What happened to Michael Flynn?
Before he pleaded guilty to lying to the FBI, before he became a folk hero to many of President Trump’s most loyal supporters, before he pivoted from accomplished military officer to purveyor of shocking stories about the evils of Islam, something changed in the tough kid who rose to be a three-star Army general.
His friends and critics agree that after winning a reputation as a master intelligence officer on the battlefields of Iraq and Afghanistan, Flynn broke with lifelong patterns of behavior. Once discreet and apolitical, he morphed into a highly partisan alarm ringer. A man once trusted to cautiously analyze information began touting wild hearsay as fact.
Flynn, 60, is expected to be sentenced in federal court Tuesday after having given prosecutors 19 interviews as part of their investigation into the Trump campaign’s relationship with Russia. Whatever punishment the court imposes, the mystery of Flynn’s transformation endures.
More than two dozen of Flynn’s friends, superiors and colleagues — including some who see him as a heroic truth teller and others who wonder how he went off the rails — agreed in interviews that Flynn’s public persona shifted dramatically. They remain at odds over why it happened.
Did he gradually absorb a new, conspiracy-minded worldview, in part inspired by his son Michael Jr.’s embrace of fringy ideas? Did he discard lifelong habits because he’d been enraged to his core when President Barack Obama’s administration in 2014 removed him as director of the Defense Intelligence Agency (DIA), his last and most senior military assignment? Or had Flynn, who retired as a lieutenant general, long harbored extreme views, successfully shielding his real opinions from those around him?
Although the explanations vary, the pivot is undeniable:
Flynn was, for many years, notably tough on Russia, saying that it and Iran were “the most active and powerful members of the enemy alliance” against the United States.
But over the past three years, Flynn took a fee from the Russian government-supported TV outlet, RT; sat next to Russian President Vladimir Putin at an RT-sponsored dinner; and spoke with Russia’s ambassador before Trump took office — and then lied about those conversations to Vice President Pence and the FBI.
For years, Flynn was a social media skeptic, writing that Facebook and Twitter must become “more socially responsible,” adding “positive messaging campaigns about the betterment of humankind.”
Then, after the 2016 election, Flynn insisted that social media were the key to building a pro-Trump, conservative “army of digital soldiers . . . irregular warfare at its finest.” He said he’d seen proof on social media that Trump had actually won the popular vote in addition to the electoral college, which is false.
Throughout his career, those who had close contact with Flynn agree with remarkable unanimity, he strictly adhered to the military’s standard of avoiding expressing partisan views. He praised superiors publicly for not tolerating criticism of American politicians by officers.
“He was as conforming to the tradition of nonpartisanship as anyone,” said retired Adm. Mike Mullen, former chairman of the Joint Chiefs of Staff, who worked with Flynn for many years.
“The saw you hear all the time that people in the military and intelligence don’t know each other’s politics turns out to be surprisingly true,” said Daniel Benjamin, coordinator for counterterrorism at the State Department under Obama and now a scholar at Dartmouth College. “I had no idea what Mike Flynn’s politics might be.”
Soon after he was fired as head of the DIA, Flynn became a very political actor, even if he was “not a political sophisticate,” said Michael Ledeen, co-author of “The Field of Fight,” Flynn’s best-selling book on the American failure to confront radical Islamists.
Flynn called Milo Yiannopoulos, the incendiary writer and speaker who marketed himself as a right-wing provocateur, “one of the most brave people I’ve met.” Flynn went on Breitbart radio to claim that he had seen signs in Arabic along the U.S.-Mexico border that had been posted to guide “radicalized Muslims” into the United States — a false assertion.
Flynn has traced his leap into partisan politics to his first meeting with Trump, in 2015. A 30-minute appointment turned into an hour and a half, and, as Flynn told The Washington Post in 2016, “I got the impression this was not a guy who was worried about Donald Trump, but a guy worried about the country.”
“I was sold,” Flynn said in a later speech. “From that moment on, my direction in life completely changed.”
And in July 2016, at the Republican convention in Cleveland, he used his prime-time speech embracing Trump to lead the crowd in a lusty shout aimed at Democrat Hillary Clinton.
“Lock her up!” Flynn cried, over and over, clapping along as the crowd’s chant crescendoed. “Lock her up! You guys are good. Damn right! Exactly right! There is nothing wrong with that. . . . Crooked Hillary Clinton, leave this race now!”
Mullen had long found Flynn “extraordinarily capable, thoughtful — an out[side]-the-box thinker. People wanted to be around him. In the field, I saw a balanced guy.”
