Chicago Fights Back
What A Day4 Nov 2025

Chicago Fights Back

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:

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DHS Dysfunction

DHS Dysfunction

It’s been about a week since the Department of Homeland Security entered a partial shutdown, with Democrats refusing to fund the agency until changes are made to federal immigration enforcement. Accor...

20 Feb 21min

Don't Bank On Trump's Tax Cuts

Don't Bank On Trump's Tax Cuts

The IRS has lost tens of thousands of employees since President Donald Trump took office – the result of DOGE, policy differences, last year’s government shutdown, and layoffs. Now that we're in tax s...

19 Feb 21min

Trump’s Iran Power Play

Trump’s Iran Power Play

U.S. officials met with Iranian envoys in Switzerland Tuesday to negotiate the fate of Iran’s nuclear program — and came away with a “set of guiding principles,” according to Iran’s foreign minister. ...

18 Feb 22min

The MAGA Health Movement

The MAGA Health Movement

It's been about a year since President Donald Trump signed an executive order, "Establishing the President's Make America Healthy Again Commission." Since then, MAHA has brought together a lot of stra...

17 Feb 23min

Democrats Shut Down DHS

Democrats Shut Down DHS

Capitol Hill was surprisingly busy this week. Republicans and Democrats yelled at one another, Republicans yelled at other Republicans, and amazingly, some actual business got done – sort of. But it l...

13 Feb 21min

Bondi's DOJ Fails Again

Bondi's DOJ Fails Again

The Department of Justice fumbled yet another attempt to prosecute President Donald Trump’s enemies on Tuesday night. This time, it failed to get an indictment of the six Democrats who posted a video ...

12 Feb 21min

ICE Warns It’s ‘Only Getting Started’

ICE Warns It’s ‘Only Getting Started’

Over the past year, the Trump administration has been eliminating policies aimed at slowing down climate change – and now, it may go even further. This week, the Environmental Protection Agency plans ...

11 Feb 20min

Epstein Files Cause Ripples Across The Pond

Epstein Files Cause Ripples Across The Pond

Getting justice for Epstein survivors seems impossible in the United States. But in the United Kingdom, the Epstein files could bring down the British government. Prime Minister Keir Starmer is facing...

10 Feb 24min

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