Trump flew deportation planes during active federal judge order then faced criminal contempt

On March 15, 2025, Trump used the 1798 Alien Enemies Act to deport 137 Venezuelan men to El Salvador's CECOT prison. He said they were Tren de Aragua gang members. That same night, Chief Judge James Boasberg held an emergency hearing and ordered any planes still in the air to turn back. The planes didn't. They landed in El Salvador while Boasberg's order was active. Trump's people told the court the planes were already out of U.S. airspace. Boasberg said that didn't matter legally.

By April 16, 2025, Boasberg found probable cause that Trump officials had committed criminal contempt. He sent it to prosecutors. The D.C. Circuit paused the contempt case while Trump appealed. Then the Supreme Court stepped in. In a 5-4 vote on April 7-8, they overturned Boasberg's temporary order but said AEA deportees needed written notice so they could file habeas corpus petitions. Boasberg picked up his contempt inquiry again in November 2025 after the appeals process finished. On December 22, 2025, he ruled the U.S. had denied due process to the deported Venezuelans. He gave Trump until January 5, 2026 to either bring them back or give them proper hearings.

The Alien Enemies Act of 1798 was supposed to be for wartime invasions by foreign governments. It had never been used against a civilian gang. The Supreme Court's April ruling didn't even decide if Trump could use the act at all, just how the injunction process worked. At the same time, there was another case: Kilmar Abrego Garcia, a Maryland resident who got deported to CECOT despite having a court order protecting him. The Supreme Court ruled unanimously in April 2025 that Trump had to "facilitate" his return. Trump resisted that order for months. This whole situation became the biggest test in modern U.S. history of what happens when a president just ignores a federal court order in real time.