Like a lot of people on the left, I’ve always had mixed feelings about House Speaker Nancy Pelosi.
On the one hand, she’s an enormously effective caucus leader, which is not easy given the diversity of the Democratic Party. But she’s also a pragmatist, and that means she chooses her battles very carefully. That instinct for compromise is often hard to accept — and sometimes looks a lot like capitulation to the impatient among us.
To conservatives, Pelosi is the face of progressivism, a dreaded “San Francisco liberal.” And because she’s such a capable legislator, she’s been a thorn in the side of House Republicans since she first became speaker of the House in 2007. Indeed, she’s arguably been the greatest obstacle to Republicans in Congress for the last decade.
The truth is that Pelosi is a bit of an enigma. For all her fame, we don’t really know that much about how she sees the world. Pelosi is still defined mostly by conservative caricatures (and lately some progressive ones). And generally speaking, she doesn’t say more than she needs to say — and that’s probably one of the reasons for her success.
A new biography of Pelosi by Time magazine writer Molly Ball throws some light on the House speaker. It’s not the first book written about Pelosi, but it may be the best one, and in any case, it’s revealing. The big takeaway from Ball’s book is that Pelosi is an old-school operator. She accepts the constraints of the political machine and navigates it methodically. It’s a skillset that doesn’t always play well in the age of Twitter, but it works.
I spoke to Ball about why she was drawn to Pelosi in the first place and what she learned about her political philosophy. We also discuss what might be the most interesting question to me: What does Pelosi regret? And what does she think of her progressive critics who say she’s too moderate or too eager to compromise to lead the Democratic Party?
A lightly edited transcript of our conversation follows.
Sean Illing
You didn’t find Pelosi all that compelling when you started covering her a couple of years ago, but at some point you clearly changed your mind. Why?
Molly Ball
I think one of the things I came to understand about her is that she is a fascinating character who’s had a fascinating life, but she’s not necessarily a great teller of her own story. She’s not a natural storyteller. You think of great politicians as orators who are always speaking in pithy anecdotes and who talk about themselves in relatable and moving and empathetic ways. She has a lot of strengths as a politician, but I don’t think that’s one of them. But my view of her changed as I started to dive into her story.
Sean Illing
She’s been pretty widely caricatured, on both sides, and it’s hard to shake that perception.
Molly Ball
Right, and I think a lot of my book is about the role of perception in politics generally, but also specifically the way that she’s been perceived over the course of her career. And I think I, as much as anyone else, was susceptible to this sort of baked-in caricature of her as a rigid partisan without a lot of depth. And I guess I what I learned is that that caricature isn’t accurate.
Sean Illing
Something that comes across really early in your book is that she likes to control things —
Molly Ball
Her staff will tell you that she line edits every press release that goes out and she’ll change a word here and there just so that it’s exactly right. Look, I don’t want to psychoanalyze her — I’m not qualified to do that. But what you see running through her life is this desire for control, whether it’s wanting to be able to control her own surroundings, her own situation, her own life.
Sean Illing
Where does that come from?
Molly Ball
She was born into a situation where women didn’t have a lot of control over their own lives and seeing how her mother was never able to be independent and be in control of her own future. And so from an early age, she’s wanted to have control and I think that manifests itself all over the place.
But look, there’s this interesting sort of paradox, where on the one hand she will tell you that she doesn’t care about her public image. On the other hand, I think she has become more aggressive about establishing her image and particularly what she sees as her strengths in recent years, because at some point she realized that her negative public image was interfering with her ability to achieve her goals.
Sean Illing
A lot of that negativity has come from her own party —
Molly Ball
Oh yeah. In 2016 and 2018, there was a lot of angst in the Democratic caucus and an attempt to oust her as minority leader and then as speaker, just because she was viewed as such a toxic and polarizing figure. Even many Democrats had concluded that she was just a liability, that she was a burden simply because of the negative perceptions that had accrued over the years.
