Lessons From 2026 (Live From Crooked Con)

Episode of Pod Save America · November 11, 2026 · 1 h 37 min

Live from Crooked Con, Jon Lovett and Democratic strategists dissect the 2026 midterm wins, then Alex Wagner interviews Senator Chris Van Hollen on Senate leadership and accountability.

Summary

This bonus episode of Pod Save America, recorded live at Crooked Con shortly after the 2026 midterm elections, featured two conversations. In the first, Jon Lovett spoke with strategists Lis Smith, Morris Katz and Danielle Butterfield about what drove Democratic victories. Butterfield argued that Democrats still underinvest in digital and search advertising, lack good metrics for whether ads break through, and must reach the roughly half of voters who ignore politics. Smith emphasized candidate recruitment through The Bench and the value of earned media, citing James Talarico, Bobby Pulido and Adam Hamilton, while Katz argued that ads should not look like political ads and that voters reject bad insiders rather than insiders as such.

The panel spent considerable time on the Michigan Senate primary, where Katz and Smith sharply criticized AIPAC's roughly $80 million in spending for Haley Stevens and Smith faulted Chuck Schumer for backing Stevens. Butterfield urged donors to fund long-term infrastructure rather than candidate-specific super PACs, and the group discussed optimizing campaign information for AI chatbots and search. In closing, Katz called for affirmative economic visions, Smith urged candidates to be themselves, and Butterfield criticized excessive consultant pay.

In the second conversation, Alex Wagner interviewed Maryland Senator Chris Van Hollen. He condemned Trump's appointment of Stephen Miller as chief of staff, said there should be no coronation of the next Senate Democratic leader, and listed his priorities: ending the war in Iran by withholding funding and the defense authorization bill, lowering costs including electricity tied to data centers, moving toward a public option and Medicare for All, clawing back ICE funding, and ending secret money in politics. He said he would vote to impeach Pete Hegseth, vowed to block Trump judicial nominees, called for ending the 'blank check' to Israel and opposing two Israel-related NDAA provisions, and said he was considering a 2028 presidential run.

Chapters

0:52
Election night and the panelists' campaigns
Lovett asks Katz, Smith and Butterfield when they knew Democrats would win and what races each worked on in 2026.
6:22
Ad spending lessons from Priorities USA
Butterfield explains how Priorities used the midterms to prepare for 2028 and why Democrats still underinvest in digital advertising.
10:59
Earned media and ads that don't look like ads
Smith and Katz discuss breaking through with earned media and authentic content, and the panel names favorite ads of the cycle.
22:04
Insiders versus outsiders
Katz argues voters reject bad insiders, citing Roy Cooper, while Smith describes recruiting Bobby Pulido and Adam Hamilton and the Kansas Senate race.
31:04
Against labels and for a big tent
Butterfield warns against bucketing candidates, and Smith argues a big tent of voters requires heterodox candidates.
39:13
AIPAC and the Michigan Senate primary
Katz and Smith criticize AIPAC's spending for Haley Stevens and Chuck Schumer's role, and the panel discusses Mallory McMorrow being squeezed out.
53:44
Outside money, super PACs and AI search
The panel discusses outside spending, Democrats' lack of infrastructure investment, and optimizing for AI chatbots and search ads.
1:00:59
Final lessons from 2026
Katz trades jokes with Lovett and each panelist offers a closing lesson, including Butterfield's critique of consultant pay.
1:04:59
Van Hollen on Stephen Miller and Senate leadership
Van Hollen condemns Miller's appointment as chief of staff and lays out the questions he would ask the next Democratic leader.
1:12:38
2028 ambitions and populist message
Van Hollen discusses considering a 2028 run and argues the left-right paradigm is outdated.
1:15:16
Accountability for Hegseth, ICE and the courts
Van Hollen supports impeaching Hegseth, clawing back ICE funding, and blocking Trump judicial nominees.
1:26:22
Israel, the NDAA and closing thoughts
Van Hollen calls for ending unconditional aid to Israel, opposes NDAA provisions, and reflects on the grassroots blue wave.

Key points

What was said, by whom, with the exact words. Timestamps jump to the moment.