Then Mullen watched Flynn at the convention. “I was as stunned as anybody else to see him on the stage and see him latch onto conspiracy theories,” he said. “I didn’t recognize the guy.”
The episode at the convention was embarrassing, perhaps, but understandable, friends say.
“He was caught up in the moment,” Ledeen said. “Hard to resist. I mean, I would have said, ‘Calm down, calm down,’ but if you’re going to be on the campaign with Trump, you’re going to say things that support him. And he’s angry. He has reason to be angry.”
The change in Flynn had been evident to some people for at least a year before the convention.
“I thought he was a really upbeat, can-do kind of guy — totally likable,” Benjamin said. In 2015, he invited Flynn to speak at Dartmouth. In such appearances, the retired general railed against negotiating with Iran. He slammed Obama for touting the killing of Osama bin Laden as a turning point in the war against terrorism. He alleged that top U.S. officials were in league with Islamist extremists, trying to make sharia law part of U.S. legal codes.
“The Michael Flynn who showed up here was a very different person from the one I had seen in Afghanistan,” Benjamin said. “He was saying stranger and stranger things. He seemed like he was becoming a bit unhinged.”
Flynn was unapologetic about his new manner.
“I am smack dab in the middle of this arena,” he said in 2016, “and I don’t mind people up in the bleachers throwing rocks at me.”
He pushed back against the tradition of nonpartisanship among retired military leaders. “What do you do when you get out of the military, you stop serving?” he said in a 2016 Post interview. “That means that you stop being an American?”
A friend who has advised Flynn for years said Flynn felt compelled to abandon the tradition of cautious neutrality to save his country. The friend, who like many interviewed for this article spoke on the condition of anonymity to protect their relationships with Flynn, said the general came to view Obama as head of a worldwide crime cartel supporting jihadist ideas.
After the 2016 election, in the only meeting between Obama and then-President-elect Trump, the outgoing leader warned against the hiring of just one person: Flynn. Obama considered Flynn to be dangerous — because of his performance as head of DIA, because of his incendiary statements about Islam, and because Flynn had appeared at the Moscow event staged in 2015 by RT.
Trump ignored his predecessor’s advice and made Flynn his national security adviser. Flynn lasted 23 days. The president forced him out after The Post revealed that Flynn had lied about discussing U.S. sanctions against Russia with that country’s ambassador to the United States.
Flynn did not respond to requests for an interview. Approached after a speech to a conservative group in St. Louis, he said: “I don’t want to talk to you. I don’t even want you here.”
America may not survive this battle over its values, Flynn said in that speech. “This turning point is about the heart and soul of the United States,” he said. “It’s time to . . . stand ready to fight for our way of life and our traditions.”
Nasty tough kid
When Flynn’s mother died in 2014, the family posted a memorial that described Helen Flynn — a lawyer and Democratic activist in Rhode Island — as a fiercely determined woman who “was fearless in expressing her informed opinions. . . . When Helen had it in her mind to do something, she found the way, embraced the challenge and stepped in with two feet firmly planted on the ground.”
Friends said Flynn and his mother were alike in that way — certain in their worldview, bold about making sure others knew what they believed. When he was a child, they attended antiabortion marches together. Always, they argued their points hard at the dinner table.
“I detest those who distort the truth,” he wrote.
Michael Flynn was never going to be one of those studious, intellectual military leaders who quote from Sun Tzu’s “The Art of War” and settle into Ivy League sinecures after taking off the uniform. The son of a veteran and brother of another senior military officer, Flynn described his young self as “one of those nasty tough kids, hellbent on breaking rules for the adrenaline rush and hard-wired just enough to not care about the consequences.”
“I’m a maverick, an atypical square peg in a round hole,” he wrote in “The Field of Fight.”
From the start of his career, Flynn made it clear he would sometimes go his own way. In 1983, when he was stationed at Fort Bragg in North Carolina, members of his platoon were ordered to Grenada to help with the U.S. invasion of the Caribbean island.
Flynn was not included in the group that was deploying. He wanted in. He went to his superior officer and talked his way into the mission.
In Grenada, positioned along a seaside cliff, Flynn heard that two U.S. soldiers were in trouble in rough waters. A former lifeguard, Flynn leaped off the cliff, a 40-foot dive into roiling waters, swam out to the struggling men, and pulled both of them back to a ledge where they could await help from a helicopter.
Flynn initially got chewed out for staging his rescue without authorization, and “that established the legend of Mike Flynn,” said an officer who served with him for two decades. “His reputation was as the guy who believed, ‘You can’t go to war without me,’ and really, he’s acted that way ever since.”
