It caught up to him as Trump’s national security adviser, resulting in a guilty plea
On Friday, it became clear that Flynn broke one rule too many.
Flynn abruptly pleaded guilty in federal court to one count of “willfully and knowingly” making “false, fictitious and fraudulent statements” to the FBI about his communications with Russia’s ambassador last December, after Donald Trump had named Flynn his national security adviser.
As part of a plea agreement, Flynn also said he was cooperating with the investigation led by special counsel Robert Mueller into whether anyone in Trump’s orbit helped Moscow’s efforts to meddle in last year’s presidential campaign, suggesting higher-ups in the White House may face legal jeopardy.
The guilty plea was the latest dip in Flynn’s roller-coaster career — an up-and-coming battlefield intelligence officer in Iraq and Afghanistan, promoted to a three-star Army general, named to head the Defense Intelligence Agency and then fired in 2014 for what the White House said was mismanagement.
His tenure as Trump’s national security adviser set a dubious record: He was ousted after only 24 days for misleading Vice President Mike Pence and others about his discussions with Sergey Kislyak, then-Russia’s ambassador to Washington, about easing U.S. sanctions on Russia.
“It’s a sad thing,” retired Army Gen. Barry McCaffrey said Friday. “We owe Flynn a lot, and he went over the line.”
Flynn’s hard-charging nature was core to his persona. In Afghanistan, his commanding officer once praised him as someone who “just busts down walls” to get the job done.
But that determination sometimes clouded his ability to make considered decisions.
“If you’re not someone blessed with the gift of good judgment, you end up in the situation he’s in,” said Derek Chollet, a former senior Pentagon official in the Obama administration.
Flynn was always pushing the limits as a kid in a working-class family in Middletown, R.I., whether surfing during hurricanes, jumping off bridges or playing sports.
“He was a lineman on our football team,” said Thomas Heaney, a childhood friend. “He was probably 155 pounds, and he would play guys 80 to 100 pounds heavier than him.”
Flynn wrote in his book that he was something of a hard case, participating in “some serious and unlawful activity” that led to his arrest and a “very unpleasant night” in a state reformatory for boys. His record was expunged after a year of supervised probation, he wrote.
He straightened out, dated a high school classmate he eventually would marry and scored an Army ROTC scholarship at the University of Rhode Island. It was a logical step for the son of a man who served more than two decades in the Army.
But Flynn also swam against political currents by enlisting in the Army soon after the Vietnam War, which had sparked protests across the country.
“We didn’t do a lot of big formations,” said Heaney, who joined ROTC with Flynn. “We didn’t do a lot of things as a group out on the campus just to not provoke any kind of negative feelings.”
He rose to prominence as an Army intelligence officer. A former commander called him “tireless, focused, serious, and thoughtful about how he went about connecting dots.”
In Iraq, Flynn teamed with Gen. Stanley McChrystal and followed him to Afghanistan as a senior aide. McChrystal envisioned a more nimble military force that prioritized gathering intelligence about insurgents in nighttime raids, then swiftly sifting the information to launch more attacks.
“It’s said that Gen. McChrystal built a killing and capturing machine,” said the former commander, who spoke on condition of anonymity because of the legal case. “This was the intelligence component of that machine.”
Flynn’s contrary nature was clear in the Pentagon. He contributed to a disparaging 2010 report saying the “vast intelligence apparatus is unable to answer fundamental questions about the environment in which U.S. and allied forces operate and the people they seek to persuade.”
But Flynn flamed out in his next assignment after President Barack Obama named him head of the Pentagon’s spying arm, the Defense Intelligence Agency, in July 2012.
Critics in the Pentagon, the intelligence community and on Capitol Hill soon described Flynn as out of his depth running the 17,000-person agency. Some said he advanced unreliable theories.
“His penchant for inventing his own facts and asking people to chase down evidence to support them — the so-called ‘Flynn facts’ — is deeply disturbing for an intelligence officer,” said Rep. Adam Schiff, D-Calif., the top Democrat on the House Intelligence Committee.
Flynn was ousted in August 2014 after clashing with James Clapper, who was director of national intelligence, and other officials.
Flynn later blamed the White House, saying Obama had failed to reckon with the growing strength of Islamist terrorists.
“I was fired as the director of the Defense Intelligence Agency after telling a congressional committee that we were not as safe as we had been a few years back,” Flynn wrote in his book.
He scorned the idea of cashing in on his military experience and contacts, like other former government officials who parlayed their public service into private-sector profit.
“Flynn used to run around bragging that his stars weren’t for sale,” according to one former intelligence official.
When Trump announced his presidential campaign in 2015, one of his aides, Sam Nunberg, thought the newly declared candidate would take a shine to Flynn and helped arrange a meeting.
“He had made the talk-radio rounds. He had criticized the Obama administration,” Nunberg recalled.
The bond gelled at the Republican National Convention, when Flynn delivered an angry speech denouncing Democratic nominee Hillary Clinton and led the crowd in chants of “Lock her up.”
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