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An extraordinary legal showdown took place last weekend over President Donald Trump’s invocation of an 18th-century wartime act to deport hundreds of immigrants, most of them Venezuelans, to a prison in El Salvador.It involved a series of legal filings, White House announcements, court hearings, deportation flights and a mocking social media post from a Central American leader who proudly calls himself the “world’s coolest dictator.”Here is a timeline of events surrounding the invocation of the Alien Enemies Act. All times are Eastern.Saturday, March 152:16 a.m.: Two legal advocacy groups — the ACLU and Democracy Forward — file suit on behalf of five Venezuelans held in immigration detention who fear they’ll be falsely labeled members of the Venezuelan gang Tren de Aragua and deported under the Alien Enemies Act, which lawyers expect to be invoked soon.9:40 a.m.: Judge James E. Boasberg issues a temporary restraining order preventing the government from deporting the five plaintiffs. He schedules a 5 p.m. hearing on whether to expand it. The Trump administration swiftly appeals the order.Roughly 4 p.m.: The White House posts the order invoking the Alien Enemies Act.5 p.m.: Boasberg convenes a hearing and asks the government attorney, Deputy Assistant Attorney General Drew Ensign, if the government plans to deport anyone under Trump’s new proclamation “in the next 24 or 48 hours.” Ensign says he doesn't know and asks for time to find out, as the ACLU warns planes are apparently about to depart. Boasberg gives Ensign about 40 minutes to find out and recesses the hearing at 5:22 pm.5:26 p.m.: An airplane with the tail number N278GX, believed by activists to be carrying deportees, leaves Harlingen, Texas, near the border with Mexico, according to the flight tracking website FlightAware.5:45 p.m.: Another airplane with the tail number N837VA, believed by activists to be carrying deportees, departs Harlingen.About 5:55 p.m.: Boasberg reconvenes the hearing. Ensign says he still has no specifics. The ACLU again warns that planes are leaving. Boasberg says he has to issue a new order to avoid anyone being immediately deported.Around 6:45 p.m.: Boasberg tells Ensign: “Inform your clients of this immediately, and that any plane containing these folks that is going to take off or is in the air needs to be returned to the United States.” He verbally issues his order, which stands for 14 days, and notes that immigrants protected by it will remain in U.S. custody.7:26 p.m.: Boasberg's written order is released.7:36 p.m.: The plane with the tail number N278GX lands in Honduras.7:37 p.m.: An airplane with the tail number N630VA, believed by activists to be carrying deportees, departs Harlingen.8:02 p.m. The plane with the tail number N837VA lands in El Salvador.9:46 p.m.: The plane with the tail number N630VA arrives in Honduras.10:41 p.m.: The plane with the tail number N278GX departs Honduras.Sunday, March 16:12:05 a.m.: The plane with the tail number N278GX arrives in El Salvador.12:41 a.m.: The plane with the tail number N630VA leaves Honduras.1:03 a.m.: The plane with the tail number N630VA arrives in El Salvador.7:46 a.m.: El Salvador’s president, Nayib Bukele, tweets a New York Post headline saying Boasberg had ordered planes turned around and adds “Oopsie … Too late” and a laughing/crying emoji.8:13 a.m.: Bukele tweets footage of the deportees arriving and being processed into his country’s showcase prison.8:39 a.m.: U.S. Secretary of State Marco Rubio posts Bukele’s tweet.9:29 a.m.: White House Communications director recirculates Bukele’s laughing postMonday, March 175 p.m.: A hearing begins over what Boasberg has called the “possible defiance” of his court order. Trump administration lawyers tell Boasberg that his verbal directions did not count, only his written order needed to be followed, that it couldn’t apply to flights outside the U.S. and that they could not answer his questions about the trips due to national security issues. Boasberg calls the arguments "one heck of a stretch.” Lee Gelernt of the ACLU, the lead attorney for the plaintiffs, warns that “I think we're getting very close” to a constitutional crisis.___Associated Press writer Tim Sullivan contributed.