A Profile of John J. Gleeson, the Trial Court’s Proposed “Friend Of The Court” in the Michael Flynn Case


In the topsy-turvy world of the Justice Department during the Trump era, the Department is seeking the dismissal of a case against a defendant, Michael Flynn, who twice has pleaded guilty but never was sentenced.

Michael Flynn, President Donald Trump’s first national security advisor, pleaded guilty in December 2017 to making false statements to the FBI about conversations he had with Russia’s ambassador to the United States during the transition to President Trump taking office. (Flynn pleaded guilty again about a year later, after the case had been randomly reassigned to the current judge, Emmett G. Sullivan.) Over the past two-and-a-half years, Flynn’s sentencing has been delayed for various reasons and now may never occur because the Justice Department has moved to dismiss the prosecution.

Disturbed about this recent development, Judge Sullivan appointed a former federal trial court judge, John Gleeson, to advise the court on how to proceed in the case. Whether Gleeson will ever act in the case remains to be seen, as Michael Flynn’s attorneys have asked the U.S. Court of Appeals for the D.C. Circuit to order Judge Sullivan to immediately dismiss the case.

Now that Flynn’s request has been fully briefed in the D.C. Circuit, the court is likely to rule promptly. This article is about the man currently on the sidelines. Who is John Gleeson? What was his record and reputation as a federal judge in Brooklyn? How did he become involved in the Flynn case? And, if the D.C. Circuit allows Gleeson to serve as a friend of the court in the case, what might he do?

Developments in the Flynn Case That Led to Gleeson’s Appointment

Gleeson is currently a partner in the law firm of Debevoise & Plimpton. On May 11, after the Justice Department announced it would move to dismiss charges against Flynn, Gleeson co-wrote an op-ed article in the Washington Post arguing that the Department’s motion need not and should not end the case.

The article noted that the “Justice Department has made conflicting statements to the federal judge overseeing the case”—indeed, it asserted that “the record reeks of improper political influence”—and that the judge “has the authority, the tools, and the obligation to assess the credibility of the department’s stated reasons for abruptly reversing course.”

One of those tools, the article stated, was the appointment of “an independent attorney to act as a ‘friend of the court,’ ensuring a full, adversarial inquiry.” Within days of the article’s publication, Judge Sullivan appointed Gleeson as a “friend of the court” tasked with presenting an argument against the Justice Department’s move to dismiss the case and also with considering whether Flynn should be held in criminal contempt for perjury for false statements he had previously made in open court.

Flynn responded to Gleeson’s appointment by petitioning the D.C. Circuit to grant a writ of mandamus ordering Judge Sullivan to dismiss the case. Judge Sullivan retained counsel to defend his actions in the D.C. Circuit; his attorneys argued that the appeals court should have the opportunity to ensure “the integrity of the judicial process.” The Justice Department, meanwhile, filed a brief supporting Flynn’s request for the appeals court to end the case.

A Prosecutor, Then a Federal District Court Judge, Now a Law Firm Partner

Gleeson, 66, was born into a large family living in a two-bedroom apartment in the Bronx and grew up in Valhalla in Westchester County. A graduate of Georgetown University and the University of Virginia School of Law, his first job out of law school was serving as a law clerk for a federal judge on the U.S. Court of Appeals for the Sixth Circuit. He then worked at Cravath, Swaine & Moore, a prestigious law firm in New York City before becoming an assistant U.S. Attorney in the Eastern District of New York.

Gleeson was a prosecutor for nine years that included a stint as chief of the criminal division. The Eastern District covers three boroughs of New York City (Brooklyn, Queens, Staten Island) and the two Long Island counties and is known for important cases involving immigration, organized crime, street gangs, and terrorism. As a prosecutor, Gleeson led the team that convicted John Gotti, the boss of the Gambino organized crime family known as “the Teflon Don.”

Gleeson was appointed to the federal bench by President Bill Clinton in 1994. After serving as a federal trial court judge in the Eastern District from 1994 through early 2016, Gleeson left the bench to become a partner at Debevoise & Plimpton, another prominent law firm in New York City.

Judge Gleeson’s Record on the Bench, Part I: Noteworthy Criminal Cases

Gleeson was a very strong judge, who more than carried his weight in both civil and criminal cases. As the Flynn case is a criminal matter, those cases receive most consideration here.

