What A Day - Chicago Fights Back

Episode Date: November 4, 2025

A federal judge once again blocked the Trump Administration from sending the National Guard to Portland over the weekend — but if Trump is successful in the courts, Portlanders can look to the great city of Chicago for a preview of what may be in store. Since ICE began operations in September, there have been violent raids on apartment buildings and near-constant activity from aggressive federal agents rounding up immigrants who are being kept in facilities reportedly full of cockroaches and with horrifying examples of overcrowding. And, in some cases, US citizens are getting detained, too. Chicago Mayor Brandon Johnson has faced the brunt of Trump’s attacks on the city, while also reckoning with Chicago’s crime rate and affordability crises that many big cities also face. We sat down with the Mayor to talk about what it’s been like to face down the President while trying to manage the nation’s third-largest city.And in headlines, President Trump’s tariffs are at the Supreme Court this week, a rundown of the high-profile Election Day races, and 20 Democratic-led states sue the Trump administration over a rule that could block certain public servants from getting their student loans forgiven.Show Notes:Call Congress – 202-224-3121Subscribe to the What A Day Newsletter – https://tinyurl.com/3kk4nyz8What A Day – YouTube – https://www.youtube.com/@whatadaypodcastFollow us on Instagram – https://www.instagram.com/crookedmedia/For a transcript of this episode, please visit crooked.com/whataday Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

It's Tuesday, November 4th, happy election day, and happy birthday to my dad. I'm Jane Koston, and this is what a day, the show celebrating House Speaker Mike Johnson's commitment to never seeing or hearing or knowing anything about anything ever. Here he is Monday with another stirring example while talking to CNN's Manu Raju. Last week, you were very critical of Joe Biden's using the auto panic, he's parted, he said he didn't even know if he was pardoning. The last time in 60 minutes, the president, President Trump, admitted not knowing he parted a crypto billion guilty to money laundering. Is that also concerning me? I don't know anything about that. I didn't see the interview.

You have to ask the president about that. I'm not sure. He never is. On today's show, it's Election Day in America. Get out to vote and plant the seeds of good news that we can harvest. for you later. And Trump hopes for terrific news from the Supreme Court that will determine the legality of his favorite stick. I did not

write that joke. But let's start with immigration and immigration and customs enforcement. A federal judge once again blocked the Trump administration from sending the National Guard to Portland, Oregon over the weekend. The preliminary injunction, in place until November 7th, comes as the judge says she is still, quote, in the process of diligently reviewing all the evidence to determine and whether or not the president can send troops to the allegedly war-ravaged city.

Portland can look to the great city of Chicago for a preview of what it might face if Trump succeeds in court. Since ICE began operations in September, there have been violent raids on apartment buildings and near constant activity from aggressive federal agents rounding up immigrants, who are being kept in facilities reportedly full of cockroaches and with horrifying examples of overcrowding. And in some cases, U.S. citizens are getting detained, too. Last week, federal officials released tear gas near the start of a Halloween parade for children, resulting in the parade's cancellation. And President Donald Trump thinks that ICE hasn't gone far enough. Here he is on 60 Minutes with Nora O'Donnell on Sunday.

More recently, Americans have been watching videos of ICE tackling a young mother, tear gas being used in a Chicago residential neighborhood, and the smashing of car windows. Have some of these raids gone too far? No, I think they haven't. gone far enough because we've been held back by the judges, by the liberal judges that were put in by Biden and by Obama. Gross. Chicago Mayor Brandon Johnson has been in office since 2023. He's faced the brunt of Trump's attacks in the city while also reckoning with Chicago's crime rate and affordability crises that many big cities also face. I wanted to ask him about what it's been like to face down the president while trying to manage the nation's third largest city.

