The FRONTLINE Interviews

Gil Duran

Harris Adviser

Gil Duran served as Kamala Harris’ communications director during her tenure as California attorney general. He has also worked for U.S. Senator Dianne Feinstein and California Governor Jerry Brown. Duran has also worked as the opinion editor of The Sacramento Bee and the editorial page editor of The San Francisco Examiner.

The following interview was conducted by the Kirk Documentary Group’s Mike Wiser for FRONTLINE on July 25, 2024. It has been edited for clarity and length.

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Harris as a Rising Political Star

So let me start at the beginning.When do you first come across Kamala Harris?

Well, in 2010, Jerry Brown, who I had also worked for, was running for governor.And he had been the attorney general.And the person running to replace Jerry as attorney general was the district attorney of San Francisco, whose name was Kamala Harris.And I had heard that name before, but I didn't really know much about her.But she ended up being locked in a very, very tight, close race with Steve Cooley, this Republican DA from LA, who was the epitome of the old-school, tough on crime, antiquated approach to public safety.

So I found myself rooting very much for Kamala Harris to pull that out, and to win.And when she did win, it was pretty historic, and gave people a lot of enthusiasm and hope.And the moment you become the attorney general of California, the AG, when people say the AG initials stand for “Aspiring Governor.” And Brown ended up going from attorney general to governor.And so Kamala Harris immediately becomes somebody who's seen as a potential for that office.

And who are you at that time?Where had you come from?Just give me a little sense of your background leading up to 2010.

Well my political career started in 2003, when I met Jerry Brown through a mutual friend at a dinner party.At the time, I was a janitor working in West Oakland, and had been sort of caught outside of newspapers when the bust happened, and ended up working at Oakland City Hall for the mayor of Oakland, who goes on to become the attorney general and the governor.I helped Jerry become attorney general, working for him in the City of Oakland.

And when all of these elections in 2010 were happening, I had become the communications director for Senator Dianne Feinstein.So I was watching this from Washington.I ended up coming back when Jerry Brown becomes governor, to be his press secretary in Sacramento.And so in Sacramento, I became a lot more aware of Kamala Harris, and her circle, and her people.… And, although it didn't seem like a logical step for someone who had had the job that I had had, they recruited me to come and be the communications director and senior advisor for Kamala Harris.

And when it became—when it became public that I was going to work for Kamala Harris, after having been press secretary to the governor, an acquaintance asked me, “Isn't this a step down, going from the governor's office to the AG's office?” And I said, “No.Kamala Harris is the future.” And that's how a lot of us saw her.Now, at the time, that meant the future governor, you know.Because in Sacramento, it's very much based on who becomes governor.But after you become governor, you start thinking about president.But obviously, fate had other plans for Kamala Harris.And she ends up in Washington instead of in Sacramento.

But even at that point, it was clear that she was a rising star on a trajectory, you know, well likely beyond the attorney general's office.

Definitely.The person who recruited me described it as an unfinished project.He said, “Here is somebody with amazing potential.This person is going to be a star.But they need people around her to kind of help bring that out.” And so I was recruited as a part of a, you know, a strategy to really bring out the best, and help create a star.And I think in the end, that that ends up being, as we have all seen, that's been the case.That's a talent Kamala Harris has always had, is a—a star power.People really believe in her, and project a lot of hopes onto her.And so, even back then, that was true.People knew she was going places.Now I realize as far back as the DA's office people knew that.But I did not know her during her San Francisco days.

What do you think it is about her that attracts that attention, that expectation?

Well, she has a talent for winning and doing so as someone who has not traditionally been represented in the political system.And I think, when you see a woman, and a woman of color being able to win elections to beat, you know, an old-school white guy, tough on crime politician from LA, that makes people think, “Wow.This is someone who can do it.” There's a lot that goes into a politician.And being able to win is probably the most important part of that, regardless of whether they're a good politician or a bad politician.And she's been able to do that.

And I think the higher she goes, the higher she has gone, the more people's hopes have been raised, that she can really pull it off.I would say people have always seen Kamala as someone who has a date with destiny.And, as we're going to see in this election, we'll see how that ends up, whether it was a good one or a bad one.And once again, all hopes are on Kamala Harris in a very tight race, where a lot is at stake.

I mean, was it back then—and then I'll ask you about your time with her.But was there, then, any talk of, she could be a future president, or thought that her future might be that high?

