The Apprentice: Trump, Russia and the Subversion of American Democracy

These were the circumstances of the man Trump would turn to in 2016 to lead his campaign.

EARLY THAT YEAR, MANAFORT SAT DOWN AT A COMPUTER AND began typing a memo to pitch his services. “I am not looking for a paid job,” he wrote, aware of Trump’s miserly impulses and volatile tendencies toward paid subordinates. The two-page missive, which he delivered through a mutual acquaintance, recited his experience running conventions and wrangling GOP delegates presenting himself as someone who could head off the threat of a convention coup. He also cast himself, remarkably, as a Washington outsider, an exile of the swamp Trump had vowed to drain. Finally he noted that he lived in Trump Tower—unit 43G—and claimed that he had once helped Trump quiet the skies over his Mar-a-Lago estate in Florida by lobbying the Federal Aviation Administration.

Former colleagues, mindful of the problematic sources of Manafort’s riches, warned him of the scrutiny that would accompany a return to the political spotlight. But Manafort was unswayed—Trump was his kind of guy. On March 29, eight days after Trump’s meeting with the Post editorial board, Manafort was brought on board.

MANAFORT JOINED AN OPERATION SO BEREFT OF FOREIGN POLICY expertise that one campaign official summarized the search criteria in stark terms: “Anyone who came to us with a pulse, a résumé, and seemed legit would be welcomed.”

Only one early Trump backer exceeded those expectations, bringing with him the kind of credentials that would ordinarily have been welcomed by any campaign. Michael Flynn’s patriotism, sacrifice, and distinguished service were beyond dispute. In the fifteen years since the September 11 attacks, he had spent almost as much time deployed to Afghanistan and Iraq as he had spent with his family in the United States. The Army traditionally favors officers who rise up by leading combat units, but Flynn had climbed the service’s intelligence ranks. His ascent to three-star general was a reflection of his effectiveness as an officer, but also the realities of a new era of conflict. Against amorphous terror and insurgent networks, the ability to process streams of data from drones, captured militants, and their laptops and cell phones was often more important than overwhelming force.

Flynn helped design a lethally effective combination of these ingredients. In concert with General Stanley A. McChrystal in both Iraq and Afghanistan, he worked to compress a nightly cycle of raids by commando units followed by rapid exploitation of information gathered at the scene. The data was used to generate targets for the next round of raids, often within hours, a tempo that proved devastating to insurgents. The approach helped pull the war effort out of a tailspin at a time when Al-Qaeda’s franchise in Iraq had driven the country into a sectarian bloodbath. In 2006, forces under McChrystal and Flynn decapitated the Al-Qaeda network, tracking its leader in Iraq, Abu Musab al-Zarqawi, to a village north of Baghdad and ending his insurgent career under a pair of 500-pound bombs.

When McChrystal was given command of the war in Afghanistan in 2009, he again turned to Flynn as his top intelligence officer. While deployed, Flynn co-authored a twenty-six-page article that delivered a blistering critique of America’s cluelessness about the cultural and religious complexities of the conflict. Titled “Fixing Intel,” it was published by the Center for a New American Security, a Washington think tank. Flynn’s report was seen by some as self-serving but it burnished his reputation as an unconventional thinker.

When McChrystal’s career was derailed over a troubling profile in Rolling Stone magazine, Flynn returned to Washington to take what many regard as the top job in his specialized field, running the Defense Intelligence Agency, a spy service that caters to the needs of the military from a base across the Potomac River from Reagan National Airport.

Then it was Flynn’s turn to implode.

He’d arrived at DIA with ambitious plans to reorganize the agency around geographically focused centers and to upgrade its overseas collection capabilities to more closely resemble those of the CIA—in effect, to raise DIA above its reputation as a backwater among U.S. intelligence agencies.3 He warned any who resisted his agenda that he would “move them or fire them.”