So I sat down with the mayor on Monday afternoon. Mayor Johnson, welcome to what a day. Hey, thanks for having me. The president's reasoning for all of this, immigration enforcement, his attempted National Guard deployment, is that Chicago is just plagued with crime, and he called it the most dangerous city in the world, which is bullshit. It just is. Chicago historically does have a higher crime rate than other cities, but what's your response to the president's claims?

Well, first of all, since I've taken office, violent crime has gone done every single year. It's my top priority. raising a family in Chicago on the west side of Chicago. I'm the first mayor in modern history to wake up in one of the most disinvested communities in the entire city of Chicago. What's so disruptive or disturbing about the president's claim not only is violence down in our city,

the president withheld $800 million that was earmarked for violence prevention, $800 million, and then he cut the ATF budget by 30%. Now, my local police, Department has worked with ATF to get illegal weapons off the streets of Chicago that are being trafficked in from states that voted for Donald Trump. Indiana, like, there's a very well-down path of guns making it from other states into Chicago. Absolutely. And just a few months ago, we were able to remove over 170 high power

weapons off the streets of Chicago. And then we actually put forth a lawsuit. We sued a manufacturing company, they were making a product that made it easier for that product to be turned into a high-powered machine gun. That lawsuit that we put forward, this company has decided to discontinue this particular weapon. Now, look, I'm working hard every single day to make the critical investments in our communities, whether that's in youth employment, where we hired over 31,000 young people for summer jobs, or expanding mental and behavior health care. And so this president is off-base completely. He's not having conversations with me

or Mayor Brandon Scott in Baltimore, or Randall Woodfin in Birmingham or Karen Bass right here in Los Angeles. He has put more money in ICE than any other president in the history of this country. In fact, the only budgets that are bigger than ice

is the United States military and China's military. This is his privatized police force to enact fear, anxiety, and terror in the streets across America, and in the city of Chicago, we're standing up in protecting people. I think it's so important to recognize how much of this, in my view, and I'd be curious as to your thoughts, is Trump's view of cities writ large, because he talks about Chicago in the same way he talks about Portland, in the same way he talks about New York, and he talks about Philadelphia,

and he talks about Baltimore. These are all cities. These are all worth mentioning, largely majority-minority cities. But what do you think are some of the specific challenges that Chicago faces with regard to crime? Well, first of all, the biggest challenge really is the fact that we have not had an administration that was dedicated and committed to investing in people. When we think about some of the neighborhoods in Chicago,

like Garfield Park, for instance, on the west side of Chicago, it has been described as a developing nation because the violence and the poverty per capita reflects that. And because the hyper concentration of poverty in the city of Chicago is quite severe and extreme. We have, you know, thousands of children who go to bed hungry, who are without homes. We've had administrations closed schools, shuttered mental health clinics, shut down public housing. And if you look at those neighborhoods where the violence was most pervasive, there's a direct correlation, I believe there, between the lack of schools, the lack of job opportunities and poverty. That's the issue.

That's the challenge. And that's why I'm demanding that the large corporations and the ultra-rich pay their fair share in taxes after receiving the greatest tax break in the history of America by President Trump. That's why in my budget, I'm investing in young people, youth employment. I'm investing in mental and behavior of health care. We're on pace to build 10,000 affordable homes by the end of our first term. These are the elements that really create long-term sustainability. And by making these critical investments in these communities, it's why you're seeing the decline of violence the way we're experiencing it

because we're going right at the root causes of these challenges, which, again, is poverty. Now, you are a mayor of a large city. And even without federal intervention, there's a lot to be done. It's a city that's facing so many simultaneous challenges that a lot of other cities are facing, but Chicago might be experiencing them first. So can you talk about some of those? Yeah. So it's affordability, environmental challenges, our education system. And so what I've done, we reinstituted the Department of the Environment, right?

