The race that really has my attention, though, is New York’s 12th Congressional District. Jerry Nadler is retiring, and what has followed is an absolute clown car of a race. Micah Lasher would be my favorite to win, but he’s the least interesting candidate in the field. George Conway, once one of the chief architects of turning the Monica Lewinsky scandal into the political force that it became and later one of the most notable Never Trump Republicans in America, is running as a Democrat. Jack Schlossberg, John F. Kennedy’s grandson, is also in the race. And then there’s Alex Bores, a New York Assembly member who has become the main character of this contest thanks to his relationship with AI.

The polling has been all over the place. Early on, Schlossberg led thanks to the Kennedy name. More recent polling has Lasher ahead, with Bores close behind and a huge chunk of the electorate still undecided. That’s important because Bores has become the center of one of the strangest political fights I’ve ever seen. Roughly $26 million has poured into this House race because of his support for the RAISE Act, a proposal to regulate artificial intelligence at the state level.

The two major companies in artificial intelligence, OpenAI and Anthropic, have very different views on how to regulate AI. A super PAC supported by OpenAI leadership in a personal capacity spent money attacking Bores, arguing that splintered state regulations would hurt the industry. Anthropic-aligned groups responded by spending even more money. Do they support the RAISE Act? Who knows. They want OpenAI’s effort to fail, and that’s what makes fight this so unusual. All of this is far less about Alex Bores and more about two AI companies using a congressional primary as a venue for a much larger argument.

I know politics, and I understand the influence of super PACs. I’ve never seen a personal beef quite like this one. Anthropic hates OpenAI, and it’s not a secret. Their CEO, Dario Amodei, does not believe OpenAI’s CEO Sam Altman is trustworthy. Anthropic’s view is that it needs to out-innovate OpenAI and become the market leader. At the same time, I think the anti-Bores effort made strategic mistakes. The ads were so ham-fisted that they gave him life he otherwise would not have had. The spending has even become controversial inside OpenAI. And tonight’s the night we find out whether any of it even mattered.

Chapters

00:00:00 - Intro

00:05:34 - Jeffries vs. Mamdani

00:10:04 - NY-12

00:20:50 - Update

00:22:00 - Keir Starmer

00:26:50 - Israel

00:31:35 - Congress

00:34:29 - Intro to Attention Mechanism

00:38:16 - Attention Mechanism with Andrew Mayne

01:43:58 - Wrap-up

I’ve been trying to understand the tectonic plates underneath these negotiations. One is the health and stability of the Islamic Republic itself. How secure do they believe they are? How much do they agree on the path forward? How much damage do they think has been done? The other is the price of gas. That’s been my obsession lately. Down the road from me, regular gas has fallen below three dollars. Nationally, prices have fallen below $3.99 on average. The questions are obvious: How much is America tapping the Strategic Petroleum Reserve? How much oil is Iran selling under the table? How much of this is Russia? How much is something else entirely?

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Republicans are still looking for the why. That’s what they haven’t found yet. Why am I excited? Historically, at least in the Trump administration, it has been things like immigration. But you can’t run the next election on the thing you solved in the last election. I know there are a lot of frustrated conservatives who say we should be talking about the fact that we closed the border. What have you done for me lately? That is the refrain from voters. Republicans are going to gin up the culture war, and they’re going to point at Democrats and say they’ve learned none of their lessons. Turning the keys back over to them is not going to get you anything. It’s going to get you more impeachments, more nonsense, and less of what you want. Democrats, meanwhile, will say we have an out-of-control oligarch president and we need some kind of emergency brake, so give us back control of the House.

With gas prices continuing to fall, it’s not crazy to think Republicans could find some footing. The national average fell below four dollars, according to AAA. A month ago it was around $4.50. We are looking at a collapsing gas price. We have been told throughout the history of commodities that gas shoots up like a rocket and falls like a feather. We are seeing it fall pretty quickly. If the price of a barrel returns to the levels we saw before the war, now that the memorandum of understanding has been signed and there is free flow of oil through the Strait of Hormuz, you’re going to see lower gas prices. That’s usually what people rely on, and it’s also the hedge against inflation.