Of course, her allies would say that’s because the Republicans created this impression of her with hundreds of millions of dollars of negative ads tying Democratic congressional candidates to this caricature of a “San Francisco liberal.” And it became this sort of vicious cycle where Democrats didn’t want to defend her because she was viewed as toxic and then the perception that even her own party didn’t support her increased the perception that she was toxic, and so it just fed itself in a loop.
At some point, if she didn’t defend herself, nobody else was going to do it.
Sean Illing
Does Pelosi think of herself as a genuine progressive?
Molly Ball
I don’t know how she would answer that question, and I can’t speak for her, but I’ll say this: She was born into a Democratic political family in Baltimore, and I think her loyalty has always been to the party as an institution rather than to any movement or issue. So she’s not a progressive in the activist sense. During the Vietnam War, she was leafleting for Democratic candidates for president. In 1968, when there were riots outside the Democratic convention, she was inside the convention hall. So she’s always been part of the establishment in that sense.
But she’s also a liberal. And she has been on the left edge of the party when it comes to things like gay rights and the environment and war. I mean, she didn’t just vote against the Iraq War, she voted against the Gulf War. She’s been on the left side of her party and pretty representative of her district in a lot of those ways.
Now, I don’t think she considers herself a socialist. She certainly is not as far left as some on the left would like her to be, but on things like reproductive rights, she went against her church and her own party to be a consistent advocate for a woman’s right to choose. So I would place her on the left, but not on the far left.
Sean Illing
What does she think of her critics on the left who say she’s a sellout or that she embodies everything that’s wrong with the Democratic establishment?
Molly Ball
She’s someone who very much sees politics as the art of the possible. And I think what she would say to anyone who’s got a cause or an issue or a movement that they’re passionate about is go out and do the work. Go build support out there among the public, go find votes here in the House of Representatives. The House Democratic Caucus is very ideologically diverse, and then they’ve got to deal with the Republicans. So you can be as far left as you want to be, but it’s not going to get you anywhere if you can’t find other people to build that movement with.
So you saw last year when she had that high profile dust-up with the Squad over the border wall funding, and she made that dismissive comment that they’re four people and that’s all the votes they got. She was speaking quite literally. She was saying of all the Democrats in the House Democratic Caucus, only four of them thought that this particular bill didn’t go far enough. And this was the border funding supplemental that caused a lot of really nasty infighting among the Democrats in 2019.
And so what she’s saying to them is, it’s great that a lot of people like you on Twitter, but if you can’t build a broader base of support, either out there among the public or internally in terms of votes in the House, you don’t really have anything.
Now, I do say in the book that I think she’s somewhat dismissive of soft power and that maybe she’s too focused on hard power, but I think she came to this lesson very honestly. She learned earlier in life that people see you differently when you have the authority, when you have the votes. And that goes all the way back to the ’70s in San Francisco when she was appointed to the Library Commission. As a woman in 1975, nobody necessarily listened to her when she opened her mouth, but people had to listen to her when she had a vote.
Sean Illing
Did you find her to be introspective at all about the mistakes she’s made as a leader of the party?
Molly Ball
She’s not a person who admits regret. She will not tell you that she regrets anything. She doesn’t do regret, and she doesn’t do fear. So you can ask her, “What are your greatest regrets in life?” And she’ll just say, “I don’t do that.”
Sean Illing
So you asked her that question, and she wouldn’t answer?
Molly Ball
Nope, she wouldn’t answer it.
Sean Illing
But she has to have thought about the reality of Trump and how we got here as a country. That’s not to say that the Democratic Party is responsible for Trump — that’s absurd. But there’s no way to tell the story of this era without grappling with the failures of the Democratic Party and, for better or worse, she’s part of that.
Molly Ball
I tried to engage her in a conversation about what she thinks went wrong in 2016 and she doesn’t want to look back on it. There are a lot of explanations for what happened, and it’s really hard to sort out what’s wrong with a party that wins the popular vote. Because you can’t say, well, we turned the American public against us and our positions are all unpopular when your candidate wins the popular vote and there are a lot of other contingencies.