Because I believe the way our economy is moving, we have to be able to create neighborhoods where they are. up for success for long-term sustainability. So we have a brand new initiative in Chicago it's called Green Social Housing. It's a part of my $1.25 billion bond investment to build affordable and sustainable housing throughout the city of Chicago so that we do not have to rely upon the federal government to initiate affordability. We also have something that's called TIF, the tax increment finance. So it basically allows for taxes to be frozen in a particular district. And And then when it's frozen, the accumulation of those dollars, that particular increment, can be used for economic development, right?

We know that there are TIF districts around the country, but particularly in Chicago, you know, TIFs were designed to go towards blighted communities, and that has not been the case historically. And so I'm using the TIF surplus, particularly in the areas where there's no longer blight, to actually reinvest in our public spaces, particularly our education system, our parks, as well. And then the other area of need is real economic development, particularly for our small businesses. And so my $1.25 billion bond investment is not just for housing, but it's for economic development as well for our small businesses. It's evident that there's work to be

done, right? But it's also evident that what Donald Trump is describing about Chicago, he is way off. It's a beautiful city. It's a diverse city. And then I also find it interesting that, you know, in 1986, when the first black mayor of Chicago was heading into his second term, it was Ronald Reagan that also declared war on American cities. And so our city has experienced this before where there's been a direct attack against Chicago, but we are battling the way Chicagoans know how, and we're doing that through our solidarity. You are now more than halfway through your term as mayor, and I know that there has been a tremendous amount of work done on,

reducing crime and a host of other issues because being mayor is hard. And you've had low approval numbers throughout your term. A recent poll shows your approval rating at 31%. What have you taken from those polls as you move forward as you're thinking about the work that you want to do, but also what you're hearing from the people who are answering those polls, what you're hearing from voters, your constituents, all of those folks? You know, people are charged to see government actually deliver on behalf of working people. And transformation is hard. You know, the city of Chicago has been through quite a bit. When I was first elected, there were buses that were being sent to Democratic-led cities across America from the state of Texas. And that caused

a great deal of tension. I mean, containing migrants. Yeah, I remember. You know, and it was a very trying time, right? When I became mayor, we had migrants sleeping on floors and police districts. That's what I inherited. There was no help coming from the federal government, and we stood firm. And though we took a strong hit there, I made a moral decision to look out for the least of these. Of course, throughout the campaign, it never really came up. But it was a crisis that I inherited. And now we have a one system initiative where we increased our shelter beds by 126%. So we took a challenge that was in front of us, and we turned it into a system that, quite frankly, Chicagoans have been calling for. And we added an additional $40 million to shelters across the city that needed,

you know, repair and transformation and upgrade. And so the numbers that I do pay most attention to are how we're investing in our public schools. How many more affordable homes are we going to be able to build? How many more young people can we hire in this budget? And I believe that as the people of Chicago continue to experience how government can be transformative, the rest will take care of itself. What have you learned that you're going to take forward to the rest of your term? Yeah. One of the things that I recognize that I should have done and what we're doing now,

I should have communicated more earlier in my administration. You know, I think I took it for granted that the work would speak for itself and that as long as the work was happening, people would just know, or see it, yeah, you see it happening. You experience it, or media would cover it mainstream, right? That was, you know, probably more optimistic than I should have been. And so now what we're doing, I'm going back to what I did to get elected and that I'm holding community meetings.

We're having town halls. Just last weekend, I went canvassing, knocking on doors again, talking to people, because I can't trust and rely upon mainstream, if you will, to deliver the story and the message to everyday Chicagoans. That's going to require me to make sure that people know the why. It's like there's a passage in the Book of Mark. My father's a pastor, so I, every now that I try to quote a scripture so that, you know, he's proud of me.

All right. There's the Book of Mark, and it was around chapter. where Jesus was talking to his disciples and he said, you know, beware of the way the Pharisees offer up their scribe. And he goes on to talk about the yeast of the Pharisees. So in other words, if you allow people who oppose you to tell the story, they're not going to tell the truth. And furthermore, those untruths spread like yeast. And I took away from that passage of scripture. or how important it is for us to tell our own stories, particularly as progressive leaders.

