A rare criminal-contempt fight is unfolding in Washington, D.C. over deportation flights that allegedly violated a federal court order. The case involves Venezuelan migrants flown to El Salvador in March 2025, despite U.S. District Judge James Boasberg’s directive to turn the planes around mid-flight. Media outlets report that Judge Boasberg is considering contempt charges against DHS and DHS officials.
Judge Boasberg has already found probable cause to believe the Trump administration willfully violated his order halting these removals, which were carried out under the Alien Enemies Act and related authorities. The judge has ordered sworn declarations from senior Department of Homeland Security officials and is weighing whether to initiate formal criminal-contempt proceedings. That step moves the dispute from a bureaucratic “compliance issue” into the realm of personal criminal exposure for federal officials.
Under Federal Rule of Criminal Procedure 42, criminal contempt is a standalone federal offense. It can result in fines or imprisonment and applies to anyone who willfully disobeys a clear and specific court order. In theory, that has always included cabinet-level officials. In practice, criminal-contempt prosecutions against senior executive-branch officials are extremely rare. Most compliance disputes are handled through civil contempt, negotiated remedial plans, or political pressure, not by threatening individual prosecution.
This matter is different because it directly tests how much control federal courts have over their own orders when they clash with aggressive executive enforcement. If the Executive Branch can disregard an injunction affecting removal flights and later argue that a written order did not clearly apply to planes already in the air, the court’s ability to provide meaningful relief is weakened. Boasberg’s push for detailed sworn statements from top DHS officials signals that he views this not as a misunderstanding of scope or timing, but as potential deliberate non-compliance.
For federal criminal practitioners, the implications are structural rather than doctrinal. First, this case shows that Rule 42 is not a dead letter. When agencies or officials ignore injunctions that protect your client’s rights—whether in immigration, prison conditions, or access-to-counsel litigation—judges have the authority to escalate from civil sanctions to criminal contempt if they conclude the violation is willful.
Second, the case underscores the importance of clear, precise injunctive language and a clean evidentiary record. The more specific the order, the harder it is for the government to invoke ambiguity later. That precision matters both for establishing contempt exposure and for preventing quiet workarounds that undermine court-ordered relief while technically staying “within the lines.”
Third, this episode is likely to affect how future administrations and agency lawyers analyze risk when they consider pushing the edge of a federal court order. If criminal-contempt proceedings against senior officials become even a credible possibility, internal advice about “hard-charging” enforcement tactics will change. Counsel inside the government will have to weigh their clients’ personal exposure alongside policy goals.