Your wingnut uncle Mikie Flynn

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.”


President-elect Donald Trump, retired U.S. Army Lt. Gen. Michael Flynn and Chief of Staff Reince Priebus walk out to speak to members of the media at the Mar-a-Lago Club in Palm Beach, Fla., on Dec. 21, 2016. Departing president Barack Obama had warned Trump against the hiring of just one person: Flynn. (Jabin Botsford/The Washington Post)

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.”