In 2010, Flynn jolted the U.S. intelligence community when he co-wrote “Fixing Intel,” a paper for a think tank that concluded that the nation’s intelligence work in Afghanistan was “ignorant,” “incurious,” “disengaged,” a massive waste of resources.
“Merely killing insurgents usually serves to multiply enemies rather than subtract them,” the paper said.
Flynn’s message read like something almost any counterintelligence professional from either party from President Bill Clinton through Obama might have said. What shocked many in the intelligence agencies was only that Flynn was the paper’s lead author.
“A lot of people in high places were upset because it was signed by an active general who put this out in public rather than going through channels,” a fellow officer said.
The paper did not halt Flynn’s rise. It may even have helped establish him as a serious thinker. Defense Secretary Robert Gates called the paper “exactly the type of candid, critical self-assessment” the military needed. Previously viewed by many as a crackerjack field commander but not executive material, Flynn was quickly moved to a top position in Washington. In 2012, the Obama White House nominated him to run the DIA.
Things did not go well, nearly from the start.
A DIA officer who regularly attended meetings with Flynn said the top brass welcomed him because “he was a legend to us, coming in as the shake-up artist.”
But soon after Flynn’s arrival, the officer said, “he started doing weird things, like bring his unsecured BlackBerry into the secure space, and he became unabashed about his beliefs. In meetings, he sounded like he was reading Breitbart and Alex Jones and random bloggers, alt-right stuff, and he’d just say, ‘Well, I heard this . . .’ ”
“We saw a serious cognitive erosion,” another agency staffer said, “like he couldn’t inhibit himself from saying things, like the filters were off.”
“He lost control of the building very quickly,” Benjamin said.
Some officials began to call his forays into speculative or conspiratorial thinking “Flynn facts.” When he decided to go to Moscow in 2013 to speak to officers at Russia’s military intelligence agency, some top advisers told their boss the move was naive, even dangerous. Flynn insisted that the battle against Islamist terrorism made it urgent to seek common ground with the Russians.
A senior DIA staffer said several people “tried to push Flynn away from that stuff in a very cordial, diplomatic way, to move him away from his extreme ideas about not talking to Iran and about Islam. He’d just say, ‘Well, you’re wrong.’ We talked all the time among ourselves about what was going on in his head. Like, was it PTSD, or was this who he was all along and now he finally had the authority to say it?”
By 2014, Flynn’s bosses had had enough. They cut his tenure short and pushed him out.
Humiliated and incensed, Flynn started a private intelligence business and signed with a speakers bureau to deliver paid addresses about leadership and the fight against Islamist extremists.
He had a new battle in mind. “He decided to take his lance and point it at the administration,” Benjamin said. “He fell in with a crowd that was out of the mainstream. His view of Islam was of it being almost a genetic failure.”
At lunch one day in the Pentagon dining room, Flynn, visiting former colleagues, loudly complained that Obama and his aides had run him out of DIA because they weren’t willing to fight the terrorists, said an official who witnessed the moment.
“Everyone knows who he is,” the official said, “and there he was, in the Pentagon dining room, ranting and raving, totally unhinged.”
In one of his first major TV appearances, on “Charlie Rose,” Flynn asserted that Iran “has killed more Americans than al-Qaeda has through state sponsors, through its terrorist network called Hezbollah.”
Rose pushed back: “Hezbollah has killed more Americans than al-Qaeda?”
Flynn doubled down. After the show, people who had been helping him establish his speaking career confronted him, telling him he had to be truthful.
“Well, I believe it to be true,” Flynn replied.
It quickly became harder to book Flynn for high-profile, mainstream venues, according to two people who worked with him in that period.
Flynn began appearing instead before Trump supporters who applauded his diatribes against America’s shifting demographic makeup. “Our lifestyle is changing,” he said. “The demographics of our country, which has changed dramatically over the last 50 years — unbelievable.”
It also became more difficult to talk to Flynn about political issues, a shift that friends said seemed to coincide with Flynn spending more time with his son Michael Jr.
“His son became much more important in the daily structure of Mike’s life,” a longtime friend said. “He was like Mike’s chief of staff. They used the same slogans. They believed the same wild things.”
The son, who did not respond to requests for comment, has a high profile on social media, where he uses more inflammatory language than his father, endorsing conspiracy theories such as Pizzagate, the false notion that a Northwest Washington pizza place was home to a child sex trafficking ring run by Hillary Clinton.
