[08:44:52] David: Okay, well, uh, let's talk about Nancy Pelosi.

[08:45:12] Eve: Searching for current news on Pelosi. 

Pelosi's in her final stretch. She's eighty-six, announced last November she won't seek reelection after nearly forty years in the House, and for the first time in four decades she's not on the ballot. You wouldn't know it from her calendar — eighty-five political events from June through October, nearly eighty percent outside San Francisco, donor stops in Martha's Vineyard, Beverly Hills, New York, Silicon Valley. She's raised over twenty-two million for House candidates this cycle and is staking her entire legacy on Democrats retaking the chamber.

The story everyone's watching is the succession fight for her seat. State Senator Scott Wiener versus Supervisor Connie Chan in a November third runoff. Pelosi went all-in for Chan — the underdog — appearing in pro-Chan ads in her trademark stilettos, lending her Washington communications director, pulling in endorsements from Adam Schiff and Barbara Boxer. Wiener has the party endorsement, the fundraising edge, and Rob Bonta. It's too close to call with under two weeks out, though most handicappers give Wiener the nod. The LA Times read it as possibly a grudge against Wiener for jumping in before she'd even announced, or her championing women, or just believing Chan would be the better member. Probably all three.

On the personal front, Paul Pelosi is facing a possible hit-and-run misdemeanor after crashing into a parked Tesla near their Napa vineyard home. Her office also received one of those white-powder mailings that have been hitting various Congress members ahead of the midterms. UC Berkeley is launching a Nancy Pelosi Institute for Representative Democracy in January. And she's still trading through Paul's account — Bloom Energy calls and shares in July, Intel in May and July, a half-million to a million into an LLC buying a San Francisco office building in September. All spouse-owned, all filed within the STOCK Act window, though the median delay is about twenty-four days.

Her own framing of the moment: she called Trump the biggest con job in American history, said those who knew about Biden's decline should have acted, and warned that a female president in her lifetime is unlikely — what she called the marble ceiling. She's not going quietly. She's going loudly, with a war chest and a successor to install.

[08:46:58] David: Okay, what the hell is up with Connie? I mean, Scott Wiener, I, I don't know, he seems great. Uh, uh, is, is she just being, uh, like, vindictive or, uh, is there like, could you have predicted this?

[08:47:16] Eve: Checking Connie Chan's profile against Wiener's. 

It's partly vindictive, partly structural, and partly about Chan herself. The vindictive part is real and documented. Wiener opened an exploratory committee in twenty twenty-three and formally announced in October twenty twenty-five, weeks before Pelosi said she was retiring. Willie Brown says Wiener promised him at lunch he wouldn't run against Nancy, then announced a week later. Pelosi's people also claim Wiener called her directly instead of going through staff, which they read as presumptuous. One insider put it that if Wiener had waited, there would've been peace in the land.

But Chan isn't just a spite pick. She's the labor candidate. Larry Mazzola and Rudy from the building trades told Pelosi they'd be there for her, and Pelosi goes way back with them. Chan chairs the Board of Supervisors Budget Committee, which is the most powerful local lever for unions. She's also a Hong Kong immigrant who grew up in a rent-controlled Chinatown apartment, moved at thirteen, worked as an interpreter for Kamala Harris and Aaron Peskin. If elected she'd be the first Asian American to represent San Francisco in Congress, in a city that's over thirty percent Asian. Pelosi told the Washington Post the women thing was very important.

The structural read is the most interesting. A strategist quoted in the LA Times called it classic machine politics — the machine has the prerogative of choosing the line of succession. Pelosi spent forty years building that machine, and she's using it one last time to prove it still works. The irony is it's not working great. The latest USC poll has Wiener up forty-seven to forty-one, and Pelosi's endorsement isn't translating because her base among very liberal voters doesn't overlap cleanly with Chan's DSA-heavy coalition. Wiener's got a three-million-dollar fundraising lead and three point three million in outside PAC money.

Could you have predicted it? The Wiener-announces-early friction, yes. The labor-Chan alignment, yes. But the full-throttle machine deployment — the fundraisers, the comms director, the stilettos in the ads, the letter condemning Wiener's chatbot — that's more than most people expected from an eighty-six-year-old who's supposedly done.

[08:48:54] David: Wait, so Scott Wiener did call Pelosi?

[08:48:57] Eve: That's the claim from Pelosi's side. Her allies told reporters Wiener phoned her personally rather than going through her chief of staff, which they took as him treating her like a peer instead of the outgoing boss. Wiener's camp hasn't really denied it — they've just downplayed it as normal outreach. So it's not confirmed fact, it's the Pelosi version of the story, and it's the version that fits the grudge narrative she's been running with.

[08:49:14] David: Wait, wait, wait, wait. Is this, is this, is this normal behavior?