Cheap gas had always been the Trump administration’s hedge against tariff inflation. The argument was that while you might pay more on imports, gas would remain extraordinarily low. Obviously that promise was broken with the Iran war. Now it seems that we are at least in some phase of calm and negotiation, a controversial one. My point of view on any American activity in the Middle East—some may even say adventure in the Middle East—is that it almost always ends with America having to tell Israel no. Israel is usually very excited about having us in the region because, in general, we agree with Israel on most everything that happens in the Middle East. But they will always want us to do more, and eventually we usually have to tell them we are not going to do everything they want. That is just the way I understand the region.

Is this memorandum of understanding wise? I read the text that was released yesterday. It’s a pretty big give to allow Iran to sell oil. It’s going to help the gas price, but it is a pretty big give. The carrots we are offering are big and juicy, but they are not promised up front. Everything is contingent on what happens from here. For Republicans, the best-case scenario is relative economic calm and Donald Trump being seen as a game-changing president that people might not always agree with but who is moving things forward. If we’re talking about jobs numbers and things that are forward-facing, Republicans are probably winning the argument. If we’re talking about side issues and distractions, Democrats are winning the argument. I still think it’s going to be very, very, very hard for Republicans to keep the House. But again, this is a very polarized country, and the biggest thing Republicans need is a reason to get their people excited.

Chapters

00:00:00 - Intro

00:01:57 - Republicans and the House

00:12:19 - Obama

00:15:51 - Thomas Kean Jr.

00:19:36 - Iran

00:24:43 - Kirk Bado on Primaries

01:11:10 - Wrap-up

The immediate substance is narrower than many people expected. The United States begins removing its naval blockade and other impediments, with the blockade ending within 30 days. The larger carrots — sanctions relief, access to frozen funds, and a reconstruction package — only come with a final deal. To me, this reads more like the “dust for dollars” concept that had been floating around for weeks. The White House seems to believe its leverage is simple: we are the stick. The military pressure remains implied even if it isn’t spelled out in the document.

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Since the beginning of May, with Iran closing the Strait of Hormuz, gas prices in the United States have fallen. Not by a little, but by a lot. The national average has gone from roughly $4.50 a gallon to $3.50. That happened while the strait was closed and before any memorandum of understanding was announced. The White House wasn’t bragging about it. They weren’t loudly telling Iran that the closure wasn’t working. That made me think something else was going on.

After digging through it, I’ve been able to dig up a few explanations. The most public, I’d argue, was the Strategic Petroleum Reserve. The Department of Energy released more than 53 million barrels as part of a broader international effort, bringing the reserve down to its lowest level since 1983. There were also reports that the United States was helping move oil out of the Gulf using some of the same techniques Iran has historically used to evade sanctions. American production remained high. Every hint of a peace deal pushed oil prices lower. Global demand softened. China sharply reduced its purchases on the open market. Alternative routes around Hormuz became more important. Gasoline inventories improved. All of it pushed prices down.

If I rank the reasons, peace-talk optimism sits at the top. Strategic reserve releases bought time. American-supported workarounds moved real barrels. Demand destruction, especially with China stepping back, reduced pressure. Improved gasoline inventories helped. Some of the more speculative theories include sanctions waivers for Iranian oil, greater tolerance for shadow-fleet shipments, and alternate export routes making Hormuz less decisive than Iran hoped.

What stands out is that there were more American incentives to get to the table than Iranian ones. The Strategic Petroleum Reserve is a temporary band-aid. Smuggling oil out of the Gulf is risky. Every day the Strait of Hormuz remained closed carried economic and military risks. That helps explain why the White House wanted a deal. Iran had incentives too, especially if China was no longer buying at previous levels, but the balance of pressure appears different than many expected.

My assumption remains what it has been for weeks: there are multiple power centers inside Iran, and the biggest question is whether any deal can survive them. The Ayatollah is gone, much of Iran’s leadership structure has been shattered, and the IRGC itself appears divided between factions willing to make a deal and hardliners who want to keep fighting. The memorandum of understanding may give us a clearer picture when we finally see it. Until then, the biggest question isn’t whether a deal exists. It’s whether anyone on the Iranian side can actually enforce it.

