The Dictatorship
ACLU asks judge to force the Trump administration to state under oath if it violated his court order
A federal judge on Monday questioned whether the Trump administration ignored his orders to turn around planes carrying deportees to El Salvador, a possible violation of the decision he’d issued minutes before.
District Judge James E. Boasberg was incredulous over the administration’s contentions that his verbal directions did not count, that only his written order needed to be followed, that it couldn’t apply to flights that had left the U.S. and that the administration could not answer his questions about the deportations due to national security issues.
Republican presidential nominee former President Donald Trump speaks along the southern border with Mexico, on Aug. 22, 2024, in Sierra Vista, Ariz. (AP Photo/Evan Vucci, File)
Republican presidential nominee former President Donald Trump speaks along the southern border with Mexico, on Aug. 22, 2024, in Sierra Vista, Ariz. (AP Photo/Evan Vucci, File)
“That’s one heck of a stretch, I think,” Boasberg replied, noting that the administration knew as the planes were departing that he was about to decide whether to briefly halt deportations being made under a rarely used 18th century law invoked by Trump about an hour earlier.
“I’m just asking how you think my equitable powers do not attach to a plane that has departed the U.S., even if it’s in international airspace,” Boasberg added at another point.
AP AUDIO: Judge questions Trump administration on whether it ignored order to turn around deportation flights
AP Washington correspondent Sagar Meghani reports on deportations to Central America.
Deputy Associate Attorney General Abhishek Kambli contended that only Boasberg’s short written order, issued about 45 minutes after he made the verbal demand, counted. It did not contain any demands to reverse planes, and Kambli added that it was too late to redirect two planes that had left the U.S. by that time.
“These are sensitive, operational tasks of national security,” Kambli said.
The hearing over what Boasberg called the “possible defiance” of his court order marked the latest step in a high-stakes legal fight that began when President Donald Trump invoked the 1798 wartime law to remove immigrants over the weekend. It was also an escalation in the battle over whether the Trump administration is flouting court orders that have blocked some of his aggressive moves in the opening weeks of his second term.
“There’s been a lot of talk about constitutional crisis, people throw that word around. I think we’re getting very close to it,” warned Lee Gelernt of the ACLU, the lead attorney for the plaintiffs, during the Monday hearing. After the hearing, Gelernt said the ACLU would ask Boasberg to order all improperly deported people returned to the United States.
Boasberg said he’d record the proceedings and additional demands in writing. “I will memorialize this in a written order since apparently my oral orders don’t seem to carry much weight,” Boasberg said.
On Saturday night, Boasberg ordered the administration not to deport anyone in its custody through the newly-invoked Alien Enemies Act, which has only been used three times before in U.S. history, all during congressionally declared wars. Trump issued a proclamation that the law was newly in effect due to what he claimed was an invasion by the Venezuelan gang Aragua Train.
In this photo provided by El Salvador’s presidential press office, a prison guard transfers deportees from the U.S., alleged to be Venezuelan gang members, to the Terrorism Confinement Center in Tecoluca, El Salvador, Sunday, March 16, 2025. (El Salvador presidential press office via AP)
In this photo provided by El Salvador’s presidential press office, a prison guard transfers deportees from the U.S., alleged to be Venezuelan gang members, to the Terrorism Confinement Center in Tecoluca, El Salvador, Sunday, March 16, 2025. (El Salvador presidential press office via AP)
Trump’s invocation of the act could allow him to deport any noncitizen he says is associated with the gang, without offering proof or even publicly identifying them. The plaintiffs filed their suit on behalf of several Venezuelans in U.S. custody who feared they’d be falsely accused of being Tren de Aragua members and improperly removed from the country.
Told there were planes in the air headed to El Salvador, which has agreed to house deported migrants in a notorious prison, Boasberg said Saturday evening that he and the government needed to move fast. “You shall 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,” Boasberg told the government’s lawyer.
