Danny Weiss: Taking Us Behind the Scenes in Washington

Although social media has enabled the public to obtain a more intimate and detailed understanding of the “real lives” of famous people, including our political leaders, this transparency doesn’t necessarily help us understand how the real work of lawmaking gets done in Washington. 

In today’s political climate, the art of dealmaking, of enacting an agenda, of reading a room, remains as mysterious as ever. 

In today’s episode of Deciding Factors, Eric speaks to one of DC’s smartest operators to give us a peek behind the curtain.

Danny Weiss is a former politics reporter who eventually left his career in media to become the communications director for the legendary California Democratic Representative George Miller. Later, Weiss served as Speaker Nancy Pelosi’s Chief of Staff. In that role, he helped navigate the famously contentious relationship between President Trump’s administration and Democrats in Congress.

These days, Weiss works in the public policy space, focused on technology, education and workforce issues, and he remains extremely tapped in to the going-ons in Washington. 

Listen along as Weiss discusses the debt-ceiling negotiations and how he thinks the White House worked with Speaker McCarthy to make a deal, reveals some of Speaker Pelosi’s work habits and quirks, explains how he thinks we can reduce extreme partisanship in Washington and much more.


Danny Weiss is a former politics reporter who switched careers to become the communications director for the legendary California Democratic Representative George Miller. Later, Weiss served as Speaker Nancy Pelosi’s Chief of Staff.

He now serves as the Chief Advocacy Officer for Common Sense Media, a global-non profit “focused on improving the digital lives of children and their families.”

Podcast Transcript

Eric Jaffe:
We make decisions every day. While some of them are small, others can have a huge impact on our own lives and those around us. But how often do we stop to think about how we make decisions?

Welcome to Deciding Factors, a podcast from GLG. I’m your host, Eric Jaffe. In each episode, I’ll talk to world-class experts and leaders in government, medicine, business and beyond, who can share their firsthand experiences and explain how they make some of their biggest decisions. We’ll give you fresh insights to help you tackle the tough decisions in your professional life.

It’s frequently said that social media has enabled the public to obtain a more intimate and detailed understanding of the quote “real lives of famous people,” including our political leaders. But even to the extent that may be true, this transparency doesn’t necessarily help us understand how the real work of lawmaking gets done in Washington.

In today’s political climate, how do you strike a deal? How do you enact your political agenda? How do you get things done inside the room where it happens? These days, these dynamics remain poorly understood, and I’m so thrilled today to welcome one of DC’s smartest operators to give us a peek behind the curtain. Danny Weiss is a former politics reporter who eventually left his career in media to become the communications director for the legendary California Democratic Representative George Miller.

Later, Weiss served as Speaker Nancy Pelosi’s Chief of Staff. In that role, he helped navigate the famously contentious relationship between President Trump’s administration and Democrats in Congress. These days, Weiss works in the public policy space focused on technology, education, and workforce issues, and he remains extremely tapped into the goings-on in Washington. Listen along as Weiss shares details on the debt ceiling negotiations, how he thinks the White House worked with Speaker McCarthy to make a deal, reveal some of Speaker Pelosi’s work habits and quirks, explains how he thinks we can reduce extreme partisanship in Washington and much more. Danny Weiss, welcome to the show, Danny.

Danny Weiss:
Thank you. Good to be here.

Eric Jaffe:
Just kind of to get us grounded here, why did you choose to go into politics, and what did you learn about politics as a reporter covering DC and in sort of your early roles in politics?

Danny Weiss:
Yeah. I had always been interested in journalism, but I was always interested in politics and advocacy. When I was in college, I did both. And when I came to Washington as a reporter, my first job was to cover Congress and the administration. So I was always dealing with political issues. I got to know members of Congress and people in the administration. And eventually, as does happen here in DC, a few different members offered me the opportunity to come to work on Capitol Hill.

And one member in particular who I had been covering, Congressman George Miller, was someone I really respected, and he recommended that I come to work for him, and I took him up on it. And the rest is history. George Miller came here as a reformer and thought that Congress should be more responsive to new voices, to younger members and to more progressive members.

He was a progressive Democrat, very successful legislator, very committed to legislation, and he was more committed to the issues than he was to his image. So I’ll never forget when we had a young reporter come in to do an interview with him who was very well-dressed for a reporter. I think he was wearing an actual suit, and he had shiny black shoes. And George mentioned afterward that that reporter had dressed really nicely, and he said to me, “Dress conservative, vote liberal.” And I think that’s a great way of summing up his career that he was mostly interested in results.