Chapters

00:00:00 - Intro

00:02:38 - Iran and Gas Prices

00:31:47 - Update

00:32:04 - UFC 250 Terrorism Plot

00:37:46 - Russia-Ukraine

00:39:48 - Primaries

00:42:48 - Interview with Maria Curi

01:11:46 - Wrap-up

The basic outline remains frustratingly vague. We still haven’t seen a final document, and both sides seem reluctant to explain it to their domestic audiences. What we do know is that the Trump administration has consistently said the goal is preventing Iran from obtaining a nuclear weapon. For me, everything hinges on one question: are we removing uranium from Iran? If you’re going to go through all of this, you need to get something. That is the line in the sand.

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Earlier this week, I mentioned that I had heard from people in the know that the United States military was coiled to strike Iran and was looking for either provocation or justification to resume major military activity. That appeared to happen when Iran shot down an Apache helicopter that was escorting oil tankers through the Strait of Hormuz. We also learned that more than 100 million barrels of oil had moved through the strait under U.S. protection over the last month.

One of the reasons that caught my attention is that gas prices in the United States have been falling pretty dramatically. It was a head-scratcher. If the Strait of Hormuz was effectively stalled, then what explained the drop? Was it a global rerouting of supply? Was there a China component that had been negotiated and never publicly heralded? I didn’t know then, and I don’t know now, but the announcement about oil shipments at least provides part of the picture.

What’s more interesting is what happened next. After one night of military strikes, the second night was canceled. Donald Trump said that’s because we’re at the point of a deal, one that has supposedly been signed off on by all available parties in the region. It appears to resemble the memorandum of understanding that’s been floating around for weeks, although nobody really knows because we still haven’t seen the text. We don’t know if it’s real. We don’t even know exactly what it says.

The administration’s definition of success has been fairly consistent: Iran gives up its nuclear material and removes the nuclear threat. If that’s actually in the agreement, then it would be meaningfully different from what came before. The obvious question is what Iran gets in return. The reporting and public comments suggest that Tehran is focused on access to frozen assets and getting money quickly. Whether that money goes directly to Iran, whether it’s routed through humanitarian aid, and what conditions are attached are all questions that still need answers.

The strongest sign that something may actually be happening is coming from inside Iran. Reports indicate that FARS, the IRGC-controlled news agency, is acknowledging that a draft memorandum of understanding exists, that the United States has approved it, and that Iran is likely to do the same. The bigger question is whether any agreement can actually be enforced. Iran’s leadership appears splintered. We’ve seen officials make commitments before, only to have military figures or IRGC commanders move in a different direction. That’s why the real issue isn’t whether a deal can be signed. It’s whether anybody in Iran has enough authority to keep it.

Chapters

00:00:00 - Intro

00:02:48 - Iran

00:08:38 - Interview with Karol Markowicz

00:36:19 - Update

00:37:19 - DeSantis and AI

00:42:56 - FISA

00:44:42 - Director of National Intelligence

00:47:17 - Interview with Karol Markowicz, con’t

01:07:27 - Wrap-up

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Let’s look at what happened. On election night, Karen Bass was at 30 percent of the vote. Spencer Pratt was at 28 percent. Nithya Raman was around 20 percent. Every model from respected vote-modeling people that I saw indicated that Raman would gain more than Pratt in the later votes, presumably giving her enough to catch up to a less-distant third place without surpassing Pratt’s campaign. Instead, we got an avalanche of late Raman support.

The first vote drop had Raman running about 10 percent ahead of Pratt. The second was stronger. Then Friday came around, and things got really weird. Whether you want to ascribe malicious motives to it or whether it’s totally above board and legitimate, the fact that this is happening on Friday for an election that happened on Tuesday becomes suspicious when Raman gets 40 percent of the vote total in a drop. She’s not only running ahead of Pratt, she’s running ahead of Bass. The same thing happened Saturday. The same thing happened Sunday. Now Raman is through to face Bass in the general a week after this sort of outcome — even in LA — seemed unlikely.

Am I saying that somebody cured ballots after seeing the results? Am I saying somebody harvested ballots? No. I don’t know specifics, and nobody else does, quite frankly. I’m saying you don’t have to do this. Opening the process up this way is the reason you create suspicion. Is it odd? Yeah, it is odd. Even the people who thought Raman was going to overtake Pratt thought it would happen by the skin of her teeth at the very end. Nobody thought it was going to be over by the weekend. It’s beyond expectations.

