
Millions of Americans were in the streets over the weekend, rallying against President Donald Trump and his administration's latest authoritarian escalations. Organizers for the 'No Kings' protests said more than 7 million people turned out to more than 2,700 pro-democracy rallies across the country. Republicans tried their best to demonize the protesters saying the "hate America" demonstrations would be filled with radicals and violence. But, as it turns out, the protests were almost entirely peaceful. Chicago, Illinois, a focal point for the administration's crackdown on immigration, was just one of the cities that saw people gather in solidarity against Trump. So to talk more about the latest regarding Immigration and Customs Enforcement, the back and forth on National Guard deployment, and what's really happening on the ground there, we spoke with Monica Eng. She covers Chicago for Axios. And in headlines, the Israel-Hamas ceasefire faces its first major test, Trump says he's ...
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Todd Zwillick
It's Monday, October 20th. I'm Todd Zwillick in for Jane Coston. And this is what a Day, the show where only a king has the power to make George Santos a queen for a day. On today's show, the Trump admin administration continues to inflict pain on everyday Americans as leverage in a still ongoing government shutdown. Israel and Hamas exchange deadly fire in Gaza, threatening the ceasefire. President Donald Trump accuses the president of Colombia of being a drug dealer while he continues to unilaterally kill people on boats in the Caribbean. And Ukraine steps up attacks inside Russia as Ukrainian President Volodymyr Zelensky waits for an answer on American cruise missiles. But let's start with the massive turnout at Saturday's anti Trump rallies. Millions of Americans took to the streets over the weekend for the no Kings protests, demonstrating against Donald Trump and his authoritarian vibes. Organizers said that more than 7 million people turned out to more than 2700 pro democracy rallies in rural towns and major cities all across America. It was the second wave of protests organized by the no Kings network of progressive organizations. The protests were almost completely peaceful. And that's not the framing Republicans were looking for. Last week on Capitol Hill, GOP lawmakers predicted hate America demonstrations filled with pro Hamas radicals in New York City, where more than 100,000 people demonstrated. The NYPD reported zero arrests. Here's House Speaker Mike Johnson reacting to the peaceful nature of the protests on abc, who on Sunday morning, I've never called anybody an enemy, but we call out Hate America rally or, you know, antifa pro Hamas. That sounds. Those are enemies. Well, there were a lot of hateful messages yesterday. I mean, we have video and photos of pretty violent rhetoric calling out the president, saying fascists must die and all the rest. I mean, I don't think that's loving speech. I don't think that's friendly speech. And I don't think it's pro American to say those kinds of things. Trump also responded to accusations of being called a king on Fox News.
Donald Trump
A king.
Todd Zwillick
This is more than king.
Donald Trump
You know, they're saying they're referring to me as a king.
Todd Zwillick
I'm not a king. Right. Not a king is not what Donald Trump's social media operations had to say. The official White House social media accounts posted pictures of both Donald Trump and Vice President J.D. vance wearing golden crowns and sitting on thrones. And if that's not gross enough for your civic sensibilities, let's try your stomach. Trump also posted an AI video to Truth Social depicting himself again wearing a Crown this time taking off in a jet fighter and bombing. No King's protests in the streets below with, and I can't believe I'm about to say this, torrents of shit. Take it as a metaphor. Take it as a threat. One of the things that folks rallied against is the ongoing threat of Immigration and Customs Enforcement officers raiding cities around the One of those cities getting a lot of attention, of course, is Chicago. You can't get on social media without seeing disturbing arrests happening in and all around the city. I wanted to know what's really happening on the streets in Chicago, so I spoke with Monica Eng, who covers Chicago for Axios. Monica Eng, welcome to what a Day.
Monica Eng
Thanks so much. Happy to be here.
Todd Zwillick
Well, there's been a lot of back and forth and a lot of attention in the last month or so about ICE operations in Chicago. Of course, we're seeing tons of videos, tons of coverage, a lot of iPhone videos from the streets, and some of them are disturbing. Set the scene for all of us. What's happening with ICE in Chicago right now?
Monica Eng
Well, I mean, you can live your life and not know anything about it. Walk around, have a great time, have 100,000 to 250,000 people march in a no kings march, have 50,000 in the Chicago Marathon and see nothing. But if you go on your social media feed and if you watch the news, you are seeing some really disturbing images. So it's sporadic and terrible, but not so noticeable in people's everyday lives.