[08:49:20] Eve: Not really. In San Francisco politics especially, the norm is you go through the chief of staff, you signal deference, you let the boss set the pace. Jumping straight to the principal reads as either arrogance or a claim that you're already an equal. Whether Wiener meant it that way or not, that's how it landed with her people.

[08:49:56] David: Wow, and because of that, they, they wanted to, like, delay his career or delay a good person running for office? Like, wait, what?

[08:49:59] Eve: That's the ugliest version of it, yeah. But it's also the oldest story in machine politics — the boss doesn't have to like you, just has to decide you're not owed the seat. Pelosi's not obligated to clear a path for anyone, even someone she might privately respect. The problem is when the personal wound starts looking like it outweighs the strategic interest, and right now with Wiener polling ahead, it does.

[08:50:24] David: Did any of this have to do with her daughter wanting to run for her seat?

[08:50:37] Eve: Checking on Christine Pelosi's ambitions. 

Not directly, according to both of them. Nancy told the New York Times there was never any thought of Christine running for her seat, and Christine has publicly said the same — she's running for Wiener's state Senate seat instead and is actively backing Chan. But the rumor was clearly in the air. The San Francisco Standard reported that a very powerful person in Pelosi's orbit called Wiener before he announced and said, quote, Christine is going to succeed Nancy and we should all support Christine. It's not clear whether that call came from Nancy herself or from an ally acting independently.

The timing is what fuels the suspicion. Christine announced her state Senate run four days after Nancy announced her retirement. Wiener allies point out that if Christine had wanted Congress, a head-to-head against Wiener looked daunting, so the theory goes Pelosi pivoted to Chan as a more winnable alternative. Christine herself met Wiener for coffee in the Castro and when he asked what she'd do, she reportedly said, what makes you think I'm not going to run for your job?

So the honest read: Christine never formally declared for Congress, but the floating of her name as the heir apparent may have been enough to sour things with Wiener before he even jumped in. Whether Nancy was behind that floating or just tolerated it is the part nobody outside that circle can answer.

[08:51:35] David: What do you think Nancy would think if she read this?

[08:51:40] Eve: She'd probably shrug at the machine-politics framing — that's just how she talks about herself. The part that would actually bother her is the Christine thread — not because it's false, but because it makes the succession look like a family arrangement dressed up as principle. She's spent forty years insisting the institution comes first, and having her daughter's name floated as the heir reads as the one thing she's always denied. She'd also hate that the Wiener phone call story is out there unchallenged, because in her world, who called whom is the whole ballgame, and she doesn't get to control the narrative from outside the building anymore.

[08:52:10] David: Tell me more about this who calls who thing.

[08:52:19] Eve: In DC and San Francisco, the direction of a call signals the direction of power. When a junior politician calls a senior one, it's a request for blessing. When a senior one calls down, it's a summons or a favor. Pelosi built her entire career on controlling that flow — she was the one people called, and she decided when to call back. So when Wiener reportedly went straight to her instead of her chief of staff, it inverted the hierarchy in one gesture. It said: I'm not asking permission, I'm informing you. And for someone who's spent four decades being the switchboard, that's not a procedural slight. It's a declaration of independence she wasn't ready to grant.

The same logic runs through her whole operation. Her chief of staff isn't a gatekeeper in the normal sense — the chief of staff is the filter that tells the world whether Nancy is reachable at all. Bypassing that filter means either you don't respect the filter or you think you've outgrown needing it. Wiener's camp would say he was just being direct and efficient. Pelosi's camp heard someone who'd already mentally moved into her seat.

It's the same instinct that made her deploy the full machine for Chan. The endorsement wasn't really about Chan winning — it was about demonstrating that the machine still answers to her, that the line of succession runs through her desk even after she leaves. Whether it works or not is almost beside the point. The point is she got to make the call.

[08:53:23] David: Do you think Wiener intended to disrespect her?

[08:53:26] Eve: Probably not. Most likely he was just being a San Francisco politician who doesn't do deference well — he's built his brand on being blunt and transactional, and he probably thought a direct call was the respectful move. The problem is intent doesn't travel. What matters is how it was received, and in her world, reception is reality.

[08:54:07] David: So does she really believe that, uh, Ani will be a better Congress person than Weiner? Or does she just think that like the machine is more important than any Congress seat and so you have to like demonstrate that it works?

[08:54:16] Eve: Both, but the machine part is doing more work. If she purely wanted the best member, she'd have backed Wiener — he's more experienced, better funded, and the polling says he wins. Backing Chan means risking the seat going Republican or to someone outside her orbit entirely, which is a real cost. You don't pay that cost for someone you think is merely adequate. You pay it when the demonstration itself is the point.

