Category: October Surprise 2016

With Donald Trump threatening to retake the U.S. presidency next week in the face of Russia’s ongoing aggression in Ukraine, it’s time to take stock of a deeply unsettling fact. After years of investigations by U.S. government bodies from the Justice Department to the FBI to Congress, the American public has no idea if Russian President Vladimir Putin has “something” on Trump—in other words, some compromising information about the would-be 47th president’s past, or what the Russians call kompromat.

Eight years after the FBI first began probing Trump’s Russia connections in mid-2016, national security officials are still puzzled by the former U.S. president’s unrelenting deference to Putin, as well as the enduring mystery of Trump’s decades-old relationship with Russian and former Soviet investors and financiers, some of whom helped save his failing businesses years ago.

So we’re asking the same questions we were asking eight years ago. Is Trump some sort of Manchurian candidate—or in this case, perhaps a Muscovian candidate—controlled by or beholden to Moscow in ways that we don’t know and likely will never know? Or is Trump’s persistently fawning treatment of Putin mainly just a manifestation of his often-expressed admiration of autocrats around the world, including Chinese President Xi Jinping and ​​Hungarian Prime Minister Viktor Orban?

Trump himself has long denied that there is any collusion between him and the Kremlin. But among key U.S. officials who were involved in these earlier investigations, there is no small amount of frustration over this disturbing question.

What has emerged from interviews in recent weeks is an idea of just how ugly and unresolved the disputes remain among the investigators, some of whom are kicking themselves for not going deeper in their probes back then. In many cases, former senior officials at the FBI and Justice Department are still blaming each other for falling short—especially when it comes to the investigation by former special counsel Robert Mueller of Russian election interference and ties between Trump officials and the Kremlin during the Trump administration.

“Here we are in 2024, and over the years since the special counsel started their work in 2017, all we have gotten is more questions, more evidence, more situations that point toward very serious questions about Donald Trump’s relationship with Russia and specifically with Vladimir Putin,” said Andrew McCabe, the former acting director of the FBI who first pushed for the Mueller probe, in a phone interview with Foreign Policy. “And none of those questions have ever been answered,” he added. “Likely because there’s never been a thorough and legitimate investigation of them.”

And that’s unlikely to change if Trump takes office on Jan. 20, 2025.

Russian interference in the November U.S. election—all apparently in support of Trump—is already more widespread and intense than in 2016, U.S. officials say. Deploying new methods such as deep fakes and paid-for news sources, Russia’s activities “are more sophisticated than in prior election cycles,” a senior official with the Office of the Director of National Intelligence told reporters in September.

According to the Washington Post, the official cited the use of artificial intelligence as well as “authentic U.S. voices” to “launder” Russian government propaganda and spread socially divisive narratives through major social media and fake websites posing as legitimate U.S. media organizations. Moscow is targeting U.S. swing states “to shape the outcome in favor of former president Donald Trump,” the newspaper said.

Perhaps the most crucial swing state that could decide the election is Pennsylvania, and on Oct. 25, U.S. officials announced that “Russian actors” were behind a widely circulated video falsely depicting mail-in ballots for Trump being destroyed in a critical county of that state—in an apparent effort to justify Trump’s regular rants about election fraud.

In late September, the U.S. Justice Department accused two employees of RT, the Kremlin’s media arm, of funneling nearly $10 million to a company that media outlets later identified as Tenet Media, a Tennessee-based company that has hosted right-wing pro-Trump commentators with millions of subscribers on YouTube and other social media platforms. The Biden administration also announced the seizure of 32 internet domains used in Russian government-directed foreign malign influence campaigns called “Doppelganger.”

According to Attorney General Merrick Garland, “Putin’s inner circle, including [First Deputy Chief of Staff of the Presidential Executive Office] Sergei Kiriyenko, directed Russian public relations companies to promote disinformation and state-sponsored narratives as part of a campaign to … secure Russia’s preferred outcome in the election.”

