Trump Targets Naturalized US Citizens

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0:41Big league reliability for your business. That's Genius. You need to make a huge presentation in an hour. Adobe Acrobat uses AI to take all your documents and generate a presentation with a single click. Build slides quickly and streamline the process. Need a last-minute pitch deck? Do that with Acrobat. Need to level up your presentation design? Do that with Acrobat. You have 30-plus documents that need to be simplified into a proposal. Do that. Do that. Do that with Acrobat. Learn more at adobe.com slash do that with Acrobat. This is Bloomberg Law with June Grosso from Bloomberg Radio. New York State is attempting to place guardrails around the Trump administration's immigration agenda with a comprehensive package of bills to limit local law enforcement from cooperating with ICE.

1:40That's led border czar Tom Holman to threaten to flood the zone and send more ICE agents to New York than you've ever seen before, although he denies that constitutes a threat. Governor Holcomb is saying, I'm threatening her. I'm not threatening her. I'm responding to the ridiculous legislation that's going to force more agents in the street. Because we lose the efficiency of the jail, we lose the efficiency of the 287G program, we've got to send more agents to New York. Rather than one agent arresting one bad guy in the safety and security of a jail, which is safer for the alien, safer for the agent, certainly safer for the community, they're going to release them into the street, which means now you've got to send a few jobs teams to arrest them because we're arresting somebody on his turf who has access to who knows what weapons.

2:25Joining me is Leon Fresco, a partner at Holland & Knight. He was the former head of the Office of Immigration Litigation in the Obama administration. Leon, start by telling us about this package of bills that New York is about to pass. Well, the bills basically would make it impossible for any jurisdiction to voluntarily cooperate with ICE by either giving ICE information about people that can be deported, or even more affirmatively by being what's called the 287G jurisdiction, which is the kind of jurisdiction that says we will actually deputize our police officers to engage in ICE tactics so they can actually be forced multipliers for ICE.

3:07And there's a lot of police offices in Florida and in Texas that do this, where if they arrest you, they're the ones who do the immigration check. And they actually will refer people to ICE, even that ICE didn't even know about or care. And they'll say, hey, ICE, here, go take this person and deport them. So what New York is trying to say is, no, we don't want any of that in New York, and we will actually prevent it. And there's actually a very interesting case law that comes out of the Fifth Circuit in Texas, where they basically said that states have this level of supremacy over localities. This time it was the opposite.

3:42The state of Texas didn't want the localities to be sanctuary jurisdictions, but it would work the other way. So if the state didn't want its localities to be 287G jurisdictions, it could similarly stop that. But what Tom Holman is saying is, okay, fine. If you don't want to let these police departments pick and choose who are the bad people so that they can refer them to us, then we're going to have to go find the bad people. And so if you won't let your people vet bad people and send them to us, then we don't have any vetting of any kind. We don't know who's here. So what you're inviting is for us to come to New York and have to start looking for whoever we can find because you're unwilling to do the work of vetting the quote unquote bad people for us.

4:30And so it's a tough argument because there is some truth to this, which is the states that sort of decide to delegate a little bit of this on their own actually do get better treatment from the Department of Homeland Security. And that is what Tom Holman is basically saying there. He's saying, look, if you don't want to give us any cooperation and you want to leave us completely blind, what do you want us to do? just not enforce anything in New York and just leave. We're not going to do that. And so you're going to leave us in a position where we're going to end up arresting all kinds of people you didn't want us to arrest because you were unwilling to engage in the vetting on the state and local land.

5:07So, Leon, New York Governor Kathy Hochul said the state would help you go after the hardened criminals, the violent, the worst of the worst. Does this bill not even leave room for that? So here is the problem. And a lot of this debate still tracks back to a time that I don't think exists anymore in America, which is there was a time maybe in the 90s or the early 2000s where people were worried that the police was out there racially profiling people. then they would mistakenly arrest people of color and then they would mistakenly then report those people of color to ICE and then ICE would deport them and they weren't even guilty of anything.

5:52The whole thing was racist from beginning to end. And what Kathy Hochul is saying is the people we want to give to ICE are people who are convicted, who have gone through the system, not people we are just arresting. But here's the point, and here's where I have sympathy for what Tom Holman is saying. If the city of New York doesn't want to refer someone to ICE, they don't have to refer someone to ICE. This idea that people are accidentally referred to ICE after a racial profiling arrest, that's the kind of thing people were worried about again in the 90s and in the early 2000s. Now all of these jurisdictions have become sanctuary jurisdictions, and they've been trained in this way, etc.

