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Trump may not be as rich as he claims, or have a poor charity record, or have money stashed offshore

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.

“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.”

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.