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Democrats had a great night. It doesn’t solve their biggest problem.

The party’s success with high-propensity voters in off-year elections is good. How they reach the rest of America is the challenge.

Welcome to Chaotic Era, a newsletter about politics, media, and online influence. From the Democratic Party’s soul-searching to our tech overlords, the changing media environment, and the new MAGA government, this newsletter will provide you with unique insights you can’t get anywhere else.

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Alright, let’s dig in.

Democrats had a great night. It doesn’t solve their biggest problem.

This morning, Democrats are celebrating a decisive victory in Wisconsin’s Supreme Court election, where the liberal candidate, Susan Crawford, beat conservative Brad Schimel by a 10 point margin. After a historic amount of money was spent in the race, the result wasn’t particularly close. Turnout in yesterday’s vote (2.3 million votes counted so far) was much higher than the 2023 State Supreme Court race (1.8 million), but obviously lower than the 2024 presidential election in the state (3.3 million). Because of the outcome, liberals will maintain their narrow ideological majority on the court, with enormous ramifications for politics and policy nationally and in the Badger State. It’s a big deal. The Democratic Party of Wisconsin, under the leadership of Chair Ben Wikler, deserves a lot of credit, as they have built a machine perfectly tuned to win these types of elections.

This time around, the judicial race was dominated by Elon Musk, who spent millions of his own money essentially bribing supporters and pummeling Crawford with attack ads. If this election was a referendum on Musk, his chaos, and his role in the administration, the anti-Musk campaign won decisively. “It's clear now that while Republicans may crave his financial support, Musk is a severe liability for the party's candidates,” wrote one POLITICO reporter.

While it's important for Democrats to pop some champagne, take credit for the win, and learn what can be repeated elsewhere, it's just as critical to recognize that the smaller electorate in non-presidential years is now biased toward Democrats. 

In the Trump era, the Republican Party has bled support among older voters, suburbanites, and voters with a college degree - the most engaged parts of the electorate that turn out in every election, no matter what. But, according to Data for Progress, Democrats lost “low-information voters” in 2024 by a 19 point margin. Another analysis from Blue Rose Research found that disengaged voters shifted significantly away from Democrats from 2020 to 2024. 

As Democrats have become the party of white, educated elites, they will continue to see small special and off-year election victories across the country. That bodes particularly well for Virginia’s gubernatorial and legislative elections this fall, where Elon Musk’s DOGE will no doubt reprise its starring role in campaign advertising. The party’s main challenge, however, is persuading the millions more disengaged, lower propensity voters to ditch MAGA in time for 2028. That will require a lot more work.

Florida, man…

Meanwhile In Florida, voters headed to the polls yesterday in two congressional special elections to replace former Rep. Matt Gaetz in FL01 and National Security Advisor Mike Waltz in FL06. The results showed a massive Democratic overperformance in both seats.

In the 6th Congressional District, Democrat Josh Weil lost, but earned nearly 43% of the vote - a margin unthinkable in a district Trump carried in November by 30 points. More shockingly in Florida’s 1st Congressional District, Democrat Gay Valimont outperformed Harris’ showing in November significantly, receiving 42 percent of the vote. These are dark red districts where Democrats are few and far between - the results shows that just like in Wisconsin, the voters who pay attention to politics do not like what they’re seeing in Washington.

But for some longtime Florida Democrats, there’s more to the story. Steve Schale, a longtime campaign and PAC operative with deep ties to the state, wrote in his newsletter this morning that We Have to Stop Doing What We did in Florida This Last Month.” In the piece, Schale argues that too often Democrats spend huge sums on moral victories and unwinnable elections, while failing to fund basic infrastructure like voter registration.

“The truth is we are really good at getting grassroots donors jazzed up about things that are tangible — and often unachievable,” Schale wrote. “But what we suck at is creating interest in long term investments - organizing, research, registration, candidate recruitment, etc. — the stuff that really matters, but doesn’t come with an emotional connection.”

Is this what hope feels like?

Michigan State Senator Mallory McMorrow just announced her campaign for U.S. Senate to succeed retiring Sen. Gary Peters. ICYMI, here’s her launch video:

Married to MAGA

This week, Republican pollster and author of The Intersection Patrick Ruffini published a fascinating look at American voters divided by race, education, marital status, and age. The data shows that White, non-college, married couples of all ages are the most likely to support Trump out of all subgroups.

“Dividing the electorate by gender and marital status produces a much more illuminating picture, with gaps between groups larger than almost all others,” Ruffini writes. Check out this chart:

Democrats’ ticking time bomb

This weekend, Lauren Egan at The Bulwark wrote about a coming “Doomsday” scenario for Democrats, when “Blue” states see a large-scale loss of electoral clout after the 2030 Census. In just a few years, typically Democratic states like New York, California, Illinois, Rhode Island, Minnesota, and Oregon are predicted to lose Congressional seats and votes in the Electoral College, while more red-leaning places like Florida, Texas, North Carolina, Utah, and Idaho are set to grow their political power.

In addition to creating some complex math for Democratic congressional majorities, it also means that Democrats’ path to the White House will shrink further, with “The Blue Wall” midwestern states no longer providing a consistent map for a Democratic presidential victory. 

If Democrats don’t start laying the groundwork for consistent wins in places like Georgia, North Carolina, and elsewhere, they may be locked out of the presidency for a generation. We’ve already seen this play out in the party’s impossible Senate math, where Democrats likely won’t retake the majority for years. 

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A big week in right-wing media

Last Thursday, the White House invited conservative podcasters and YouTubers to attend a “podcast row” event to record interviews with various administration officials. Some of the podcasters in attendance: Michael Knowles from the Daily Wire, Natalie Winters from Steve Bannon's War Room, Ask Dr. Drew host Dr. Drew Pinsky, Blaze Media’s Sara Gonzales, Jack Posobiec, Libbey Dean, and Sage Steele.

At the same time, former FOX anchor turned right-wing podcaster Megyn Kelly announced she’s building a media network centered around video and audio podcast products. Some of the personalities she’s brought in already include disgraced former political journalist Mark Halperin and Link Lauren, a TikTok creator who was all in on RFK Jr.’s presidential campaign last year. 

Not all is going great for conservative media endeavors, however. According to Oliver Darcy, cultural and entertainment juggernaut The Daily Wire is going through a period of upheaval after the sudden departure of CEO Jeremy Boreing last month. In addition to Boreing leaving, the company’s top communications executive has departed, and numerous staff have been laid off, including its entire team focused on children’s programming. 

More on this from Darcy’s newsletter:

“With Boreing out as co-chief executive, Cordova gone, and much of the Bentkey staff apparently laid off, the vision of The Daily Wire as a full-spectrum entertainment company appears to be in retreat. For years, the company hyped its ambitions to become a conservative counterweight to Hollywood—boasting that it could build the next Disney. But as of early 2025, that dream appears to be on pause, if not altogether abandoned.”

More things you should read:

One last thing: Political Podcasts by Partisanship

Democrats and progressives continue to face an uphill battle when it comes to cultivating talent and building out long-form programming via podcasts and YouTube shows. The below chart is a snapshot of the top-ranked political and political-ish podcasts on Spotify last week that I somewhat subjectively categorized according to partisan lean.

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