Flynn drew judge’s ire with 'guilty-but-not-really' filing: Experts

When a federal judge unleashed a tongue-lashing on former White House national security advisor Michael Flynn Tuesday, legal experts saw a dramatic push back to Flynn’s eleventh-hour attempt to seed doubts about the FBI’s conduct during his questioning and arrest.

“It’s very unusual for sentencing that was supposed to be uneventful, to go so far off the tracks,” former federal prosecutor Robert Mintz told ABC News. “Here, in the eyes of the court, the defendant really tried to minimize culpability. That obviously struck a bad chord with the judge.”

Mintz was referring to a court filing Flynn’s defense team made last week, after prosecutors had already recommended he be spared prison time, in which Flynn’s team strongly suggested that Federal Bureau of Investigations (FBI) agents had been duplicitous in their treatment of Flynn when they interviewed him at the White House about his contacts with the then-Russian ambassador. “The agents did not provide General Flynn with a warning of the penalties for making a false statement … before, during, or after the interview,” the filing said.

That insinuation -- that the FBI tricked Flynn into lying -– quickly became a narrative embraced and circulated by Flynn’s supporters -– including close allies of President Donald Trump. Two days after Flynn's filing, the president criticized in a tweet how Flynn had been "treated" by the FBI.

The filing prompted U.S. District Judge Emmet Sullivan to request additional records, and today to ask Flynn flatly if he wished to ”challenge the circumstances in which you were interviewed by the FBI?"

The judge then asked Flynn’s lawyer if he believed Flynn was entrapped by the FBI.

Both replied with a definitive, "No, your honor." But, legal experts told ABC News, it appeared the damage had been done. The judge began a lengthy up-braiding of the former lieutenant general.

"You made those false statements while you were serving as the national security advisor, the President of the United States’ most senior security aid. You can't minimize that,” Sullivan said. "I want to be frank with you, this crime is very serious."

"As I stated it involves false statements to FBI agents in the White House, in the West Wing!" the judge continued. "By a high-ranking security officer who up to that point had an unblemished career of service to his country. It's a very serious offense."

“I'm not hiding my disgust my disdain for this criminal offense,” he said.

In addition to his comments in court today, the judge issued an order prohibiting Flynn from traveling outside of a 50 mile radius of Washington D.C.

Kendall Coffey, another former federal prosecutor and current white collar defense attorney, said Flynn’s earlier filing likely played a part in Sullivan’s heated remarks.

“Most federal judges are not interested in a plea of ‘guilty-but-not-really,’” Coffey told ABC News. “Judges don’t want individuals coming in unless they are truly believing they are guilty and accepting responsibility. One concern would have been whether Flynn was trying to have it both ways.”

“The judge was basically saying you’re one or the other,” Mintz said. “Withdraw your guilty plea if you think you’re innocent. If you believe you haven’t committed a crime, I’m giving you an opportunity to withdraw your plea… The judge found off-putting the tightrope that Flynn was trying to walk here.”

White collar defense attorney and former federal prosecutor Shan Wu said he thought Flynn’s team “miscalculated the effect of their effort to portray Flynn in a sympathetic light” with regard to the FBI interview. “In my opinion, they should’ve stuck with the 50 letters of reference and the Bronze Star.”

Douglas Berman, a leading expert on federal sentencing and professor at the Ohio State University Moritz College of Law, said, however, he wouldn’t be “too judgmental” about how the defense “tried to navigate around some difficult terrain here.”

“It sounded like Judge Sullivan is mightily concerned about the seriousness of Flynn’s conduct,” Berman said.

Sullivan dialed back his remarks after a short break at mid-day, explaining to the court that he may have misspoken when he went as far as to ask prosecutors if they ever considered Flynn’s conduct to be “treasonous.” (Prosecutors said they hadn’t.)

Sullivan also appeared to have mistakenly believed that Flynn had worked as an unregistered agent of the Turkish government into his White House tenure. Flynn had ceased operating in that role in mid-November 2016, prior to entering the White House. The undeclared foreign work by Flynn while he was an advisor on the Trump campaign clearly bothered the judge, but he walked back his initial statements about that topic.

"There are a lot of conspiracy theorists out there," he said. "I am not taking the elements of any of the uncharged offenses under consideration at the time of sentencing."

Sullivan has served on the U.S. District Court in Washington, D.C. since he was appointed to the bench there by then-President Bill Clinton in 1994. Prior to that, Ronald Reagan and George H.W. Bush appointed him to spots on D.C. court benches.

A past case suggests Sullivan is especially incensed by potential misconduct in his court. A decade ago he oversaw a public corruption case against former Senator Ted Stevens. In that case, Sullivan named a special prosecutor to investigate whether the Justice Department improperly withheld important evidence.

Then, too, he gave an impassioned speech to the court, saying he had “never seen mishandling and misconduct like what I’ve seen” by the Department of Justice in that case, according to a 2009 New York Times report.

In 2015 Sullivan made some headlines for his criticism of Hillary Clinton's use of private email during a hearing about one of numerous Freedom of Information Act lawsuits seeking court-ordered access to her records. The judge reportedly said that her private email use violated government policy.

Sullivan recently had an oblique foray into the Trump orbit when he ruled in September that congressional Democrats can sue Trump over claims he violated the emoluments clause of the Constitution by doing business with foreign governments.

After recognizing the judge’s pique with Flynn today, defense attorney Robert Kelner requested the sentencing hearing be postponed. The judge agreed, and set a status update for March.

Coffey said Kelner’s request for a delay made sense, even though they will eventually be back before him.

“Based on the judge’s comments, this was not a day to seek a sentence,” Coffey said.

ABC News’ James Gordon Meek, Katherine Faulders, Ali Pecorin contributed to this report.