“In some respects, this payment of media sources to put out stories is even more brazen than some of the activities we investigated,” said Andrew Goldstein, a former senior Justice Department lawyer and the co-author of a new book titled Interference: The Inside Story of Trump, Russia, and the Mueller Investigation.

“Americans should be concerned about the fact that Russia interfered in a very substantial way in 2016 on Trump’s behalf, and they’re doing it again by every measure we’ve been able to see publicly,” Goldstein added. “People should be continuing to try to get the bottom of that.”

The most urgent issue, these former officials say, is what might happen if Trump gets elected and follows through on his promise to resolve the Ukraine war quickly. Trump has hinted that he will give Putin at least some of what the Russian president wants—in particular, the parts of Ukraine that he has conquered as well as a pledge to keep Ukraine out of NATO.

“On a foreign-policy level, that is clearly the biggest concern,” McCabe said. “His promise to end it [the war in Ukraine] in one day can only possibly end it one way, and that will be an absolute travesty that could spell the end of NATO, and on and on. There’s a million other things, though. He’s the only president to ever have repeated one-on-one unmonitored, unwitnessed interactions with Vladimir Putin who then gets up in front of the world and tells them he believes Putin over his own intelligence agency.”

Those conversations with Putin continued after Trump left the presidency, according to a new book by Washington Post journalist Bob Woodward, titled War. Woodward reported that Trump spoke to Putin as many as seven times after he left the presidency and that at one point, in 2024, Trump told a senior aide to leave the room at his mansion in Mar-a-Lago so “he could have what he said was a private phone call” with the Russian leader.

According to Goldstein, “given the difference in the candidates’ views of the war in Ukraine, there is an even greater incentive now for Russia to intervene, wanting Trump to win and not wanting [Democratic nominee and Vice President Kamala] Harris to win.”

Trump himself, asked to confirm the Woodward account of his alleged conversations with Putin since he left the White House during an interview with Bloomberg editor in chief John Micklethwait in mid-October, responded: “I don’t comment on that. … But I will tell you that if I did, it’s a smart thing. If I’m friendly with people, if I can have a relationship with people, that’s a good thing and not a bad thing in terms of a country.”

So what do we actually know about Trump’s ties to Russia? A great deal. But while there is a great deal of smoke, it’s still difficult to find any fire—that is, any kind of hard evidence of a tit-for-tat relationship that would cause Trump to side with Putin. The investigations simply didn’t go far enough to know if there is one.

What’s clear is that some three decades ago, when Trump’s businesses were buckling under failure after failure and repeatedly declaring bankruptcy—causing him to be toxic to U.S. banks—foreign money played a significant role in reviving his fortunes.

In particular, Trump benefited from investment by wealthy people from Russia and the former Soviet republics, some of them oligarchs linked to Putin. The overseas money came initially in the form of new real-estate partnerships and the purchase of numerous Trump condos—but Trump also benefited from help from the Bayrock Group, run by Tevfik Arif, a Kazakhstan-born former Soviet official who drew on unknown sources of money from the former Soviet republic; and Felix Sater, a Russian-born businessman who pleaded guilty in the 1990s to a massive stock-fraud scheme involving the Russian mafia. Some of the overseas banks and investment groups that Trump used also had alleged ties to the Kremlin and Russian money launderers linked to Putin, according to U.S. officials.

Trump’s own family has acknowledged his dependence on Russian money, without ever saying where in Russia it came from. In September 2008, at the “Bridging U.S. and Emerging Markets Real Estate” conference in New York, his eldest son, Donald Trump Jr., said: “In terms of high-end product influx into the United States, Russians make up a pretty disproportionate cross-section of a lot of our assets. … We see a lot of money pouring in from Russia.”

