Bulwark Takes – “What It Was Like To Face Off Against Nancy Pelosi”

Date: November 6, 2025
Guests: Former Rep. Barbara Comstock (R-VA), Jonathan Cohn (Bulwark writer)
Host: Sam Stein

Overview

This episode is a timely response to Nancy Pelosi’s announcement of her impending retirement from Congress. Sam Stein is joined by former Republican Congresswoman Barbara Comstock and political journalist Jonathan Cohn to reflect on Pelosi’s remarkable legacy. Through personal anecdotes and deep-dive analysis, the conversation explores Pelosi’s skills as a legislator and party leader, her tenacity and effectiveness, her relationships across the aisle, and the ways in which her leadership style shaped the U.S. House of Representatives over four decades.

Key Discussion Points & Insights

1. Personal Reflections on Pelosi – Early Impressions and Rivalries

[03:20] Barbara Comstock recalls working on Capitol Hill in the '90s:

• Pelosi, even as a young member, was known for being impeccably “put together” and gracious, despite their ideological differences.
• Early in her career, Pelosi even partnered across the aisle, e.g., with Frank Wolf, on China-related human rights issues.
• Comstock notes the irony: despite being Pelosi’s political “top target,” post-Congress they’ve had friendly encounters.

Notable Moment:

“When we were trying to be in the majority... it’s like, vote for this woman so you don’t have this woman – Nancy Pelosi – as speaker. She was a foil for everybody. But it was also because we knew how formidable she was.”
— Barbara Comstock [07:52]

2. Pelosi’s Legislative Effectiveness – Behind the Scenes Mastery

[08:26] Jonathan Cohn outlines why Pelosi stands out:

• Pelosi’s true genius was her behind-the-scenes mastery, not her public speeches.
• She passed enormous legislation with narrow majorities in both the Obama and Biden eras.
• Her “blocking and tackling” skills: Cohn highlights that she was pivotal not only in passing bills, but in blocking Republican priorities, e.g., stopping Social Security privatization in 2005 and ACA repeal in 2017.

Notable Quote:

“The criteria for a successful speaker legislatively is not what they do in front of the cameras – it’s what they do when the cameras are not on.”
— Jonathan Cohn [08:26]

[11:30] Sam Stein shares a story about Pelosi’s shrewdness:

• Recounts the Jack Murtha anti-Iraq War moment: Pelosi knew that for Murtha’s dissent to have the most impact, she needed to stay quietly supportive offstage, rather than publicly aligning with him.
• Her loss rate: Out of all the votes she brought to the floor, only one (TARP) failed the first time – and she quickly rectified it.

Notable Quote:

“She only lost one vote she ever brought to the floor, which is crazy.”
— Sam Stein [13:25]

3. Relationships, Fundraising, and Caucus Management

[14:23] Barbara Comstock on why Pelosi’s fundraising was about relationships:

• Pelosi wielded her fundraising as a way to build authentic, lasting relationships in the caucus.
• Even her GOP adversaries—privately—in Congress recognized she was far more organized and effective than her reputation often admitted.

Notable Quote:

“She was always… scorned, like, oh yeah, she doesn’t know what she’s doing. And it’s like, what do you mean? She’s beating you guys all the time.”
— Barbara Comstock [14:55]

• Comstock recalls Pelosi’s reputation as “the grown-up in the room”—the only leader willing to confront President Biden directly about electoral realities when others wouldn’t, doing so directly yet kindly.

4. Lead with Authority (Even Against Her Own Side)

[17:55] Sam Stein:

• Discusses Pelosi's confrontation with AOC and "the Squad" on immigration: when they tried to break with party discipline, Pelosi famously downplayed their influence with a sharp quip.
• The panel credits her for keeping the Democratic caucus unified, in contrast to frequent Republican divisions.