According to the filing, two planes that had taken off from Texas’ detention facility when the hearing started more than an hour earlier were in the air at that point, and they apparently continued to El Salvador. A third plane apparently took off after the hearing and Boasberg’s written order was formally published at 7:26 p.m. Eastern time. Kambli said that plane held no one deported under the Alien Enemies Act.
El Salvador’s President, Nayib Bukele, on Sunday morning tweeted, “Oopsie…too late” above an article referencing Boasberg’s order and announced that more than 200 deportees had arrived in his country. The White House communications director, Steven Cheung, reposted Bukele’s post with an admiring GIF.
Later Sunday, a widely circulated article in Axios said the administration decided to “defy” the order and quoted anonymous officials who said they concluded it didn’t extend to planes outside U.S. airspace. That drew a quick denial from White House press secretary Karoline Leavitt, who said in a statement “the administration did not ‘refuse to comply’ with a court order.”
The administration argues a federal judge does not have the authority to tell the president whether he can determine the country is being invaded under the act, or how to defend it.
After Boasberg scheduled a hearing Monday and said the government should be prepared to answer questions over its conduct, the Justice Department objected, saying it could not answer in a public forum because it involved “sensitive questions of national security, foreign relations, and coordination with foreign nations.” Boasberg denied the government’s request to cancel the hearing, which led the Trump administration to ask that the judge be taken off the case.
Kambli stressed that the government believes it is complying with Boasberg’s order. It has said in writing it will not use Trump’s invocation of the Alien Enemies Act to deport anyone if Boasberg’s order is not overturned on appeal, a pledge Kambli made again verbally in court Monday. “None of this is necessary because we did comply with the court’s written order,” Kambli said.
Boasberg’s temporary restraining order is only in effect for up to 14 days as he oversees the litigation over Trump’s unprecedented use of the act, which is likely to raise new constitutional issues that can only ultimately be decided by the U.S. Supreme Court. He had scheduled a hearing Friday for further arguments, but the two organizations that filed the initial lawsuit, the ACLU and Democracy Forward, urged him to force the administration to explain in a declaration under oath what happened.
As the courtroom drama built, so did international fallout over the deportations to El Salvador. Venezuela’s government on Monday characterized the transfer of migrants to El Salvador as “kidnappings” that it plans to challenge as “crimes against humanity” before the United Nations and other international organizations. It also accused Bukele’s government of profiting off the plights of Venezuelan migrants.
“President, I respectfully say to you, are you going to support this cruelty, this injustice … of imprisoning noble, hard-working migrants, good people, without trial, without having committed crimes in El Salvador, without any kind of sentence issued by a Salvadoran court?” President Nicolás Maduro said on state television. “Is this legal? Is it fair? Is it humane?”
Trump’s proclamation alleges Tren de Aragua is acting as a “hybrid criminal state” in partnership with Venezuela.
The Trump administration has transferred hundreds of immigrants to El Salvador even as a federal judge issued an order temporarily barring the deportations under an 18th century wartime declaration targeting Venezuelan gang members, officials said. President Trump defended the deportations, commenting ‘these were bad people.’
Families of some Venezuelans in U.S. custody scrambled to find out if their loved ones had been sent to El Salvador. Multiple immigration lawyers said they had clients who were not gang members who were being moved for possible deportation late Friday.
Franco Caraballo was held by immigration authorities during a routine check-in Feb. 3. His immigration lawyer, Martin Rosenow, said Caraballo not been accused of a crime. Caraballo’s wife believes he’s been wrongfully accused of belonging to the gang because of a tattoo he got marking his daughter’s birthday,
He called his wife Friday night in a panic because he was being handcuffed and put on a plane to an unknown destination in Texas, from where flights to El Salvador departed.
That was the last the family heard of him and he’s disappeared from the federal immigration detainee locator system. “I’ve never seen anything like this,” said Rosenow.