Even though he served as a prosecutor, Gleeson cannot be characterized as pro-prosecution or pro-police. He presided over a number of difficult prosecutions of terrorists that took place in the Eastern District. Among them was that of Brooklyn-born Betim Kaziu, convicted of conspiracy to commit murders in a foreign country. Gleeson also had the case of Adis Medunjanin, a Flushing High School graduate, who was convicted for plans to bomb the New York City subway. And he sentenced Agron Hasbajrami—who was on his way to the Middle East when apprehended at JFK Airport—to 15 years in prison for sending money to a terrorist group in Pakistan.

Gleeson also presided over a case involving civil rights claims brought by eight non-U.S. citizens who were arrested after 9/11 and detained under harsh conditions in New York City. In litigation with many stages, perhaps Gleeson’s most important contribution was his rejection of the government’s claim that the lawsuit should be dismissed because the threat of foreign terrorism exempted the government from following rules made in peacetime. Gleeson held that while the government had wide latitude under immigration law to detain non-citizens indefinitely, the conditions of confinement nevertheless were improperly abusive and unconstitutional. (Several years after Judge Gleeson left the bench, the Supreme Court held that high-ranking government officials could not be sued for damages for policies adopted after 9/11.)

Perhaps more visible to the general public in the long run was his handling of prosecutions of those involved in Stratton Oakmont securities firm who had participated in a conspiracy to manipulate stock prices of 34 public companies. Led by Jordan Belfort, the “Wolf of Wall Street,” the firm underwrote substantial amounts of the stock of public companies and then sold it at fraudulently inflated prices through high pressure sales tactics. After the stock was in the hands of Stratton’s customers, the price typically collapsed. At sentencing, Gleeson predicted that Belfort, whose jail term was lessened because of his cooperation with the government, would go on to earn a considerable amount of money after release from prison. That he did with the publication of a book, which became a major motion picture.

Two other cases related to the criminal law deserve mention. In the first case, Gleeson held that the Constitution requires that certain convicted defendants be allowed access to evidence of DNA testing. Then, in a case of first impression, McKithen v. Brown, the U.S. Court of Appeals for the Second Circuit remanded a section 1983 case to Gleeson to determine “the extraordinarily important and delicate constitutional issue as to whether the Constitution requires the state to disclose physical evidence to prisoners for the purpose of post-conviction DNA testing.” Gleeson issued an opinion holding that the prisoner had a due process right to such evidence. Although the Second Circuit praised his “thoughtful and careful decision on a difficult constitutional issue of first impression,” it nevertheless rejected Gleeson’s work because of an intervening Supreme Court decision.

Judge Gleeson’s Record on the Bench, Part II: Sentencing

Gleeson’s most important and creative work as a judge was in the area of sentencing. In the Eastern District Gleeson had many colleagues unhappy with and strongly speaking out against the federal sentencing guidelines. However, his own contributions were remarkable. Known as a fearless and effective prosecutor, but also vividly aware of the defendant’s situation—he had been Chairman of the U.S. Judicial Conference Committee on Defender Services—Gleeson wrote a series of opinions, speeches, and law review articles that detailed the injustices of the sentencing regime.

Gleeson emphasized that most of the time “miscarriages of justice occur in small doses.” He attributed the problem to combining mandatory minimum sentences with sentencing guidelines. This combination meant that the defendant’s sentence would essentially be set in a deal between defense and prosecution with leverage in the hands of an inexperienced and possibly overzealous assistant U.S. attorney. This would force the defendant to serve the mandatory minimum sentence based largely, if not completely, on the estimate of the quantity of drugs in the criminal transaction.

This led Gleeson to state in one case where he was the sentencing judge that “there was no judging going on at Vasquez’s sentencing.” Indeed, he added, the sentencing proceeding had “all the solemnity of a driver’s license renewal.”

One of Gleeson’s most remarkable efforts in the sentencing area occurred in Holloway v. United States. In a series of opinions, he convinced U.S. Attorney Loretta Lynch to vacate two counts of the 57-year sentence that Gleeson had given years before, as required by mandatory sentences and sentence enhancements. This resulted in a total sentence that amounted to a longer sentence than a murderer might have been given.