There were some people who saw her as a future president.The term “future”—or there were some people who saw her as a future president.The term “The female Obama” was floating around out there in some circles.That was the kind of talk we really tried to kind of push away, because you always have to be focused on the office that you're in, and not creating huge expectations that might seem arrogant or egotistical.So I do think people saw that.But we really thought that that path was going to go through Sacramento and the governor's office.Which ironically, her main rival for that was Gavin Newsom.And they were sort of eyeing each other for years, because they knew they were after the same prize.And they were on the same timeline to try to get it at the same time.Even had the same campaign advisors.

And when Senator Barbara Boxer decided to retire, unexpectedly, that opened up a lane for the Senate.And Newsom was perceived to have won that fight by immediately announcing he would not run for Senate.Which meant that Kamala Harris had to now announce that either she's going to run for Senate, or she's going to plan to run against Gavin Newsom for governor.She ended up taking the Senate job.It seemed like, at the time, maybe she had made a mistake, or was no longer on track for the big job.But it ended up being this express circuit to the White House.Whereas, Newsom is now mired in a massive budget deficit, and large amounts of homelessness, and other issues here, that would be—and those issues would make him a candidate with many vulnerabilities in a presidential race.Now Kamala has none of that.So, in a weird way, she drew a winning hand, though at the time, it probably didn't seem that way.

Yeah, it's a remarkable rise.So let's bring you in.You've heard all of these expectations about her.And you have your own excitement about who she is and what she represents.And tell me about meeting her, and taking the job, and who you find.

I was really excited to take the job, because the main part of my experience had been working for elderly white politicians in California, Dianne Feinstein and Jerry Brown.And I really wanted the opportunity to try to work to promote and help someone who was more like the state's future, a woman, a person of color.And I thought that this would be an amazing opportunity to work with somebody at the beginning stages of their career, as opposed to meeting them when they've already risen to a certain level.Jerry Brown had already been governor and secretary of state of California when I met him.He was governor when I was born, in 1976.So he, you know, and when he was mayor, that was, you know, many years behind him.Feinstein had been a household name in California forever.

So, with Harris, I thought, here is a chance to get in on the ground floor, and help somebody who's not well known become more well known.I ended up only lasting five months.It was a pretty short stint.I did not find it to be an atmosphere conducive to me doing my best work.It's not secret that her office environment tends to be very tough, very demanding, and in some ways, dysfunctional for many staffers.And it's not an environment that I felt was conducive to me doing my best work.And so I left and went on to consulting, and doing the quiet kind of well-paid work you do after you leave politics.And no longer in some thrilling campaign, but just, you know, having multiple clients, and getting paid very well, quietly do the consulting thing.

But, in a weird twist, in 2018, I was recruited back to journalism as editorial page [editor] of the Sacramento Bee.And it was the last thing I ever expected to happen.And when I returned to the Sacramento Bee, it turns out to be one month before Kamala Harris launches her presidential campaign.And so, here is a twist.A boss you didn't get along with, and didn't like.And now you're in a position where you're going to be asked to be an honest and insightful critic of that person.It's sort of like every employee's fantasy, right.The tables are turned now.And I knew that, by playing that role, my career in politics would be done for good.Not just because of Kamala Harris, but because of, you know, I'd been in Democratic politics.But that was also what made my work interesting.

And so a month after I get named editorial page editor of the Sacramento Bee, the premiere political newspaper of California, Kamala Harris launches her campaign.And from the very beginning, I was skeptical.Respectful but skeptical.Her launch was amazing.A lot of people were tremendously excited.But I raised the questions of whether she could hold it all together, and whether it would be a success in the end.

Harris as a Boss

I want to understand the Kamala Harris that you saw as a boss, and what she was like.Can you help me there with a little bit more detail of what it was that was this sort of, the chaos and the environment that you described?

Sure.I think she's a leader who has always been highly aware of the expectations and the pressures on her.And that there was a possibility she would go much higher in politics.And I think this resulted in a deliberative style, where you can kind of think too much about exactly what you want to do, and what you want to say.And that made it a bit complicated sometimes, to get a decision on an issue, an issue that should have been sort of quickly decided.But you know, and—and there were times, and she's been criticized for this a lot, where she didn't take a position on something clearly that would have been important to the progressive base in California, a position you would have expected the first woman of color attorney general to take a position on.