But Flynn, who had helped devise the formula for subduing insurgent organizations, seemed overwhelmed by the complexity of the organization he now led. From the outset, the hallway murmurs were that he was struggling to adapt outside the supportive structure of McChrystal’s combat apparatus, where orders were executed with the snap of a salute and the mission was both clear and all-consuming. The DIA, by contrast, was a sprawling agency of 17,000 employees, half of them civilians. Its mission was diffuse, its structure bureaucratic, and its rhythms nothing like the raid-exploit-raid repetition Flynn knew on the front lines. Subordinates left meetings confused by his instructions; members of Congress were alarmed by his inability to answer basic questions about the agency’s budget. Flynn made so many unfounded pronouncements—about the Islamic State, North Korea, and other subjects—that aides coined a term for his puzzling assertions: “Flynn facts.” Senior aides began warning the director of national intelligence, James Clapper Jr., a gruff Air Force general who had spent half a century around U.S. spy agencies and was now in charge of all of them, as well as the Pentagon’s top intelligence official, Michael Vickers, that Flynn’s disruptive approach was damaging morale.

As the months passed, Flynn’s views about Islam appeared to harden, and he became fixated on Iran. He pushed analysts to scour intelligence streams for hidden evidence of Iran’s ties to Al-Qaeda, connections that most experts considered minimal, and search for proof of Iranian involvement in a variety of events where there seemed to be none, including the 2012 attacks on U.S. compounds in Benghazi, Libya. No matter the evidence, Flynn kept pressing, always seemingly convinced of connections to the country he considered America’s greatest enemy.

The DIA chief had an inexplicable admiration for another American adversary, however. In June 2013, Flynn traveled to Moscow for meetings with General Igor Sergun, his counterpart at the GRU, the military intelligence agency that three years later would help disrupt the U.S. election. Prior DIA chiefs had made similar visits, but Flynn was convinced that he had been accorded special treatment and developed a rapport with the Russians that might enable a cooperative breakthrough.

Flynn “was brought into the inner sanctum,” recalled U.S. Army brigadier general Peter Zwack, who was the U.S. defense attaché in Moscow and accompanied Flynn throughout his three-day visit. Flynn was allowed to lay a wreath at Russia’s Tomb of the Unknown Soldier. He was taken to the GRU’s gleaming modern headquarters on the outskirts of Moscow, where—in a remarkable gesture—he was invited to deliver an hour-long address on U.S. counterterrorism methods to a collection of majors and colonels who, Zwack surmised, “had never before encountered an American intelligence general.”

That evening Flynn hosted a dinner for Sergun at Zwack’s residence at the U.S. embassy, decorated with a LeRoy Neiman painting of Red Square. The assembled officers began raising glasses of vodka, culminating in a final toast to making “the airlocks fit,” a reference to the 1975 joining of the Apollo and Soyuz spacecraft. Sergun returned the gesture the next night by hosting a dinner for Flynn at the historic Sovietsky Hotel, providing the American general a personal tour of the room where Stalin’s son had lived.

Flynn saw such promise in the encounter that he returned to DIA and began planning a reciprocal visit that would bring Sergun and his GRU entourage to the United States. He continued to pursue the idea even after U.S.-Russia relations went into a protracted skid over Moscow’s military incursions into Ukraine. Eventually Flynn had to be told by his bosses to abandon the plan—an intervention that only added to their growing vexation with him.

DIA directors are expected to serve terms of at least three years. But by early 2014, Clapper and Vickers had had enough, and told Flynn that his troubled tenure would run out after two. Flynn, only fifty-five, was forced to retire.

Flynn’s wife, Lori, wore a festive floral dress with a lei around her neck to his farewell ceremony on August 7, 2014, as if anticipating the coming freedom that she and her husband, an avid surfer, were soon to enjoy. And Flynn, in an Army dress uniform draped with the many medals he’d won during his career, ended his remarks to the five hundred in attendance at DIA headquarters with an expression more associated with sailors than soldiers, a wish for “fair winds and following seas.”

Beneath the surface, he seethed.

FLYNN’S REMOVAL HAD BEEN DELAYED BY MONTHS TO ALLOW HIM to make one final move up in rank and secure his third star. Despite that accommodation, Flynn became increasingly bitter toward those he blamed for his ouster. He began claiming that he was pushed out not because of any leadership deficiencies, but because Obama and his top aides “did not want to hear the truth” that Flynn was speaking about militant Islam. He started a company, Flynn Intel Group, a consulting and lobbying firm that pursued international clients willing to shell out six-figure sums for his overseas expertise and access in Washington. He also began working on a book—half memoir, half call to arms against Islamists—with the neoconservative author Michael Ledeen. Flynn joined a speakers’ bureau and began making appearances on Fox News, NBC, CNN, and other cable news channels. The outlet that seemed most eager to provide a platform for the forced-out former general was RT, an international English-language television channel funded by the Russian government.