As far as the times being different, George Miller was here at a time when Democrats had a bigger majority in the Congress and could get more legislation passed because of that, but there was also more comedy between the Republican members and the Democratic members. So it was a very different time in that regard.

I think one way to say it is there’s a little less genuine personality to Washington these days than there used to be. I think members of Congress, for example, were more comfortable being themselves back in the day. There are probably a number of good reasons for that. One is that you didn’t have as much media scrutiny in, let’s say, the ’70s and ’80s that you do today, and you certainly didn’t have social media back then.

And so, the idea that you might, let’s say, go out and have a couple of drinks and be a little bit rowdy at night after a long day at work wasn’t necessarily going to result in a photograph that was then going to be tweeted and seen by the world. So members were probably a little bit more capable of being themselves and comfortable being themselves. I can just tell you that even Congressman Miller said to me one time because he was really an ideas person.

He cared about early childhood education. He cared about the environment. He cared about working families and labor unions. He would work with Republicans. And he said, “I was talking to one of my Republican friends on the Appropriations Committee, and I was saying to him, ‘I’ve got this really good idea. We could work together on an early childhood issue.'” And he said that that Republican member looked both ways. He looked left, and he looked right, looked behind him, and he said, “George, I can’t talk to you.”

And that was assigned to George. That was, I would say, in the 2010s. That was really assigned to George, the things that really changed so much that it wasn’t going to be that possible to get big things done.

Eric Jaffe:
Most historians point to Newt Gingrich’s entrance into Congress in the ’90s as being the time where it became hyperpartisan, and then it’s just sort of been a downward trend from there. Is that how you see it?

Danny Weiss:
I 100% subscribe to the view that the demarcation point in hyper-partisanship in Washington is 1994 with the Republican takeover of the House under the leadership of Newt Gingrich.

Eric Jaffe:
Now, you worked as Nancy Pelosi’s Chief of Staff from 2017 to 2019 while President Trump was in office, perhaps the least bipartisan, most partisan time in recent history. You were up close on that. I wonder is there anything that would surprise you or surprise us rather about Speaker Pelosi and President Trump’s relationship, which was a famously acrimonious one? And also, is there anything about the way that White House staff and you and your staff work together that might surprise our audience?

Danny Weiss:
If you know Nancy Pelosi or if you’ve been able to observe her closely, this might not be surprising, but if you only know her as a caricature through cable television, then you might be surprised that she is an enormously respectful person of people that she disagrees with or agrees with. She has very strong opinions. There’s no question about that.

And she is willing to speak against somebody in public, but she also feels sort of an obligation almost to do that with a level of respect that elevates her opponent to an extent, but it also elevates her in that dynamic. And I can say, for example, one meeting at the White House in particular, the way she would speak directly to the President, she would even lean over during the president, say, “Mr. President, with all due respect,” and she’d put her hand on top of his hand in a sort of gentle fashion. And then, she might say something extremely direct to challenge his point of view with her point of view, but by placing her hand on his hand in a way to suggest that there’s a place where we could get together here and reach an agreement or at least understand each other better.

Eric Jaffe:
And what about at the staff level? When you and your colleagues were interacting with White House staff, what was that like behind the scenes?

Danny Weiss:
So staff try to turn down the temperature that might exist between the members. So if things are particularly hot or if things are particularly stuck, it is the job of staff in the end to help move things forward, provide a good path for whoever they’re representing at that point.

So when I would meet with White House staff, I intentionally avoided anything that sounded like it was just being said for partisan purposes, that was not going to get us anywhere. It didn’t necessarily get us far, but I think it was a better approach to say that this is really about substance, and it’s not about me proving my partisan bonafides to my opponent. It’s about trying to get something done. I think a lot of good staff work that way.

The other thing about staff working with each other is you have to come armed with good information. Better armed you are with information, the more likely you are to be successful. Whether you have better data or whether you have prepared negotiating positions ahead of time, coming prepared with that makes a big difference.

Eric Jaffe:
We just went through this period on the debt ceiling where it seems like the temperature every day leading up to the deal that was eventually struck was it was very hot for outsiders. It was a little bit hard to understand. Was there a constituency on the Republican side who genuinely wanted to breach the debt ceiling? If they did, what was the reasoning behind that? Could you take us behind the scenes?

