The 21 biggest unanswered questions about the Trump investigations

As a tsunami of scandal threatens to flood Mar-a-Lago, it’s worth stepping back to look at the enormity of the situation and lay out the remaining mysteries.

The 21 biggest unanswered questions about the Trump investigations
[Photo: Jamie Squire/Getty Images]

The ever-expanding universe of Trump investigations–it’s now up to 17 separate federal and state probes–presents a huge challenge to journalists, lawyers, investigators, and the public. There is such a preponderance of unanswered questions covering so many angles on so many topics that it’s hard to get a sense of it all. (We’re going to need a bigger corkboard, Carrie!)


At this point, when you read a new headline about one thread of the case, it’s beyond not being able to see the forest for the trees. It’s more like not seeing the forest–and the trees and the branches–for the leaves. For the average citizen, it’s almost impossible to step back and get the full picture.

When the scandals first started to pile up, even before he took office, commentators often explained Trump’s immunity to controversy and his improbable victory by citing scandal fatigue. That’s a reference to the Clinton impeachment saga, in which questions about an Arkansas real-estate deal morphed into stains on a blue dress, all of it dominating headlines for months. The public was so exhausted by the whole saga that they started to lose interest and even sympathize with Clinton, boosting his approval numbers and staving off his almost-inevitable impeachment.

But Whitewater feels like a crude chalk drawing next to the Trump saga’s pyramid, with all of its angles, optics, reactions, plot lines, international intrigue, and questions. So many questions.

If Trump weren’t so impulsive and childish, it would seem like a calculated strategy to overwhelm his antagonists. And it worked for a long time, with many Americans just too exhausted by it all to be that outraged–complexity leads to complacency–and his base doubling down on their support.

But in recent weeks, it feels like we’re at a tipping point, with the public’s fatigue turning into frustration and fury. This growing tsunami of scandals is about to mess up the president’s coif and flood the patio at Mar-a-Lago.

All that said, if you’ve got the stamina, keep reading. To give you a better sense of the enormity of it all and a look at the most dramatic parts of the big picture, here are the main unanswered questions about the Trump investigations.


If you start to struggle and need to come up for air, that’s fine. Take a break, drink another pot of black coffee, and come back for more.

Did Trump know about the Trump Tower meeting?

The president has vigorously insisted he wasn’t aware that his son, son-in-law, and campaign manager met with a Russian lawyer promising dirt on Hillary Clinton in Trump Tower just weeks before the Republican convention in the summer of 2016. But no one outside of his administration and his fiercest defenders really believes him. Even Rob Goldstone, the British publicist who set up the meeting, told me that he assumes Don Trump Jr. told his father before and after the meeting.

It’s a key question because it gets to the heart of the collusion question–if the candidate himself was okay with getting damaging info on his opponent from a foreign country considered an adversary, that may be a serious crime. And when he later drafted a memo to obscure his knowledge of the meeting, that could be considered obstruction.

  • Related questions:
    • When Don Jr. and Emil Agalarov–an Azerbaijani-Russian singer whose family was in talks to develop a Trump Tower in Moscow–had their phone call to set up the meeting, what did they talk about?
    • What was really discussed at the meeting? Goldstone insists it lacked drama and just focused on adoption and an American law that sanctions Russians, without any mention of Hillary Clinton.

Related: The man who sent “the most famous email in history” still has plenty of questions

Did Michael Cohen go to Prague and meet Russian officials there?


That was one of the claims made in the infamous Steele dossier, much of which has been corroborated. When the dossier was first made public, Cohen vigorously denied traveling to Prague in late August 2016 to meet with Russian officials as part of an effort to cover up connections between Kremlin and the Trump campaign. Per the dossier, Cohen met with Russian official Oleg Solodukhin to discuss “how deniable cash payments were to be made to hackers who had worked in Europe under Kremlin direction against the CLINTON campaign and various contingencies for covering up these operations and Moscow’s secret liaison with the TRUMP team more generally.”

Cohen tweeted a photo of his passport and later showed it to a BuzzFeed News reporter to show that he hadn’t visited Prague. When a McClatchy story later reported that Mueller had evidence of the visit, Cohen called it a “false story” and asserted that he was in L.A. with his son at the time.

Why was a computer server at Trump Tower pinging Russia’s Alfa Bank?