People will know what you're doing, but people have to know why you're doing it. And so now I'm doing a much better job of taking the message directly to the people so we don't have to worry about dismantling untruths that they can hear directly from my administration. So you're not going to hide your light under a bushel basket.

Oh, check you out. Come on. Speak the word. Yes, exactly. Mayor Johnson, thank you so much for joining me. You're welcome. Thanks for having me. That was my conversation with Chicago Mayor Brandon Johnson. We'll get to more of the news in a moment, but if you like the show, make sure to subscribe, leave a five-star review on Apple Podcasts, watch us on YouTube, and share with your friends. More to come after some ads. What a day is brought to you by OneSkin.

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level for a stronger, smoother, and more youthful-looking complexion. For a limited time, try OneSkin for 15% off using code Wad at OneSkin.co slash Wad. After you purchase, they'll ask you where you heard about them. Please support our show and tell them we send. you. Here's what else we're following today. Headlines. Good morning, everyone. We're on day 34 of the Democrats shutdown. Day 34, it's now officially the second longest shutdown in U.S. history. This is day 34 of the Trump Republican shutdown. And opposition as Democrats remain the same.

We will sit down with any Republican shutdown. with any Republican who is prepared in good faith to find a bipartisan path forward. That was House Speaker Mike Johnson and House Minority Leader Hakeem Jeffries, each speaking at separate press conferences on Monday. But now it's day 35 of the shutdown showdown, as the impasse between Democrats and Republicans has dragged into a new month. With no end in sight, the government shutdown is poised to become the longest ever this week. Thankfully, President Trump has been doing every.

everything he can to figure out a collaborative solution, right? Wrong. In that 60 Minutes interview that aired Sunday, Trump said he won't be extorted by Democrats who want to extend the expiring Affordable Care Act subsidies. I can fix health care. Give them better health care for less money. Obamacare is hurting people. Obamacare was a disaster from day one.

I can fix it and make it good. I'd really rather start with a fresh plate. but if it's required to keep it, we can make it much better. Then do it! And not in like two weeks. In other shutdown news, the Trump administration said on Monday it will partially fund the Supplemental Nutrition Assistance Program for November. That's after two judges issued rulings requiring the administration to keep snap up and running.

The government says the emergency fund it will use to do so has enough money to cover about half the normal benefits. Senate Majority Leader John Thune on Monday expressed optimism that the Senate could reach a deal to end the shutdown this week. That remains to be seen. Folks, in case you've been living under a rock, the general election is today. I know that you're probably still recovering

from the horrors of last year's election, and I am too. But it's more important than ever to get out and vote because the results of this election are not just a preview of next year's incredibly important midterms. This is also a chance to make your voice heard in response to the Trump administration's agenda. Here are a handful of high-profile races we're keeping an eye on.

The Virginia governor's race. This one is a big opportunity to turn a red governor's mansion blue. And in New Jersey governor's race is a chance to keep the governor's mansion blue. The Virginia and New Jersey governor's races happen one year after the presidential election, and they're seen historically as a sort of barometer for how people feel about whoever's in the White House. Here's Virginia Democratic gubernatorial candidate Abigail Spanberger at a rally Monday. In Virginia, we need a governor who will stand up against the chaos and endeavor to create stability, steadiness, and job growth here on the ground. And I'm excited about this moment because we have the opportunity to show the rest of the country what it is that we do.

There's also the election for mayor of New York City, between the progressive Democratic nominee, Zaramam Dani, independent former New York Governor Andrew Cuomo, and Republican Curtis Sliwa. Is Mamdani's populist Democratic socialism the jolt the Democrats need to win the midterms next year, or is it alienating moderate voters? This race is going to shape the narrative one way or another. Then there's Prop 50 in California, which would redraw the state's congressional districts in an attempt to give Democrats more seats in next year's midterms. Republicans are doing the same in places like Missouri, Texas, and North Carolina.

