6 big questions

The 6 big questions we may now get answered on Donald Trump's taxes

Analysis by Chris Cillizza

We're going to see Donald Trump's taxes. Or, to be totally clear about it, we are very likely to see the former president's taxes -- following a Friday ruling by the Justice Department's Office of Legal Counsel's office that said that the returns must be turned over to Congress.

"The Chairman of the House Ways and Means Committee has invoked sufficient reasons for requesting the former President's tax information," read the opinion, which is the latest development in a two-year fight between the Trump administration and House Ways and Means Committee Chairman Richard Neal over the billionaire businessman's tax returns.

While Trump's lawyers will no doubt fight the Justice Department ruling, the chances of Congress getting its hands on Trump's returns went WAY up last Friday. And because Congress is Congress, if it gets the returns, you can be certain that some (or all) of the information in them will find its way into the public eye.

Which means that after six years or excuses, delays and obstruction, some of the most pressing questions about Trump's financial strengths -- and weaknesses -- may well be revealed.

Below, a look at the five biggest questions the release of Trump's tax returns could show.

1. How wealthy is he really?: There's no doubt that Trump is less wealthy than he says publicly. But how much less wealthy? Forbes says Trump is worth $2.4 billion, making him the 1,299th richest person in the world. Why does it matter? Well, Trump premised his entire campaign on the idea that he had done extremely well for himself in the business world and that he could do the same for America. "I have total net worth of $8.73 billion," he said back in 2015. "I'm not doing that to brag. I'm doing that to show that's the kind of thinking our country needs."

2. Who does he owe money to?: We know -- thanks to amazing reporting by The New York Times, which got its hand on Trump's tax return data for more than two decades -- that he is on the hook for hundreds of millions of dollars of personally guaranteed loans that come due in the next few years. But, to whom does he owe all that money? And has he paid them anything as a sort of good-faith indicator that he plans to pay off the debts?

3. Does he have Russian ties?: Given everything we know about what happened in 2016 -- the Russians ran a complex and coordinated campaign to interfere in the election to help Trump and hurt Hillary Clinton -- there have long been questions about whether Trump has financial ties to the foreign power. As George Will suggested in July 2016: "Perhaps one more reason why we're not seeing his tax returns is because he is deeply involved in dealing with Russian oligarchs and others. Whether that's good, bad or indifferent, it's probably the reasonable surmise."

4. Is there an organized crime connection?: No, this isn't a joke. In fact, during the 2016 campaign, not one but two prominent Republicans suggested Trump's taxes might reveal his ties to La Cosa Nostra. "There have been multiple media reports about Donald's business dealings with the mob, with the mafia," Texas Sen. Ted Cruz said in February 2016. "Maybe his taxes show those business dealings are a lot more extensive than has been reported." Mitt Romney also touched on Trump's potential mob ties in a May 2016 Facebook post -- noting: "While not a likely circumstance, the potential for hidden inappropriate associations with foreign entities, criminal organizations, or other unsavory groups is simply too great a risk to ignore for someone who is seeking to become commander-in-chief."

5. Has he paid taxes?: Thanks to The New York Times, we know much of this answer. "Mr. Trump paid no federal income taxes in 11 of 18 years that The Times examined," the paper wrote in September 2020. "In 2017, after he became president, his tax bill was only $750." In the wake of the Times report on Trump's taxes, a lawyer for the then-president said this: "Over the past decade, President Trump has paid tens of millions of dollars in personal taxes to the federal government, including paying millions in personal taxes since announcing his candidacy in 2015." So, which is it?

6. Does he donate to charity?: People of Trump's wealth -- presuming he is actually a billionaire -- typically give considerable sums to charity. But given the absolute boondoggle of his personal charity -- as expertly exposed by The Washington Post's David Fahrenthold -- there's reason to be skeptical. "Mr. Trump is generous both with his money and with his time," a Trump spokesman said in the fall of 2016. "He has provided millions of dollars to fund his Foundation and a multitude of other charitable causes." So, again, which is it?