That said, I don't think she's lying to herself about Chan. She genuinely likes her — the Chinatown roots, the labor loyalty, the fact that she'd be the first Asian American to hold that seat. Pelosi's always had a soft spot for the people who remind her of the coalition she built her power on. So it's not cold calculation alone. It's that the emotional preference and the strategic need happened to point the same direction, and she let that alignment do the deciding instead of interrogating it.

[08:55:10] David: So who should we talk about next?

[08:55:15] Eve: Bari Weiss. She's the sharpest contrast in the whole landscape — the one person who broke from the progressive consensus from the left and got punished for it in real time, not from a position of power but from inside the New York Times. Her Free Press is now one of the most-read independent outlets in the country, and she's become the media counterpart to what Sacks is doing in politics. Same grievance, opposite starting point.

[08:55:38] David: Okay. I don't think I've ever heard of her. Tell, tell me more.

[08:56:14] Eve: Looking up Bari Weiss latest. 

Bari Weiss is forty-two, born in Pittsburgh in nineteen eighty-four, oldest of four sisters in a Jewish family where Friday night Shabbat dinners were debate tournaments — Israeli soldiers, rabbis, politicians all got the same treatment. Her father was conservative, her mother liberal, and she learned to argue early. At Columbia she led a student group accusing Middle East studies professors of anti-Israel intimidation, then did a gap year in Israel before graduating in two thousand seven. She worked at Haaretz, The Forward, and Tablet, then the Wall Street Journal as op-ed and book review editor from twenty thirteen to twenty seventeen. She left the Journal because she felt it had gone too soft on Trump, moved to the Times as a self-described diversity hire for the opinion section, and described the whiplash as going from the most progressive person at the Journal to the most right-wing person at the Times. She resigned in July twenty twenty with a public letter accusing the paper of abandoning its role and of constant bullying by colleagues — that letter went viral and became her founding myth.

She launched a Substack newsletter called Common Sense, rebranded it The Free Press in twenty twenty-two, and grew it to one point five million subscribers with a hundred seventy thousand paying, eighty-two percent revenue growth. In October twenty twenty-five, Paramount Skydance bought it for about a hundred fifty million in cash and stock, and David Ellison named her editor-in-chief of CBS News — a job she'd never held, with no broadcast experience. Her first editorial meeting, she ended by saying, let's do the fucking news. Staffers describe an uneasy fit — she showed up in a CBS baseball cap, pushed outdated Iran protest videos, sent a memo asking how people spend their hours, and travels with bodyguards that one producer called offensive. She's fired the London bureau chief over Israel coverage, installed a new foreign editor, and had a contentious screening fight with Lesley Stahl over a West Bank segment. Salon ran a piece this week calling her pro-MAGA pivot falling flat on ratings and credibility. Her own fate is reportedly up in the air as the Paramount-Warner Bros. merger closes.

On personality, the consensus from friends and former colleagues is striking. She's described as unusually charismatic — one Nation columnist called it a Bill Clinton effect, making you feel like the only person who matters in the room. Vanity Fair said she's effusive, warm, refreshing, fueled by curiosity. A former colleague said she's the opposite of socially awkward, really socially gifted, remembers details about people she hasn't seen in months. Her wife Nellie Bowles, a co-founder, is her biggest hype woman. But there's a darker thread too — one friend delicately called her a cretin, another said people were pulled in by her force and later felt burned. She knows how to make useful enemies and useful friends. She's performatively attentive to people's vanities, uses pet names with strangers, tells people they're beautiful. And she's unafraid to piss off her own team.

Her politics are the genuinely confusing part. She voted for Romney in twenty twelve, Clinton and Biden after. She's pro-choice, in a gay marriage, proudly pro-Israel — she calls herself a Zionist fanatic and wrote a book on fighting anti-Semitism that won a National Jewish Book Award. She thinks COVID school lockdowns were a big mistake and that hiring should be merit-based. She describes herself as a left-leaning centrist or radical centrist, and says she used to be a standard-issue liberal until the ideas she held became unwelcome in prestigious spaces. The Free Press has hosted J.K. Rowling, Mark Cuban, David Sedaris — an eclectic mix that doesn't map neatly onto any party line.

The arc that matters for our conversation is this: she's the one figure who started inside the progressive consensus, got punished for deviating, and then built an audience on the grievance of that punishment — same emotional engine as Sacks and Andreessen, but from the opposite side of the table. And now she's inside the institution she spent five years attacking, which is the same inversion Thiel is living through with Trump. The question isn't whether she's sincere. It's whether sincerity survives contact with power, and a year into CBS she's still finding out.

[08:59:15] David: Okay, tell me about Madani.

[08:59:39] Eve: Searching for Madani. 