This mystery has bedeviled reporters and computer security geeks alike, ever since late October 2016, when Slate’s Franklin Foer first reported that a server belonging to the Trump organization was communicating with a pair of servers at the bank in Moscow. The anomaly was discovered by researchers and caught their attention since it didn’t appear to be malware or automated communications and it occurred at irregular intervals. Thousands of words have since delved into the details of this mysterious occurrence–and it’s still unclear whether it’s evidence of collusion or just a random manifestation that defies explanation.

It arouses so much interest because it offers the tantalizing possibility of a “collusion” smoking gun–evidence that the Trump campaign, whose data firm Cambridge Analytica had harvested data on millions of Americans via Facebook, may have transferred that info to the Russian government “to help guide its targeting of American voters before the election.” Or it could show that Trump was in hock for millions to the Russians. It could also show nothing at all.

  • Related questions:
    • Did Cambridge Analytica use the servers at Trump Tower to upload or download data?
    • Why did Cambridge Analytica share data on American voters with Lukoil, the Kremlin-owned oil company?
    • What’s the deal with Sam Patten, the longtime Republican operative who was a contractor for Cambridge Analytica and reportedly had ties to Russian intelligence? He attracted the interest of Mueller’s investigators and pleaded guilty to one felony count of failing to register as a foreign lobbyist while working–like Paul Manafort–for a pro-Russian Ukrainian political party. As with Manafort, Patten received payments through an offshore account in Cyprus.

Did foreign donors contribute to the inaugural committee and how did it spend the $120 million it raised?

Ever since it was reported that Trump’s inaugural committee had raised $107 million, a stunning amount that far surpassed previous inaugurations, questions have swirled about who contributed money and how the money was spent. Just last week, it was reported that federal prosecutors are looking into whether anyone from Qatar, the United Arab Emirates, and Saudi Arabia illegally contributed funds to the event via straw donors.

The inaugural committee also spent money at Trump International Hotel in D.C. and Ivanka Trump talked about charging $175,000 per day for use of the space, though organizers complained that the fee seemed excessive. One of those raising concerns with the president’s daughter was Stephanie Winston Wolkoff, an event planner and friend of First Lady Melania Trump, who was herself paid $26 million for her services during the inauguration. If the price negotiated for the hotel was above market rate, it might reportedly be a violation of tax law.

Inauguration chair Thomas Barrack Jr., who aroused some suspicion due to his own close business ties to Saudi Arabia and other Gulf countries, confirmed his that he was interviewed in 2017 by Mueller’s team. But he said that his lawyer reached out to the special counsel last week and was assured that he was “not under investigation.”

Related: How Trump’s D.C. hotel works to help swamp the drain

What’s in the president’s tax returns?


It’s the perennial question, and the one which the president has successfully managed to avoid for over three years. As a billionaire with a global business empire (presenting plenty of potential conflicts of interest), his tax returns would be immensely informative, shedding light on everything from possibly fraudulent tax avoidance schemes to any loans to Russian or Chinese banks.

But Trump has so far refused to release the returns, despite the fact it’s been standard practice for presidents for decades, insisting that “you get far more” from his already-public financial disclosure forms. Tax experts dispute that contention, explaining that the actual tax returns reveal much more information about his businesses and sources of revenue. In Trump’s case, it might be less about what’s included in the return than what’s not in there–like a far lower net worth and smaller charitable deductions than he’s claimed.

Does Russia–or any other country–have kompromat on Trump?

The further we get from the publication of the Steele dossier, the less you hear about the “pee tape,” even on late-night talk shows. So far, there’s no evidence for that salacious allegation. While it’s possible that there’s other compromising info on Trump, whether personal or financial, that is holding on to blackmail him, it seems increasingly doubtful. Despite his praise and kind words for Putin, Trump has been tougher than expected on Russia, bombing their troops in Syria and sending lethal weapons to the Ukraine. (Though pulling troops out of Syria and dropping sanctions against Russian oligarch Oleg Deripaska has warmed Putin’s heart.)

[Photo: Flickr user Hillel Steinberg]
Who allegedly threatened Stormy Daniels and her daughter?


The porn star has slipped from the headlines ever since losing her defamation case against Trump. But last summer, during her 60 Minutes interview, she raised eyebrows with her claim that an unidentified person threatened her in a parking lot in Las Vegas while she was with her daughter and while she was trying to sell her story about an affair with Trump to a supermarket tabloid. “Leave Trump alone,” he said, according to her account, and looked at her daughter, adding, “That’s a beautiful little girl. It’d be a shame if something happened to her mom.”