Which is all to say, no matter where you live, this year's elections could have huge consequences for next year and beyond. So once again, get out there and vote. The president must have the emergency authority to utilize tariffs. Look at what President Trump has been able to do by leveraging tariffs and leveraging the might of the United States economy. White House Press Secretary Caroline Levitt spoke ahead of Wednesday's Supreme Court hearing over whether President Trump overstepped federal law.

How? by using emergency powers to impose tariffs on U.S. trading partners. Earlier this year, multiple federal courts found that Trump could not use the 1977 International Emergency Economic Powers Act to set tariffs. That power the Constitution reserves for Congress. Remember Congress. Some judges on the court disagreed, saying the law allows the president to regulate imports during emergencies without specific limitations, and to decide what constitutes an emergency.

The courts left the tariffs in place while the Supreme Court mulls over the issue. In the meantime, Trump has continued to wield tariffs by using them to pressure or punish other countries on matters related and unrelated to trade. A ruling against him could limit or even take away that swift and blunt leverage that much of his foreign policy has relied on. Levitt told Sunday morning futures that the Trump trade team is working on contingency plans in case things don't go their way. But she said they're hopeful the high court will, quote, rule on the right side of the law. Us too, Caroline. Us too. More than 20 Democratic-led states are suing the Trump administration over a new rule that could block certain public servants from getting their student loans forgiven. The Trump administration recently overhauled the public service loan forgiveness program, which wipes federal loans after 10 years of payments in public or nonprofit jobs.

But the new policy lets officials deny forgiveness if they decide an employer has a, quote, substantial illegal purpose. Huh? Critics say this language is conveniently vague enough to target nonprofits that support immigrants, transgender youth, or any other boogeyman in Trump's closet. Somewhere within the brittle husk of what used to be the Department of Education, Education Undersecretary Nicholas Kent defended the role as a safeguard against taxpayer funds going to groups engaged in, quote, terrorism, child trafficking, and transgender procedures.

Yes, the Biden-era crisis no one saw coming, a member of Al-Qaeda for kids applying for PSLF. The rule basically hands sweeping discretion to the education department to decide which public servants count. In other words, your student loan debt could be forgiven, but only if you drink the red Kool-Aid. And that's the news. Before we go, if you want to understand what Trump 3.0 could mean for the courts, check out the latest episode of strict scrutiny. Kate, Leah, Melissa dig into the legal battles over ICE, the National Guard, and Kim Davis's unwelcome return to the spotlight, and preview the SCOTUS case that could expand Trump's presidential powers. Listen to strict scrutiny every Monday wherever you get your podcasts or watch on YouTube.

That's all for today. you like the show, make sure you subscribe, leave a review, learn more about Miami's 13-way mayoral race, and tell your friends to listen. And if you're in a reading, I'm not just about how the race is technically nonpartisan, but it's being viewed as a bellwether for how Democrats can perform in a red state with a rapidly growing population, but seriously, 13 candidates? What is this the last supper? Like me, Waterday is also a nightly newsletter. Check it out and subscribe at crooked.com slash subscribe. I'm Jane Koston. And Democrat and Miami-Dade County Commissioner, Eileen Higgins, has a slight lead in the polling.

So, hey, wouldn't it be cool if you went out and voted right now? What a day is a production of Crooked Media. It's recorded and mixed by Desmond Taylor. Our associate producers are Emily Four and Chris Alport. Our video editor is Joseph Dutra. Our video producer is Johanna Case. We had production help today from Greg Walters, Matt Berg, Caitlin Plummer, and Ethan Oberman. Our senior producer is Erica Morrison, and our senior vice president of news and politics is Adrian Hill.

We had helped today from the Associated Press. Our theme music is by Colin Gilliard and Kashaka. Our production staff is proudly unionized with the Writers Guild of America East. Thank you.