Trump is on a losing streak in the courts. How will he respond?

Vox

27-03-2025

President Donald Trump isn't a fan of judges who rule against him. During his first term, he famously attacked Judge Amy Berman Jackson, who sentenced his ally and adviser Roger Stone, by saying she was 'totally biased' and had 'hatred' for both Trump and Stone.
Now, Trump has only ratcheted up the attacks on judges. This feud reached a new high-water mark after US District Court Judge James Boasberg ordered the Trump administration to stop deporting certain Venezuelan immigrants. Boasberg also pressed the administration on the timing of flights from the US to El Salvador, where the immigrants were moved to a mega-prison.
In response, Trump called Boasberg a 'Radical Left Lunatic of a Judge, a troublemaker and agitator.' In concert, Attorney General Pam Bondi said the judge had 'no right' to be asking about the flights. Similar attack lines have been used by an array of Trump administration officials and allies.
For more on Trump's grudge with judges, Today, Explained's co-host Sean Rameswaram spoke with Kate Shaw. She's a professor at the University of Pennsylvania's Carey Law School, and co-host of the legal podcast Strict Scrutiny.
Click the link below to hear the whole conversation. The following is a transcript edited for length and clarity.
Kate, what is going on with Trump and the judges?
Trump has fared remarkably poorly in litigation in the last two months. He really is on an impressive losing streak. He's zero for three in the courts of appeals in trying to defend the constitutionality of his birthright citizenship executive order. He has been losing in cases challenging various aspects of Elon Musk's role in government and the activities of DOGE. In the only two cases to reach the Supreme Court so far, both very early-stage procedural matters, he lost both of them.
He's notched a couple of wins in the lower courts, but mostly on procedural issues. So, he's losing a lot and he's clearly really unhappy about it.
And the biggest controversy in all of the losses is perhaps this situation with El Salvador.
I think it's the one that Trump is the most incensed about. That seems clear, right? And so the administration invoked this 1798 statute: the Alien Enemies Act. That's been used three times, always in wartime: 1812, World War I, World War II.
Now, they try to make an argument that this Venezuelan gang, Tren de Aragua, is somehow working in concert with the Venezuelan government in ways that makes them a state actor that we're basically engaged in active hostilities with. That's the [reasoning] for invoking this old statute, and that allows designating individuals as alien enemies and expelling them, essentially, to this prison in El Salvador.
That has been challenged and is before this judge, Judge Boasberg. There have been some preliminary determinations made, but it's pretty clear the administration is gonna lose big in front of Judge Boasberg. This is the one that I think has Trump the most spun up based on his social media.
He has taken to Truth Social and basically called for Boasberg to be impeached. He has called him a radical left lunatic of a judge, a troublemaker, and an agitator. I don't know this judge, but, no, that is not an accurate characterization of him.
He was put on the DC local court by George W. Bush and then on the district court by President Obama — and then also designated to serve on the Foreign Intelligence Surveillance Court by Chief Justice John Roberts. This is not a judge who is in any way a radical left lunatic.
It's a preposterous characterization, but calling for his impeachment based on this preliminary set of rulings is an enormous escalation of the way Trump has been talking about and acting toward the judiciary.
And calling for a judge's impeachment — has that been reserved for Judge Boasberg, or does that apply to a number of these court battles that the Trump administration is facing?
He has been criticizing federal judges. Others, I think including Musk, have called for other impeachments. I think this might be the first that Trump has called for [impeachment] himself.
How do judges fight back when a president or an all-but-official vice president call for their impeachments?
It's a good question and judges are very limited in what they can do. They can't take to public-facing communications channels. They don't have a bully pulpit the way the president does. They cannot tweet or skeet or truth or whatever in their own defense. They have a lot of power in a very limited domain.
There's defending themselves in the court of public opinion, but then there's also the possibility that they could actually have to end up defending themselves in the actual United States Congress against impeachment.
How often do we see judges getting impeached? Remind us.
Pretty infrequently. There have been 15 impeachments of federal judges. Only eight of them have resulted in conviction.
Impeachment is a two-step process. We say somebody has been impeached if a majority of the House of Representatives has voted to approve one or more articles of impeachment against them. It just requires a simple majority in the House and then, colloquially, we say the person has been impeached.
But then they actually just go to the other House of Congress, the Senate, and that's where an actual trial happens. It requires a two-thirds supermajority to actually convict someone in a Senate trial, which results in their removal from office.
So impeachment, again, is the first half of the two-step process in the Constitution. And it does not seem impossible to me that we might see federal judges actually subject to real impeachment proceedings in the House, although 67 votes in the Senate is very hard for me to see ever occurring.
But that's still playing within the boundaries of what's legally acceptable. What about if they just openly defy the courts? That's what is at stake with this case, with Boasberg and the flights to El Salvador. Do we have concrete evidence that that has happened?
I don't think so. I think we are close. [There's] this delicate dance in front of Judge Boasberg, in which the administration does suggest that it is complying with a narrow — and I think probably wrong, but at least defensible in legal-sounding language — argument that they weren't subject to this order. They weren't defying the order, they were trying to comply with the order.
So they are at least not saying to the court: you essentially have no power over us. They are maybe inching a little closer to that. I think it matters a lot that they're continuing to make legal arguments and that they're continuing to appeal. I think in some ways, the real red lights start flashing if they stop doing that and simply don't comply.
I think they're likelier to do it here than in the context of a challenge to the dismantling of USAID or the Department of Education or an order targeting law firms. Where the president is making claims about national security, the president's power is always understood to be at its apex, and so they think they have the strongest legal footing for suggesting a court has no power over them here, [compared to] other spaces where it's obvious that courts absolutely have the power to review and maybe invalidate things the executive branch has done.
Interestingly, one source of that vast executive power comes from Chief Justice John Roberts, who last year helped expand our views of presidential power in this country. But in this case, especially when it comes to this fight between Trump and this DC judge, Boasberg, there's a bit of tension there.
Yeah. So as you just referenced, July 1 of last year, Roberts authors this opinion granting sweeping new authorities and immunities to presidents and ex-presidents.
And I think it hangs over virtually everything that we've seen in the last two months in terms of these extravagant assertions of executive authority and disdain at the idea that courts or any outside institution could act to check a president in any way.
There's a straight line between some of the descriptions of presidential power in that Trump v. United States case and the predicament we find ourselves in. So I do think that John Roberts bears a ton of responsibility for the way the administration has comported itself and broadcast its vision of essentially boundless executive power.
It is interesting that Roberts kind of came out swinging after Trump [suggested] on Truth Social that Boasberg should be impeached. Roberts issued this very unusual statement, kind of a rebuke of President Trump.
The chief justice rarely wades into the political fray in any way other than issuing his opinions. So he was obviously worried enough to speak up.
Any response from the Trump administration?