“There is a saying I love: truth fears no questions,” Flynn said in one of his RT interviews. He may have loved the saying, but, as it would turn out, didn’t always adhere to its message.

PAGE, PAPADOPOULOS, MANAFORT, AND FLYNN CAME TO THE CAMPAIGN from different directions, but each saw their association with Trump as a way to reach or recover influence. At the time there seemed little downside. If Trump won, a job at the White House or elsewhere in his administration wasn’t out of the question. If he lost—as seemed almost inevitable—the contacts they made and attention they got could only enhance their post-election fortunes.

Moths to Trump’s flame, all four would end up burned, whatever futures they envisioned eventually reduced to a single imperative: staying out of jail.

AS TRUMP GAINED MOMENTUM IN THE REPUBLICAN RACE, HE BEGAN facing pointed questions about how he could continue heaping praise on Putin when so many of the Russian leader’s adversaries ended up disfigured or dead. Trump’s defiant responses were unlike anything ever uttered by a major party candidate. “I think our country does plenty of killing also,” he said in mid-December 2015 on MSNBC’s Morning Joe program. Putin is “running his country and at least he’s a leader, unlike what we have in this country.” Two days later, on ABC, Trump said that murdering journalists would be “horrible. But, in all fairness to Putin, you’re saying he killed people. I haven’t seen that. I don’t know that he has … I haven’t seen any evidence that he killed anybody.”

The consistency of his deference to Putin seemed out of character: whether on social media or standing before a packed arena, Trump seemed incapable of stringing together more than a few sentences without insulting or demeaning a rival, a demographic, or an entire country. Unscripted and unapologetic, Trump often seemed to offend even when he didn’t intend to. Yet, with Putin, Trump was disciplined and on-message, never even inadvertently critical.

The pattern was perplexing to Trump’s political adversaries as well as national security officials in Washington. Some saw his early statements about Putin as the uninformed comments of a political neophyte, someone who had only a cursory understanding of world affairs. It was Trump being Trump—staking out a provocative position that he might abandon when it became politically advantageous to do so, or better-informed advisers got through to him.

As Manafort, Page, Papadopoulos, and Flynn came on board, the Trump campaign’s entanglements with Russia—and questions about their purpose—intensified. The search for answers would eventually occupy U.S. intelligence agencies, committees in Congress, and a team of FBI agents and prosecutors led by special counsel Robert S. Mueller III. Before those organizations were fully engaged, however, there was a far smaller, independent inquiry under way.

CHRISTOPHER STEELE HAD PERSONAL EXPERIENCE WITH THE ruthless side of the Kremlin that Trump could not bring himself to see, stationed in Moscow in the early 1990s under diplomatic cover for Britain’s Secret Intelligence Service.

Steele and Putin were nearly espionage contemporaries, Steele in Moscow, after the Soviet Union collapsed, while the future Russian leader was based in East Germany for the KGB when the Eastern Bloc began to unravel. Putin was permanently scarred by what had happened when the Berlin Wall came down in 1989. Crowds stormed the Dresden offices of the East German secret police and then turned their attention to the nearby headquarters of the KGB. Putin, by his own account, radioed a Red Army tank unit to ask for protection. “We cannot do anything without orders from Moscow,” came the reply. “And Moscow is silent.” Putin, sickened by the fecklessness of his government, returned to Russia and had begun pursuing a career in St. Petersburg politics when Steele arrived in Moscow. Their paths would intersect several times in the ensuing decades.

THE SOVIET UNION WAS IN ITS DEATH THROES AT THE START OF Steele’s Moscow assignment, and he would witness the hammer-and-sickle flag lowered for the last time, opening a chaotic new era for Russia and the former Soviet republics. Steele had joined MI6 after graduation from the University of Cambridge, where his success as a student allowed him to transcend his family’s working-class roots. His father worked for the United Kingdom’s weather service; a Welsh grandfather had mined coal. Steele excelled at Cambridge and became president of the prestigious debating society, the Cambridge Union. His path to espionage began when he saw a newspaper ad seeking applicants interested in overseas adventure. Only when he responded did Steele learn the ad had been posted by MI6.