And so there were situations like that, where I just kind of felt it was hard for me to do my job productively, if we couldn't keep these things on a—on an appropriate timeline, or get them done.But I think that, as she moved higher up in the levels, and got a little more comfortable in her role, in her power, in her ability to succeed, I think maybe that got a little better.I think at the early part of your career, you can be a bit deliberative and scared and anxious about making a decision, because there's always a different decision.

Jerry Brown used to say, “Never make a decision until you have to.Something better might come along.” And I see a lot of that in many politicians.But also, the older and more experienced you get, the more you get comfortable in your own skin.So I would describe her back then as someone who was a bit uncomfortable in her own skin, suddenly in a big position, and not fully sure, at that point, how to handle it.Still really working on it.

And I found that very frustrating.It wasn't a pleasant office atmosphere.I've never really gone into detail about that.Others have.There have been many stories about the dysfunction in her office, about people feeling they were berated or treated unfairly.But I've never gone into detail about my own experience.I just decided that it wasn't for me.And I left.And I got in a position, later, by you know, just out of—as fate would have it, I returned to journalism, and am able to apply my insight in a very public way, to analyzing her campaign.

Let me just break down those two things.I mean, and one of them is that sort of indecisiveness that you saw.I mean, did she say what her reasons were?People are calling me, asking me for where you stand on this.Did she have a reason?Or was it sort of a hesitation on her part that you perceived?

Yeah.I think, as—as someone trained as a lawyer, I think she's trained to look at all sides of an issue or a debate, and to act very judiciously, and to do all the research.And, you know, if you're a researcher, or a journalist, or a lawyer, there's… an endless amount of research you can do.But sometimes, in certain situations, you do have to kind of narrow it down to a decision pretty quickly.Most of us don't have the high stakes that politicians have when they're up-and-comers, where they have to maybe live with it forever.And so I think there was a bit of that deliberativeness.I felt, you know, there were some—there were some things, not on all things.On some things, she was great.On marriage inequality, she was leading the fight against Proposition 8.I was always impressed that she doesn't take money from oil companies, and was pretty committed to fighting climate change.And some politicians have a more mixed record on that.They're having it both ways.She seemed to have some really clear principles.

And I think maybe there was an incident earlier in her career, when she was DA, that maybe burned her a little bit, when she had pledged that, as DA, she would not enforce the death penalty.And then, somebody shot a police officer and killed him.And there was a lot of pressure on her to do the politically popular and expedient thing, and to seek the death penalty against the killer.And she held her ground.She held onto her principle.And she paid a heavy price for it.And it was probably one reason why the race was so close in 2010.Even Senator Dianne Feinstein, at the officer's funeral, called out Kamala Harris and called for the death penalty

So she realized that, when you stake out some of these positions, it can get really dangerous really fast.And so I think, at that point in her career, it made her very deliberative and very cautious, I think is a word you could use.And looking back, now, in a weird way, some of the caution is now working to her benefit.There was a major ballot initiative in 2014 called Proposition 47, which was a major criminal justice reform in California, changed the sentencing guidelines for a variety of crimes.¹

Superior Court of California: Prop 47 Resentencing

And Kamala Harris didn't take a public position on it.And people expected her to.How could this smart-on-crime progressive prosecutor not take a position on the most meaningful criminal justice reform legislation to come down the pipeline?And then Lieutenant Governor Gavin Newsom was a huge supporter.Almost everyone else was in support of Prop 47.Harris didn't take a position, with some sort of mealy-mouthed excuse about the AG has to stay out of these kinds of things.

And well, lo and beyond, flash forward to 2024.Proposition 47 is now unfairly being blamed for every crime in California, even though crime is at historically low levels.Fox News has made Proposition 47 an entire product line of everything wrong in California can be traced to it.And, try as they might, nobody can say that Kamala Harris is to blame for Proposition 47, because she didn't take a position on it.And going into this presidential race, it is strangely providential that she wimped out on that one.

So in politics, you never know.Something that is a deficit at one point could be a surplus at another.Something that is a weakness or a flaw at one point could turn out to be a lucky break.So I've been thinking about that one a lot, as I reflect on my own criticism and critiques of Harris, because you never know, you know.Fate and luck play a big role in these things sometimes as well.And maybe a decision that people thought reflected weakness in her then, was actually rooted in something a bit more like a wisdom, about the role she would have to play in the future.

And you said you haven't talked a lot about your own story.But there are stories out there about sort of turmoil, and what she's like as a boss.And it seems pretty relevant to a question of her leadership skills.I mean, what can you say about that, from your experience inside her office?