Trump’s former longtime architect, the late Alan Lapidus, confirmed this in a 2018 interview with me, saying that in the aftermath of Trump’s earlier financial troubles, “he could not get anybody in the United States to lend him anything. It was all coming out of Russia. His involvement with Russia was deeper than he’s acknowledged.”

In the view of U.S. investigators, these historical connections to Russia looked suspicious and helped to explain why during the 2016 presidential campaign, some of the people in Trump’s orbit—including Trump’s son, daughter, and son-in-law—were contacted by at least 14 Russians at a time when it was clear that the Kremlin was interfering in the U.S. election in Trump’s favor. Parts of this relationship were hyped as open collusion by the so-called Steele dossier produced by a former British intelligence agent, Christopher Steele, which was later mostly debunked.

All those suspicions in turn led to the FBI probe and then the Mueller investigation, along with a massive bipartisan report from the Senate Intelligence Committee that identified a close associate of former Trump campaign chairman Paul Manafort—Konstantin Kilimnik—as a Russian intelligence officer.

“Manafort’s high-level access and willingness to share information with individuals closely affiliated with the Russian intelligence services, particularly Kilimnik and associates of [Russian oligarch] Oleg Deripaska, represented a grave counterintelligence threat,” read the 2020 Senate report. The report also delved into Trump’s relationships with women in Moscow during his trips there starting in the mid-1990s.

But the Senate investigation was limited by partisan infighting and insufficient subpoena power, and the FBI and Justice Department never followed through fully as the narrowly focused Mueller probe got under way.

One key reason why we don’t know more about Trump’s ties to Russia appears to be that Trump and his lawyers aggressively interfered with the Justice Department investigation—and in particular, reports suggest that they pressured former deputy attorney general Rod Rosenstein, who was overseeing the Mueller probe.

Trump’s efforts to obstruct the investigation were extensively detailed in the Mueller report itself, which came out in April 2019. According to McCabe and others, Trump and his team were intent on ensuring that the president’s past financial ties to Russia did not become part of the probe, and they made that clear to Rosenstein, who was described in several accounts as rattled by the pressure and unsure what to do.

“I think Rod desperately didn’t want to get fired. I think Rod navigated a lot of those pressure situations with his first and strongest eye on self-preservation,” McCabe told me.

Some of these tactics were reported in a 2020 book by New York Times reporter Michael S. Schmidt, Donald Trump v. The United States: Inside the Struggle to Stop a President. Schmidt wrote that Rosenstein quietly curtailed the investigation by making it strictly about whether Trump or his campaign officials committed criminal offenses through colluding with Russia or by covering up such collusion. Apparently bowing to pressure from Rosenstein, Mueller dropped the original counterintelligence probe into Trump’s long-term business ties to Russia—in other words, ignoring any questions about what might have motivated Trump to favor or collude with Moscow.

McCabe said he was unaware that Rosenstein was doing this. “Had I known at the time that there would be no investigation of the counterintelligence concerns, I would have continued that work at the FBI,” he said.

Andrew Weissmann, another member of the Mueller team and a former FBI general counsel, also wrote in a 2020 book that fears of dismissal—and unrelenting pressure from the White House—had a lot to do with the limits on the investigation. Trump had already fired then-FBI Director James Comey, partly for pursuing the Russia probe, and behind the scenes, the president was threatening to get rid of Mueller as well, according to several news accounts as well as the final Mueller report.

In his book Where Law Ends: Inside the Mueller Investigation, Weissmann wrote that the Mueller team “was put on notice” that “a broad-based financial investigation might lead to our firing.” He wrote that at one point, Mueller told his investigators, “if the president were in the tank with Putin, ‘It would be about money’—that is, that Trump was motivated by money and his fawning behavior toward Putin could be explained by his seeking to make a buck in Russia. We all knew we had to dig deeper.”

