dan pfeiffer on thinking bigger than 2024

ALSO: a dating app provided free gas to get people out of the house, reality TV vs. Kalshi and Polymarket, your WiFi is lowkey maybe spying on you, and more

May 29, 2026

Happy Friday, May 29th!

FYSA, every Tuesday and Friday, I’ll be in your inbox with the latest in politics, tech & social media, culture, and other relevant topics – and I’ll share some notes and tips on what I’m keeping my eye on.

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Today’s texter needs no introduction, BUT here’s one anyway: Dan Pfeiffer is, among many things, the co-host of Pod Save America and author of the new Substack, Message Box Pro, a newsletter about political strategy. Enjoy!!

LR: There has been a lot of talk about 2024 autopsies these days. Putting aside for a moment what has and hasn’t happened, on a macro level, what’s your 2024 autopsy report? If you were building out more comprehensive research, what would you look at first?

DP: There are so many voter groups to dissect — the Biden voters who stayed home, the Biden voters who flipped to Trump, the first-time voters who broke for Trump. But the reasons behind those specific 2024 decisions may already be behind us, and therefore not particularly instructive for what comes next.

Here’s where my personal obsession kicks in: Democrats got our asses handed to us in the information wars. Trump and the Republicans dominated the conversation and successfully defined Harris and Walz before we could define ourselves. I want a deep dive into how that happened — not just the tactics everyone has fixated on, like the Rogan interview, but the bigger question. Where were the less-engaged voters who don’t actively follow the news actually getting their information? Who and what shaped their opinions?

Answer that, and you have a real foundation for 2028 and beyond.

LR: Acknowledging there’s no universal playbook… if you had to name three talking points that every Democrat running in 2026, regardless of where they fall on the ballot, should be able to communicate clearly on, what would they be?

DP: The Trump administration is such a shitshow that there is almost too much to talk about, and Democrats end up talking about everything and communicating nothing.

I’ve been pushing politicians to organize their messaging around three things: Costs, Corruption, and Chaos. I kind of hate the alliteration — it sounds like it came out of a bad consulting brainstorm — but these really are the pillars of a coherent and compelling story about how Trump and the Republicans have failed America.

This is something I have been hammering home to the candidates and operatives who subscribe to my Message Box Pro product.

LR: What political issue or opinion have you changed your mind on the most in the past five years?

DP: The essential value of field organizing was an article of faith on the Obama campaigns. Obama was an organizer. Plouffe was an organizer. We lionized the staffers on the frontlines — knocking doors, making calls, registering voters, recruiting volunteers.

A combination of technological shifts (spam detectors, iOS updates, Ring cams) and cultural ones (more fear, more polarization) has rendered that model much less effective than it used to be. I now believe we need to build campaigns around something new: more efficient, more effective, natively digital, and built on relationships and trust.

LR: What is the most memorable episode of Pod Save America you’ve recorded? Bonus: Who are the top three guests you’ve interviewed?

There have been a lot of fun ones over the years, especially the live shows at places like the Greek in LA and the Ryman in Nashville. And this has been somewhat erased from history, but back in 2018, four of our shows aired on HBO.

But the most memorable episode, unfortunately, is the one we recorded in the immediate aftermath of the Biden-Trump debate. We basically turned off the TV, turned on the mics, and what came out was our authentically raw response in real time.

Top three guests:

Barack Obama. I probably can’t show up to the Obama library opening next month without putting the boss at the top of the list. We’ve interviewed him a number of times, but the conversation we had on his last full day in office in 2017 — about his legacy, Trump’s win, and what was coming next — really stands out.

Steve Kerr. Back in 2017, I interviewed Kerr at the Warriors’ practice facility after Trump disinvited the team from the White House. Steve is an incredibly decent, thoughtful, and interesting person.

Stacey Abrams. I first interviewed Abrams in Atlanta in front of an insanely raucous audience during her run for governor. I’ve probably interviewed her half a dozen times since, in various settings, and I always come away feeling like I’ve learned something profound about how to think about politics, history, and the country.

LR: You’re chatting with a college-age Gen Z-er who wants to get into electoral politics (probably after watching The West Wing three times). They are driven and passionate about the work, but scared by the lack of job security in this economy, rising political violence, the general clusterf*ck of modern politics, etc. What would your advice to them be?