Well, I'll say this.Politicians are not normal people.They are largely driven by ego and by a sense that they deserve to be in charge of things in a way that most people aren't.Most of us don't wake up thinking, “I should be the governor.I should be the mayor.I should be the president of the United States.” It takes a certain kind of person to do that.And I think that results in some personality characteristics that are necessary to that particular calling, politician.And politicians, most of them, almost all of them I would say, that I have worked for, certainly, would not be perceived as very nice people behind the scenes, because of the way they talk, because of the way they act, and because of the way the people around them are expected to filter out the pressures that they are under.You kind of largely become the—the receptacle of all the stress and pressure they're feeling.

And ultimately, I think that that's an element that all politicians have.Kamala Harris certainly does.I think there are a lot of people who expected to find something very different.When I first went to work with Jerry Brown, I had seen him on the cover of a Buddhist magazine looking very meditative.He was more like the Tasmanian devil behind the scenes, you know.It's very different.

And so Kamala is no different in that way.And I think, you know, I think people can feel-- you know, you're under the withering gaze of someone who's been a prosecutor.And I've seen it quoted.I have never said this.People have said they feel like they're being prosecuted.But, you know, part of that, if you were to speak in her defense, could be, she's demanding more and more and more out of the staff.Give me every detail.Do a better job.And there's a role for that.But I think sometimes, people feel that it was a bit unfair.At the same time, being philosophical, the proof will be in the pudding if she can pull this off and win the most momentous competition in American democracy's history, right.I don't count against it, that there might be a purpose for all of that in there.

So I also think this.There's a lot of criticisms one could give of Kamala Harris behind the scenes.Like all people, she's flawed.But she also has been a leader at a time when this stuff actually matters in the press.It didn't matter before, right.I think after the #MeToo movement, people felt more comfortable coming forward, and telling a story, not only about serious things that were crimes, or deserved to be heard, and people held accountable.But I think it morphed into the workplace, where people now felt there has to be a different standard of behavior and rules.And we've seen a lot of stories about people going through staff, and losing staff.And I don't mean to defend that kind of behavior.But only to say that it's not unique.

I mean from what you saw, did it raise, you know, to the level of where you would be—you know, have serious concerns about her leadership skill?Does it raise to the level where it was beyond what you would expect in a workplace environment, the kind of tension or treatment of staff that you saw?

At the time, I had just worked on such a high level already, that I felt, you know, what?I'm not going to kind of be—I'm not going to waste my time on this.I'm just going to go do other things now, you know.Someone once told me, “If you were in your 20s, this wouldn't—you wouldn't have left after five months, right?” And that's true, you know.… And I think one thing I would say about Kamala Harris that's a great skill of hers, is the people I worked with in that office were the smartest people I have ever worked with.Really brilliant lawyers, really brilliant thinkers, brilliant policy people.She has a way of attracting really brilliant people to her.And a lot of those people are still in her circle.

And I think a president is more than just the person on top.It's the people they bring in, and the people they put into positions.And I have no doubt that she has the judgment and the wisdom to bring the very best people with her into the White House.

From what you could see, or what you've observed, was it difficult for her to go into that office as a Black woman?I mean, was she facing skepticism, or the opposite, walking into that position?

Oh, when she became attorney general, I think there was tremendous excitement.And I think that she understood that she had a duty to carry out, and also some relationships to repair.A lot of the police groups were against her and skeptical.And she managed to really make that into something, and to be a good attorney general, who played a role in the national stage, in things like marriage equality, and the mortgage settlement.You know, she found a way to make a difference, while still running all the business that the state does, which is, you know, it's the biggest, like, law firm in the state, a lot of responsibilities, 1,000 lawyers.

And so she got reelected, and then went onto the Senate.So the people voted.They promoted her.I don't think she was ever in doubt, in terms of doing the job she had.You know, I think the question has always been, what about the job in the future?And how does what we do now impact that?And again, that's a normal thing in politics.

Did she have clear ambitions for what was next and what was beyond?

No.And the way that you know a politician has clear ambitions is they don't talk about them.But we all—we all knew.We all knew what the goal was.And at the time, again, it was governor.And you know, a lot of our positioning of her on marriage equality was because, ostensibly, she was going to be going up against Gavin Newsom in the governor's race.And he was the guy who declared, you know, marriage equality legal in San Francisco.And so you know, how do we make sure that she's the grand marshal of the parade, when the law changes?So I think there was that level of understanding.But I never heard her say anything about who she planned to be.It was very much focused on that office, and using that office.