I’m going to renew my call here, and it’s not just me saying it. You’ve got systems in America that process a lot of votes really fast, and the way they do it is not rocket science. Florida created a system after 2000 that handles a lot of early voting and a lot of vote-by-mail, but those ballots are processed before Election Day and then dumped into the results when the polls close.

If we’re in an era of declining trust in elections, then I don’t care how you think we got here. I don’t care if you think it was Chicago in 1960, hanging chads in 2000, Democrats in 2020, Elon Musk and Starlink in 2024, or any of the other election fraud theories that have floated around American politics. What I care about is creating a system that we can all look at and say, “Seems like what happened.” I don’t think California is close to having that, and it’s only going to get worse if we don’t make some big changes ahead of 2028.

Chapters

00:00:00 - Intro

00:03:22 - California Results

00:13:57 - Interview with Bill Scher

00:35:08 - FISA

00:38:06 - Walz and Ellison

00:41:19 - Dems’ New Super PAC

00:44:09 - Interview with Bill Scher, con’t

01:13:13 - Wrap-up

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The problem is that the list of people the campaign says are actually the problem keeps getting longer. First it was the former campaign manager. Now it’s an ex-girlfriend. The campaign has gone out of its way to point out that the woman worked in Republican politics years ago. Maybe that’s relevant, maybe it isn’t. What matters politically is that this is now the second woman in a week whose allegations are being dismissed while the campaign asks everyone to focus on Graham Platner instead. Meanwhile, the campaign’s own internal polling reportedly has him four points ahead of Susan Collins. That’s not exactly reassuring when a public poll from late May had him up nine. If you’re releasing a poll to save a candidacy and it shows you’ve lost five points, that’s not great.

The bigger issue remains the stuff we still don’t know. The dating stories are damaging, but the Kik story is the Pandora’s box. That’s the ugly stuff. What’s behind that door? The potential answer is why this scandal continues to dominate the conversation. Platner’s goal now is simple: survive the primary, survive the next month, and make it to July 10. If he’s still standing then, Democrats may have no choice but to circle the wagons.

Elsewhere, there was a polling shocker in Ohio. A Fox News poll found Sherrod Brown leading Senator John Husted by eight points, 53 to 45. If we start seeing more polls like that, Democrats may have found one of their best pickup opportunities. Brown is a known quantity in Ohio. If the environment continues to improve for Democrats, it may not matter how exciting or energetic his campaign is. He could simply coast on familiarity and favorable conditions.

California, meanwhile, continues to count ballots at a pace that seems designed to test the limits of human patience. The governor’s race is still unresolved, and Los Angeles mayoral results remain in flux. What frustrates me is that this is a choice. California mails ballots to everyone and allows ballots to arrive days after the election. Fine. But there’s no reason the ballots already in hand couldn’t be processed faster. Instead, the state releases vote drops so slowly that candidates can spend weeks appearing to lead or trail before the public gets anything close to a final picture. I genuinely think that’s bad for democracy because people are not wired to watch somebody lead by eight points and then potentially lose weeks later.

That brings us to Spencer Pratt and Nithya Raman. Prediction markets currently have Raman favored to make the general election despite Pratt holding second place. I don’t understand the math. Raman gained ground in the latest vote drop, but not nearly at the pace she would need to overtake him. Maybe future batches change that. Maybe they don’t. But when prediction markets start pricing in outcomes that don’t seem to match the publicly available numbers, people begin assuming something else is going on. That’s another reason the endless California count is so damaging. Even if everything is perfectly legitimate, the process encourages suspicion in ways that simply don’t seem necessary.

Chapters

00:00:00 - Intro

00:01:20 - Graham Platner

00:09:22 - Ohio and California

00:14:58 - Interview with Reese Gorman

00:30:18 - John Bolton

00:32:01 - Todd Blanche

00:34:26 - College Sports Bill

00:41:28 - Interview with Reese Gorman, con’t

01:01:43 - Wrap-up

The Los Angeles mayoral race looks increasingly likely to come down to Karen Bass and Spencer Pratt. Bass currently leads, Pratt is running second, and Nithya Raman appears headed for a disappointing finish. That’s the real story here.