Danielle Butterfield
Butterfield says campaigns must grapple with the fact that half of voters do not follow news or politics.
“just really grappling with the notion that 50% of voters don't pay attention to news or politics”
Listen from 8:33 · Political advertising
Danielle Butterfield
Butterfield argues Democrats are wrongly congratulating themselves for spending about half their budgets on digital when voters spend most of their time online.
“we're giving ourselves a pat on the back for spending half of our budget on digital in a world where voters are spending more than 80% of their day online”
Listen from 9:06 · Political advertising
Lis Smith
Smith says the candidates who succeeded focused on earned media rather than relying on paid advertising.
“something I saw work really well this cycle are the candidates who really focused on breaking through and earned media versus just trying to communicate via paid media”
Listen from 11:12 · 2026 United States midterm elections
Morris Katz
Katz says that if one of his ads looks like a typical political ad, his team has failed.
“if it looks like a political ad, I don't want, like we have done a bad job”
Listen from 14:48 · Political advertising
Danielle Butterfield
Butterfield argues that attention cannot be bought with money and must be earned even through paid media.
“We can't buy attention. We have to earn it. And so even when we're running paid media programs”
Listen from 16:29 · Political advertising
Morris Katz
Katz argues that voter hunger for outsiders stems from the poor quality of most insiders, not insider status itself.
“The reason there's such a hunger for outsiders is because most insiders suck”
Listen from 23:08 · 2026 United States midterm elections
Lis Smith
Smith rejects the post-2024 idea that Democrats must match Trump's nastiness, arguing no one can beat him at that game.
“that really no one is ever going to beat Donald Trump at that game”
Listen from 26:10 · 2026 United States midterm elections
Lis Smith
Smith says internal analysis showed Roger Marshall was weak and poorly known, making Kansas winnable.
“Roger Marshall's numbers were not really good. He was not super well known”
Listen from 29:45 · 2026 United States Senate election in Kansas
Danielle Butterfield
Butterfield argues Democratic labels like moderate or progressive are vague compared with MAGA, which contains a clear verb.
“the thing that's different about the MAGA label with the labels that we use on our side is that MAGA has a verb in it”
Listen from 31:09 · 2026 United States midterm elections
Lis Smith
Smith argues Democrats need ideologically diverse candidates to win a broad coalition and should stop prescribing a single model.
“a big tent of voters requires a big tent of candidates. And we should stop trying from stages like this”
Listen from 35:45 · 2026 United States midterm elections
Morris Katz
Katz argues that candidates who accept AIPAC support cannot be trusted, citing Haley Stevens as an example.
“you cannot trust candidates who are in bed with AIPAC because if they are willing to sell out Gaza”
Listen from 41:48 · American Israel Public Affairs Committee
Lis Smith
Smith questions whether Chuck Schumer, who backed Haley Stevens behind the scenes, should lead Democratic Senate recruitment.
“is this the person who really should be in charge of all the recruitment for Democratic candidates?”
Listen from 43:32 · 2026 United States Senate election in Michigan
Lis Smith
Smith says $80 million was spent supporting Haley Stevens in the Michigan Senate primary.
“They put $80 million behind her in the primary, across TV ads, across mail, all that, $80 million”
Listen from 50:12 · 2026 United States Senate election in Michigan
Danielle Butterfield
Butterfield argues Republicans are far ahead in using outside money to build lasting infrastructure while Democrats fund individual candidates.
“Republicans, they're a decade ahead of us on using outside money to actually build things”
Listen from 54:53 · Campaign finance in the United States
Morris Katz
Katz warns that AI chatbot answers will be a key 2028 battleground and Democrats will be outmatched without investment.
“absent a real investment in the kind of AI tools and tactics for 28, we're gonna be outmatched by them”
Listen from 57:04 · Artificial intelligence
Danielle Butterfield
Butterfield says Democrats spend under 2% of paid media budgets on search advertising, far less than corporate advertisers.
“Democrats invest less than 2% of their paid media budgets on search advertising”
Listen from 57:32 · Political advertising
Danielle Butterfield
Butterfield argues the Democratic consulting class has its own oligarchy problem and is overpaid.
“in politics, should not afford you the ability to buy a lake house”
Listen from 1:03:11
Chris Van Hollen
Van Hollen calls Trump's choice of Stephen Miller as chief of staff a sign of contempt for voters who repudiated his administration.
“a complete sign of contempt for American voters after an election where the people repudiated the Trump administration”
Listen from 1:06:36 · 2026 United States midterm elections
Chris Van Hollen
Van Hollen says the next Senate Democratic leader should not be chosen without a full caucus discussion.
“There should be no coronation of the next Democratic leader”
Listen from 1:09:02 · Senate Democratic Caucus leadership election
Chris Van Hollen
Van Hollen says he ultimately supports Medicare for All but that Democrats should at least move toward a public option.
“I ultimately believe we need to get to Medicare for all. But we certainly need to begin moving toward a public option”
Listen from 1:09:54
Chris Van Hollen
Van Hollen says Democrats should refuse further funding for the Iran war and hold up the defense authorization bill.
“we're not going to vote to spend one more dime on the war in Iran”
Listen from 1:10:06 · United States war with Iran
Chris Van Hollen
Van Hollen argues the traditional left-right ideological paradigm is outdated and the winning message was populist.
“the sort of traditional paradigm of left versus right or progressive, moderate, conservative is outdated”
Listen from 1:12:53 · 2028 Democratic Party presidential primaries
Chris Van Hollen
Van Hollen says he would vote to impeach Defense Secretary Pete Hegseth under Thomas Massie's proposal.
“Tom Massey has proposed impeachment of Hegseth, I would vote yes to impeach Hegseth”
Listen from 1:16:03 · United States war with Iran
Chris Van Hollen
Van Hollen says he has opposed every Trump judicial nominee as a threat to the rule of law.
“I have voted against every one of Trump's judicial nominees because I think they represent an attack on the rule of law”
Listen from 1:25:51 · Supreme Court of the United States
Chris Van Hollen
Van Hollen calls for ending unconditional U.S. taxpayer aid to Israel, citing complicity in Gaza and the West Bank.
“we should end the American taxpayer blank check to the government of Israel”
Listen from 1:26:38 · United States military aid to Israel