I think you described her as thin-skinned.Is that a trait of Kamala Harris?

Well, it's a trait of a lot of politicians.They're very sensitive to criticism.And it's amazing, you'll have a politician show you some obscure tweet, and be like, “Did you see this?” And you're like, “Don't pay attention to that.That person has five followers.” Kamala never did that, but I've had people do that before.I think she's affected by criticism.I think she's stung by criticism.Partly why I have written in the past about the improvements she's needed to make as a candidate, is because I know she'll read it.And I have hoped that she would take it to heart.And never in anything I've written have I ever doubted that she had some kind of importance in the future.It was a lot of me sort of advising her to be ready for it when it comes.And now it seems like it has come.

It is interesting, though, because in public, I mean she has what she's been exposed to, certainly since she's been on the national stage, has been pretty brutal, and you know, racist, or sexist, you know, attacks.And a lot of people thought she had got really thick-skinned, right.That she just moves beyond that.I mean, is there a contradiction between the public Kamala Harris and the private Kamala Harris?

Oh, there usually is.And that's true of most politicians.But I would assume that, as she's risen to the levels—again, I haven't talked to her in over a decade—that she has gotten a little more thick-skinned.Because you get used to it.You know, I remember, there was somebody buzzing critically about her in the background when she was AG.And there was a meeting, and this came up.And everyone was worrying about it.And I said, “Excuse me.Excuse me.Why do we care what that person thinks?Like is the New York Times writing a story about it?Tune it out.Like if you let things matter, they matter.” But I had already been with people like Feinstein and Jerry Brown, where it's like, we're not going to worry about something unless it's a big, big deal.But she was at an early stage of her career, where those things mattered.And certainly, for local politicians, every little rumor and attack and tweet is serious.So she was coming from that local background.

I would assume, now, having been a senator, and having been vice president, and being a globally known person, that she's a bit more impervious to these attacks, these pernicious sexist and racist attacks, which it appears the Trump campaign is going to really quadruple down on in the coming months.And that's important, because it's going to be important for her to focus on her message, and be on the attack.And this is where I would say that I am happy to know the full extent of her prosecutorial skills.Because if she can prosecute the case against Donald Trump, then it will all have been worth it.

Harris’ Background as a Prosecutor

I mean, it is interesting that she comes to politics from being a prosecutor.And you know, the other people you worked with came from different backgrounds.How does that change her as a politician?

Well, I think that, again, she is somebody who's going to study the facts of the case, to the best of her ability.And I think she's going to proceed in a logical way.And in a way, it's perfect.It seems like she's already in Trump's head.He gave a speech recently where he said, “They're framing this as the prosecutor versus the criminal.” And I think we're going to see a lot of that framing coming up.

But I also think that, in addition to being a prosecutor, an important part of Kamala's story is that she's an unlikely prosecutor.She's someone who is a woman of color, who comes from an activist background.Her parents were civil rights activists.And so she sees the practice of law as an extension of that.And how do you use a prosecutorial position to do better for people?Or at least that's the ethos of a progressive prosecutor, which she hasn't always lived up to, some of her critics would say.But again, that's a double-edged sword.

So I think she can't lean only on prosecuting the case.I think that'll be a substrate of the campaign.It's a great meme for Twitter.But I think to the mass audience, people are going to be looking for a different kind of inspiration.And that is, what Kamala Harris' other major gift is, is that people project onto her a lot of hopes and dreams and aspirations.And she's a symbol of the fact that the United States has changed, and that the glass ceiling can be broken, and that we can be led by a woman of color.

And I think that this is generating a lot of enthusiasm and excitement.And, as one of her critics, someone who has known her, I really hope she can live up to that destiny.Because it's not just about her.And it really never has been.I think what the Kamala Harris phenomenon is about, is about people seeing history changing before their very eyes, and seeing someone who's success means we have made a certain level of progress in American society.

And while I am cautious and naturally pessimistic, whenever it comes to politics, I really hope she can do it.I'm really pulling for her to summon the greatness that so many of us have seen in her, at so many different parts of her career.

You mentioned one of the mysteries about Kamala Harris, which is, she comes from this background with her parents, and the civil rights background, and decides to become a prosecutor.And she spends a lot of time sort of explaining why she made that decision.Why do you think she took that route?