Michael Jr. began accompanying his father to events, including to Russia for the RT appearance, and has been perhaps his father’s most devoted advocate, attacking the special counsel, campaigning for public support to clear his father’s name, and raising funds for his defense.
As his son’s rhetoric became more radical, the father, too, ratcheted up his attacks on the forces he blamed for destroying America. The father told a crowd that Obama “didn’t grow up as an American.” Two friends said Flynn told them he agreed with his son about Pizzagate.
Some of Flynn’s old allies — including Gen. Stanley McChrystal, with whom Flynn had worked closely in Iraq and Afghanistan, and two other military leaders, according to two of Flynn’s friends — asked him to tone it down. Flynn insisted he was doing what was right and necessary.
‘He got played’
In late 2015, RT proposed to hire Flynn to attend its 10th anniversary bash in Moscow. He would be paid $33,750.
Ledeen’s daughter Simone, who worked closely with Flynn as he crafted his post-military career path, tried to talk him out of the trip.
“Don’t do this” to your friends in the Army, she pleaded, according to Flynn’s associates. “Don’t do this to yourself.”
Flynn defended his decision on Twitter: “Know my values and beliefs are mine & won’t change because I’m on a different piece of geography.”
Simone Ledeen “saw what it would look like,” her father said. “Whereas Flynn was surprised by the reaction.”
At the RT dinner, Putin sat next to Flynn at the head table. Putin spoke, and when he was done, Flynn joined the crowd in standing to applaud.
Flynn would later emphasize that he never praised Putin, never wavered from his position that Russia was the enemy.
Whether it was naivete, a desire to build his career as a speaker or an urge to get involved in policymaking even though he was no longer in government, Flynn’s decision to put himself in a room where he would be seated next to Putin proved problematic.
“He was playing with some very sophisticated players,” said a senior U.S. official who worked closely with Flynn. “He got played.”
Flynn didn’t “know why people make such a big deal,” he told The Post last year. “So I get asked by my speakers bureau to go do a speech. Here’s the topic. Yep. Take it.”
His tweets, speeches, TV appearances, bestseller and convention address all fed a campaign of agitation against Obama and Clinton. As he warned against the country’s moral decay, Flynn became a folk hero to Trump’s burgeoning base.
Flynn fixated on the damage Clinton could do. When he first “got into this political nonsense,” he said at a Massachusetts synagogue, he felt compelled to warn against Clinton because “she has zero accountability.” His audience cheered, his eyebrows bobbed, his forehead tightened. Over waves of applause, he pushed on: “She has none, she has none, she has absolutely none. She has no personal responsibility.”
Last December, Flynn pleaded guilty to lying to the FBI about his conversations with Russian Ambassador Sergey Kislyak. Flynn’s friends say he admitted lying to halt the hemorrhaging of money from being on the wrong end of a federal investigation.
“His wife was miserable, his siblings were miserable,” Ledeen said. “This was how he could stop it.”
Even after he admitted lying, pleaded guilty and cooperated with the investigation, Flynn remained a folk hero to many in Trump’s base. A singing trio calling itself The Deplorable Choir recorded a country tune, “Our General Flynn,” that paid tribute to his loyalty, with proceeds going to his defense fund.
But the past week’s revelation that Flynn repeatedly met with special counsel Robert S. Mueller III’s prosecutors — for a total of 62 hours — challenged the notion that Flynn has stood firmly with Trump.
Flynn “made a serious error in judgment, for which he has shown true contrition,” his lawyers wrote in a memo to U.S. District Judge Emmet G. Sullivan on Tuesday. But the lawyers also contended that Flynn was lulled into lying by FBI agents who wanted him “to be relaxed” and therefore didn’t warn him that making false statements to investigators was a crime.
To family and friends, Flynn remains an unrepentant hero, standing tall against political correctness, liberal folly and media bias.
Flynn’s brother Joseph tweeted in October: “Thank God for Patriots like @GenFlynn who sacrificed everything to ensure @HillaryClinton did not get elected . . . with absolutely NO REGRETS.”
His supporters viewed the special counsel’s recommendation last week that Flynn serve no prison time because of the “substantial assistance” he provided not as a sign that their man had been flipped, but that he had been vindicated.
“The judge should just throw the thing out,” Flynn’s friend Michael Ledeen said. “Give him a medal and be done with it.”
Karen DeYoung in Washington and Kurt Shillinger in St. Louis contributed to this report.
Illustration by Mitch Gee. Design and development by Joe Moore.