WASHINGTON — Federal prosecutors had scored a stunning victory in 2008 with the successful conviction on corruption charges of Senator Ted Stevens of Alaska, a powerful Republican, when months later they were astonished as Judge Emmet G. Sullivan turned the tables on them.
Judge Sullivan dismissed the verdict against Mr. Stevens and appointed a special prosecutor to investigate whether the government lawyers themselves had committed criminal wrongdoing.
In an angry courtroom lecture, Judge Sullivan, of the United States District Court for the District of Columbia, accused the Justice Department team of withholding exculpatory evidence. “In nearly 25 years on the bench,” he said, “I’ve never seen anything approaching the mishandling and misconduct that I’ve seen in this case.”
The case cemented Judge Sullivan’s reputation for fierce independence and low tolerance for government misconduct — a reputation in the spotlight again now that he is entertaining a challenge to the Justice Department’s extraordinary motion to dismiss its criminal case against Michael T. Flynn, President Trump’s former national security adviser.
On Tuesday night, less than a week after prosecutors filed a motion to drop the case against Mr. Flynn, who had pleaded guilty to a felony charge of making false statements to federal authorities, Judge Sullivan indicated he was willing to hear from outside legal experts before he decides how to rule.
That appears to leave the door open for critics who claim that the motion is politically motivated. The department’s reversal followed months of pressure from Mr. Trump and his allies.
Judge Sullivan showed the extent of his concern on Wednesday when he appointed a retired federal judge, John Gleeson, to present arguments against the government’s decision to drop the case, and to address whether Mr. Flynn may have committed perjury by seeking in January to withdraw his 2017 guilty plea.
Judge Gleeson, a former United States District Court judge in Brooklyn, co-wrote an op-ed Monday in The Washington Post urging Judge Sullivan to “assess the credibility of the department’s stated reasons for abruptly reversing course,” and, potentially, to deny the motion and “proceed to sentencing.”
Criminal defense lawyers and legal analysts in Washington said it was hard to predict how Judge Sullivan might act. While he has expressed personal “disgust” in court for Mr. Flynn’s actions, he has also displayed a low tolerance for the sort of prosecutorial misconduct that the Justice Department claims as a justification for ending its case against Mr. Flynn.
“He’s not afraid to cross anybody,” said Robert D. Luskin, who has represented several high-profile Washington political clients and argued before Judge Sullivan.
“He’s ferociously independent,” said Reid H. Weingarten, a prominent criminal defense lawyer and partner at the Washington firm of Steptoe & Johnson who has also argued before the judge. “He doesn’t suffer fools.”
A Washington native and Howard Law School graduate, Judge Sullivan was nominated to the federal bench by President Bill Clinton, a Democrat, but first appointed to the Superior Court of the District of Columbia by President Ronald Reagan and promoted by President George Bush, both Republicans.
Judge Sullivan, 72, can be withering when he believes the government has overstepped its bounds or failed to honor legal procedure. In 2017, he threatened to hold the attorney general at the time, Jeff Sessions, in contempt after the Justice Department deported a pair of Central American women as they were seeking asylum to enter the country. Judge Sullivan ordered that a plane taking them out of the country turn around in midair.
Lawyers for Mr. Flynn, who argue that their client was essentially entrapped by federal prosecutors who had no legitimate reason to question him, may have hoped that Judge Sullivan would be sympathetic to the defense arguments that Mr. Flynn was a victim of government misconduct, much like Mr. Stevens. The former senator was accused of accepting undisclosed gifts and services from an Alaska business.
But legal analysts said that Judge Sullivan’s announcement that he would set a schedule for outside parties to present arguments about the government’s move to dismiss the case was highly unusual, as was his move on Wednesday to enlist Judge Gleeson. Together, his actions suggest to some that he disagrees with the Justice Department’s reversal in the Flynn case.
“He’s a stickler,” said Paul Rosenzweig, a senior fellow and national security analyst at the R Street Institute, a Washington think tank. He added that Judge Sullivan “takes very seriously the obligation of the government to abide by the rules.”
Mr. Rosenzweig said the Justice Department’s move appeared to be “a seemingly colluded and politically motivated decision that both challenges his authority and the integrity of the judicial process and perhaps offends him at a personal level.”
More than 2,300 former prosectors have argued in an open letter that Attorney General William P. Barr has “assaulted the rule of law” and that his “purported justification for doing so does not hold up to scrutiny.”
During a December 2018 hearing, Judge Sullivan was scathing in his courtroom commentary about the former Trump aide, who served less than a month at the White House before the president fired him for lying to Vice President Mike Pence about the nature of conversations he had with the Russian ambassador at the time, Sergey I. Kislyak, during the 2016 presidential transition.
Mr. Flynn pleaded guilty to lying about those conversations to the F.B.I. Intercepts of the December calls by the National Security Agency established that Mr. Flynn had asked Mr. Kislyak that Russia hold off on retaliating to Obama administration sanctions on Russia, something he denied during the F.B.I. interview. He later attempted to withdraw his plea, saying he only admitted guilt because his lawyers had advised him to do so.
Judge Sullivan has made clear how grave he considers Mr. Flynn’s case to be. “I am not hiding my disgust, my disdain for your criminal offense,” he told Mr. Flynn during a December 2018 court hearing. “The aggravating circumstances are serious. Not only did you lie to the F.B.I., you lied to senior officials in the incoming administration.”
The judge also condemned Mr. Flynn for accepting payments from the government of Turkey, which sought his help in securing the extradition of the prominent Turkish cleric Fethullah Gulen, who lives in Pennsylvania and whom the Turkish government accuses of plotting a coup. Mr. Flynn has also pleaded guilty to failing to disclose his lobbying work to the Justice Department, as required.
“All along, you were an unregistered agent of a foreign country while serving as the National Security Adviser to the President of the United States. That undermines everything this flag over here stands for,” Judge Sullivan told Mr. Flynn. “Arguably, you sold your country out.”
Mr. Flynn’s legal team has already challenged Judge Sullivan’s decision to allow briefs from outside parties. “This court has consistently — on 24 previous occasions — summarily refused to permit any third party to inject themselves or their views into this case,” the defense said in a motion filed on Tuesday night. “Only the Department of Justice and the defense can be heard.”
Mr. Luskin represented Nicholas Marsh, a Justice Department lawyer who committed suicide after coming under scrutiny for the Stevens prosecution, something Mr. Luskin called “one of the worst experiences of my professional life.”
He said that Judge Sullivan had “overreacted, but I never thought that there was anything intellectually dishonest, nothing that smacked of a grudge about his approach.” He said the Stevens affair suggested that Judge Sullivan would demand voluminous information and “insist on getting to the bottom of whatever is in there before making a decision.”
The Justice Department’s motion to withdraw charges against Mr. Flynn cites “newly discovered and disclosed information” about his case, and argued that the federal investigation had no legitimate counterintelligence or criminal purpose and that his admitted lies had no “material” effect on the Russia investigation directed by the special counsel, Robert S. Mueller III. No career prosecutors involved in the Flynn case signed on to the motion.
While cautioning against predictions, Mr. Rosenzweig said he thought it was most likely that Judge Sullivan would grant the Justice Department’s request, while writing “an extensive opinion granting the motion, dismissing the case — and cataloging chapter and verse why he thought Flynn was guilty in the first place.”
Noting Judge Sullivan’s previous condemnations of Mr. Flynn, he added, “I don’t have any reason to think that he would change his mind.”
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