The mob, al-Qaeda and the Duchess of York

Mychael Schnell

A federal judge on Thursday appointed Judge Raymond J. Dearie to serve as special master in the case involving documents the FBI seized from former President Trump’s Mar-a-Lago residence last month.
The decision to install Dearie — a 78-year-old New York native and semi-retired judge from the U.S. District Court of the Eas-tern District of New York — came in response to Tr-ump’s request for an independent mediator to determine what, if any, materials recovered by authorities are protected by attorney-client or executive privileges.
U.S. District Judge Aileen Cannon, who is presiding over the Trump documents case, granted Trump’s request for a special master and directed both his legal team and the Justice Department to provide a list of contenders for the job. Dearie was the only individual both sides agreed upon.
The longtime judge is now tasked with examining the more than 11,000 documents the FBI seized by Nov. 30.
Here are five things to know about Dearie.
Dearie is a former Reagan nominee
Dearie received a bachelor’s degree from Fairfield University in 1966 before earning his juris doctor from St. John’s University School of Law in 1969.
After working in private practice for two years, Dearie moved to the U.S. Attorney’s Office for the Eastern District of New York in 1971.
Starting out as an assistant U.S. attorney, the New York native moved up the ladder at the Manhattan office, leading the appeals division, general crimes section and criminal division before assuming the role of chief assistant U.S. attorney in 1980 and, in 1982, U.S. attorney for the Eastern District of New York.
In 1986, then-President Ronald Reagan nominated Dearie to serve on the U.S. District Court of the Eastern District of New York.
Dearie was elevated to chief judge of the district court in 2007, a position he held until 2011, when he received senior status and took a reduced caseload.
Dearie decided to move to inactive status in August, but one of his staff members told NPR that it is unclear when the change will take effect. Inactive status is just shy of formal retirement, according to the outlet, and Dearie can return to the court if needed.
“I’m going to miss it,” he told the New York Law Journal in August.
Served on the FISA court, ruled in Carter Page case
Supreme Court Chief Justice John Roberts appointed Dearie to serve on the U.S. Foreign Intelligence Surveillance Court in 2012, where he remained until 2019.
The FISA court, as it is often referred to, examines applications from the U.S. government requesting warrants for electronic surveillance, physical searches and other investigative efforts related to foreign intelligence.
Dearie was serving as a FISA judge in October 2016 when the court approved a wiretap on Carter Page, who had previously served as a foreign policy adviser on Trump’s presidential campaign. The Justice Department requested the surveillance on the belief that Page was acting as a foreign agent on behalf of Russia. His surveillance was renewed three times.
The eavesdropping was part of the FBI’s “Crossfire Hurricane” investigation, which looked into potential links between Trump’s campaign and Russia. The probe has been a frequent target of criticism by Trump and his Republican allies.
In December 2019, the Justice Department’s inspector general Michael Horowitz issued a report that said the FBI had reason to open the “Crossfire Hurricane” investigation, but outlined issues with how the investigative bureau handled applications for the Page wiretap.
Justice Department says Dearie has ‘substantial judicial experience,’ but raises potential concern
Dearie was the only individual both Trump’s legal team and the Justice Department agreed on to serve as special master in the Trump documents case. Trump’s team initially proposed him as a candidate, and the department said it was open to the selection.
In a filing on Monday, the department said Dearie, in addition to its two proposed candidates, “each have substantial judicial experience, during which they have presided over federal criminal and civil cases, including federal cases involving national security and privilege concerns.”
The Justice Department did, however, raise one potential concern regarding Dearie serving as special master. Limits exist on how much outside work federal judges are permitted to take part in, as well as compensation they can receive. For senior status judges, however, those constraints are fewer, according to Bloomberg.
“The government’s understanding is that Judge Dearie currently remains on ‘senior active’ status,” the Justice Department wrote in its filing. “If this Court were to select Judge Dearie as the special master, the government would defer to the Court and Judge Dearie to determine whether the special master role would constitute outside employment and what rules and/or restrictions, if any, would apply to his serving in this capacity.”
Judge Cannon did not address that concern in her filing announcing Dearie’s appointment as special master.
The mob, al-Qaeda and the Duchess of York
Dearie presided over several cases during his 36-year tenure on the federal bench, including matters related to the mob, al-Qaeda and the Duchess of York.
The judge handled a number of matters involving the mob when he was U.S. attorney in the 1980s. At the time, the judicial field in Brooklyn had been cracking down on mobsters, gang chiefs and individuals committing financial crimes, according to The Washington Post.
But in 2009 and 2010, Dearie’s focus was centered on al-Qaeda: the then chief U.S. district judge presided over the case involving Najibullah Zazi, a legal permanent American resident from Afghanistan who pleaded guilty to providing material support to al-Qaeda.
And back in 1996, Dearie was at the helm of a trial involving the Duchess of York, who lost a necklace and matching bracelet worth hundreds of thousands of dollars. The jewelry was a wedding gift from Queen Elizabeth II.
Investigators ultimately identified Gilbert Terrero, who was a baggage handler at Kennedy International Airport in New York, as the individual behind the case. Authorities arrested Terrero, 19 at the time, and recovered most of the jewelry. He confessed to stealing the necklace and bracelet from a handbag at the airport.
Dearie sentenced Terrero to four years’ probation, according to The New York Times.
Previously called for reforming federal sentencing laws
Dearie drew headlines in 2016 when he called for reforming federal sentencing laws.
Speaking at an event sponsored by the New York Criminal Bar Association, the longtime judge who had senior status at the time said “I must admit that at times I’ve wanted to scream out in frustration, sadness and anger when I have been required to impose a mandatory sentence or have been prevented from doing the sensible thing,” according to the New York Law Journal.
“Let’s stop tinkering with this system of ours and collectively demand in the name of decency meaningful change, intelligent change,” he added.
The judge argued that most offenders are “not evil incarnate,” but commit wrongdoings because of “weakness, need, sometimes desperation,” according to The New York Times.
“So many defendants I see are without schooling, skills, hope or direction, and no term of years is going to change that,” he said.
“Why this love affair in this country with lengthy incarceration, to our great embarrassment as a civilized nation?” he added.