Danny Weiss:
Yeah. And, of course, on the debt ceiling specifically, it ended up being a very small group of people, which is not uncommon for a high level negotiation. But usually, there would be four or five parties at the table. You’d have the top Republican Senate staffer, the top Democratic Senate staffer, similarly in the House, the top Democratic and Republican House staffers, and then someone from the White House.

And there’d be paper and ideas and discussions shared among the five of them. In this case, it was just the president and Speaker McCarthy and his staff. So that was a little bit unusual. The way that the White House had to approach that, my understanding, is that they didn’t necessarily know if Speaker McCarthy was going to be able to control those members of the house who had said they would rather default than give in to so-called give in to demands from the White House.

So they had to be careful about that. They did make an assumption that Speaker McCarthy would accept a deal because it would elevate Speaker McCarthy in Washington. That was a very important leverage point for the White House, that they knew that there was something McCarthy wanted outside of the details.

And one of the things that he wanted was to be elevated in the stature of Washington. Now, up until recently, the speaker went from being in January the laughing stock of Washington with the Republican Conference because it took 15 rounds for him to get elected speaker to then getting their operation going and running the House in a relatively normal fashion, and then getting to the point where the White House invited the speaker for negotiations.

That was a huge narrative shift for Speaker McCarthy. I think that was clever for the White House to do that, and it was a benefit to McCarthy. It will remain to be seen how much of a benefit it is for McCarthy because he still has people in his conference who want to, shall we say, burn the house down and maybe take McCarthy with it.

Eric Jaffe:
From your inside perspective, what about our legislation making actually does work and is working reasonably well?

Danny Weiss:
We are still able to name post offices. I believe that goes relatively well. Bunch of those happen all the time. Surprising that some post offices don’t have real names, so they have to still get named. But in seriousness, there’s not a lot you can point to except when sort of the political climate is right.

And, for instance, when a new president takes office, there’s a lot of energy around a new president. And what we found with President Obama, President Trump and President Biden is they each got two years to work with a majority from their own party. And then the remainder of their term was spent with Congress in the opposition. So one of the things that does work is that when there is a majority, you can get stuff done. President Trump passed the Tax Cut and Jobs Act in late 2017 because he had a Republican majority.

It’s not easy to work even with your own party, but it’s certainly that is when you do have a majority in the White House and in Congress, both parties are able to get stuff done. When you don’t have a majority, you have to be willing to accept smaller deals and compromises.

One thing about this Congress, the 117th Congress that we’re in now, is that we don’t know if it’s going to produce more bipartisan compromise or not. We have one basic bipartisan compromise, which is the debt deal, which had to get done, but we don’t have anything else to point to at the moment that I’m aware of. So it remains to be seen what’s going to happen with the remainder of this Congress.

Eric Jaffe:
What have you found the most successful leaders have in common in their approach to making sure that they really use the time that they have in office to drive impact?

Danny Weiss:
Well, things have changed a little bit because of the pace of work. If you go back to maybe Tip O’Neill, former Speaker of the House, Tip O’Neil from Massachusetts, he was considered a very effective person, famously worked with President Ronald Reagan on the other side of the aisle. But life moved a little more slowly back then. Back then, you could get together over drinks, or you could have long conversations. You could take a little bit more time to make decisions. Politics now operates in a pressure cooker. You get very little time to make decisions.

So one of the things that effective leaders do today is they have to be decisive. You have to be willing to work really hard. You have to be willing to work very long hours. In the case of Speaker Pelosi, she does not drink alcohol, and she doesn’t really even drink coffee. She was working with a lot of other people who still wanted to have a drink, and they might go off and have dinner and have a drink, and she’d go back to her office or to her house and work the phones. And she was able to outwork people.

So I do think effective leaders are able to make decisions in a pressure cooker environment, make them quickly, are willing to work very hard, and know that their moment of power might be fleeting, and they should take full advantage of it while they have it.

Eric Jaffe:
No coffee. Wow, I didn’t know that about the speaker. How does she operate with no caffeine?

Danny Weiss:
She does eat dark chocolate, and she does have ice cream with dark chocolate coating, so she gets a little bit of caffeine.

Eric Jaffe:
Could you just talk about our media structure? Does it, in your view, address the information needs of our citizens, and how would you want it to change if you were in charge of all of the major media outlets?

