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WASHINGTON — Fired by one American commander in chief for insubordination, Michael Flynn has now delivered his resignation to another.

President Donald Trump had been weighing the fate of his national security adviser, a hard-charging, feather-ruffling retired lieutenant general who just three weeks into the new administration had put himself in the center of a controversy. Flynn resigned late Monday.

At issue was Flynn's contact with Moscow's ambassador to the United States. Flynn and Ambassador Sergey Kislyak appear to have discussed U.S. sanctions late last year, raising questions about whether he was freelancing on foreign policy while President Barack Obama was still in office and whether he misled Trump officials about the calls.

The center of a storm is a familiar place for Flynn. His military career ended when Obama dismissed him as defense intelligence chief. Flynn claimed he was pushed out for holding tougher views than the Obama administration about Islamic extremism. But a former senior U.S. official who worked with Flynn said the firing was for insubordination, after the Army lieutenant general failed to follow guidance from superiors.

Once out of government, he disappeared into the murky world of mid-level defense contractors and international influence peddlers. He shocked his former colleagues a little more than a year later by appearing at a Moscow banquet headlined by Russian President Vladimir Putin. Given a second chance by Trump, Flynn, a lifelong political Democrat, became a trusted and eager confidant of the Republican candidate, joining anti-Hillary Clinton campaign chants of "Lock Her Up" and tweeting that "Fear of Muslims is RATIONAL."

As national security adviser, Flynn required no Senate confirmation vote or public vetting of his record, and his tenure was brief but turbulent.

The Washington Post and other U.S. newspapers, citing current and former U.S. officials, reported last week that Flynn made explicit references to U.S. sanctions on Russia in conversations with Kislyak. One of the calls took place on Dec. 29, the day Obama announced new penalties against Russia's top intelligence agencies over allegations they meddled in the U.S. election process to help Trump win.

While it's not unusual for incoming administrations to have discussions with foreign governments before taking office, the repeated contacts just as the U.S. was pulling the trigger on sanctions suggests Trump's team might have helped shape Russia's response. They also contradicted denials about such discussions of the sanctions by several Trump administration officials, including Vice President Mike Pence.

Flynn later backed off his adamant denials. On Friday, he said he "no recollection" of discussing sanctions policy but "can't be certain," according to an official, who wasn't authorized to speak publicly on the matter and demanded anonymity.

He apologized to Pence, who, apparently relying on Flynn's denials, vouched for him on television. In his resignation letter, Flynn said he held numerous calls with the Russian ambassador to the U.S. during the transition and gave "incomplete information" about those discussions to Pence.

For days, Trump was publicly and unusually quiet on the matter. While his aides were declaring the president had confidence in Flynn, Trump privately told associates he was troubled by the situation, according to a person who spoke with him recently.

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INSUBORDINATION:

Flynn's sparkling military resume had included key assignments at home and abroad, and high praise from superiors.

The son of an Army veteran of World War II and the Korean war, Flynn was commissioned as a second lieutenant in May 1981 after graduating from the University of Rhode Island. He started in intelligence, eventually commanding military intelligence units at the battalion and then brigade level. In the early years of the Iraq war, he was intelligence chief for Joint Special Operations Command, the organization in charge of secret commando units like SEAL Team 6 and Delta Force. He then led intelligence efforts for all U.S. military operations in the Middle East and then took up the top intelligence post on the Joint Staff in the Pentagon.

Ian McCulloh, a Johns Hopkins data science specialist, became an admirer of Flynn while working as an Army lieutenant colonel in Afghanistan in 2009. At the time, Flynn ran intelligence for the U.S.-led international coalition in Kabul and was pushing for more creative approaches to targeting Taliban networks, including use of data mining and social network analysis, according to McCulloh.

"He was pushing for us to think out of the box and try to leverage technology better and innovate," McCulloh said, crediting Flynn for improving the effectiveness of U.S. targeting. "A lot of people didn't like it because it was different."

It was typical of the determined, though divisive, approach Flynn would adopt at the Defense Intelligence Agency, which provides military intelligence to commanders and defense policymakers. There, he quickly acquired a reputation as a disruptive force. While some applauded Flynn with forcing a tradition-bound bureaucracy to abandon old habits and seek out new, more effective ways of collecting and analyzing intelligence useful in the fight against extremist groups, others saw his efforts as erratic and his style as prone to grandstanding.

In the spring of 2014, after less than two years on the job, he was told to pack his bags.

According to Flynn's telling, it was his no-nonsense approach to fighting Islamic extremist groups that caused the rift.

A former senior Obama administration official who was consulted during the deliberations disputed that account. Flynn was relieved of his post for insubordination after failing to follow guidance from superiors, including James Clapper, Obama's director of national intelligence, said the official, who asked for anonymity to discuss personnel matters.