6:35And so this fear that we still have in 2026, that jurisdictions are unwittingly or helplessly referring people to ICE who are innocent, and all the person did that was they were brown, and they were arrested by the local police, and now they're being deported. I just think the jurisdictions have a lot more control over that than people are giving them credit for. So it is a little weird that you wouldn't report people who you arrested, even if they weren't convicted, if you thought they were actually really, really bad people. So it is a fair argument to say, hey, do something, local jurisdictions.

7:13Don't just do nothing. And don't just intentionally try to keep ice in the blind. But that's what's happening. And it's because they are basically conceding a point, which is we believe that our local jurisdictions are incapable of being able to explain who is actually a threat and should be referred to ICE, as opposed to who is not a threat and shouldn't be referred to ICE. The governor is also moving to ban federal, state, and local law enforcement from wearing masks while on duty. A similar law was passed in California and a judge struck it down. But I mean, a different judge in New York might uphold it or no?

7:56Well, so this is going to be tough because even in the Ninth Circuit, it was a very liberal court that said, hey, you know, this is regulating federal police enforcement and you can't do this in any way. It doesn't matter what your intention is. Even if your intention is, look, you need to wear a helmet if you're going to be doing unsafe things. That's for the federal government to decide. That's not for the state government to decide. And so I do think it would suffer the same fate if it's passed in New York, as they can symbolically say no masks, but at the end of the day, the courts are going to say, no, we're not going to allow the states to suddenly start putting these regulations on federal enforcement officers conducting federal enforcement.

8:40Look, a district judge can do anything, but I find it very unlikely that the Second Circuit would permit it. And definitely, I don't think it would ever get to the point where the Supreme Court would permit it. And now, the DHS has been fully funded with the exception of ICE and CBP. But nevertheless, that's still part of the appropriations process. So if the Republicans end up funding it for the next three years, then they won that debate. And that's not the issue. But if somebody individually can show that their civil rights were violated by a masked person, then they still have those lawsuits and abilities to file those cases.

9:20Since we're speaking about ICE making arrests in cities, let's turn to D.C. and a judge's order there. Judge Beryl Howell ordered the federal government in December not to arrest anyone in D.C. for civil immigration offenses without an administrative warrant. Tell us first what ICE normally needs to arrest someone. Well, this is where it gets very complicated because it depends where the arrest is occurring. So normally before the Trump administration, or we were just talking about the last 30 years of the country without really getting into post-Trump and injunctions and everything else, If you wanted to go into someone's house or into a private location, obviously you needed a warrant to be able to engage in that arrest.

10:11But if you were patrolling out in the street, then all you would need generally is a reasonable suspicion that the person is not here legally in order to arrest them if you were ICE. And in fact, that is the decision that Justice Kavanaugh wrote in the most recent Supreme Court decision in this topic. But what had happened in the D.C. district court litigation is that the district judge had said that there weren't these pre-arrest individualized escape determinations that were made for people who were randomly being arrested out on the street. And so what they wanted was, and let me just explain this for your listeners in plain English, what they want to limit ICE to do is basically go off of a list every day that they would get warrants for these people's arrests and they would then go off of their list and do it, but not randomly start picking people off of the street and making arrests.

11:14So now what the court had ordered, and this was in December of 2025, the court had actually issued a preliminary injunction saying that you couldn't just arrest people in the street if you thought they were here without a status unless you actually made a probable cause finding that the person is likely to escape before a warrant can be obtained. So that was the new sort of standard. So they didn't say you needed a warrant to arrest people out in the street, but you at least needed some type of probable cause finding that would be done vis-a-vis some sort of paperwork that you can then show after the fact.

11:54And then now the more recent debate is, well, what does this mean, likely to escape? And the government position was that they were assessing you by looking at you and saying you were going to run away. And what the court held is, no, it's not that. It's are you actually trying to avoid legal process? And only if you could prove that, that basically you were in hiding, you were a fugitive, could you actually be arrested out on the street without a warrant? And so that's where we are at right now. What did the judge find? Well, what the judge said was ICE wrote a memo that was defining what an escape risk is.

12:35And the actual definition is likely to escape before a warrant can be obtained. And so you have to actually make that determination. And so then ICE said, fine, we're going to write a memo training our officers. and the training of the officers, their memo had to do with factors that made someone an escape risk in terms of how you observed the person. And that's not what the court thought was sufficient. They said you actually had to know that the person was a fugitive, essentially, and that they had no residence, no family, no employment, other things tying them here, because any of those things tying them here would mean that they weren't an escape risk because they had the residents you could always visit or the family you could always visit or the employment you could always visit.