Todd Zwillick
So let's talk about Broadview. People might have heard that name. What is Broadview? How does it operate, and why is it important in this story?
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Monica Eng
Broadview is an ice processing facility that's been there for at least 19 years. And it's been the subject of weekly Friday prayers by clergy. Friday for at least 19 years, where they pray for the people inside. And, you know, they said in the past they've actually been able to visit them, bring them things, sit on the bus with them as they're taken to detention. In more recent months, it has actually become a detention facility, which is actually illegal in Chicago in Illinois, to have. But we're told that they're not kept there for that many days. Congressional representatives for Illinois have asked repeatedly shown up in person, to please be able to go inside to see what it's like. They've not had the opportunity. So it's become a focal point, especially on Friday mornings, for not just those clergy who've been going for years, but for protesters. Not an organized group, I should say. I was told by the Department of Homeland Security. This is all organized and they're busing people in. I haven't found a single person who's been bussed in. It's a very ragtag, disorganized group that shows up. They can't even agree on what chance they're going to do. There's a very elderly hippie clergy group that likes to sing songs from a song sheet that are adapted from Bible songs. And then there's your usual group of people or single people who want to shout obscenities at law enforcement. So it's very much a decentralized and disorganized group. But when I interview them, they all say that they are there to protest what's going on inside. They like more transparency and more accountability about what's happening in this process facility that has become in many ways a de facto detention facility.
Todd Zwillick
So what you're describing sounds very, very different from the story coming from the Trump administration, which would, which would tell you to expect antifa affiliated terrorist aligned agitators outside of Broadview. That's not what you're seeing. But what's been happening when ICE interfaces with whatever protests are there? What kind of tactics? What does it look like?
Monica Eng
Well, it's a great question. End of September, I was there. Hundreds of people showed up on a Friday morning. And those hundreds of people, again, ragtag, very disorganized, but they would try to approach the facility. There were ICE agents on the other side who without any rhyme or reason, would start shooting rubber bullets, pepper spray and throw tear gas canisters. No one knew exactly when this was going to happen. When I went on Friday, by order of a judge, the fence came down finally. But there are now barricades and it's the Illinois State Police that is enforcing the barricades and the restrictions on how close protesters can get. They brought out the Illinois State Police, who did have batons and did push people back, but they were able to get them to go on the grass or the sidewalk without tear gas, without rubber bullets, without any pepper spray, which it seemed the federal authorities really felt they needed or deployed constantly, without rhyme or reason. This was very clear. If you do not move to the sides of the street, you will be arrested. And there were some arrests. But this idea that, oh, federal agents, they need help because they're being attacked. And so we need to send in the National Guard. The Illinois State Police did this in about two minutes, no problem. Everybody stood on the side and then they sang Bible songs.
Todd Zwillick
So let's move beyond Broadview and add onto the streets of Chicago where ICE is interfacing with people on the streets, American citizens, immigrants and undocumented immigrants. To be sure. We've already mentioned that the video tactics might have a distorting effect. Everyday people in Chicago aren't seeing this. We on the Internet definitely are seeing it. Can you start to categorize the quality or what interactions between ICE and people on the streets, who they want to apprehend, look like? What happens when ICE finds somebody who they're interested in?
Monica Eng
Well, the typical scenario seems to go ICE apprehends someone or ICE goes on a street and then people come out. Now, if someone has a whistle around their neck, you know, they are of a certain ilk. It's whistlemania in Chicago. People are carrying whistles on them because it's three blows. And if you see ice, a long blow, if they're actually apprehending someone. So when that signal goes out, there are rapid response teams and then there are others who simply know in those neighborhoods to come out, sometimes they surround cars, sometimes they say, what are you doing? They ask the person what their name is, what their birthday is, so that they can track them. And then it seems, even in some cases without apprehensions, ICE will toss out a canister of tear gas. The temporary restraining order by federal Judge Sarah Ellis says you must issue two clearances, audible warnings, before using any tear gas. And you cannot use tear gas on journalists or peaceful protesters. Also, they're supposed to absolutely very clearly identify themselves with a serial number or identification. They also cannot throw people down to the ground unless it's absolutely necessary for their apprehension and they pose an immediate threat. And yet Sarah Ellis is calling all parties back into court on Monday saying, I'm seeing some disturbing things that make me think that my TRO is not being abided by. What DHS is saying is, oh, these incidents, this was all Customs and Border Protection guys. So you don't even want to talk to the ICE guys. And a lot of people don't know the distinction. Customs and Border Protection usually works around the border. Ice, they go all over the place. Governor JB Pritzker said, wait a minute. Why is Customs and Border Protection here in Chicago? We're not on a border. Guess what? Hundred mile zone, maritime border. I am working with a lot of immigration experts and lawyers to say how often has this hundred mile zone constituting Chicago as the border because of Lake Michigan really been invoked to bring Customs and Border Protection to Illinois and Chicago? I mean, to the point where the Governor Was like, I don't understand why Border Protection is here. But the DHS officials tell me that, yes, Chicago is in the hundred mile zone and so fair game.