They never did dig deeper, and even now, they are still arguing about why that never happened. Weissman blames Aaron Zebley, Mueller’s chief deputy and a co-author, with Goldstein, of Interference. Weissmann accused Zebley of fretting about retribution from Trump and the White House if the Mueller team dared, for example, to subpoena the president or his son Donald Trump Jr. as part of the inquiry. (They never did.) In the end, Weissmann wrote, the Mueller probe was doomed by its reluctance to fully examine Trump’s financial history and ties to Russia.

“The inability to chase down all financial leads, or to examine all crimes, gnawed at me, and still does,” Weissmann wrote. “Our investigation and report do not resolve those issues once and for all. But we, as a country, are entitled not to have to wonder what the facts would have revealed.”

In interviews with me in the past month, Zebley and Goldstein denied that they were ever directly pressured to narrow the investigation.

“There were definitely no red lines,” Zebley told me. “There was never any sort of decision not to examine something financial, or anything else, when there was cause to do so.” Nonetheless, those who worked with Mueller acknowledge that the special counsel was directed only to conduct a purely criminal investigation, dispensing with the counterintelligence component that McCabe wanted to pursue.

Rosenstein, who is now in private law practice, responded to a request for comment by indicating, in an email, that he did not wish to comment about the scope of the investigation. But he said that he “did what I thought was right and consistent with my oath to faithfully execute the duties of the office, which often angered Trump and some of his key allies.” Defenders of Rosenstein say he did his best to keep the investigation going—even as he was under constant threat of being fired by Trump.

“He was incredibly concerned about what Trump might be up to from both the counterintelligence and the criminal side,” said McCabe, who confirmed an earlier report that at several points during the probe, Rosenstein even offered to wear a wire to the White House to help the investigation into Trump. “That really says it all. Rod is a sphinx. He is a survivor, a guy who is capable one day of writing the memo that justifies the firing of Jim Comey and two days later asking me for Comey’s cell phone number because he desperately wanted to talk to him to get his advice on what to do.”

Early on, Rosenstein did defy Trump by appointing Mueller as special counsel, leading to angry reactions by the president and his GOP defenders, who called the probe a “witch hunt.” But in the end, Rosenstein also appeared to bow to the Trump administration’s wishes by endorsing Attorney General Robert Barr’s controversial statement on March 24, 2019—after the Mueller report was completed but before it was released the following month—saying that the Mueller team had found no evidence of crimes by the president.

As the journalist Jeffrey Toobin described it in his book True Crimes and Misdemeanors: The Investigation of Donald Trump, Barr’s statement “was an obvious and unjustified act of sabotage against Mueller and an extraordinary bequest to the president.”

It is true that the 22-month investigation led by Mueller did not find sufficient evidence to justify criminal charges that the Trump campaign coordinated with Moscow to tip the election, nor that Trump tried to cover up his own role. But the Mueller investigators were also explicit in saying that enough evidence existed to make it impossible for them to exonerate Trump.

That part of their conclusion was ignored by Barr and Rosenstein. Contradicting Trump’s claims that Russian interference on his behalf was a “hoax,” the Mueller report concluded that Russian interference was “sweeping and systematic” and “violated U.S. criminal law,” resulting in the indictment of at least 26 Russian citizens and three Russian organizations.

The Trump White House sought to quash other inquiries into his past as well. In 2019, when the House Financial Services Committee tried to subpoena Deutsche Bank’s records on Trump, the president sued and ultimately won a decision from the Trump-aligned Supreme Court saying the subpoena was not justified. Deutsche Bank, one of the few major banks that would still lend to Trump after his financial debacles, has been heavily fined by U.S. and U.K. regulators for sham trades that could have been used to launder billions of dollars out of Russia.

Most of these former officials believe that a second Trump term would certainly involve fresh threats of dismissal against any Justice Department or FBI officials who don’t fall into line, whether on Russia or Trump’s threats to use the Justice Department to go after his domestic political enemies.

“One thing we learned about Donald Trump in our investigation: What you see is what you get,” Zebley said. “There aren’t two Donald Trumps. If he says he’s going to behave in a particular way, that’s what he’s going to do.”