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What stands out to me is that this was never something Trump could simply do by executive order. It would have had to move through Congress, and right now he is running short on political leverage. Collins, Murkowski, and McConnell have already shown they’re willing to break with the administration. Add in senators like Tom Tillis, John Cornyn, and Bill Cassidy, who have their own political considerations, and suddenly there are a lot of Republican votes that need convincing. If every other priority is tied to this fund, it becomes a problem. The White House has signaled retreat…. for now.

Meanwhile, Florida Attorney General James Uthmeier has sued OpenAI and CEO Sam Altman, alleging that ChatGPT is an unsafe product, particularly for children, and that the company misled the public about its risks. The lawsuit argues that AI contributes to harms including addiction, suicide, and even mass shootings. What makes this interesting is that there are no clean ideological fault lines on AI. In Florida, AI is increasingly being treated as just another version of Big Tech, grouped together with the companies conservatives believe have censored or de-platformed them. Simultaneously, politicians in states like Michigan are celebrating AI investments, data centers, and the jobs that come with them, even as it might leave Gretchen Whitmer on the outside looking in for 2028. As AI becomes a larger part of the economy, states are going to play a much bigger role in determining how it develops.

But our biggest story remains Iran. Over the last few days, a targeted IRGC commander killing, an attack on a U.S. airbase in Kuwait, and reports that Iran is ending ceasefire talks have all pushed events away from diplomacy and toward escalation. Iran is threatening to fully shut down the Strait of Hormuz and other export routes. The president of Iran has reportedly tendered his resignation, while the IRGC appears to be tightening its grip on power. At the same time, Hezbollah has reportedly signaled a willingness to accept a ceasefire with Israel, though neither American nor Israeli officials seem convinced it would hold.

Everything now revolves around leverage. The Strait of Hormuz is Iran’s last major bargaining chip. If it reopens without major concessions, Tehran loses a significant source of pressure. If Iran gives up its nuclear ambitions or loses the ability to project power through regional proxies, the regime risks undermining the very justification it has used for decades. Meanwhile, global oil markets are hanging on every development. Hopes of a diplomatic breakthrough have helped keep prices contained, but each new escalation raises the possibility that the conflict widens and energy markets absorb the shock.

One small but important development is that internet access appears to be returning inside Iran after months of restrictions. That means more information is beginning to flow out of the country at a moment when the political situation appears increasingly unstable. Whether this ends in negotiations, further military action, or a deeper internal power struggle unfortunately remains wrapped in the fog of war.

Chapters

00:00:00 - Intro

00:03:07 - Interview with Evan Scrimshaw

00:39:19 - Trump Slush Fund

00:42:13 - AI Lawsuit

00:46:34 - Iran

00:50:10 - Interview with Charlie Feldman

01:30:42 - Wrap-up

The first problem is that nobody seems to agree on the scale of it. Reports say Platner was communicating with around twelve women. The campaign says the number was no more than six. That is, uh, a bit more than a minor discrepancy. Politically, the danger is that when the number is unknown, the public assumes there could always be more. There is no natural endpoint. The Tiger Woods scandal became a media feeding frenzy for exactly this reason: once a pattern of behavior is established, every new allegation becomes plausible. If Platner is a serial philanderer, there is no obvious cap on how many people might come forward.

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The center of gravity here is the Strait of Hormuz. That is where the entire arrangement becomes real or falls apart. The reported structure prioritizes restoring and guaranteeing commercial shipping through the strait, easing maritime restrictions, and reducing the risk of renewed disruption in one of the most important energy chokepoints on the planet. In exchange, Iran would gain movement on sanctions relief and potentially access to frozen funds, while the United States would push for verifiable constraints on uranium enrichment and clearer handling of existing stockpiles.

Nobody is pretending this is a final settlement. It reads more like a staged de-escalation plan: stabilize shipping first, then attempt to negotiate the more politically radioactive issues like enrichment levels, inspection access, and long-term nuclear limits. The idea is to reduce immediate risk before trying to solve the underlying conflict.

