Flynn sketch 1218 -1
CNN  — 

Michael Flynn’s attorney and conservative commentator Sidney Powell sent Judge Emmet Sullivan a copy of her book in 2014, about a criminal case he handled where he obliterated the Justice Department’s work. Writing to the judge she’s called a hero, the Texas-based lawyer inscribed on the third page: “Judge Emmet Sullivan, to all those who seek, hallow, and do Justice. With the greatest respect and gratitude for your honorable service.”

Five years later, Powell stood face-to-face with Sullivan in her first hearing representing Flynn, President Donald Trump’s former national security adviser who pleaded guilty to lying to the FBI days into the new administration. It was a short meet-and-greet type of hearing. Sullivan held up the book in his Washington, DC, courtroom, acknowledged he had read the complimentary parts about him, thanked her for sending it and moved on.

Powell left the courtroom glowing.

But that glow may not last a full year. Despite Justice Department efforts to drop the case against Flynn last week, Sullivan still stands between the guilty plea of Powell’s client and his exoneration. For Flynn, the court proceedings before Sullivan have been rocky – with the retired general moments away, multiple times, from the end of his criminal case.

Sullivan’s judicial flex

Sullivan – in his 36 years as a judge, and in handling Flynn’s case for the last two-and-a-half – has mastered the art of surprise.

On Wednesday night, Sullivan jolted the case – and political and legal commentators on both sides – yet again with an announcement that he would hear from a federal judge-turned-private-attorney about why he shouldn’t dismiss the Flynn case and whether he should hold Flynn in criminal contempt for perjury.

In late 2018, Sullivan stunned Flynn by questioning whether he was treasonous (he wasn’t, prosecutors said) at what was supposed to be the sentencing. And now, Flynn’s team has clawed through attempts to unravel his guilty plea by slamming the Mueller investigation and the FBI, with the judge rejecting many of their attacks and slowing down a case that hasn’t yet been dismissed.

Sullivan is jovial in person, often surrounded by his clerks and colleagues as he walks through the courthouse. On the bench, the judge keeps a long memory, frequently questions authorities before him and embraces the drama his federal courtroom lends.

That’s why, to many Washington lawyers, it wasn’t a surprise when Sullivan opened the door on Tuesday to third party arguments in the Flynn case before commenting on the Justice Department’s move to drop it. Sullivan apparently was reacting to legal arguments sent to the courthouse by 16 former Watergate prosecutors, who reasoned the judge could still sentence Flynn. And they warned him of corruption within the Justice Department.

It wasn’t over yet, Sullivan’s order essentially meant.

“It’s very Sullivan,” one Washington lawyer said of the judge’s move, declining to give his name because he represents clients in the court.

The Wednesday order puts Sullivan again in the political spotlight for days to come, and potentially gives him a platform to scrutinize the Justice Department’s approach and to rail against Flynn’s contradicting statements of both innocence and guilt.

The Watergate prosecutors were echoed by almost 2,000 former Justice Department employees condemning Barr in an open letter and by several newspaper op-eds from prominent lawyers. But it was one in The Washington Post that appeared to guide Sullivan the most.

In that column, three accomplished former prosecutors, including ex-federal Judge John Gleeson, outlined options Sullivan could pursue. They suggested he question a prosecutor who had exited the case, force the Justice Department to release the phone call transcripts Flynn had lied about or appoint an independent attorney for “a full, adversarial inquiry.”

“Courts often inquire as to the reasons for a government motion to dismiss, but this is the rare case that requires extra scrutiny, to ensure that, in the Supreme Court’s words, ‘the waters of justice are not polluted.’ “

They also said that Sullivan, in theory, could still sentence Flynn.

Sullivan selected Gleeson, one of the three op-ed writers, on Wednesday to look at Flynn’s possible perjury and argue against the case dismissal.

The mention of third-party voices in the Flynn case was the first word from the judge five days after Attorney General William Barr and the DC US Attorney Timothy Shea announced they would seek to dismiss the lying charge against Flynn, a shocking about-face in a major case special counsel Robert Mueller had brought, Flynn had pleaded guilty to and Sullivan had certified. Barr and Shea’s decision, which they said was backed up by internal FBI documents and a legal analysis that Flynn shouldn’t have been investigated or approached in the first place and that his lies weren’t “material,” unleashed intense criticism that the Justice Department political appointees are undermining the rule of law to help a judicially rogue President.

During the silence from Sullivan over the weekend, many across Washington started wondering what the judge would do. Would he rubber-stamp the motion to dismiss? How much could he push back to learn more? Was a hearing or witness testimony in the works?

Might he even appoint a special investigator, a move he has made before? At least one DC firm started considering whether they could possibly be in the running for such a job.

Those who know Sullivan’s record predicted he wouldn’t rubber-stamp anything.

The 72-year-old judge was born, raised and educated in DC, and as a Clinton appointee, is the senior-most active judge in the DC District Court, the federal trial bench in the nation’s capital. His long career among Washington’s political class frequently has made him the arbiter of cases about the clash of government powers. He has not shrunk from the spotlight, nor from direct challenges by other federal officials.