Her lawyer, Michael Avenatti, released a composite sketch of the man who allegedly made the threat. When Trump mocked Daniels’s claim as a “total con job,” Avenatti sued Trump on her behalf but lost, with the judge demanding that Daniels pay Trump almost $300,000 in legal fees.

Does Trump owe money to Russian oligarchs or banks?

These were the allegations that first piqued the interest of many reporters, some of whom were told about such loans–or guarantees of his existing loans to Deutsche Bank–by sources. So far, he’s asserted that he has “nothing to do with Russia–no deals, no loans, no nothing.”

But there’s more than nothing. The Trump organization was “actively negotiating” a business deal in Moscow with VTB, a sanctioned Russian bank, during the 2016 campaign, according to a memo released by Democratic lawmakers.

And it’s pretty clear that many Russians have put money into Trump real-estate developments from New York to Palm Beach to Panama in recent years, with Don Jr. telling investors in 2008, “Russians make up a pretty disproportionate cross-section of a lot of our assets. We see a lot of money pouring in from Russia.”


How much revenue does the Trump organization get from foreign governments?

Though Trump put his business assets into a trust managed by his two oldest sons, he didn’t divest those assets, leading to concerns about conflicts of interest between his decisions as president and the business interests of the Trump organization. Last April, the company gave $151,470 to the Treasury Department, claiming that was the sum total of the profits its hotel and resorts have received from foreign governments, but there is no way to ascertain the accuracy of that number.

Earlier this year, it was reported that two foreign government-owned companies pay almost $2 million a year in rent to two Trump properties. And the Trump International Hotel in Washington, D.C., just a few blocks from the White House, was paid $270,000 by Saudi Arabia, when diplomats booked 500 rooms there in late 2016 and early 2017, and other countries including Kuwait and Turkey have spent mucho dineros to put up their officials at the swanky hotel.

Did the Trump campaign know that WikiLeaks was about to dump thousands of emails connected to Hillary Clinton’s campaign?

Like a leaky faucet, this angle keeps dripping with new revelations. In recent weeks, new details have emerged about how Trump consigliere and notorious dirty trickster Roger Stone wrote to conservative theorist Jerome Corsi in July 2016, instructing him to contact WikiLeaks founder Julian Assange at the Ecuadorian embassy in London to get Clinton campaign emails. Stone has said he had heard about the impending leak from New York comedian Randy Credico, but recently added that he had also been tipped off by viewing an email from James Rosen, then a Fox News reporter, to blogger Charles Ortel. Ortel confirmed to The Washington Post that he had forwarded Stone the email.

Corsi, according to prosecutors, sent Stone’s request to Ted Malloch, a London-based author. A week later, Corsi informed Stone that Podesta’s emails were about to be leaked. Corsi, who claims that he was not in touch with WikiLeaks, recently rejected a plea deal with Mueller, filed a complaint with the Justice Department alleging prosecutorial misconduct by Mueller, and is suing Mueller for $350 million, accusing the special counsel of lying to him about Trump. And Stone claims that he was not in touch with Corsi about Podesta’s emails until after they were published by WikiLeaks.


Recently, the Guardian reported that Manafort visited Assange in London in March 2016, soon after joining the Trump campaign, though that report has not been confirmed by other outlets.

  • Related:
    • Is the suicide of Republican donor Peter W. Smith related to the Mueller investigation?
    • The mystery of Smith, a longtime GOP donor who spent much of 2016 trying to get his hands on the 33,000 emails deleted by Clinton in order to help the Trump campaign, deepened a few months ago when it was reported that he had met Flynn the year before. In a document he circulated to raise funds for his effort, the former businessman mentions Flynn, Steve Bannon, Kellyanne Conway, and Sam Clovis, a Trump appointee, but all of them later denied any knowledge of Smith and his initiative. A few months after the inauguration, Smith killed himself.

[Photo: Flickr user Gage Skidmore]
Why did Michael Flynn lie?

The former national security adviser convicted of lying to federal agents about his pre-inauguration conversations with Russian ambassador Sergei Kislyak just saw his sentencing delayed (after a withering put-down by the judge). His lawyers have claimed that he was not told in advance that lying to the FBI was a crime (which seems a little hard to believe given his decades-long career in government), but Mueller’s team asserted in a memo that Flynn was given multiple chances by agents to correct his false statements.

