Judge Theodore Chuang Returns to the Spotlight as Bolton Faces Felony Charges

U.S. District Judge Theodore Chuang, an Obama-era appointee based in Greenbelt, Maryland, is once again at the center of national attention — this time overseeing a case involving former National Security Adviser John Bolton. Known for his past rulings that have limited presidential power, Chuang’s involvement in yet another politically charged dispute has reignited debates over the judiciary’s role in checking the executive branch.

Chuang first rose to prominence in 2017, when he issued a nationwide injunction against the Trump administration’s second travel ban, which sought to restrict entry from six Muslim-majority countries. In that decision, the judge argued that the executive order could not be separated from then-President Trump’s prior campaign rhetoric.

“A reasonable observer,” Chuang wrote, “could conclude that the policy was motivated by anti-Muslim sentiment.”

He added that campaign statements do not simply vanish from public memory once a candidate takes office, writing, “A decision-maker’s statements during a campaign do not disappear from the reasonable memory of a reasonable observer.”

The ruling quickly made Chuang a polarizing figure. Supporters praised him for defending constitutional protections, while critics labeled the decision judicial overreach, accusing him of using political arguments to override the executive’s national security authority.

A History of Clashing with the Executive Branch

Chuang’s influence extended beyond immigration. During Trump’s presidency, he presided over several key cases involving the U.S. Agency for International Development (USAID) and other government agencies. One notable dispute involved Trump’s plan to reorganize USAID in an effort to streamline operations and reduce bureaucratic waste.

Chuang temporarily blocked the restructuring, saying the court needed more time to review the legality of the move. To conservatives, the decision symbolized a growing pattern of federal judges stalling or halting executive actions based on political disagreement rather than clear constitutional grounds.

Now, the Maryland judge is set to preside over John Bolton’s criminal case, a proceeding that promises to draw intense national scrutiny. Bolton, who served as Trump’s national security adviser during his first term, faces 18 felony charges related to the alleged mishandling and unauthorized disclosure of classified information.

A critical hearing is scheduled for November 21, and the outcome could have implications for both the former diplomat and broader questions of how far executive privilege extends once an official leaves office.

Bolton Claims Political Retaliation

Bolton, who famously broke with Trump over foreign policy disputes, argues that the charges represent political retribution rather than genuine legal violations.

“I’ve become the latest target of a weaponized Justice Department,” Bolton said in a statement. “These charges distort the facts and revive claims that had already been reviewed and dismissed.”

The Justice Department’s pursuit of Bolton dates back to 2020, when prosecutors filed a civil lawsuit to block the release of his memoir, The Room Where It Happened. Officials alleged that Bolton had failed to complete the required pre-publication review meant to protect classified information.

Although the court allowed the book to be published, Judge Chuang found that Bolton had “likely disclosed classified materials” and “exposed both his country and himself to potential harm and legal liability.” The Department of Justice later launched a criminal investigation into the matter but dropped it in 2021, under the Biden administration.

At the time, Bolton declared the decision a victory. “This is a complete vindication,” he told Axios. “They’re just giving up.”

Renewed Legal Firestorm

Despite the closure of the previous investigation, a federal grand jury recently returned an indictment alleging that Bolton again mishandled sensitive information. The case has drawn renewed media attention because of the judge’s prior rulings that frequently curtailed Trump-era policies.

According to the indictment, Bolton’s representative notified the FBI in July 2021 that one of his personal accounts had been hacked by Iranian actors. However, investigators found no indication that classified materials were compromised or distributed. Bolton maintains that the Justice Department had long been aware of the cyberattack and that “in four years of the previous administration, after these reviews, no charges were filed.”

“These charges are not about documents or diaries,” Bolton said. “They’re about intimidation — an effort to silence dissent and control the narrative about [Trump’s] conduct.”

He added that his book had undergone a thorough review process, which he said was approved by “experienced, career clearance officials.”

The Broader Constitutional Clash

The Bolton case once again places Judge Chuang in the middle of a larger power struggle between the judiciary and the executive branch. His history of rulings limiting presidential discretion — especially in cases involving Trump — has made him a lightning rod in Washington’s ongoing debate over judicial independence.

As the November hearing approaches, observers say the case will test not only Bolton’s defense but also the broader question of whether judges like Chuang are acting as neutral arbiters or as participants in the country’s political conflicts.

Regardless of the outcome, one thing is clear: Theodore Chuang remains a judicial figure whose decisions continue to shape — and challenge — the limits of executive authority in modern America.