DP: I have spent my entire adult life in politics in one form or another. It’s not easy. It can be frustrating and disappointing. But there is no better way to positively impact more people’s lives than through politics. It’s how you make things better in this country. It’s how you help people at scale.

And there is no better feeling than fighting the good fight, winning, and knowing that people’s lives are actually better because of what you did.

Ballots Have Been Seized Across the US. No One Knows What Will Happen Next

The seizures began in January when FBI agents armed with a warrant raided an election facility in Fulton County, Georgia, and grabbed 600 boxes of ballots from 2020. This was followed in March by the Department of Justice obtaining ballot images from 2020 in Maricopa County, Arizona, and—citing claims about supposed fraud in 2020—demanding ballots from the 2024 election in Wayne County, Michigan. (WIRED, 5/28 – free version)

Why Democrats prefer their own messy primaries

The irony: Democrats have overcorrected to fix their “anti-democratic” image. The DNC spent half of last year fighting over David Hogg’s vice chair position because party chair Ken Martin was trying to institute, then enforce, rules that prevented any DNC member from intervening in primaries. The Democratic Congressional Campaign Committee is more hesitant than Trump about endorsing candidates because when it does, the candidates it’s not endorsing run to microphones, denouncing the “meddling.” (Semafor, 5/27)

Meta launches Instagram, Facebook, and WhatsApp subscriptions, with more to come, including AI plans

For a few dollars per month, consumers subscribing to Instagram Plus ($3.99/mo), Facebook Plus ($3.99/mo), or WhatsApp Plus ($2.99/mo) will gain access to extra features, like profile customization, super reactions, and story insights, among other things. (TechCrunch, 5/27)

The AI fight brewing inside The New York Times

Unionized staff with the Tech Guild say Times management has refused to provide the union with information related to how the company has used AI, its plans for AI use in the future, and how it will affect employees’ jobs and workflow. (The union filed an unfair labor practice charge earlier this month.) (The Verge, 5/27 – free version)

Ordinary WiFi can now identify people with near perfect accuracy

Researchers in Germany are warning that ordinary WiFi networks could become a powerful new form of invisible surveillance. Using standard wireless signals and artificial intelligence, they demonstrated a system capable of identifying people with striking accuracy, even if those individuals are not carrying an active device. (Science Daily, 5/22)

A Dating App Is Giving Away Free Gas to Convince People to Get Out of the House

As part of the promotion, BLK is providing $500 gas gift cards to 10 people who download the app and tag three friends in the campaign post across its social channels. “Dating should not have to compete with the price of a full tank,” Amber Cooper, BLK’s head of brand, said in a statement. (WIRED, 5/27 – free version)

Lucy’s note: shot…

Wealthy Retirees Are Buying ‘Med-à-Terres’ to Be Near Their New York Doctors

A growing faction of affluent, older New Yorkers who relocated during the pandemic are buying second properties back home to anchor themselves to elite medical specialists, according to real-estate experts. Meanwhile, new retirees are hanging on to or investing in urban real estate before migrating elsewhere. (WSJ gift link, 5/28)

Lucy’s note: … chaser

Kalshi and Polymarket Are Spoiling Reality TV Shows — and Studios Don’t Know What to Do About It

When a “Survivor 50” market opened on Kalshi six weeks before the Feb. 25 season premiere, preliminary trades forecast Bracco to have a 61% chance of winning — nearly double the odds of her next closest competitor. By Jan. 28, she had jumped to 83%. And on Feb. 28, just days after the premiere and before Bracco had accumulated much screen time, a user bet $45,500 she would win the season (which later earned them a profit of $4,500). (Variety, 5/22)

Is ‘out of control’ US tipping culture spreading overseas?

“Since tips go straight to staff, it is quite likely that restaurants are using tips as a way to increase salaries without footing the bill,” says Harris. “The UK hospitality industry is on its knees, with restaurant owners being squeezed by VAT, increased minimum wage, national insurance, and increased food and utility bills. (BBC, 5/27)

T. rex had massive jaws but tiny arms: Scientists now know why

If that means sacrificing the size of the arms for a stronger head, which is the primary weapon for the animal, then that’s likely what will happen.” The researchers developed a new methodology to quantify skull robustness, considering factors such as skull dimensions, bite force, tooth shape, and cranial bone-fusion patterns. (The Independent, 5/29)