Todd Zwillick
So wait, you say that. Does that mean that for the purposes of ICE agents in Chicago, the border is the Lakeshore, Lakeshore Drive.
Monica Eng
Well, for the purpose of Customs and Border Protection agents who are separate from ICE agents and those CBP agents, they can conduct warrantless seizures. They have extra powers that ICE officers do not have. And so that is what I am investigating right now is it seems like lots of warrantless searches have happened.
Todd Zwillick
Monica, what about Americans, American citizens? ProPublica had a report just before the weekend saying that 170Americans. Minimum. Minimum. That was only the estimate they could come up with. So just total basics. If I'm on the corner of somewhere in the Loop, I'm in Chicago, ICE walks up on me and says, do you have proof of citizenship? And I say, I don't. I'm not carrying my passport. Can they handcuff me and hold me until I can prove to their satisfaction that I was born here?
Monica Eng
Well, they've certainly handcuffed people who had not committed a crime. I mean, according to the tro, you cannot arrest someone who is not suspected of a crime. I don't know what crime older person, Jesse Fuentes was suspected of when they handcuffed her. The crime that supposedly Debbie Brockman was killed suspected of was throwing something at an ICE car. She claims she did not. So, you know, I wouldn't tell anyone that they were 100% immune to arrest if they didn't have papers proving that they are an American citizen when they're standing in Chicago.
Todd Zwillick
So now at the federal level here in Washington, Donald Trump has gone to the Supreme Court asking for them to give permission to move National Guard troops in. We've seen temporary restraining orders. You have a hearing on Monday governing ICE and Border Patrol tactics. What's your take on the legal posture right now and what kind of boots on the ground Chicago could be seeing in the next week or so?
Monica Eng
Well, I mean, it really depends on how this Supreme Court issue goes. Both the appeals court and the federal court. Judge April Perry said, you know, when I look at the accounts, I've been in Chicago News for 40 years, and I've seen some fibs and some tweaks coming of the truth coming out of government. I have never seen any government press releases that were so far off from the truth I've seen on the ground as the ones that I've gotten from dhs. And this is what the judge pointed out. She just says that the information that DHS is providing is unreliable. And let's just see if the Supreme Court also feels it's as unreliable in whether they grant or they deny the deployment of National Guard troops in Chicago.
Todd Zwillick
Well, before we go, just talk about that a little bit more. I mean, you've been on the streets and in the houses of Chicago for many, many decades. People will know that there have been lots of protests in Chicago going back over the years, including the last few years during the Trump era, all the way back to 1968 and the Democratic National Convention riots at that time. Is this fundamentally different than anything that you've seen before in terms of protests, protest and how federal agents are responding?
Monica Eng
Well, the federal response is nothing like I've ever seen. You know, we've never had the National Guard being threatened. We've never had anyone threatening to deploy the National Guard on Illinois against the will of our governor. I mean, it's, you know, we're seeing one unprecedented thing after another. I was here covering the Laquan McDonnell protests, the George Floyd protests, and those were very, very, very strong. You know, what we saw with the no Kings protest, so peaceful. Huge, enormous, but very peaceful. But people, I think part of that is the ICE tactics in Chicago and people in Chicago are fed up. But by and large, what I have seen is completely peaceful. And this characterization, and I read it in the press releases, that rioters are attacking federal law enforcement is just not compatible with what I see with my own eyes.
Todd Zwillick
And federal judges don't seem to believe it either. They've said so in their rulings.
Monica Eng
Exactly. And several courts, I mean, what April Perry said was, we've had four courts just this week tell us that what you are charging is not compatible with the truth. So why should I believe it? So that's what we're seeing at this point.
