An intense legal clash unfolded last weekend following President Donald Trump’s use of the Alien Enemies Act, an 18th-century law, to deport a large group of immigrants, predominantly Venezuelans, to a prison facility in El Salvador. This development featured a series of legal maneuvers, official statements, judicial interventions, and deportation flights, culminating in social media commentary by a Central American leader who cheekily brands himself as the “world’s coolest dictator.”
The sequence of events began on Saturday, March 15. At 2:16 a.m., two legal advocacy organizations, ACLU and Democracy Forward, filed a lawsuit on behalf of five Venezuelan detainees in immigration detention. These individuals feared being wrongly categorized as members of the Venezuelan gang, Tren de Aragua, under the Alien Enemies Act. Anticipating the law’s invocation, the suit sought to protect their rights.
By 9:40 a.m., Judge James E. Boasberg had issued a temporary restraining order to prevent the government from deporting these individuals, scheduling a hearing for 5 p.m. to discuss extending this order. Nonetheless, the Trump administration promptly challenged this order. Mere hours later, around 4 p.m., the White House announced the activation of the Alien Enemies Act.
The situation escalated at 5 p.m. when Boasberg convened a hearing, inquiring whether the government intended to deport anyone under the new proclamation within the next 24 to 48 hours. Government representative Deputy Assistant Attorney General Drew Ensign admitted he lacked this information and requested time to investigate. As ACLU reported imminent departures, Boasberg granted Ensign about 40 minutes to obtain clarity. The hearing paused at 5:22 p.m.
Shortly after, at 5:26 p.m., a plane, tail number N278GX, suspected by activists to carry deportees, departed Harlingen, Texas, near the Mexico border. Another plane, tail number N837VA, left Harlingen at 5:45 p.m. Reassembling the hearing around 5:55 p.m., Boasberg found Ensign still uninformed. As the ACLU reiterated that planes were en route, Boasberg decided a new order was imperative to prevent immediate deportations.
By approximately 6:45 p.m., Boasberg instructed Ensign to inform clients promptly, stating that any plane with detainees must either remain on U.S. soil or return if already airborne. The verbal order, effective for 14 days, ensured those protected remained in U.S. custody. A written version of this order was available by 7:26 p.m.
As events continued to unfold, the plane with tail number N278GX landed in Honduras at 7:36 p.m., and another, tail number N837VA, landed in El Salvador by 8:02 p.m. Meanwhile, yet another aircraft, N630VA, took off from Harlingen, subsequently arriving in Honduras at 9:46 p.m., before eventually heading to El Salvador.
Early on Sunday, March 16, El Salvador’s President, Nayib Bukele, took to Twitter to mock the U.S. court’s turnaround orders, sharing footage of the deportees’ processing into the country’s prison. His tweets quickly garnered attention, being shared by U.S. officials.
The legal scrutiny continued into Monday, March 17, with a 5 p.m. hearing on whether the Trump administration defied Boasberg’s order. Government lawyers contended that only written orders were valid and couldn’t apply to foreign-departed flights, citing national security for their non-disclosure of flight details. Boasberg described these arguments as “a heck of a stretch,” while ACLU’s representative, Lee Gelernt, highlighted the possibility of approaching a constitutional crisis.