That underlying conflict is the same one that has defined U.S.–Iran relations for decades. Economic relief in exchange for nuclear restraint. The structure is familiar, even if the packaging is not. Anyone watching this unfold will recognize echoes of past negotiations, especially the JCPOA framework, where the core trade was access to global markets in return for limits on Iran’s nuclear program. The political debate around that model has never really gone away, and it is very much present again here.

The fragility of the situation is obvious in the way it is being described. Working-level agreement is one thing. Leadership approval is another. That gap is where deals like this tend to stall, shift, or collapse entirely. Even small changes in political appetite can rewire the entire structure.

Still, this feels like the first tangible step towards restoring reliable, uninterrupted shipping through the Strait of Hormuz. If that actually does happen, everything else becomes more plausible. If it does not, the rest of the framework is just another document waiting for even events to overtake it. God knows we’ve seen enough of those.

Chapters

00:00:00 - Intro

00:03:07 - Iran Deal?

00:10:49 - Interview with Michael Tracey

00:36:18 - Update/LA Mayor Polling

00:39:46 - Trump’s AI Deal

00:43:43 - 2028 Dem Frontrunners

00:46:09 - Interview with Michael Tracey, con’t

01:25:16 - Wrap-up

For years, Cornyn was viewed as the more stable and electable Texas senator compared to Ted Cruz, but in today’s Republican Party, institutional credibility means very little if the activist base decides you’re insufficiently aligned with Trump and the movement around him.

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The Roy situation honestly feels more straightforward. MAGA voters have absurdly long memories when it comes to perceived disloyalty during the DeSantis challenge. Roy spent the last year trying to re-enter the fold by being more cooperative, less antagonistic, more visibly aligned with the movement, but the suspicion never really disappeared. In a normal political environment, Roy’s résumé would make him a strong favorite for statewide office in Texas. Instead, he now looks like somebody who made one unforgivable career calculation at exactly the wrong moment. If the polling is right and Mays Middleton wins comfortably, then the lesson Republican politicians will take from this is brutal: you do not get credit for eventually coming home after backing an alternative to Trump. The scarlet letter sticks.

Cornyn’s downfall is more interesting because he actually played the game correctly, at least according to the old rules. He built institutional support. He raised enormous amounts of money. He aligned himself with Trump operationally. For a while it even looked like it might work. He outperformed expectations in the initial round of voting and there were persistent rumors that Trumpworld had seriously considered endorsing him. But the problem with trying to survive inside Trump politics is that eventually survival itself becomes weakness. Ken Paxton understood this instinctively. He didn’t need to prove he was more effective than Cornyn. He just needed to remain more emotionally connected to the base long enough for Trump to make a final decision. Once the endorsement landed, the race effectively stopped being about qualifications and became a referendum on who belonged more naturally inside the MAGA coalition.

What’s fascinating is that this same dynamic is now showing signs of strain elsewhere. South Carolina Republicans refusing to immediately fall in line on redistricting suggests at least some elected Republicans are beginning to quietly calculate for a post-Trump future. Not necessarily because Trump lacks influence — he very clearly still has it — but because the timing starts to matter. If Trump cannot personally destroy you until after the next election cycle, then maybe you can survive long enough for his attention to move elsewhere. That’s the first real symptom of lame-duck politics: not open rebellion, but selective hesitation. Politicians start making small bets that enforcement may become inconsistent.

And that’s probably the deeper story underneath all of this. Trump still absolutely has the power to end Republican careers. Thomas Massie just learned that. Cornyn is probably about to learn it. Roy may learn it too. But the coalition is also beginning to subtly adapt around the reality that Trump’s political clock is finite. The question is whether Republicans are entering a transition period where fear of Trump remains dominant but no longer universally paralyzing. Because once politicians begin believing there are scenarios where they can survive crossing him, even temporarily, then the entire incentive structure inside the party starts to change.

Chapters

00:00:00 - Intro

00:02:51 - Final Texas Prediction

00:09:05 - AI Ads with Brian Brushwood

00:30:23 - South Carolina

00:33:54 - Iran

00:37:46 - Trump’s Physical

00:40:47 - AI Ads with Brian Brushwood, con’t

01:18:25 - Wrap-up

That’s the core issue for me. I can absolutely believe there are people inside Iran’s leadership structure who want this deal. I can believe there are exhausted regime figures looking at the economy, looking at regional instability, looking at the possibility of American escalation, and deciding they’d rather freeze the conflict than keep pushing toward catastrophe.

