowledges how complicated his tax returns are refuses to release them,” Thorndike tells me.

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Thorndike and a second expert I spoke with today — Robert Willens, an independent tax consultant and professor at Columbia Business School — offered several reasons why Trump might be refraining from releasing them.

First, it’s possible that Trump wants to obscure his charitable giving patterns. “If he isn’t doing much charitable giving, that’s relevant, and potentially could have an impact,” Thorndike notes. “He has claimed he is a very generous philanthropist. The tax returns would demonstrate whether or not that’s actually true.”

The second possible reason is that Trump may have lots of money parked overseas, and if so, this would come out in the returns. “If you have foreign accounts, you have to disclose them and check boxes confirming you have them,” Willens tells me. “It could be embarrassing.”

Trump, of course, has cheerfully admitted he has long been one of those elites who milks the system to their advantage. Indeed, he has pointed to this as an argument for electing him president. He has openly boasted that he has bought and paid for politicians himself, so no one knows how to end the problem of bought-and-paid-for politicians better than he does, dammit! Trump is going to use his financial wizardry, and his inside knowledge of how elites scam the system, to put an end to that elite scamming and make America as rich as he is. As Trump has put it: “I’ve always been greedy. I love money, right? But you know what? I want to be greedy for our country.”

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So Trump might respond to revelations about parking money abroad by saying: Damn right I milked the system to my advantage, and got filthy rich doing it. Now I’ll make sure people like me can’t get away with it anymore.

But at a certain point, this might no longer work. Trump has said that in his first 100 days as president, he’d get on the phone and browbeat CEOs into bringing jobs back to America. But if it comes out that Trump has money placed abroad, would he then pledge to bring it back? If not, Willens says, “that certainly dilutes your message.”

Third, these experts note, it’s possible that Trump’s returns might reveal that he isn’t quite as rich as he likes to claim he is.

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“I’m leaning towards the idea that he’s income poor but asset rich,” Willens says. “The tax returns wouldn’t convey that. They would only convey the shortage of income without conveying the other side of the coin, his real estate holdings.”

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If there is one thing we know about Trump at this point, it is that he values being seen as a winner above all else. Trump may believe that if he is perceived as a loser (relative to his self-inflating boasts, that is), it could dramatically undercut what he believes is a winning argument for the presidency — i.e., that he is the greatest winner ever, and therefore can make America a bigger winner than it’s ever been before.

Whatever the motive here, what Trump is doing may be unprecedented in one important respect. The tradition of presidential candidates releasing their tax returns dates back to Richard Nixon. As Philip Bump documents today, Nixon released his tax returns while president, even though he was under audit. Thus, Trump — who had previously said he would not release his returns until an ongoing audit is complete, and is now suggesting he may not release them at all — is not even willing to do what Nixon did.

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Worse, as Thorndike points out, Trump may well decline to release them, even though he is likely to have far more complex returns than Nixon did. “It’s disturbing,” Thorndike says. “Complexity can hide a multitude of sins. There’s going to be a lot going on in those returns, even if it is all legitimate. But we have no way of knowing whether it’s legitimate unless we can actually see them.”