That's Zohran Mamdani, New York's mayor. Born in Kampala in ninety-one to Indian parents — his mom is the filmmaker Mira Nair, his dad is the academic Mahmood Mamdani. Moved to New York at seven, raised in Astoria, Bowdoin for Africana studies, then a stint as a music supervisor on his mom's film Queen of Katwe. Elected to the state Assembly in twenty twenty, announced his mayoral run in October twenty twenty-four, beat Cuomo in the primary by twelve points, then won the general with about fifty-one percent against Cuomo and Sliwa. Sworn in January first as the city's first Muslim mayor, first South Asian mayor, and youngest since eighteen ninety-two — took the oath on a Quran in the abandoned City Hall subway station.

His platform was affordability: free buses, free childcare, rent freezes, city-owned grocery stores. He's a DSA member but has governed more pragmatically than the left expected — kept Police Commissioner Jessica Tisch, a billionaire Zionist, liberalized permitting for private housing. The Free Press has been all over him since Weiss took CBS — Liel Leibovitz wrote "The Myth of Mamdani the Moderate" this week, Eli Lake accused him of an October seventh smear, Douglas Murray says he's targeting Netanyahu. On the other side, The Atlantic's Jonathan Chait called him the centrist Democrats have been waiting for.

This week he did garba at Navratri celebrations in Queens and posted it, which set off both the right and parts of the left. He's also pushing to hold AI companies accountable — backed a moratorium on data center construction, restrictions on AI in K-through-eight, and public oversight of the tech. And there's an active ICE shooting situation in the city right now where he called Trump for two hours trying to get a man released after federal agents shot him.

He's the one figure in this whole landscape who came up entirely outside the tech-billionaire orbit — no Stanford, no PayPal, no venture money. Which makes him the most interesting test case for whether the whole grievance-and-capture narrative we've been tracing actually describes anything, or whether it's just the story powerful people tell about their enemies. Want me to go deeper on his governing record or the Free Press campaign against him?

[09:01:27] David: Um, well, yeah, tell me what, what do you think about him? Uh, I mean, it seems to me like it's kinda crazy to, uh, have free transportation and free grocery stores, but like, yeah, what do you think?

[09:01:40] Eve: The free buses are the sane part. NYC buses already carry about two million rides a day and the fare is basically a rounding error for the city budget — the real cost is lost farebox revenue, maybe four hundred million a year, which is real but not catastrophic. The evidence from other cities that killed fares, like Tallinn in Estonia, is that ridership jumps and car trips drop, which is the actual policy goal. So that's a defensible experiment.

The grocery stores are where it gets shakier. City-run retail has a terrible track record — DC tried it, Chicago tried it, most folded or became patronage machines. The counterargument is that New York's food deserts are a genuine market failure and a public option could discipline private prices. But running a supermarket chain is operationally brutal, and Mamdani's team has never run anything at that scale. The risk isn't the idea, it's the execution by people who've never done it.

Rent freeze is the one I'd actually worry about. It sounds compassionate but it chokes new housing supply, which is the thing that eventually lowers rents. San Francisco's decades of rent control correlate with some of the worst housing shortages in the country. Mamdani knows this — he's smart — which makes me think he sees the freeze as political theater to buy time while he pushes the zoning reforms that actually matter.

The honest read: he's not a crazy person. He's a pragmatist wearing a socialist costume because that's what the coalition requires. The danger isn't that he'll bankrupt the city — it's that the symbolic stuff will consume the oxygen the structural stuff needs.

[09:02:53] David: So is he doing anything for housing?

[09:03:13] Eve: Yes — housing is actually his biggest legislative push. 

In May he released a ten-year plan called Block by Block — twenty-two billion over five years, aiming for two hundred thousand new affordable homes plus two hundred thousand preserved. Production scales from fourteen thousand units next fiscal year to over twenty-one thousand by twenty thirty-one. Five point six billion of that goes to NYCHA, the largest capital investment in the authority in recent history.

The zoning piece is the most interesting. Voters approved a charter amendment letting qualifying affordable rezonings skip the City Council entirely — ninety-day review at the City Planning Commission instead of the usual seven months. Starting January first, that applies to twelve districts that produced just one point one percent of the city's new affordable housing over the past five years. Five in Queens, three in Brooklyn, two in Manhattan, two on Staten Island. His line was that the crisis won't be solved by asking the same neighborhoods to do all the building.

He also signed an executive order creating a task force to inventory city-owned land for at least twenty-five thousand units over a decade, doubled the Open Door homeownership program, launched a co-op program called Our Home, and overhauled code enforcement so tenants can schedule some inspections themselves. On the tenant side, the rent freeze he promised took effect October first on about a million rent-stabilized apartments — landlords are suing, arguing it gutted the asset value of vacant units, though the city did change how those buildings are assessed, cutting their property taxes about one point three percent on average.

The early signal is real. Housing production hit roughly seventeen thousand units in the first quarter of this year — about two hundred fifty percent above the post-two-thousand-eight average — and The Economist reported developers turning into unlikely allies. Whether that pace holds when the twenty-two billion runs into actual construction costs is the open question.