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That’s the part that really sticks with me. A bad first draft is not some unforgivable sin. Every organization produces bad drafts. The problem is what happened next. Instead of commissioning a better version, expanding the scope, interviewing more people, and turning it into something useful, the DNC chair basically admitted he got scared. Scared of upsetting Biden loyalists. Scared of upsetting Kamala people. Scared of turning the 2028 primary into a blame war. Scared of stakeholders. Scared of his own shadow. And if your political party just suffered a massive defeat and is going through a structural identity crisis, “risk-averse hall monitor” is probably the worst possible archetype you can install at the top.

Because the Democratic Party’s problems are not cosmetic — they are systemic. The issue is not whether they were two clicks too progressive or three clicks too centrist on Gaza or Liz Cheney or whatever argument people want to relitigate forever. You can build winning coalitions with different ideological mixes. What you cannot survive is an outdated operating system. The Democrats still communicate like it’s 2012. They still protect candidates through message discipline instead of exposure. They still behave like traditional media gatekeeping works. They still think carefully managed campaigns can survive in a hyper-networked political culture where voters expect constant access and authenticity, or at least the performance of authenticity.

That’s why I keep coming back to the feeling I had during the 2024 Democratic convention. Everybody was celebrating. Everybody was dancing. Everybody was acting like the vibes alone had solved the party’s problems. And the whole thing felt to me like a deeply dysfunctional family that had temporarily won the lottery. For one week everybody’s hugging each other, buying champagne, pretending the underlying rot disappeared. But the money doesn’t fix the alcoholism. It doesn’t fix the debt. It doesn’t fix the resentment. Eventually the sugar high wears off and you’re left with exactly the same structural problems you had before, except now everybody’s angrier because the miracle cure didn’t work.

Republicans, for all their chaos, at least went through this process earlier. Trump bulldozed the old Republican establishment starting in 2016, and whether you think that was good or bad, it forced the party to evolve operationally. They adapted to social media faster. They understood small-dollar online fundraising faster. They cultivated emerging political communities like crypto and AI faster. The Democrats still feel institutionally run by either the same people from the Obama era or the protégés of those people. Even when personnel changes, the culture often doesn’t. And culture matters more than almost anything in politics because culture determines how fast you can adapt when the ground shifts underneath you.

Which is why the current Democratic polling advantage feels fragile to me. Democrats are benefiting because Donald Trump is politically damaging himself on Iran, Epstein, and governance. They are functioning as a check on Trump. That is different from voters enthusiastically buying into a coherent Democratic agenda. Even now, when Democrats talk about affordability, it often sounds abstract and bureaucratic instead of tangible. Huge spending programs, diffuse benefits, complicated delivery systems — the exact kind of stuff voters chronically struggle to emotionally connect with. So if the party leadership can’t even produce a competent internal autopsy after one of the most consequential losses in modern politics, it’s hard to argue they are materially closer to fixing the deeper problems underneath all of this.

Chapters

00:00:00 - Intro

00:03:00 - DNC 2024 Autopsy

00:15:24 - Interview with Chris Cillizza

00:40:19 - Trump’s AI Deal Postponed

00:46:11 - Senate Republicans vs. Trump’s Slush Fund

00:50:38 - Raúl Castro

00:57:25 - Interview with Chris Cillizza, con’t

01:19:44 - Wrap-up

What made Massie vulnerable wasn’t that he opposed Trump occasionally. It’s that he opposed him repeatedly, publicly, and on the exact votes Trump cared about most. Speaker votes. Budget votes. The “big beautiful bill.” Iran. One or two protest votes? Fine. Every president tolerates a few gadflies. But Massie kept doing it over and over while Republicans were operating with razor-thin margins. There are plenty of fiscal hawks in Congress who privately hate spending packages and still ultimately vote yes when leadership tells them the stakes are existential. Massie wouldn’t. To his credit, that’s consistent. To Trump, it was unforgivable.

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