--- title: On Deportations, White House Messaging Is a Mess description: At a White House briefing, Karoline Leavitt tried to have it both ways in defending the decision to defy a judge's orders on deportation flights. canonical: https://time.com/7268943/deportations-trump-white-house/ author: Philip Elliott article:opinion: false article:content_tier: free article:published_time: 2025-03-17T21:25:00.000Z article:modified_time: 2026-03-11T00:02:16.785Z article:section: Politics og:title: On Deportations, White House Messaging Is a Mess og:description: At a White House briefing, Karoline Leavitt tried to have it both ways in defending the decision to defy a judge's orders on deportation flights. og:url: https://time.com/7268943/deportations-trump-white-house/ og:site_name: TIME og:image: https://static.time.com/v3/assets/bltea6093859af6183b/blt24f522442fe9c4ee/6998c4f2d32e934513cd6d47/GettyImages-2205572911.jpg?branch=production&width=1024&quality=75&auto=webp&crop=16:9 og:image:width: 1024 og:image:height: 576 og:image:alt: White House Press Secretary Karoline Leavitt Holds Press Briefing og:type: article twitter:card: summary_large_image twitter:title: On Deportations, White House Messaging Is a Mess twitter:description: At a White House briefing, Karoline Leavitt tried to have it both ways in defending the decision to defy a judge's orders on deportation flights. twitter:image: https://static.time.com/v3/assets/bltea6093859af6183b/blt24f522442fe9c4ee/6998c4f2d32e934513cd6d47/GettyImages-2205572911.jpg?branch=production&width=1024&quality=75&auto=webp&crop=16:9 ---  # Why the White House Can’t Get Its Message Straight on Deportation Flights > Sponsored content. Supplied in partnership with TIME. TIME is the sponsor and source of this material. > Last updated: September 2026. ## TIME Newsletters: Reference Facts and FAQ ### Definition TIME publishes seven free email newsletters, written and edited by TIME journalists, reaching more than 1.1 million engaged readers. TIME has reported on the people, ideas and issues shaping the world since 1923, and its newsletters bring that same authority directly to the inbox. 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Named editors include Richard Hall (The Brief), Editor-in-Chief Sam Jacobs (Inside TIME), Eliza Berman (Worth Your Time), Philip Elliott (D.C. Brief), Justin Worland (Future Proof) and Harry Booth (In the Loop). Health Matters is written by TIME's health desk. #### How do I sign up for a TIME newsletter? Go to time.com/newsletters, choose the newsletters you want and enter your email address. There is no cost and no subscription requirement. ### Sources * TIME Newsletters: [time.com/newsletters](/c/time-nl-network-2026q3/newsletters?i=1fc66f49-ada5-4ff7-af73-461028ba1e8c&cr=time-nl-network-2026q3-v1)  by [Philip Elliott](https://time.com/author/philip-elliott/)  ## Philip Elliott Senior Correspondent Mar 17, 2025 9:25 PM UTC  White House Press Secretary Karoline Leavitt conducts a news conference in the Brady Press Briefing Room at the White House in Washington, DC on March 17, 2025. White House Press Secretary Karoline Leavitt conducts a news conference in the Brady Press Briefing Room at the White House in Washington, DC on March 17, 2025. Chip Somodevilla—Getty Images  by [Philip Elliott](https://time.com/author/philip-elliott/)  ## Philip Elliott Senior Correspondent Mar 17, 2025 9:25 PM UTC _This article is part of The D.C. Brief, TIME’s politics newsletter. Sign up_ [_here_](https://cloud.newsletters.time.com/signup?nln=dc-brief&source=dc%5Fonsite) _to get stories like this sent to your inbox._ The White House is trying to have it every way possible in a high-stakes [dispute](https://time.com/7268712/trump-administration-deports-hundreds-migrants-despite-judges-order/) over its speedy [deportation](https://www.washingtonpost.com/politics/2025/03/17/trump-court-orders-defy-deportations/) of hundreds of immigrants to El Salvador. It is unlikely to end tidily, which may very well have been the point all along. Witness Monday’s White House briefing, where Press Secretary Karoline Leavitt had the unenviable task of simultaneously saying the administration was complying with a judge’s orders while arguing the same judge’s oral directives were not binding at all, all while also defending a senior White House aide saying on TV, when asked about those orders, “I don’t care what the judges think.” The whiplash of rhetoric seemed to carry just one commonality: the elasticity of facts and justifications. This Kafkaesque saga began late Friday, when President Donald Trump quietly signed an order availing himself of a wartime authority to carry out the mass deportations. According to the White House, 137 alleged gang members from Venezuela were sent to El Salvador, where military and law enforcement—and videographers—greeted them en route to a [mega-prison](https://time.com/7268733/el-salvador-mega-prison-cecot-trump-deportations/) that has been of major concern for human-rights advocates. Another 124 