Todd Zwillick
Protest is not rebellion. I think is a quote from one of the judge's writings in those.
Ad Host / Advertiser
Right. Yeah.
Todd Zwillick
Monica Eng, thank you so much for joining us.
Monica Eng
Thank you.
Todd Zwillick
That was my conversation with Monica Eng. She covers Chicago for Axios. We'll link to her work in the show Notes. We'll get to more news in just a moment. But if you like the show, make sure to subscribe. Leave a five star review on Apple Podcast. Watch us on YouTube and share it with your friends. More to come after some ads.
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Todd Zwillick
Here'S what else we're following today.
Monica Eng
Headlines I know that things feel like they're going well, but we don't have any data. The government is shut down. How long is this going to last?
Donald Trump
Look, the Democrats are kamikazes right now. They're kamikaze pilots right now. They have nothing going. They have no future. They have incompetent candidates.
Todd Zwillick
Encouraging words there from the President of the United States as the government shutdown nears its third week with no end in sight. Democrats want to extend health insurance subsidies, but Republican leaders refuse to negotiate until Congress approves short term funding to reopen the government. Hence the standstill. In a pre recorded interview that aired on Sunday, Trump proudly told Sunday Morning Futures host Maria Bartiromo that the shutdown unties his hands.
Donald Trump
Now what we're doing is we're cutting Democrat programs that we didn't want because I mean, they made one mistake. They didn't realize that that gives me the right to cut programs that Republicans never wanted. You know, giveaways, welfare programs, et cetera. And we're doing that and we're cutting them permanently.
Todd Zwillick
The thing about cutting programs Republicans never wanted, these programs exist because Trump and Republicans agreed to them and signed deals, including them. So one interesting question lingering behind this shutdown can you make a deal with the guy who'll break it whenever he wants anyway, Trump is trying to fire, not just furlough, thousands of federal workers across the Environmental Protection Agency, the Department of Education and other agencies. Congressional Republican leaders have mostly shrugged, saying that's the cost of not doing business. Israel's military carried out a wave of deadly strikes in Gaza Sunday, killing at least 36 Palestinians across the territory, including children. Israel accused Hamas of violating a recently brokered ceasefire by attacking Israeli troops Earlier in the day. Israel says Hamas killed two soldiers and injured three others. The Israeli Defense Forces also said the transfer of aid to Gaza was halted. Hamas, which has not yet given up its weapons, is accusing Israel of arming Palestinian gangs it calls criminal looters operating in the Israeli controlled half of the Gaza Strip, an anonymous source told the Associated Press. The Israeli military resumed enforcing the ceasefire and an official confirmed that aid deliveries would resume today. A little over a week has passed since the start of the US Proposed ceasefire aimed at ending two years of war. The violence is the first major test of the fragile ceasefire between Israel and Hamas. Ukrainian drones struck a major gas processing plant in southern Russia, forcing it to suspend imports from Kazakhstan, authorities said on Sunday. Kyiv has ramped up attacks in recent months on Russian energy facilities, which it says both fund and directly fuel Moscow's war effort. The strike comes after Trump hosted Ukrainian President Volodymyr Zelensky at the White House on Friday. Now, contrary to Zelenskyy's hopes, Trump did not commit to giving Ukraine Tomahawk cruise missiles that could strike deeper inside Russia. Here's Zelenskyy speaking with NBC News after the meeting Friday. It's good that President Trump didn't say.
Monica Eng
No, but for today, didn't say yes.
Todd Zwillick
Now you might be feeling a little bit of whiplash. Just a week ago, Trump had floated the idea of sending Ukraine Ukraine new weapons. Then last Thursday, Russian President Vladimir Putin called and voila. Trump now appears to have edged back in the direction of no cruise missiles and pressing Ukraine to give up land lost to Russia in exchange for an end to Moscow's aggression. In an interview, Trump said as much to Maria Bartiromo of Fox News. Here he is talking about Putin.
Donald Trump
Well, he's going to take something. I mean, they fought and he has a lot of property. I mean, he's one certain property. If you say that he's one certain property. We're the only nation that goes in and wins a war and then leaves.