Tireless in his efforts, Gleeson, in his published memorandum announcing the result, shrewdly lauded Lynch and the assistant U.S. Attorney in the case for demonstrating the difference between a Department of Prosecutions and a Department of Justice.” It should be noted, though, that while Gleeson was seeking to undo the result in Holloway, the U.S. Attorney could hardly have overlooked Gleeson’s statement in a Gleeson opinion in the case that, if the U.S. Attorney’s Office did not act, he would address a pending application to reopen a collateral challenge to the conviction and might “direct a closer inspection” of a claim of ineffective assistance of counsel.

Beyond opinions and other writings, Gleeson inspired POP (the Pretrial Opportunity Program), created by the Board of Judges of the Eastern District at his behest. Given the success of drug courts in the states, as well as the large number of reentry drug courts in the federal court system, POP was founded on the premise that many substance abusers are arrested for behavior grounded in their drug or alcohol addictions. POP provides a framework for more intensive supervising of the defendants, combining judicial involvement with the efforts of the pretrial services offices and treatment providers. The POP program contemplates the possibility that the rehabilitation of the participants might be sufficiently extraordinary that outright dismissal of the charges on the motion of the U.S. Attorney would be appropriate. However, in the usual case, POP participation may reduce the length of prison time.

Judge Gleeson’s Record on the Bench, Part III: Noteworthy Civil Cases

Gleeson handled a number of significant cases involving elections and voting. In 2003, he held unconstitutional a New York voter enrollment scheme directed at minor parties that would have cost the parties their assured place on the ballot. Local boards were not authorized to delete information that was useful for the minor parties.

In another case, brought under the 1965 Voting Rights Act and Amendments, Gleeson held that the at-large system used for electing the members of the Town Board of Hempstead was unconstitutional because it invidiously excluded African-American voters from effective participation in the political life of the town. The Second Circuit affirmed.

Gleeson’s record in election and voting cases is not without reversal, however. The Supreme Court unanimously reversed a Gleeson decision holding that the method by which New York selected most of its judges—by nominating conventions dominated by party leaders—deprived voters of their right to vote as well as other First Amendment rights. Even though the Court of Appeals affirmed Gleeson, the High Court was not convinced.

If Allowed to Serve, What May Judge Gleeson Do in the Flynn Case?

The man whose advice Judge Sullivan has requested is a tough-minded, experienced attorney. John Gleeson is no “showboat.” Indeed, he can come across as austere. As a judge, he was energetic, passionate, and willing to be a pain-in-the-neck to achieve fairness. Neither reflexively pro-government nor pro-defendant, Gleeson was deeply concerned about the “little guy” defendant, someone who may have committed a crime but may have been lost in the criminal justice system or overcome by the overwhelming power of the government to execute the law. Gleeson was willing to employ all legitimate tools available to a judge to achieve fairness. And while he was unafraid to go to the edge of his power, Gleeson also would go no further.

There are two issues raised by Gleeson’s role in the Flynn case. The first is whether he is the proper person to advise Judge Sullivan. On the one hand, he cannot truly be viewed as a neutral, disinterested party because he already has spoken out about the case. On the other hand, as a friend of the court, he fills the vacuum for Judge Sullivan, who has no one else before him to respond to what may be a real abuse of power by a government agency.

The second issue is, assuming John Gleeson is allowed to serve the role he has been assigned, what is he likely to do? One can hardly make a prediction given the extraordinary posture of this case. At most, courts can have only a small role in overseeing the government’s decision not to prosecute. Yet, in the McNabb case decided more than some 75 years, ago, under very different circumstances, the Supreme Court explained that courts have a supervisory power to oversee the government’s conduct in a criminal trial.

Gleeson, in an article published in 1997, shortly after he left the bench, was dubious about the exercise of such power. The power to execute the laws is clearly that of the Executive branch. Yet, even where the Constitution has delegated power to one branch, the genius of that document is that in critical times an implied power has been found in another branch to prevent a great injustice, especially if there are profound implications for the Constitutional system.

In the partisan ethos of today, one can be sure that Gleeson will not hold back in considering the fair and proper way to deal with Michael Flynn’s case. He will neither flinch at proposing strong medicine if it is proper, nor indulge solutions that are truly outside our separation of powers.

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