13:25So if you weren't taking those things into account, you couldn't just arrest someone in the middle of the street. So it's only if you didn't have any idea where to find these people and they were fugitives and you just happened to run in front of them, could you arrest them without a warrant? Otherwise, you need to get a warrant. Now, I don't know if such a sort of hamstringing order is ultimately going to be affirmed when it gets to the Supreme Court. But this is sort of the way these civil litigation matters have been working is the district court puts in pretty tough standards on ice. And then they work their way through the courts and we see what we end up with.

14:06Have any other judges put similar kinds of orders in place? Well, what's been happening is in places like Los Angeles and in Portland and in other places, they've tried to say just generally that ICE can't have arrests without warrants. So they're all trying to do the same thing where they're trying to say, ICE, you need to work off of a list. You can't just start arresting people in the middle of the street. Those were concerned with racial profiling and other things of that nature. But those injunctions were subsequently overturned by Justice Kavanaugh in a decision in the shadow docket where he said, no, no, no, there can be a reasonable suspicion.

14:46And here you can look at are they in a location where it's common that undocumented people are there? Are they in a profession where it's common? And people started calling those Kavanaugh stops. And there's some belief that maybe he has come to regret that based on the events that have happened. But in any case, it hasn't been overturned. And so this decision, if it gets back to the Supreme Court, will probably tee up again this larger issue of what is ICE permitted to do and when is ICE permitted to do it. Coming up next, I'll continue this conversation with Leon Fresco. The Trump administration is now targeting naturalized American citizens.

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17:57Here today, roam tomorrow. Join now at Sonesta.com. Terms and conditions apply. The Trump administration appears to have a new target in its aggressive immigration agenda. naturalized U.S. citizens. The Justice Department filed 11 denaturalization cases in federal courts across the country on Friday. It's a procedure that's rarely been used by prior administrations. In fact, between 1990 and 2017, the government filed an average of 11 cases per year. I've been talking to immigration law expert Leon Fresco of Holland and Knight. Leon, how have prior administrations treated the denaturalization process?

18:41For example, when you were in the Obama administration. There were two famous kinds of cases where denaturalization occurred. The first and the most famous were for Nazi war criminals. So people, you didn't know they were Nazis. They got to America somewhere after World War II. You don't know exactly where. And then it turns out because you did a bunch of genealogical research, You realize, oh, no, no, no, this person was a Nazi or was working in a war camp. And sometimes they'd be 85 years old, 90 years old or whatever. And it was just a matter of, hey, you lied about being a Nazi. You're getting deported.

19:16End of story. We're denaturalizing you. Those would happen a few times a year. That was the main one. The second one and one that started becoming more common was after the U.S. became a technologically dependent country where we started getting fingerprints of people and we started taking DNA, we started realizing that there were a large number of people who had been deported, changed their name and come back in and tried to create a new identity. And so that was a large group of people that the government also tried to prioritize because it said, wait a second, I mean, you can't just do that.

19:53That defeats the whole point of the immigration system if you're going to get deported and you're going to say well i was john smith when i first came but now i'm going to avoid this by saying i'm jerry smith and that's the end of that so no that was the second but now the trump administration appears to be basically trying to say what we want to be able to do is have this as a law enforcement tactic to make people very worried that they're never secure in the united states such that you could always be denaturalized for any reason. And what they're basically saying is if you do something that really makes us concerned about your behavior, we're going to start looking at everything that was filed in the past to find something where you wrote something inaccurately so that we can then say you lied on your citizenship application or your green card application and denaturalize you.

20:46And the thing is, if you really look at any application closely, you could probably find something. And the The materiality test really matters here because, for instance, there's a very famous question about organizations. And a lot of people put, I wasn't in any organizations. And they might say, well, why didn't you say that you were in the Red Cross? Or why didn't you say that you were in this fraternity or something like that? And you're like, well, I didn't think that was what you meant. I didn't think that was a big deal. So it's things like that where they can really start to bear down and find things out and say, well, you didn't put those on your application, so you lied to us, and now we're going to try to denaturalize you.

21:27And then it'll be up to the adjudicator to decide if that was a material misrepresentation. I mean, what they're doing now seems to be targeting naturalized citizens. Last year, DHS officials were told to refer upwards of 200 cases for denaturalization a month, just like immigration officials were given targets of 3 ,000 immigration arrests a month. Correct. So normally, again, these would be very, very serious cases that would come to the attention of the department for some sort of national security reason, where you said, wait a second, somebody slipped through the cracks because they made up a name or whatever they got through the system.