Todd Zwillick
Yeah, why can't we pillage more like Vladimir Putin does? Trump's attitude is, hey, Putin deserves the land he attacked. I deserve a trophy like a Nobel Prize. President Trump said in a Truth Social Post on Sunday that he'll be ending financial aid to Colombia, one of the United States closest Latin American allies. Trump's announcement comes in response to Colombian President Gustavo Petro accusing him of murder over extrajudicial U.S. airstrikes against alleged drug traffickers in the Caribbean Sea. Trump called Petro, quote, an illegal drug dealer who does nothing to stop the production of drugs in his country. He said Petro better end drug operations or the U.S. will, quote, close them for him and it won't be done nicely. Petro responded on social media saying, quote, trying to promote peace in Colombia is not being a drug trafficker. Also on Sunday, Defense Secretary Pete Hegseth announced US Forces attacked a Colombian ship tied to a leftist rebel group, although he provided no evidence for that claim. Meanwhile, survivors of one of the airstrikes in the Caribbean are being repatriated to Colombia instead of being held or charged in the United States. Petro has pushed back against Trump's characterization of his country and claims the strikes are a violation of Colombian sovereignty. He says one of the attacks in September killed a fisherman with his distress signals activated, and he questioned Trump's motives in a statement over the weekend. Petro says there when it comes to dealing with the issue of the Caribbean Sea, which has nothing to do with fentanyl, what the United States is is saying is that it wants oil from Venezuela and Guyana. Oil greed is behind the strategy that is firing missiles at fishermen. And that's the news. Before we go In Bravo America, a special Love it or Leave it series, John Lovett dives into the reality TV universe to figure out how our nation's trashiest pastime took over not just our screens, but our entire culture, from the politics of fame to the performance of authenticity. He's getting real about what happens when real life becomes entertainment. This week, he's talking to Survivor legend Parvati Shalow, the black widow who turned flirtation into strategy and outwitted almost everyone. They'll get into how she stumbled into stardom right after college and how her reality TV Persona followed her off screen. That's Bravo America every Tuesday on the Love it or Leave it feed and on YouTube. Subscribe so you don't miss one darn episode. That's all for today. If you like the show, make sure you subscribe, leave a review, contemplate what you can accomplish in just seven minutes and tell your friends to listen. And if you're into reading and not just about how robbers took just seven minutes to break in and steal the crown Jewels from inside the Louvre in broad daylight. Like me, what a Day is also a nightly newsletter. Check it out and subscribe@crooked.com subscribe I'm Todd Willick. Someone brazenly stealing in broad daylight. Has anyone checked on George Santos? What a Day is a production of Crooked Media. It's recorded and mixed by Desmond Taylor. Our associate producers are Emily Foer and Chris Allport. Our video editor is Joseph Dutra. Our video producer is Joanna Case. We had production help today from Greg Walters, Matt Berg, Sean Ali and Tyler Hill. Our senior producer is Erica Morrison and our senior vice president of news and politics is Adrienne Hill. Our theme music is by Colin Gilliard and Kashaka and we had help today from the Associated Press. Our production staff is proudly unionized by the Writers Guild of America East.
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Podcast: What A Day (Crooked Media)
Host: Todd Zwillick (in for Jane Coaston)
Episode Title: Over 7 Million Americans Protested Against Trump
Date: October 20, 2025
This episode dives into the massive nationwide protests—dubbed the "No Kings" rallies—against President Donald Trump's increasingly authoritarian policies and rhetoric. Host Todd Zwillick breaks down the surprising scale and overwhelmingly peaceful nature of these demonstrations, unpacks political and media reactions, and leads a detailed interview with Chicago reporter Monica Eng exploring on-the-ground realities about ICE (Immigration and Customs Enforcement) operations and federal responses in Chicago. Additional segments touch on the government shutdown, foreign policy crises, and escalating tensions in immigration enforcement.
“We have video and photos of pretty violent rhetoric calling out the president, saying fascists must die and all the rest. … I don't think that’s pro American.” — House Speaker Mike Johnson [01:59]
“Take it as a metaphor. Take it as a threat.” — Todd Zwillick [02:49]
“Now what we’re doing is we're cutting Democrat programs that we didn't want ... and we're cutting them permanently.” — Donald Trump [20:19]
“Well, he's going to take something. ... He’s won certain property. If you say that, he's won certain property. We're the only nation that goes in and wins a war and then leaves.” — Donald Trump [23:36]
For listeners seeking a clear-eyed snapshot of America’s political landscape in late 2025, this episode provides essential context, vivid street-level reporting, and an unvarnished look at the gap between official narratives and ground realities.