Danny Weiss:
Yeah, media is key to politics and policymaking. I’ve always said that a good staffer on the Hill will understand both the policy, the politics, and the communications element of every issue. And if you’re only thinking about the details of the policy and you’re missing the politics and the communications, it’s not going to work.

There are specialists on the Hill to be sure, but at the same time, even among the specialists, they have to understand the media component. So today, the media environment is extremely fractured and, at the same time, extremely narrow. Your leading newspapers are read by a very small number of people. They do as good a job as they can in the current environment. But at the same time, people are getting their information, and even more people get their information from what’s left of cable television, which is also diminishing, and social media, and much, much less than ever before from their local newspaper.

And that is a threat to our democracy. It’s just a plain, simple threat to democracy that there is less independent information available to the average citizen where they live about their own community. And that is the result of these hedge fund companies that have bought up local newspapers or bought up newspaper chains and have harvested them for profit. Now, you can add artificial intelligence to the equation, and you can have newspapers that are run with no reporters at all. That is a threat.

Ideally, the average citizen… I don’t expect Americans to spend most of their time or even half of their time paying attention to public policy fights. That’s not the expectation. That’s the job for people in media. It’s the job for people in government. It’s the job for some people in the private sector. ut most people are going about their day-to-day lives, raising their families, trying to earn a living, and that’s totally understandable.

But the absence of local independent media is a threat to our democracy. And the rise of social media as a delivery platform for information with virtually no regulation, I think, in the end net-net, I would say it’s turning into a net negative in terms of how well-educated Americans are about what’s happening in the country.

Eric Jaffe:
For political leaders, you might say social media is great because, now, it allows them to directly connect with the public. You might also say it’s bad because it has become so all consuming that it’s a distraction, and it’s only exacerbated the challenges on members of Congress being focused on their image rather than on the issues. Where do you come down? Is social media good, bad, or somewhere in between?

Danny Weiss:
Probably in between, but I would say in between and leaning toward bad because in social media, we all know you live in a bubble. So if a member of Congress or a candidate wants to talk to the bubble, then, they know where to go, and they can hire a firm to make sure that their content gets delivered to that bubble.

If you need to get outside the bubble, you have to be clever, maybe hire a firm that’s very good at reaching independent voters. But on social media, it’s very easy to get trapped in bubbles, which then, in a way, limits your reach even though people think that it’s expanding their reach.

So I still think it’s important for people to get out there, candidates, challengers, elected office holders, and actually talk to people. Candidates do still rely very heavily on television advertising to carry their messages, but the airwaves are saturated at this point. So you’re just basically creating kind of a general noise that may or may not be leading people to or away from the polls. We need to learn more about that. But social media is probably going to go through an evolution, and it looks to me like it’s still evolving into a more negative direction unless new regulations are put on it.

Eric Jaffe:
Nice. And maybe final question here, if there were one thing we could do or the president could do, or one change that’s near term in the country to say, “Bring back some of that spirit of bipartisanship,” what would it be?

Danny Weiss:
I would say create more opportunities for members of Congress to meet with each other privately away from the cameras, almost like in a retreat setting where the agenda is only to get to know each other better and to reach a greater understanding of why different members come to the issue the way that they do.

I can tell you for a fact that both George Miller and Nancy Pelosi, two of members of Congress I respect the most, they both did that in their careers. They had that opportunity, and they used those relationships that they built in private to their benefit legislatively.

Certainly, Pelosi did that over many years. She had a famous relationship with Congressman Wolf, a moderate Republican on the Appropriations Committee from Virginia. The two of them were able to get a lot of stuff done together, and George Miller did the same thing. So if I had one idea, it would be let members of Congress spend a little more time together in a constructive setting away from the cameras, and get to know each other.

Eric Jaffe:
Danny Weiss, thank you so much for being on Deciding Factors. We really appreciate you coming on the show today.

Danny Weiss:
All right. Thank you, Eric. Great to talk to you.

Eric Jaffe:
We hope you’ll join us next time for a brand new episode of Deciding Factors, featuring another one of GLG’s network members. Every day, GLG facilitates conversations with experts at across nearly every industry and geography, helping our clients with insight that leads to true clarity.

Feel free to leave us a review on Apple Podcast, we’d love to hear from you, or email us at decidingfactors@glgroup.com if you have feedback or ideas for future show topics. For Deciding Factors in GLG, I’m Eric Jaffe. Thanks for listening.



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