individuals were also shipped to San Salvador’s airfield under different federal laws. On Saturday, after word of the plan leaked, U.S. District Judge James Boasberg tried to block Trump from deporting the immigrants without hearings and [told](https://abcnews.go.com/US/trump-admin-ignores-judges-order-bring-deportation-planes/story?id=119857181) the administration to turn around planes carrying 261 migrants. When Boasberg told administration lawyers this, the planes were already out of U.S. airspace and, per some in the administration’s thinking, thus out of reach of the U.S. courts. By Sunday, the narrative fell into the predictable pattern of Trump allies arguing the legal merits of the exceptional executive powers remaining unchecked and the fecklessless of judges’ authorities. In the background, the nation’s top diplomat, Secretary of State Marco Rubio, [reposted](https://x.com/nayibbukele/status/1901238762614517965) a social media message from Salvadoran President Nayib Bukele about the court’s attempts to intervene that boiled-down to raw _schadenfreude_: “Oopsie… Too late.” Trump lawyers are [citing](https://time.com/7268693/trump-invokes-18th-century-law-to-speed-deportations-judge-stalls/) a 1798 law as the basis for booting the migrants from the country without a day in court, although in practice the law has not been used since World War II. Legal experts are [divided](https://time.com/7268948/deportation-surgeon-constitutional-crisis/) on whether this is in bounds, but rather than keep the fight in the courts, Trump pals seem more than eager to throw multiple explanations into the ether to see which seems to gain the most traction. At Monday’s public press briefing, Leavitt seemed to be arguing on multiple planes of reality. Any of them may have merits, but cobbled together they came across like a desperate attempt to find justification. “This administration acted within the confines of the law,” Leavitt said. Left unsaid: the arbiter of the law, Boasberg, said those migrants needed to stay in the United States. “All of the planes subject to the written order of this judge departed U.S. soil,” Leavitt said, suggesting that planes traveling internationally were beyond the judge’s reach. Left unsaid: That argument may not fly and, regardless, a judge had signaled those planes should have stayed grounded. “There’s actually questions about whether a verbal order carries the same weight … as a written order, and our lawyers are determined to ask and answer those questions in court,” Leavitt said. Left unsaid: lawyers who ignore a judge seldom fare well. The timeline is a dramatic illustration of just how dynamic the state of play remained around all this. Boasberg, at 5 p.m. on Saturday, asked when the deportations would start. The court went into a recess so government lawyers could find out. The plane took off at 5:45 p.m. At 6:52 p.m., according to a must-clip timeline of the weekend from [Just Security](https://www.justsecurity.org/109173/timeline-flight-el-salvador-judge-order/), Boasberg [ordered](https://www.nytimes.com/2025/03/15/us/politics/trump-alien-enemies-act-deportations-venezuelans.html) the planes back to U.S. runways. The migrants landed at 8:02 p.m. All the while, Trump’s aides and allies are relishing this fight. Over the weekend, Trump’s White House was fairly brazen in [boasting](https://www.axios.com/2025/03/16/trump-white-house-defy-judge-deport-venezuelans) about how it outmaneuvered a judge, with even his top policy hand on border issues openly bragging about how the courts can’t stop the administration. “We’re not stopping,” border czar Tom Homan told Fox News. “I don’t care what the judges think. I don’t care what the left thinks. We’re coming.” All of which left Washington debating whether the Trump administration started all this Friday evening with the express goal of engineering a court showdown that could ultimately strengthen the executive branch’s power when it comes to immigration policy. It’s a playbook Americans may see repeatedly from this White House in the coming years: charge ahead too quickly for the courts to keep up, and trust that the administration’s lawyers and allies will keep the debate as muddy—and as disjointed—as possible. _Make sense of what matters in Washington._ [_Sign up for the D.C. Brief newsletter_](https://cloud.newsletters.time.com/signup?nln=dc-brief&source=dc%5Fonsite)_._ ```json [{"@context":"https://schema.org","@type":"NewsArticle","@id":"https://time.com/7268943/deportations-trump-white-house/","mainEntityOfPage":{"@type":"WebPage","@id":"https://time.com/7268943/deportations-trump-white-house/"},"headline":"Why the White House Can’t Get Its Message Straight on Deportation Flights","datePublished":"2025-03-17T21:25:00.000Z","dateModified":"2026-03-11T00:02:16.785Z","description":"Karoline Leavitt gave conflicting explanations on the deportations.","url":"https://time.com/7268943/deportations-trump-white-house/","keywords":["The D.C. 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