People

In the conversation

Jon LovettCo-host of Pod Save America; diarization split of the same speaker during the economics segment
Alex WagnerMSNBC host who hosts episodes in the Pod Save America feed
Jon FavreauCo-host of Pod Save America and former speechwriter for President Barack Obama
Lis SmithDemocratic strategist and adviser to the candidate-recruitment group The Bench
Morris KatzDemocratic ad maker and partner at Fight Agency
Danielle ButterfieldPresident of the Democratic super PAC Priorities USA
Chris Van HollenDemocratic U.S. senator from Maryland

Discussed

Chuck SchumerSenate Democratic leader
Haley StevensU.S. Representative running for Senate in Michigan
Abdul El-SayedDemocratic Senate nominee in Michigan
Mallory McMorrowMichigan state senator running for U.S. Senate
James TalaricoDemocratic Senate nominee in Texas
Adam HamiltonMethodist pastor in Kansas described as running for office
Roger MarshallRepublican U.S. senator from Kansas
Bobby PulidoLatin Grammy-winning Tejano musician and Democratic nominee in Texas's 15th congressional district
Roy CooperFormer North Carolina governor running for Senate
Stephen MillerWhite House deputy chief of staff and architect of the administration's immigration agenda
Pete HegsethU.S. Secretary of Defense overseeing the Iran campaign
Donald TrumpPresident of the United States whose conduct of the Iran war is the episode's main subject
Samuel AlitoSupreme Court justice rumored to be considering retirement
Elon MuskEntrepreneur behind X, xAI and SpaceX, discussed in AI competition
Benjamin NetanyahuPrime Minister of Israel
Bob BrooksFirefighter and union leader elected to Congress from Pennsylvania

Topics

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From the publisher

Live from Crooked Con, Lovett talks with top Democratic strategists Morris Katz, Lis Smith, and Danielle Butterfield about what ads and messages worked in the field, their favorite content from other campaigns, and what pissed them off the most. Then, Alex Wagner sits down with Senator Chris Van Hollen to talk about the Senate leadership fight, holding Trump accountable, and whether he has his eye on 2028. Hate listening to ads? Become a Friends of the Pod subscriber for ad-free episodes of Pod Save America, Pod Save the World, Lovett or Leave It, Runaway Country, Offline with Jon Favreau, and more—plus exclusive content, including bonus episodes of Pod Save America. Subscribe now at crooked.com/friends , on Apple Podcasts, or through the Pod Save America YouTube channel. You can request a transcript by emailing transcripts@crooked.com . Include the podcast name, episode title, and air date. Please allow 48 hours for delivery.

Summary, chapters and key points were generated from the episode transcript on November 12, 2026. Quotes are checked word for word against the transcript.

Categories: Politics·News Commentary