Notable Anecdote:

“They had four votes. It was the Squad. And the quote was... they don't have any following. They're four people and that’s how many votes they got. And it was just like sticking the knife in, in a way.”
— Sam Stein [18:43]

5. The Affordable Care Act – Pelosi’s Tour de Force

[19:00] Jonathan Cohn explains Pelosi’s critical role in passing Obamacare:

• Pelosi wrangled her caucus through brutal intra-party disagreements, both early (abortion language) and late (getting liberals to accept the Senate's weaker version after Scott Brown's election).
• She convinced skeptical liberals to swallow unpleasant compromises because they trusted her—she had fought for them, they believed her whip counts.

Notable Quote:

“When Nancy Pelosi comes to me and says, I can’t do any better, I’m gonna believe that.”
— Jonathan Cohn [21:23]

• The panel laments that this kind of demanding, behind-the-scenes legislating is a “lost art” in today's Congress.

6. Confronting Trump and Navigating the Modern Era

[23:47] Sam Stein:

• Recaps Pelosi’s iconic showdowns: the “all roads lead to Russia” Oval Office moment, the State of the Union speech rip, and leading two impeachments.
• Despite her efforts, Trump ultimately returned to power—a bittersweet note as Pelosi retires.

[24:57] Barbara Comstock reflects:

• While the Trump resurgence is a blow, Pelosi’s impact endures: e.g., women from her 2018 class rising to become governors.
• Acknowledges Pelosi’s frustration with Biden's slow exit and Trump's political resilience, but maintains her legislative achievements will outlast both.

7. Legacy: The Iron Fist in a Gucci Glove

[27:55] Sam Stein:

• Shares lighter memories: Pelosi’s fondness for Giardello chocolates and hot dogs.
• Summarizes her style as “an iron fist in a Gucci glove.”

[28:22] Jonathan Cohn and Barbara Comstock:

• Cohn hails her as “the most effective speaker of the modern era.”
• Comstock notes her resilience—even after a hip replacement and the violent attack on her husband.

Timestamps for Key Segments

• [03:20]: Barbara Comstock’s early impressions and stories as staffer and member
• [07:52]: Pelosi as the perennial Republican political “foil”
• [08:26]: Jonathan Cohn on Pelosi’s legislative skills
• [11:30]: Jack Murtha & TARP vote anecdotes
• [14:23]: How fundraising and relationships fueled Pelosi’s leadership
• [17:55]: Handling AOC and the Squad’s rebellion
• [19:00]-[23:22]: The Affordable Care Act, compromise, and trust
• [23:47]: Trump years, Pelosi’s opposition, and the pain of his return
• [27:55]: Reflections on legacy and lighter personal stories
• [28:22]: Final thoughts on resilience and effectiveness

Notable Quotes & Memorable Moments

• “The criteria for a successful speaker legislatively is not what they do in front of the cameras – it’s what they do when the cameras are not on.”
  — Jonathan Cohn [08:26]

• “When Nancy Pelosi comes to me and says, I can’t do any better, I’m gonna believe that.”
  — Jonathan Cohn [21:23]

• “Nobody does that anymore… It’s an art that seems to be vanishing.”
  — Jonathan Cohn [23:27]

• “She was a foil for everybody. But it was also because we knew how formidable she was.”
  — Barbara Comstock [07:52]

• “She was being like a nice grandmother doing it to a fellow—somebody who, you know, she didn’t want to do that. But none of the guys were stepping up and doing it, none of their grownups in the room who would do it. And that’s—I mean, she’s been here in a time when whether it’s Trump or Schumer or any other of these other guys won’t stand up and do the right thing. And she has been the grownup…”
  — Barbara Comstock [15:38]

• “Someone said she is an iron fist in a Gucci glove, which I think sums it up.”
  — Sam Stein [27:55]

Tone and Takeaways

The conversation is frank but affectionate, crossing party lines to recognize Pelosi’s rare effectiveness and grit. There’s admiration for her toughness, occasionally rueful acknowledgment of her skill as a political adversary (especially from Comstock), and a sense that a certain kind of leadership—rooted in relationships, mastery of legislative detail, and trust—is fading from Congress. The episode makes a compelling case that Pelosi’s legacy, both personal and legislative, will be felt for decades beyond her departure.