22:08Now there is this effort to say, how do we find people that we can denaturalize, essentially? And I think the key is, like anything in life, is how is this going to be used at the end of the day? If it's going to be used because we're really taking a focus at people who are really national security risks that we weren't looking at, okay, I can maybe understand it. But if it's going to be used to basically say, this is a person I want out and I can't get them out, let's look for a reason to get them out, then that's not a traditional way that the denaturalization process has been used. Having said that, if the lie was material enough, then the denaturalization is appropriate.

22:50So, for instance, if you were in the middle of a trial for some criminal proceeding and you didn't report it and they said, you know, had you reported it, we might have not given you the citizenship. That's the kind of thing that is material. That is the kind of thing where they're going to be looking and giving it a lot of scrutiny, where it starts to get more problematic. And again, I am of two minds on all of these things because you can find one argument for one argument against. Is let's say somebody has an opinion that they are holding out now on May 11, 2026, that you don't like and that you think is destructive to the concepts of America.

23:33up, but they're a naturalized citizen. The question is, can you say on the basis that they're articulating that opinion now that they lied on their citizenship application at the time because they held those views at the time and should have disclosed that they held those views? That's the key question. And that's going to end up being one of these cases at some point. And that's, I'm sure, going to get adjudicated. It's a long process, isn't it, to try to denaturalize someone? It's not easy. Well, you have to file a complaint in the district court and you have to have a probable cause memo that gets attached saying what is the evidentiary basis for the material misrepresentation that was done on the citizenship application.

24:16And so when it's straightforward is you said you had never been convicted of a crime, but it turns out we found this record in Montana in 1981 that you had been convicted of, you know, child molestation. okay you're out that's going to be an easy one but for these where we're trying to defer your intent based on things that happened after your citizenship let's just say that they say you lied on the question of do you fully intend to support the united states and take an oath of allegiance let's just say it's that one which is a very broad range question and then now you start articulating sentiments oh america's the worst we're doing wars in a bunch of places and things like that and i'm not saying i support those sentiments i'm just trying to give a fact pattern here so if you start articulating those sentiments, can they then say, well, now that you're articulating those, that shows that you clearly lied, that you were attending to have allegiance and support to the U.S.

25:10And if we end up getting cases like that, that's going to be very interesting to see how the courts rule on those. They're not going to net high numbers here that they can tout. So what's the real purpose of this? It seems like it's going to make a lot of naturalized citizens feel uncomfortable and like second class citizens? I think there's two points here. The first point is to say to everyone who was not born in the United States, don't rest on your laurels. If you get us angry enough, you could be deported. It doesn't even matter that you're a citizen. So don't just think that you're going to be able to say I'm a citizen and I can start doing things that might attract attention.

25:48So that's one. It's sort of this larger deterrent umbrella that's trying to be built, telling everyone who was born outside of the United States, be very careful how you're behaving here, because you could come under the attention of people who will then denaturalize you. So I think that's number one. But then number two, it's saying to everyone going through the process, hey, this is never going to be done. So you've got to be careful. There will never be a time where you can rest easy in the United States. So just know that while you're going through this system. And so I think it's designed to create uneasiness in both of those areas.

26:25I remember that before they actually met in the Oval Office that Trump threatened Mayor Zoran Mandami, New York City Mayor Zoran Mandami, who's a naturalized citizen with this. And that would have been that exact kind of case we discussed, which is if there's things you don't like about what someone is saying now, can you say that when they were saying that they supported fully the United States at the time of their naturalization that they were being honest. And I think that's going to be one that would be very interesting for litigation. Finally, and we've talked about this before, that is the Trump administration's policy of mandatory detention for non-citizens.

27:06So non-citizens not being able to get a bond hearing. And that issue has already split the circuit courts. And now it appears it's going to split them even more. So there's been a couple of decisions. The Seventh Circuit has said that ICE is incorrectly determining that if you snuck into the country and you've been here for some large amount of time, that when the government finds you, it can keep you in detention for the entire time that your deportation case is going on without giving you a bond hearing. And we discussed this last time about, well, why is that a big deal? What does it matter?

27:41Well, The reason it's a big deal in 99 % of criminal cases, if you are accused of a crime, you still get a bond hearing. You still get the chance to say that, hey, I'm not a danger to society. I'm not a flight risk. Let me out while my criminal case is pending. So deportation is not even a criminal case. It's what's called a civil case. So the government has even a less constitutional ability to put you in what's called civil detention as opposed to criminal detention. So the question is, if constitutionally the government is going to put you in civil detention, the idea is that it should be a very, very, very clear statement from the Congress that says that they wanted you to do this.