Bolton Case Assigned To Judge Who Has History With Trump
U.S. District Judge Theodore Chuang, an Obama appointee based in Greenbelt, Maryland, is once again in the national spotlight — this time presiding over the high-profile criminal case against former National Security Adviser John Bolton. The judge’s long record of rulings against President Donald J. Trump’s executive authority has made him a recurring figure in the broader clash between the judiciary and the presidency — a struggle that has only intensified since Trump’s return to the White House.
Judge Chuang first rose to prominence in 2017, when he issued a nationwide injunction blocking the Trump administration’s second travel ban, which sought to restrict entry from several majority-Muslim nations as part of a national security initiative. In that decision, Chuang argued that a “reasonable observer” could interpret the policy as motivated by anti-Muslim bias — citing Trump’s campaign-era statements as evidence.
“Simply because a decision-maker made the statements during a campaign does not wipe them from the ‘reasonable memory’ of a ‘reasonable observer,’” Chuang wrote.
Conservatives at the time condemned the ruling as an egregious example of judicial activism, arguing that it blurred the line between political speech and legitimate executive policy. That interpretation — effectively treating campaign rhetoric as legally binding — helped set the stage for a series of courtroom battles aimed at undermining Trump’s authority throughout his first term.
Judge Chuang later intervened in other policy areas, including the U.S. Agency for International Development (USAID), where he blocked Trump’s plan to restructure and streamline foreign aid operations. Critics said it was yet another case of an unelected judge obstructing the constitutional powers of an elected president.
Now, Chuang finds himself presiding over one of the most politically charged cases of the year — the federal prosecution of John Bolton, who faces 18 felony counts related to alleged mishandling of top-secret materials.
The case has reignited debate over the politicization of the Department of Justice, especially given Bolton’s long and public feud with President Trump following his departure from the administration.
“I have become the latest target in weaponizing the Justice Department to charge those [Trump] deems to be his enemies with charges that were declined before or distort the facts,” Bolton said Thursday.
The indictment comes years after Bolton’s controversial 2020 memoir, “The Room Where It Happened,” which the Trump administration had sought to delay for national security reasons. The Justice Department at the time filed a civil suit accusing Bolton of publishing without completing the mandatory pre-publication review for classified material.
Although the court allowed Bolton to release the book, the judge ruled that he “likely published classified materials” and “exposed his country to harm and himself to civil (and potentially criminal) liability.”
Bolton has since maintained that the book underwent full clearance from “experienced career officials” before publication. He also claims the FBI was informed in 2021 that one of his personal accounts was hacked by Iran but insists there is no evidence that classified information was ever accessed or shared.
Bolton framed the current charges as politically motivated, saying, “These charges are not just about [Trump’s] focus on me or my diaries, but his intensive effort to intimidate his opponents, to ensure that he alone determines what is said about his conduct.”
The irony is hard to ignore: a judge who has repeatedly hampered President Trump’s constitutional authority is now overseeing the prosecution of one of Trump’s most vocal adversaries. For conservatives, Chuang’s involvement underscores the deep entanglement between the federal judiciary and partisan politics — a tension that continues to test the limits of executive power in Trump’s second term.
The case is set for a pivotal hearing on November 21, with the nation watching closely to see whether Judge Chuang’s courtroom once again becomes a battlefield in the broader war over presidential authority and the politicization of justice.