dealings with Russians also began to catch up to him. Deripaska, the oligarch he’d worked with on the $18 million cable television transaction, became convinced that he’d been cheated by Manafort and began a years-long campaign in courts to get his investment back. Deripaska sought entry into the United States but, fortunately for Manafort, was denied a visa because of his alleged links to organized crime.
Despite hemorrhaging funds, Manafort was unable or unwilling to stanch spending on a lifestyle that by now included homes from the Hamptons to Palm Beach, vacations in the South of France, a horse farm in Florida, and projects for his filmmaker daughter. Instead, he turned to even more legally dubious financial maneuvers, taking out multimillion-dollar loans on properties he’d acquired with money he’d never reported as income. A later criminal indictment accused him of submitting doctored financial statements, diverting loan proceeds, and lying about credit card bills as part of a sprawling scheme to dupe banks.
His personal life was also spiraling out of control. In late 2014, he was caught cheating on his wife of thirty-six years, according to a trove of text messages exchanged by his daughters that was stolen by hackers (possibly Ukrainians seeking revenge on Manafort) and posted online. In the messages his daughters—Andrea, who was then twenty-nine, and Jessica, then thirty-three—spoke of their father with a mix of sympathy and revulsion. Andrea hinted at the financial crunch her father was facing, complaining that he was “suddenly extremely cheap” in conversations about her wedding budget and strapped by a “tight cash flow.” They expressed admiration for his accomplishments but described him as manipulative and cravenly dishonest. In the most damning passage, Andrea bluntly acknowledged the moral stain of the Manafort fortune. “Don’t fool yourself,” she wrote to her sister. “The money we have is blood money.”
The affair appeared to add to the financial strain. According to the texts, he had rented a $9,000-a-month apartment as well as a home on Long Island for his new girlfriend, a woman thirty years younger than him. When the affair was exposed, Manafort agreed to couples counseling. After that failed, he checked into a therapy facility in Arizona, where he often sobbed during daily ten-minute phone calls home.
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,