Steele had seemed poised for a series of foreign assignments when his undercover career was derailed. During a four-year posting in Paris in the late 1990s, he was one of dozens of British spies whose true identities were published online by a disgruntled former MI6 agent.4 Steele came back to MI6 headquarters in London and rose up the intelligence service’s ranks until, in 2006, he was placed in charge of its Russia desk.

He was soon greeted with a brutal demonstration of the Russian intelligence service’s resurgence under Putin, then in his sixth year as president. That November, Alexander Litvinenko, a former FSB officer and Putin critic who had defected to Britain, was taken to a hospital with a mysterious ailment. British authorities concluded that he had been poisoned by a cup of tea laced with radioactive polonium. Three weeks later he was dead. Putin issued a statement of mock remorse, saying, “Mr. Litvinenko is, unfortunately, not Lazarus.”

Steele was put in charge of the MI6 investigation. His findings contributed to a broader official UK inquiry that took nearly a decade to finish and release to the public. It concluded that Litvinenko’s murder had “probably” been ordered by Putin. To Steele, there was never any doubt.

For all of his expertise and accomplishments, Steele had his detractors, and his departure from MI6 in 2009 was interpreted by some as a sign that he had realized that he was not likely to rise any higher in the spy agency. He also faced a personal crisis: his wife, with whom Steele had three children, was gravely ill—British press reports said she had cirrhosis of the liver—and died later that year.

After his retirement, Steele launched a London-based consulting firm, Orbis Business Intelligence Ltd., an increasingly common path for ex-spies whose contacts and inside knowledge of foreign governments and markets were in demand among corporate clients. One of Steele’s first contracts had him working for the English Football Association on an investigation into corruption at FIFA, soccer’s global governing body. U.S. investigators were also involved, eventually filing corruption charges against fourteen soccer executives. As a result of this partnership, Steele found himself working closely with FBI agents and sharing his research with the Justice Department—developing relationships that he would turn to again as troubling Russia connections began to surface in an American presidential election.

Steele’s involvement with that election began with a June 2016 call from Glenn Simpson, a former Wall Street Journal reporter who had founded his own private research company in Washington, Fusion GPS. Steele and Simpson had met years earlier when Simpson was an investigative reporter for the Journal based in Brussels and pursuing stories about Russian organized crime and its spread into Europe. One of Fusion’s business lines was opposition research, a euphemism for digging up dirt on political candidates.

Fusion had initially been hired in late 2015 to investigate Trump’s business record—including any ties to Russia—by the Washington Free Beacon, a conservative paper. It was an unusual move for a news organization: media outlets generally don’t pay for stories, let alone hire private investigative firms to root around in politicians’ or celebrities’ lives. But the Beacon in this case was doing the bidding of one of its prominent funders, Paul Singer, a wealthy New York investor and major GOP donor who at the time was determined to stop Trump from winning the party’s nomination.

The money for Fusion dried up as Trump racked up wins in major primaries and establishment candidates including Jeb Bush and Rubio were forced from the race, but Simpson found a new source of support: Perkins Coie, the law firm representing the DNC as well as the Clinton campaign. With Trump’s praise of Putin already an issue, Perkins Coie was intrigued by Fusion’s tantalizing early reports and eager to pick up the tab, via DNC funds, to see what else the company could find on the Republican candidate and the Kremlin.

The new funding stream enabled Fusion to expand its probe. The firm’s research typically involves scouring public records, court filings, and media reports to produce a comprehensive profile of a subject—much the way Simpson had worked as an investigative journalist. To scrutinize Trump’s ties to Russia, public records searches wouldn’t be enough. Simpson needed sourcing that could get him closer to the Kremlin, and turned to the ex-British spy he had met in Brussels.