McCabe agreed. “He’s said it repeatedly many different ways,” he said. “He’s committed to this revenge tour. He’s committed to using the lever of power for his own purposes, whatever those might be, whether lawful or unlawful, now cloaked with immunity from the Supreme Court.” (In a historic but controversial July 1 decision, the Supreme Court granted Trump and future presidents broad immunity from prosecution.)

And that means the FBI and Justice Department will likely go along with whatever a newly elected President Trump wants, McCabe added. “The question is whether people will break within my old organization or the [Justice] Department. Of course they will. At some point they will.”

During all this time, Trump has consistently defended Putin—or at least refused to criticize him. This goes back to that infamous moment at their first formal summit in Helsinki in July 2018, when Trump took Putin’s point of view after he was asked whether he believed the Russian president or his own intelligence agencies about the allegations of Russian meddling in the 2016 U.S. election (which have since been amply documented).

“President Putin says it’s not Russia” that is meddling, Trump replied. “I don’t see any reason why it would be.” Later, in November of that year, when his own U.N. ambassador, Nikki Haley, condemned Putin’s violent intervention in Ukraine after Russian ships fired upon, wounded, and seized Ukrainian sailors—Haley called it “yet another reckless Russian escalation”—the then-U.S. president also declined to criticize Putin personally.

Instead, Trump appeared to blame both sides. “Either way, we don’t like what’s happening, and hopefully, it will get straightened out,” Trump said.

Even on the day of Putin’s full-scale invasion of Ukraine four years later, Trump actually praised the Russian leader for his aggression. “I said, ‘This is genius.’ Putin declares a big portion of the Ukraine … as independent. Oh, that’s wonderful,” Trump told a right-wing radio program on Feb. 22, 2022.

And this September, asked at his only debate with Harris whether he wanted Ukraine to win, Trump answered simply: “I want the war to stop.”

Even Trump’s former director of national intelligence, Dan Coats—also a former conservative congressman—admitted that he was worried by the former president’s consistently positive views of the Russian dictator. “His reaching out and never saying anything bad about Putin. For me … it’s scary,” Coats told Woodward.

It is entirely possible, of course, that Trump’s fawning attitude toward Putin is simply another manifestation of his career-long habit of praising people who flatter him and buy his products, no matter what else they might have done, as well as his open admiration for “strong” autocrats.

By his own admission, Trump tends to favor anyone who invests in his businesses, including foreigners. As he said about the Saudis at a campaign rally in 2015: “Saudi Arabia, I get along with all of them. They buy apartments from me. They spend $40 million, $50 million. Am I supposed to dislike them?”

It was hardly a surprise that even after the CIA blamed Saudi Crown Prince Mohammed bin Salman for the 2018 murder of Washington Post columnist Jamal Khashoggi, Trump appeared to absolve the crown prince as readily as he often does Putin. In a statement, Trump quoted Saudi officials as describing Khashoggi as an “enemy of the state” and said only, “The world is a very dangerous place!”

“The problem with every one of these things is that there is, in the background, a reasonable or nonnefarious explanation,” said McCabe. “Like the massive inflow of Russian money buying up these high-priced condos, that’s also happening all over in places with safe currency, so it’s hard to disaggregate. Is it throwing him [Trump] a financial lifeline, or is it just him benefiting from this trend in high-end real estate?”

In other words, is Trump just a narcissistic former businessman who caters to his investors—some of whom may now represent the United States’ rivals and adversaries? Or is the explanation far more nefarious than that?

We may never know. And if Trump is elected, many new questions are likely to emerge.

“How on earth can we share human source-derived intelligence about Russia with a president who we think might have an inappropriate relationship with Russia?” said McCabe. “How do you do that without putting those people’s lives in jeopardy? But as president, he has the right to access any of that information. So how do we manage the potential risk there?”