In a 2014 speech about a fellow judge, Sullivan joked about his choice to be a judge instead of a politician. “More than once (Judge Paul Friedman) has recommended that I should resign and do something that would require me to hire a campaign manager, raise money and kiss babies. He can be quite persuasive and flattering, but I love my day job, at least for now,” Sullivan said.

Questioning the executive branch

Consistently, Sullivan’s been an excruciating questioner of the executive branch.

His most well-known criminal matter was the 2008 trial and its aftermath of the late Republican Sen. Ted Stevens of Alaska. In that case, Sullivan took in the revelation that the Justice Department had withheld exculpatory evidence from Stevens. He dismissed the case, overturning a jury’s guilty verdict.

In what’s become a legendary court proceeding in Washington where Sullivan blasted the Justice Department’s work, he appointed a special prosecutor to retread the case, looking for potential obstruction by the department.

Sullivan wrote to the federal judiciary requesting revisions that would give defendants access to evidence and set new policies for his own courtroom, which, in the Flynn case, ultimately gave Powell’s team an avenue to try unsuccessfully for access to more FBI records and even classified material.

Just last year, Sullivan used a tactic similar to what he’s doing this week with Flynn, allowing prosecutors, former lawyers on a long-running case and even the public to weigh in on the possible release from prison of a cocaine-trafficking defendant.

Sullivan also once threatened to punish the IRS Commissioner in a battle over access to the agency’s email during a political scandal.

“I will haul into court the IRS commissioner to hold him personally in contempt,” Sullivan said, facing the possibility the IRS was ignoring his orders in a public records case.

That’s one 2014 moment that prompted Powell to write that Sullivan was a hero judge.

But will he be that for Flynn now?

‘You sold your country out’

Flynn has misjudged the judge before.

In his plea deal, Flynn was primed for leniency and a light sentence – likely no prison time at all. He pleaded guilty to one count, for lying to the FBI about multiple interactions with Russia on behalf of the Trump transition, and admitted to other problematic conduct, including omitting his lobbying firm’s work for Turkey in 2016 from a federal disclosure form.

Mueller and other investigators interviewed him 19 times, and Flynn told Mueller key stories about the attention toward WikiLeaks on the campaign, contact with Russia and details about the President’s attempts to obstruct the Russia investigation. He also told a grand jury in Virginia how he and his former lobbying partner had worked on Turkey’s behalf in 2016.

Flynn’s efforts earned what’s called a downward departure or 5K letter from the Mueller team before his scheduled December 2018 sentencing, a document sought after by criminal defendants that tells the judge he was especially helpful and deserved no prison time. Not even Richard Pinedo, a low-profile Californian who had committed identity fraud online and helped Mueller crack a Russian online propaganda conspiracy, had gotten a 5K.

But when Flynn stood before Sullivan in December 2018 to reiterate his guilt, the judge seethed with anger and put Flynn under oath to discuss his crimes. A prison sentence – probably between a few days to six months – looked likely.

A note of doubt about Flynn’s guilt in his written request for leniency before the sentencing apparently had set off Sullivan.

The judge, at times nearly yelling from the dais and gesturing to the large DC and US flags behind him, said Flynn’s action “undermines everything this flag over here stands for. Arguably, you sold your country out.”

Sullivan later apologized for thinking Flynn had been a paid agent of a foreign government while serving in the White House – that work had happened while Flynn was with the Trump campaign – then added that he believed another general, David Petraeus, should have been punished more harshly after lying to the FBI.

Flynn asked the judge not to go forward with his sentencing.

Powell and Sullivan meet again

About six months later, Flynn fired his lawyers and brought in Powell.

Over the past year, Powell’s team has accused the FBI of misconduct, demanded what they believe could be exculpatory evidence and floated theories that had been circulating among conservative circles to undercut the Russia investigation. They’ve done this in court filings, but Powell has also disclosed she’s contacted Barr directly.

In January, Flynn told the judge he now believed he was innocent.

His new defense team appears not to have bet on the possibility that Sullivan’s critical eye could turn toward Barr and, by extension, Flynn.

This week – after the months-long process of Flynn turning on his prior defense lawyers, the Mueller team and the FBI – his lawyers hinted they’re ready to go to battle with the judge too.

“Separation of powers forecloses (third parties’) appearance here. Only the Department of Justice and the defense can be heard,” Powell’s team wrote in the court case. “For the Court to allow another to stand in the place of the government would be a violation of the separation of powers.”

That is, Sullivan shouldn’t do anything more than dismiss the case.

The judge threw out Flynn’s pleading and the Watergate prosecutors’ request as premature on Wednesday, reminding them he’s getting ready to hear from others on the case.

But Flynn’s supporters and family and even Powell have begun tweeting attacks on Sullivan this week as they ask the President for a pardon. The once-hero judge, they write, will be no match for Powell, their “Warrior for Justice” and “Lady Liberty.”

A reporter on Wednesday afternoon asked Trump if he thought Sullivan should leave the case “for being biased against Mr. Flynn.”

The President dodged commenting on the judge, instead simply saying about Flynn, “He’s going to be OK. He’s going to be just fine.”