Why lie, given the extraordinary consequences of such a step? Some speculate that Flynn assumed he may have violated the Logan Act, which makes it illegal for private citizens to conduct unauthorized negotiations with foreign governments, and sought to cover it up.

How much does Vice President Mike Pence know (and when did he know it)?

Maybe it’s not the elephant in the room, but the question definitely lingers in the back of many of these controversies. Pence may seem like he blends into the wallpaper, when he’s not appearing comatose during West Wing meetings, but he’s a canny politician who’s said to harbor his own ambitions for the presidency. And he’s not stupid. So it seems likely that he was at least half-aware of some of these shenanigans, from the Trump campaign’s outreach to shady Russian officials and players to the Trump Tower meeting to who was donating the millions that went to the inauguration.


Why did Erik Prince meet with a Russian financier days before the inauguration?

The Trump donor and founder of Blackwater, the infamous private security company, met with George Nader, an adviser to the leader of the United Arab Emirates, and Kirill Dmitriev, who manages a Russian sovereign wealth fund and is considered close to Vladimir Putin, in the Seychelles islands on January 11, 2017. The meeting aroused suspicion due to the players and the timing–just weeks after Jared Kushner reportedly told Russians about his desire to set up a back channel for communications–with sources telling reporters that it was a way for Trump’s team to secretly negotiate with the Kremlin. Some also saw the meeting as a way for the Emirati and Saudi crown princes to exercise influence the incoming administration. Prince testified in Congress that it was just a business meeting, but the purpose of the meeting has intrigued Mueller’s team. Nader is cooperating with the probe and testified before a grand jury.

Related: Two Princes: How a secret meeting signaled the UAE’s pull in Trump’s D.C.

What’s on the Apprentice tapes?

Ever since Trump permanently tainted the reputation of Tic-Tacs in the Access Hollywood video, there’s been chatter about the existence of outtakes from The Apprentice that show Trump making racist and sexist comments. Fired aide Omarosa Manigault Newman and comedian/magician Penn Jillette, who appeared on the show in 2012, both claim that such tapes exist. And Tom Arnold has made a comeback with a show, The Search for the Trump Tapes, devoted to just that question, claiming that he’s heard outtakes in which Trump says “every dirty, every offensive, racist thing ever.” And one of the show’s producers, Bill Pruitt, claimed in a tweet that the Access Hollywood tape was nothing, hinting at much worse language in other tapes. The Apprentice’s producer Marc Burnett insists that there are no such tapes, adding that because he sold the show to MGM, the archives are their property. Even so, Burnett claims that they cannot be released because the archives are “contractually confidential.” Trump has vigorously denied making any such offensive comments on the show.

Did Supreme Court Justice Anthony Kennedy have other reasons to resign?

Chief Justice Anthony Kennedy

When the Supreme Court justice resigned last summer, it sent shockwaves through Washington, elating conservatives and depressing liberals since it handed Trump his second pick for the high court. But questions were immediately raised about Kennedy’s resignation, since he wasn’t in ill health, and once it was revealed that his son Justin Kennedy once led the real-estate division at Deutsche Bank, which loaned $1 billion to Trump for various real-estate projects when other banks wouldn’t deal with him. Also, Justin Kennedy once escorted Ivanka to watch the Supreme Court hearings. When Trump greeted Kennedy after his first State of the Union speech, he told him, “Say hello to your boy. Special guy.”

There’s also been speculation that Kennedy resigned as part of a deal to protect his son from any Russia investigation since Deutsche Bank’s records have been subpoenaed by Mueller, a claim deemed “not proven” by

Was Trump connected to the payment of yet another Playboy model?

Everyone knows that Trump got Michael Cohen to pay AMI $150,000 to squash a story by former Playboy model Karen McDougal about her alleged affair with Trump. But The Atlantic’s David Frum has raised questions about former GOP deputy finance chair Elliot Broidy’s $1.6 million payment to former Playboy model Shera Bechard, which was arranged by Trump’s then-lawyer Michael Cohen. Broidy made the first installment of that payment just days before a private meeting with Trump, at which he encouraged the president to crack down on Qatar, the rival of his lobbying client, the United Arab Emirates.