Steele signed on with Fusion in early June 2016. “I didn’t hire him for a long-term engagement,’’ Simpson later testified before Congress. “I said take thirty days, twenty or thirty days, and we’ll pay you a set amount of money, and see if you can figure out what Trump’s been up to over there, because he’s gone over a bunch of times, he said some weird things about Putin, but doesn’t seem to have gotten any business deals.” Steele was told the client was a law firm but not which one or its connection to the DNC. The ex-spy, his biography undoubtedly known to Russian intelligence, never entered Russia himself as part of the investigation. Instead, he worked through a collection of cutouts— intermediaries used to relay communications without raising suspicion. Among them were native Russians both in and out of the country who were already on contract with Orbis and in position to make contact with their own sources, some of them close to influential oligarchs or the Kremlin.

Steele and Simpson expected to turn up information tying Trump to shady business operatives, accessing unsavory sources of money, or otherwise entangled in Moscow’s ubiquitous corruption. But from the start, the information that flowed back to Orbis from Steele’s network of sources was more fundamentally unnerving, alleging that the Kremlin had spent years cultivating Trump, not necessarily as a future presidential candidate but an influential American sympathetic to Moscow; that Russia was providing helpful information to the Trump campaign; and that Russian intelligence possessed compromising information on Trump and episodes of sexual perversion during his 2013 Miss Universe trip to Moscow.

Verifying some of the most salacious leads would prove elusive for legions of reporters and investigators for the next two years. But in some ways the most alarming report from Steele’s sources proved accurate and prescient: in one of the first entries of what became known as the “Steele dossier,” he warned that Russia was waging a covert influence campaign aimed at disrupting the 2016 election and defeating Clinton.

He also almost immediately came across disturbing information about Carter Page.

ONCE ON THE TRUMP TEAM, PAGE BEGAN GRANTING INTERVIEWS in which he presented himself as the campaign’s “Russia adviser.” He played up his business ties to Moscow and urged campaign officials to have Trump make contact with the Kremlin. His status with Trump earned him a speech invitation from the New Economic School in Moscow, a prestigious institution where Obama had once given a talk. In May, Page emailed others on the campaign to propose that Trump go in his stead “if he’d like to take my place and raise the temperature a little bit.”

In June, Page used his credentials as a member of the Trump campaign to attend an event at Blair House, a historic residence just across Pennsylvania Avenue from the White House where foreign guests of the president often stay. At a gathering for Indian prime minister Narendra Modi, Page startled the assembled foreign policy experts and academics by praising Putin as a stronger leader than Obama, and vowing U.S.-Russia relations would recover when Trump was in office.

In the ensuing weeks, Page had a flurry of interactions with campaign officials about his pending trip to the Russian capital. He sent emails submitting drafts of his speech and asking for feedback from campaign manager Corey Lewandowski, spokeswoman Hope Hicks, and J. D. Gordon, a former naval officer serving as a foreign policy adviser.5 At a dinner for members of Trump’s national security team at the Capitol Hill Club, a watering hole for Republicans, Page greeted Alabama senator Jeff Sessions and told him he was heading to Russia in a matter of days. The campaign maintained that he was going to Russia on his own, and not as a Trump representative. But organizers of the New Economic School event made clear that they were not necessarily interested in the independent opinions of Page.

“Carter was pretty explicit that he was just coming as a private citizen, but the interest in him was that he was Trump’s Russia guy,” said Yuval Weber, a Harvard professor who said he was with Page for much of his time in Moscow, and whose father, Shlomo Weber, was the rector at the New Economic School and had extended Page the invitation.

Page’s July 7 remarks in Moscow were astonishing. “Washington and other Western capitals have impeded potential progress through their often hypocritical focus on ideas such as democratization, inequality, corruption, and regime change,” he said. He cited the Occupy Wall Street movement, the Bernie Madoff scandal, and the collapse of Enron as evidence of irreparable cracks in the American system. Putin, by Page’s account, was a force for global enlightenment, fostering a system of international relations “focused on mutual respect, equality and mutual benefit and tolerance, and access to resources.”

Page kept the same campaign advisers apprised of developments on his trip in a series of emails. Relaying an apparent interaction with Russian deputy prime minister Arkady Dvorkovich—chairman of the board of the New Economic School—Page said Dvorkovich “expressed strong support for Mr. Trump and a desire to work together.” In a July 8 email to Gordon and another campaign adviser, Tera Dahl, Page said he would “send you guys a readout soon regarding some incredible insights and outreach I’ve received from a few Russian legislatures and senior members of the presidential administration.”