She has said various times that she thinks there’s a lot of anger in the populace in large part due to worsening income inequality and to the hangover from the 2008 financial crisis, which she would’ve liked to have done more to address but couldn’t do it because of Republican opposition in Congress.
Sean Illing
The thing is, and you point this out in the book, you can look at Pelosi’s approach here and call it blind or a refusal to reflect on what’s gone wrong, but this is just her philosophy.
Molly Ball
Yeah, I think that’s right. Ultimately, she’s much more concerned with what she can do about something than with theories about why things are the way they are. A word that one of her mentors used for her was “operational.” She’s always focused on what she can do in a certain situation given the constraints she’s facing. That’s just how she approaches her job.
Sean Illing
But she clearly has ideas about how to win in 2020 and beyond —
Molly Ball
I’ve talked to her quite a bit about how she thinks the Democrats should run in 2020 and what she thinks the elements of a successful campaign are. And you can see the seeds of a critique there of what she thinks Democrats were insufficiently focused on before. She was a big part of developing the Democrats’ strategy in 2018, and it was very much about ignoring Trump and staying focused on kitchen-table issues, particularly health care and economics. The message was, “We’re going to protect Medicare, we’re going to expand Medicare.” It was a very New Deal campaign message.
She does not think that Democrats are going to win the Electoral College by campaigning on Medicare-for-all. And she says that when you say you’re going to take away people’s health care, even if it’s to give them something better in the long run, they view that as “menacing.” So she does believe that Democrats need to run to the middle if they’re going to win a national campaign and win the Electoral College.
Sean Illing
For all her pragmatism, there are issues on which she refuses to compromise, even if it means the Democratic Party loses those non-college-educated white men in the middle of the country.
Molly Ball
I think that there are certain values that she thinks are non-negotiable, like gay rights. She represented San Francisco in Congress in 1987 when the AIDS crisis was reaching its height and when a lot of politicians in both parties did not want to speak for that marginalized population, and she always saw that as her role. Now, she wasn’t in leadership at the time. She was representing her district, and that was very much a problem for her district and for her constituents, but she’s never wavered on her commitment to things like that. She was a big part of bringing the Democratic convention to San Francisco in 1984, and that was really the origin of the whole idea of “San Francisco liberals.”
And she’s always viewed that as essentially a homophobic slur. She believes that when Republicans say “San Francisco Democrat,” what they’re saying is a dog whistle for gay rights.
Sean Illing
What does she make of all the hate for her on the right? Isn’t it the ultimate sign of respect?
Molly Ball
That’s her view of it. I mean, her line is, “If I weren’t effective, I wouldn’t be a target.” And I think there’s some truth to that. I think if she were as hapless as speaker of the House as some of her predecessors, she wouldn’t be such an obstacle to Republican policy goals. If it is true that without her, Obamacare wouldn’t have passed, well, then she’s the reason there’s this big, new program that spends a lot of money giving health care to poor people.
So a lot of Republicans, particularly who are on the inside of the legislative process, have a sort of grudging respect for her because she’s good at her job and because she is a tough negotiator and because she’s always able to keep her caucus in line behind her.
Sean Illing
What do you think her legacy will be?
Molly Ball
I think it’s her historic accomplishment as the first woman speaker of the House — that’s a really big deal. And she’ll go down in history for that. I think people often lose sight of what a monumental achievement that is. And she had to fight pretty hard to get there.
And then there’s her general effectiveness as a leader, right? You talk to experts on Congress and they will tell you that she is one of the most effective congressional leaders in modern history, no matter how you measure it.
You have to go back to a Sam Rayburn or an LBJ to see a legislator who was so effective at working the levers of power. As Rahm Emanuel said to me in one of my interviews with him, “A lot of Democrats are uncomfortable with the use of power. Nancy Pelosi is not.” And she never has been.
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