__
Cano reported from Caracas, Venezuela. Joshua Goodman in Miami, Michael Kunzelman in Washington, D.C., and Nicholas Riccardi in Denver contributed to this report.
The Dictatorship
Justice Jackson keeps calling out what she sees as needless Supreme Court interventions
Justice Ketanji Brown Jackson continues to speak out when she believes her colleagues are misusing their power. The latest example came Monday, when the Biden appointee dissented from a Supreme Court ruling in favor of law enforcement in a Fourth Amendment case.
In District of Columbia v. R.W.the high court majority disagreed with a ruling from D.C.’s appeals court that said a police officer violated the amendment by stopping a person without reasonable suspicion. In an unsigned through the court opinion, the justices said the D.C. court failed to properly consider the “totality of the circumstances.” The justices summarily reversed the lower court.
Jackson, however, saw the maneuver by her colleagues as heavy-handed.
In her dissent, she wrote that if the court’s intervention “reflects disapproval” of the D.C. court’s “assessment of which particular facts to weigh and to what extent, I cannot fathom why that kind of factbound determination warranted correction by this Court.” She deemed the move “not a worthy accomplishment for the unusual step of summary reversal.”
A notation at the end of the majority’s opinion said that Justice Sonia Sotomayor would have denied D.C.’s petition for high court review, but she didn’t join Jackson’s dissent or write her own to elaborate.
Jackson’s dissent follows a lecture she gave last week at Yale Law School in which she criticized what she saw as her colleagues’ disrespect of lower courts’ work.
Monday’s ruling appeared among several high court actions on a 25-page order lista routine document containing the latest action on pending appeals. The list is mostly unexplained denials of petitions for review, but sometimes it contains opinions and justices writing separately to explain themselves.
In another case on the list, Sotomayor, Jackson and the court’s third Democratic-appointed justice, Elena Kagan, all noted their dissent from the majority’s unexplained summary reversal in favor of law enforcement in a qualified immunity case.
It takes four justices to grant review of a petition. That simple math underscores the lack of power wielded by the three Democratic appointees, especially on the most contentious issues.
On that note, one of the new cases the court took up on Monday involves its latest foray into religion in public life, which the religious side has been winning at the court. The new case is an appeal from Catholic preschools in Colorado that want public funding while still admitting, as they wrote in their petition“only families who support Catholic beliefs, including on sex and gender.” The case will be heard in the next court term that starts in October.
Jordan Rubin is the Deadline: Legal Blog writer. He was a prosecutor for the New York County District Attorney’s Office in Manhattan and is the author of “Bizarro,” a book about the secret war on synthetic drugs. Before he joined MS NOW, he was a legal reporter for Bloomberg Law.
The Dictatorship
The White House’s personal, financial and diplomatic lines keep blurring
About a month ago, when Donald Trump spoke at a conference for Saudi Arabia’s sovereign investment fund, it was hard not to notice the complexities of the circumstances. On the one hand, Riyadh has helped steer the White House’s policy in Iran. On the other hand, the president’s son-in-law, having already received billions of dollars from Saudi Arabia, recently turned to the Middle Eastern country for more money for his private investment firm.
All the while, Saudi officials remain focused on private dealings with Trump’s family business, as the Republican extended his public support to the sovereign investment fund, ignored Pentagon concerns about selling F-35 fighter jets to Saudi Arabia and designated Saudi Arabia a “major non-NATO ally” as part of a new security agreement.
The trouble is, it’s not just the Saudis.
The New York Times reported on wealthy interests in Syria with ambitions plans for the nation’s future who needed the U.S. to drop the economic sanctions that crippled the country during Bashar al-Assad’s reign. One Syrian-born businessman, Mohamad Al-Khayyat, secured a meeting with Republican Rep. Joe Wilson of South Carolina, who recommended that plans for a luxury golf course carry the Trump Organization brand as a way of getting the American president’s attention.
