Judge Emmet Sullivan of the U.S. District Court for D.C. Photo by Diego M. Radzinschi/NATIONAL LAW JOURNAL

Michael Flynn and federal prosecutors were aligned: President Donald Trump’s former national security adviser shouldn’t receive prison time for lying to the FBI.

Soon after Flynn walked into court Tuesday in Washington, past the throngs of television cameras and photographers, it became abundantly clear the sentencing hearing would be far from simple and routine.

Prosecutors and defense lawyers know that judges are not bound by sentencing recommendations, though there are guidelines that restrict how low—or how high—a judge might want to go. Flynn’s fate was in the hands of a veteran Washington federal trial judge, Emmet Sullivan, long known for speaking his mind.

What began as a routine sentencing—with questions to ensure Flynn was satisfied with his defense counsel and accepted responsibility—crumbled into a dramatic moment marked by the judge’s admonishments and, at one point, a question of whether the special counsel’s office had considered charging the former lieutenant general with treason.

The sentencing hearing would end without a sentence of any kind, as Flynn took Sullivan up on his offer to delay the proceeding. Flynn’s lead defense lawyer, Covington & Burling partner Robert Kelner, said the additional time would allow the former Trump adviser to “eke out the last modicum” of credit for cooperation.

Here are three takeaways from an extraordinary hearing:

➤ Know your judge.

Even with prosecutors and defense attorneys united on Flynn not serving prison time, Sullivan declared Tuesday he could not rule out prison time for the retired lieutenant general. It was a reminder that judges—not plea deals—control the punishment of any defendant. And the hearing would be a reminder that Sullivan, like a handful of other judges on Washington’s trial bench, can make big, bold pronouncements that would make any prosecutor—or in this case, a defendant and his lawyers—cringe.

Sullivan opened Tuesday’s hearing by pressing Flynn on whether he really wanted to plead guilty. The judge lambasted Flynn, saying he could not hide his “disgust” and “disdain.”

At one point, Sullivan pointed to a flag and said Flynn’s offense arguably undermined “everything this flag over here stands for.” He added: “Arguably, you sold out your country,” and later openly pondered whether Flynn could have been charged with treason. A special counsel prosecutor later said the government did not consider charging Flynn with treason.

For all the incendiary statements, the judge would issue an apology at the hearing. After returning to the bench following a brief recess, Sullivan said he was mistaken when he stated that Flynn had been working as an unregistered agent for Turkey while serving in the White House. (His engagement with Turkey predated his three-week tenure as national security adviser.) And he walked back the earlier talk about treason.

“I wasn’t suggesting he committed violations. I was just curious as to whether or not he could have been charged, and I gave a few examples,” Sullivan said. “And, you know, there are a lot of conspiracy theorists out there. I’m not taking the elements of any of the uncharged offenses into consideration at the time of sentencing. I was just trying to determine the benefit of and the generosity of the government in bestowing a benefit on Mr. Flynn.”

➤ Careful what you say in those sentencing memos to the court.

Kelner, a veteran election-law attorney, and his Covington white-collar colleague Stephen Anthony earned praise as they steered Flynn through his legal woes. Flynn was one of the early cooperators with Robert Mueller, the special counsel investigating Russia’s interference in the 2016 election.

But the defense team took a big hit Tuesday when Sullivan pressed Kelner and Anthony about a sentencing memo, filed earlier this month, in which they noted that Flynn had not been warned that lying to the FBI was illegal. The filing also pointed out that Flynn did not have counsel present during the interview. The memo appeared to rankle Sullivan, who pressed lawyers on how the memo squared with Flynn’s acceptance of responsibility.

He even asked Kelner whether the FBI had a legal obligation to warn the former Trump adviser that lying to federal agents was a crime, and whether the FBI had entrapped Flynn. “No, your honor,” Kelner would reply.

Amid the questioning, the defense attorney said the language in the sentencing memo was intended to distinguish Flynn from two other defendants—former Trump campaign adviser George Papadopoulos and Alex van der Zwaan, a former associate at Skadden, Arps, Slate, Meagher & Flom. Papadopoulos was sentenced to 14 days and van der Zwaan got 30 days for lyings to agents.

Kelner later told Sullivan that he and Anthony were responsible for Flynn’s memo and how it was framed, and that those decisions “should not and do not diminish in any way General Flynn’s acceptance of responsibility in this case.”

The exchanges underscored what white-collar defense lawyers described as a delicate balance between giving explanations and excuses for a defendant’s alleged crimes. “If they had to do it over, I’m sure they wouldn’t have that language in there that really triggered the judge,” one white-collar defense lawyer said.

As former federal prosecutor Michael Stern wrote in a USA Today column on Tuesday: Flynn’s debacle is a lesson for other Mueller defendants: Don’t blame the FBI for your crimes.

➤ What’s next: Does Flynn still face the possibility of a prison term?

Yes, he does. The delay in his sentencing allows Flynn to continue cooperating with the government. Flynn could be asked to testify in a separate criminal case in Alexandria, Virginia, involving two of his former business associates. Bijan Rafiekian and Kamil Ekim Alptekin were charged with acting as unregistered agents of the Turkish government and lying to the FBI.

The judge will take that cooperation into consideration when he does—eventually—sentence Flynn. We’ll learn some more about Flynn’s fate in roughly three months. Sullivan on Tuesday set a March 13 deadline for a status report.

“There is little chance that circumstances will change for Flynn. Had the government wanted or expected significant additional cooperation from Flynn, it would not have proceeded to sentencing in the first place,” former federal prosecutor Liam Brennan wrote Wednesday in a post at the legal affairs site Just Security.


Read more:

Judge Emmet Sullivan Delays Flynn Sentencing After Threatening Prison

Who Is Emmet Sullivan, the Judge Who Will Sentence Michael Flynn?

Mueller Trumpets Flynn’s Help, Says Don’t Lock Him Up

‘Turn That Plane Around’ and Other Times Judge Emmet Sullivan Was Outraged