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Meet the federal judge who pulled a surprise in the Flynn case

The fate of former national security adviser Michael Flynn lies in the hands of a federal judge with an established reputation of being a fiercely independent thinker.

U.S. District Judge Emmet Sullivan, who was appointed to the bench in 1994 by former President Clinton, will determine whether to grant the request by the Department of Justice (DOJ) to drop charges against Flynn, who pleaded guilty in December 2017 to lying to federal agents about conversations he had with then-Russian ambassador Sergey Kislyak.

On Tuesday evening, Sullivan pulled a surprise, announcing in a court filing that he would allow interested parties to weigh in on the case with amicus briefs, an unusual move for a criminal prosecution, and enter a scheduling order “at the appropriate time.” The move was opposed by Flynn's lawyers, who argued that it would be inappropriate to allow third parties to weigh in on the case.

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Sullivan has several options for responding to the DOJ motion beyond Tuesday’s action. 

Sullivan could eventually move to dismiss the case with prejudice, meaning Flynn’s case would be permanently dismissed and he could never be charged again for the same incident. Or, the judge could grant dismissal without prejudice, which would allow the case to be considered again — particularly if the White House flips in November.

Another option is for Sullivan to collect as much information as he sees fit before making a decision, which could include calling the U.S. attorney for D.C., Timothy Shea, and even Attorney General William BarrBill BarrNew DOJ rule could allow executions by electrocution, firing squad Clyburn: Biden falling short on naming Black figures to top posts Five federal inmates scheduled for execution before Inauguration Day MORE to testify.

He could also deny the motion, block the withdrawal of Flynn’s guilty plea and choose to proceed with sentencing the retired Army lieutenant general.

Nancy Gertner, a former judge for the U.S. District Court in Massachusetts who was appointed to the bench in 1994 and now teaches at Harvard, said she expects Sullivan to press the DOJ on their decisionmaking.

“I actually expect him to call witnesses and demand that the government justify taking what is an extraordinarily unusual position, extraordinarily unusual, and find out why,” said Gertner.

Legal observers describe Sullivan as courageous, challenging and hard-working. Most importantly, they say, he is not afraid to challenge the government.

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“I often call him a lion in criminal justice circles. I have always maintained that he is fiercely independent — no nonsense,” said Glenn Kirschner, a former federal prosecutor in the U.S. attorney’s office in D.C.

“I would say if I had to pick one judge to deal with this unprecedented issue,” it would be Sullivan, he added.

A Howard University graduate, for both undergrad and law school, Sullivan was the first judge in Washington, D.C., to be appointed by three presidents to different judicial positions. Before Clinton, he was appointed by former Presidents Reagan and George H.W. Bush.

Mark Zaid, a national security lawyer with decades of experience going head-to-head with the U.S. government, recalled a particular case in which he was surprised that Sullivan railed against the government’s counsel for the position they were taking.

“He had a lot of harsh words,” said Zaid, who was challenging the Pentagon’s mandatory anthrax vaccine immunity program in the early 2000s.

“In the decade or so that I had already been practicing, and that, given the nature of the work that I handled against the U.S. government — I was routinely the one who got yelled at by the judge. And it was an incredibly welcoming experience to actually have the shoe on the other foot,” Zaid added with a laugh.

The Flynn investigation and prosecution has involved two administrations.

Flynn pleaded guilty to lying about conversations with Kislyak about the Obama administration’s sanctions against Moscow during the presidential transition. Earlier this year, Flynn moved to withdraw his plea, claiming that his case had been tainted by “the government’s bad faith, vindictiveness, and breach of the plea agreement.”

The DOJ later released documents that provided a behind-the-scenes look at how his prosecution had unfolded, prompting accusations among Republicans that FBI officials tried to entrap Flynn. A short while later, the DOJ filed a motion to dismiss the case.

Shea has argued Flynn’s comments to the FBI were not material to the bureau’s counterintelligence investigation into Russia’s election interference, which examined whether members of the Trump campaign and Russia coordinated or conspired to help President TrumpDonald John TrumpGeraldo Rivera on Trump sowing election result doubts: 'Enough is enough now' Murkowski: Trump should concede White House race Scott Atlas resigns as coronavirus adviser to Trump MORE win the election.

He has also said the government cannot prove “either the relevant false statements or their materiality beyond a reasonable doubt,” which some legal experts say increases the likelihood that Sullivan will grant the motion to dismiss.

Some legal experts have highlighted what they characterized as red flags in the government’s latest move, particularly that none of the prosecutors on the case signed their name on the motion.

They also noted that in the motion to dismiss the case, Barr and Shea cited an interview with former acting Assistant Attorney General for National Security Mary McCord multiple times to suggest that the bureau’s interview with Flynn was unwarranted. But in a New York Times op-ed Sunday, McCord accused the DOJ of being “disingenuous” and twisting her words in order to argue that Flynn should not be prosecuted.

Still, other legal experts have argued that Flynn’s case has not been handled fairly.

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Jonathan Turley, a criminal defense attorney and law professor at George Washington University Law School, called for the case against Flynn to be dismissed almost a week before the DOJ filed its motion.

An opinion contributor for The Hill, Turley in late April pointed to several concerns he had with the case, including the recently released field notes showing how FBI agents discussed how to handle a January 2017 interview with Flynn.

One bureau agent asked in a handwritten note whether it was their goal “to get him to lie, so we can prosecute him or get him fired.”

Such documents have led Flynn’s lawyers and his allies to argue that he was a victim of prosecutorial misconduct.

Trump has claimed Flynn was “essentially exonerated” by the new documents, and Barr has defended the DOJ’s decision, saying it was his “duty under the law” to dismiss the case. He said he was not influenced by Trump to drop the charges.

Former President Obama, meanwhile, privately blasted the decision as a sign that the basic rule of law is at “risk.”

Sullivan has also been criticized for his treatment of Flynn during a mid-December 2018 sentencing hearing, when he made remarks about Flynn possibly being charged with treason and his working as an unregistered foreign agent. Flynn was not charged with either violation, and Sullivan later apologized, saying he felt “terrible.”

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Nevertheless, Sullivan scolded Flynn for his conduct at the time.

“You lied to the FBI about three different topics and you made those false statements while you were serving as the national security adviser, the president of the United States’s most senior national security aide. I can’t minimize that,” Sullivan said. “Arguably, that undermines everything this flag over here stands for. Arguably, you sold your country out.”

Former federal prosecutors and legal experts have argued that the tactics used by the FBI were law enforcement 101 and that they were fairly applied in this case.

Going forward, however, experts are now questioning whether other defense lawyers are going to seek to use the DOJ’s new interpretation of the law to bolster their legal arguments.

“Defense lawyers all across the country are salivating about this memo because if this applies in other cases, a lot of people are going to walk free. But of course, it won’t apply in other cases,” said Gertner. “I think people are certainly going to try to use it, but the point of this is Shea distorted the law in order to move to dismiss the accusations against Flynn.”