The Apprentice. Greg Miller
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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