Michael Flynn is not the first presidential adviser to find himself in such deep legal trouble

Defense Intelligence Agency Director Lt. Gen. Michael Flynn listens on Capitol Hill in Washington, Jan. 29, 2104, as he testifies before the Senate Intelligence Committee hearing on current and projected national security threats against the US. (AP Photo/Pablo Martinez Monsivais/File)

In the 24 to 48 hours that passed since former National Security Adviser Mike Flynn filed a guilty plea on charges of lying to federal agents about his contacts with the Russian ambassador, the shock of the plea announcement has been replaced by the shock of just how good a deal Flynn received from Special Counsel Robert Mueller’s office.

The retired three-star Army General was reportedly under scrutiny for a whole slate of possible legal infractions. This included Flynn’s business with the Turkish government, his failure to disclose payments from foreign actors on vetting forms, his acceptance of a payment for a speaking engagement at the Russia Today television network without Pentagon approval, and his consulting firm’s lobbying during his time as a national security adviser to the Trump campaign.

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In the end, Flynn’s lawyers copped a deal that would require him to plead guilty to providing misleading and false statements to federal investigators in exchange for his full, unfettered, untainted cooperation with Mueller’s Russia investigation.

The tragedy of Mike Flynn’s fall from renowned al-Qaeda fighter to disgraced convicted felon is as miraculous as it is tragic for Flynn himself. He’s now damaged goods, and no politician would think about hiring him as an advisereven informallyever again. While it’s highly unlikely Flynn will serve time in prisonassuming he doesn’t break his contract with the Special Counsel’s officehe will be forever known for lying to the FBI in the course of a federal criminal investigation.

If it’s any penance to Flynn, he’s not the first national security adviser to have admitted legal wrongdoing in a court of law. Three of his predecessors were in even deeper legal trouble.

Robert McFarlane, President Ronald Reagan’s  national security adviser from October 1983 to December 1985, was a central cast member in the Iran-Contra scandal. The affair engulfed Reagan’s administration in controversy and led some at the time to wonder if Reagan himself would be impeached and removed from office.

During his time at the White House, McFarlane was an advocate of selling arms to Iran in order to free Americans who were then held captive by Iranian-sponsored militias in Lebanon. He was also ordered by the White House to keep the Contras in Central America flush with cash, which meant organizing financial assistance from foreign donors.

When public reports uncovered the Reagan administration’s Contra support initiative in December 1985 and the House Intelligence Committee asked for an explanation, McFarlane misinterpreted to lawmakers what was going on and withheld documents.

He would plead guilty in 1988 to four misdemeanor counts.

McFarlane’s successor as national security adviser, Admiral John Poindexter, would be an even more involved player in the Iran-Contra initiative. Unlike McFarlane, Poindexter approved Oliver North’s diversion of funds from Iranian arms sales to the Contras and was briefed on what North was doing.

Poindexter testified to the Iran Contra special committee that he destroyed documents on the Iran arms sales to protect Reagan from political embarrassment. He would eventually be prosecuted and convicted for five counts of lying to Congress, obstructing a congressional inquiry, and destroying government documents (an appeals court would later overthrow those convictions, arguing that witnesses testifying in Poindexter’s criminal trial were prejudiced by his earlier immunized testimony to Congress).

Last but not least is Sandy Berger, national security adviser during President Bill Clinton’s second term. This was a downright odd story, involving theft of classified documents from the National Archives.

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As the Clinton administration’s representative to the 9/11 Commission, Berger was responsible for collecting and submitting relevant material to the panel. What he did instead was steal five different versions of the same document related to the Clinton administration’s handling of the 2000 U.S.S. Cole bombing; brought them to his law office, and cut three of them up. When he was confronted about the theft from archivists, he first denied any involvement before admitting that he mistakenly removed the items from the building.

To avoid prosecution, Berger would go on to enter a plea of knowingly removing classified documents from the Archives.  He would resign from John Kerry’s presidential campaign and give up any hopes of serving in a Kerry White House. He was also forced to hand over his law license as a result of the guilty plea.

Mike Flynn’s circumstances are very different, involving a series of interactions weeks before President Trump was sworn in. But he’s now an inductee into unique club.

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