The Times’ report, which has not been independently verified by MS NOW, added that the businessman was way ahead of the congressman. He’d already planned to propose a Trump-branded resort. The same businessman’s brothers, who enjoy the backing of Thomas Barrack, the American president’s special envoy to Syria, were also negotiating a real estate partnership with Ivanka Trump and Jared Kushner.
The Times summarized the broader context nicely:
Such a mixing of personal and diplomatic affairs has long been the norm in Middle Eastern nations, where a small set of players have historically run, and profited from, their dominant role in society. But it has become the way Washington operates in Mr. Trump’s second term, too.
Business discussions involving the president’s family … are consistently blurred with important policy decisions or consequential nation-to-nation negotiations.
Not to put too fine a point on this, but developments like these aren’t supposed to happen in the U.S. If a foreign country wants a change in federal economic sanctions, it’s supposed to go through proper diplomatic and economic channels as part of a formal process to prevent corruption and potential conflicts of interests.
In 2026, that model has been torn down — and replaced with what the Times described as “a warped system of executive patronage,” which is awfully tough to defend.
The article added:
Mohamad Al-Khayyat returned to Washington late last year toting a special stone celebrating the proposed golf course, carved with the Trump family emblem. He presented it to Mr. Wilson in his Capitol Hill office to deliver to the White House. Mr. Al-Khayyat then joined meetings with other lawmakers to push the sanctions repeal.
Weeks later, legislation for a permanent repeal won approval in Congress and was signed into law by Mr. Trump in late December.
This was no doubt noticed by officials and monied interests elsewhere, sending a clear signal about how to interact with the U.S. government (at least until January 2029).
Steve Benen is a producer for “The Rachel Maddow Show,” the editor of MaddowBlog and an MS NOW political contributor. He’s also the bestselling author of “Ministry of Truth: Democracy, Reality, and the Republicans’ War on the Recent Past.”
The Dictatorship
Monday’s Campaign Round-Up, 4.20.26: Obama makes one last pitch ahead of Virginia race
Today’s installment of campaign-related news items from across the country.
* This week’s biggest election is in Virginia, where voters will decide whether to advance a Democratic redistricting effort. Ahead of Tuesday’s balloting, Barack Obama filmed one last pitch to the electorate in the commonwealth.
* With former Rep. Eric Swalwell out of California’s gubernatorial race, billionaire Tom Steyer is spending heavily to claim the front-runner slot. The Associated Press reported“Data compiled by advertising tracker AdImpact show Steyer has spent or booked over $115 million in ads for broadcast TV, cable and radio — nearly 30 times the amount of his nearest Democratic rival.”
* On a related note, the California Teachers Association, which had backed Swalwell, threw its support behind Steyer’s bid last week.
* When Donald Trump held an event in Nevada last week, many watched to see whether Joe Lombardo, the state’s Republican governor who is facing a tough re-election fight in the fall, appeared at the gathering. He did notthough Lt. Gov. Stavros Anthony spoke at the event.
* In Pennsylvania, Democratic Sen. John Fetterman isn’t up for re-election until 2028, but Punchbowl News asked every other Democratic member of the state’s congressional delegation whether the incumbent senator should run for a second term as a Democrat. Not one said he should.
* Jack Daly, a political operative who pleaded guilty in 2023 to defrauding thousands of conservative political donors, has lost some Republican clients of late, but the National Republican Senatorial Committee has continued to use the services of Daly’s firm.
* And in Tennessee, Republican Rep. Andy Ogles appears to be running for re-election, though his fundraising is badly lacking: As of the end of March, the far-right incumbent only had around $85,000 cash on handwhich lags his GOP primary opponent, former Tennessee Agriculture Commissioner Charlie Hatcher, who has around $150,000 in his campaign account.
Steve Benen is a producer for “The Rachel Maddow Show,” the editor of MaddowBlog and an MS NOW political contributor. He’s also the bestselling author of “Ministry of Truth: Democracy, Reality, and the Republicans’ War on the Recent Past.”
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