Morning radio is a weird beast. Most people just want the weather or a traffic update so they don't lose their minds on the Kennedy Expressway, but then there are the listeners who tune in specifically for the friction. That’s exactly what drives the Dan and Amy podcast, the digital home for the "Chicago’s Morning Answer" show. If you’ve spent any time driving through the suburbs or sitting in a cubicle in the Loop, you know the voices: Dan Proft and Amy Jacobson.
They aren't there to play Top 40 hits. Honestly, they aren't even there to be "nice" in the way traditional morning shows pretend to be.
It’s about the argument.
The show, which airs on AM 560 The Answer (WIND), has carved out a massive, often controversial space in the Chicago media landscape. It’s a mix of local politics, national grievances, and a very specific brand of conservative commentary that feels less like a polished news broadcast and more like a debate at a diner where the coffee is too strong and everyone has an opinion on the school board.
What Actually Happens on the Dan and Amy Podcast?
If you're looking for a bipartisan "both sides" breakdown of the news, you’re in the wrong place. The Dan and Amy podcast is unapologetically right-of-center.
Dan Proft is the intellectual engine of the pair. He’s a former gubernatorial candidate, a political strategist, and someone who genuinely seems to enjoy the "intellectual combat" of political discourse. He speaks in long, complex sentences, often weaving in historical references or specific policy critiques that require you to actually pay attention. He doesn't do soundbites; he does arguments.
Then you have Amy Jacobson. Her background is in hard news—she was a long-time reporter for WMAQ-TV—and she brings that "boots on the ground" energy to the mic. She’s the one digging into the local stories, talking to parents about curriculum changes, or questioning city officials.
The chemistry works because they don't always agree on the approach, even if they usually agree on the philosophy.
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The Shift to Digital
The reason the Dan and Amy podcast exists is that radio isn't just about the car anymore. People want to hear the segment they missed at 7:10 AM while they’re at the gym at 5:00 PM. The podcast feed captures the full four-hour broadcast, but it's often chopped up into interviews.
Think about the guests. They get everyone from local aldermen to national heavyweights like Victor Davis Hanson or Florida Governor Ron DeSantis. Because the show is based in Chicago—a city that is famously a Democratic stronghold—the podcast often feels like a "resistance" broadcast for the surrounding collar counties. It’s where the "silent majority" (or at least the very loud minority) goes to feel heard.
Why the Show Stays Relevant (and Controversial)
You can't talk about the Dan and Amy podcast without talking about the heat it draws.
Chicago politics is a blood sport. Proft and Jacobson treat it that way. They’ve been at the center of several firestorms over the years, ranging from their coverage of COVID-19 mandates to their critiques of the Chicago Teachers Union.
Some people find it abrasive. Others find it necessary.
There was a notable moment a few years back where the show faced significant pushback for certain political advertisements played during the broadcast, which led to a broader conversation about the role of independent media and corporate sponsorship. But here’s the thing: the more the "mainstream" media or political establishment pushes back, the more their audience grows. It’s a classic feedback loop.
The podcast serves as an archive of these moments. When a guest says something that makes headlines in the Chicago Tribune or the Sun-Times the next day, the podcast traffic spikes. People want to hear the context. They want to hear the "unfiltered" version.
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The Audience Profile
Who is actually listening?
It's not just "angry conservatives."
It’s small business owners. It’s parents who are frustrated with the public school system. It’s people who moved to Indiana but still work in Chicago and want to know why the city they love feels like it’s changing so fast. The Dan and Amy podcast taps into a specific type of Midwestern pragmatism—or frustration, depending on who you ask.
The show isn't just a news delivery system; it's a community. They host live events, they interact with listeners via text and social media, and they’ve built a brand that survives even when the political winds aren't blowing in their favor.
The Mechanics of the "Morning Answer"
Most podcasts are recorded in a quiet studio with hours of editing. This is different.
Because the Dan and Amy podcast is a repurposed radio show, it has a specific rhythm. It’s fast. It’s interrupted by commercial breaks (though many are edited out for the digital feed). It has a "live" energy that you just can't fake in a post-produced show.
- The Interviews: Usually 10 to 15 minutes long. They don't let guests off easy.
- The Rants: Proft is known for his monologues. Some listeners call them "prof-essorial."
- The Local Focus: While they talk about DC, the heart of the show is always Cook County and the surrounding areas.
How to Get the Most Out of the Show
If you’re new to the Dan and Amy podcast, don't try to listen to the whole four-hour block. It’s too much.
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Start with the guest segments. Look for names you recognize or topics that actually impact your life—like taxes, property values, or crime statistics in the city. The show is best consumed as a series of deep dives into specific issues rather than a background noise "variety show."
It’s also worth following their social media clips. They’ve become very good at "visual radio," filming the segments so you can see the reactions. Sometimes Amy’s face when Dan goes on a tangent is the best part of the segment.
A Note on Perspective
Every media outlet has a bias.
The Dan and Amy podcast doesn't hide theirs. They wear it like a badge of honor. To get the most out of it, you have to realize you're listening to a specific viewpoint. Even if you disagree with every word they say, it’s a vital window into what a huge portion of the Illinois electorate is thinking and feeling. You can't understand Chicago politics if you only read the headlines from one side of the aisle.
Actionable Steps for New Listeners
If you're ready to dive into the world of Dan Proft and Amy Jacobson, here is the best way to do it without getting overwhelmed:
- Subscribe to the "Chicago's Morning Answer" feed. This is the primary home for the podcast content. You can find it on Apple Podcasts, Spotify, or the Audacy app.
- Look for the "Big 3" segments. Usually, the first hour of the show covers the top three stories of the day. These are the best for a quick catch-up on what’s happening in the city.
- Check the Guest List. If you see a guest like Matt Taibbi or a local investigative reporter, those are usually the high-value episodes that offer more than just partisan bickering.
- Use the "Skip" button. Since it's a radio-style show, there's a lot of "housekeeping" (weather, traffic, station promos). Don't feel guilty about skipping to the meat of the conversation.
- Cross-Reference. When they cite a specific bill in Springfield or a city council resolution, look it up. The show is a great jumping-off point for doing your own research into how local government actually works.
The media landscape is fractured. People are moving away from the "voice of God" news anchors and toward personalities they feel they know. Dan and Amy have survived for years in a brutal market because they’ve leaned into that personality-driven, high-stakes style of communication. Whether you find them enlightening or infuriating, you can't deny they’ve mastered the art of the Chicago conversation.