I think she's being honest when she says she saw an opportunity to go into an office that had traditionally been an oppressive position, and to try to use it to create a new model, where prosecution wasn't only about oppressing people or locking them up, but about making sure that the system of justice recognized the underlying inequalities that have led to dramatically poor outcomes for the poor, for brown and Black people.I think that she was an early version of the progressive prosecutor movement that has now become so more widespread, and also reviled by some on the right.

And so I believe that was an idea people had, like Kamala Harris early on, that we can use this office, not as a tool of oppression, but in order to start creating a definition of justice that recognizes the underlying vulnerabilities that people in poor communities have because of the—the system, and how it treats them.So I believe that.And I don't think she entered into law and into the district attorney office because she thought it would make her president.I think it just happened along the way, that opportunities opened up, and she saw a path for herself through politics.

And I think that, in a weird way, it started with office drama.I don't know if you know the story of how Kamala Harris became the DA of San Francisco, but it's one of the more exciting and impressive stories in California politics, I think.

Harris Elected as San Francisco District Attorney

What is that story?

She was working for Terence Hallinan, Terence “KO” Hallinan, a boxer who became a prosecutor, a counter-cultural figure, very well known in the city, part of the old school Irish network in San Francisco.And he ran a pretty bad office, with a lot of dysfunction in it.And he had a deputy who was kind of the under-boss, who had a lot of friction with other people.And there were some divisions in the office.And one side ends up getting pushed out.And Kamala was part of the group that got pushed out.

And so, in a very interesting and fateful move, she goes out there, gets some supporters, and decides to run for office against Terence Hallinan, one of the most well-known, well-established names in San Francisco politics.And she wins.And then she takes over the office.And this is a pretty dramatic arc.And I think, when she saw that she could do that, probably, she realized there was a lot more she could do.Because that was the kind of thing that really doesn't happen in San Francisco, where there's long-time established people.And to be an outsider to that doesn't really work out.

Of course, she had some allies too, like Willie Brown, who was behind her, and supported her.And so she was able to do that.And I think her entry into politics, in this way, beating an older white dude, who people didn't think she could beat, was the beginning.And she did that again in the attorney general's race, running against Steve Cooley.And now we're going to see if the third time is a charm.

The Willie Brown Relationship

What do you think of the relationship with Willie Brown?Because that's obviously become a focus again in the race now.

Yeah.I mean, this was something that the Republicans seem to think has a lot of value.I mean, people date a lot of people when they're young.Willie Brown was a dashing figure in the city, an important guy.And it doesn't surprise me that she would have found him interesting.But that was a long time ago.And I don't think it really matters anymore, as much as some people try to make it matter.

I mean, but does it give her, you know, entree into a world of politics, and a training of how to operate in San Francisco?

Sure.I would say her relationship with Willie Brown gave her a real birds-eye view of how politics works, in a way that most people don't ever see.Willie Brown is one of the most brilliant political minds of a generation.And so I think being exposed to that, you would naturally develop a greater interest in politics and how it works, and probably feel a bit more interested in pursuing it yourself, if you're the kind of person who people see as a—as a politician.There are people who are politicians.And then there are people who are not.I've been a political staffer.And people often ask me, “Do you want to run for office someday?” I'm like, “No.I'm not one of those people.Those people, you can tell, they're always well kept.They're always in suits.And they're shaking every hand, everywhere they go.Those are the staffers who are trying to be the politicians.You know.And then there are the ones in the background.”

I think that that time was probably formative and gave her a glimpse into the world of politics, and how it works, and probably gave her a little bit more [confidence] in herself to pursue that path when the opportunity presented itself in this most unusual way, basically overthrowing your previous boss, and taking his place.

I mean, it's obviously something she doesn't want to talk about.She feels, why are people talking about it?He helped Gavin Newsom.He helped other people.And she seems to be intensely private about it, about her private life in general.Is she more private than other politicians?

I think she's very private.And I think that the reason people fixate on that so much is because it's the one thing they have to try to use against her.And other than that, I think her private life is pretty normal and pretty quiet.She's married now, and now being the vice president, there's more social media with her husband Doug Emhoff.

Now, we all get influences in different ways in our lives.If I hadn't been introduced to Jerry Brown at a dinner party, who knows where I would have ended up.So I also got into politics in a completely accidental way, based on a chance encounter, developing a relationship with somebody who made me more interested in politics.And so I think that, you know, it's kind of a non-issue for the most part, except on, you know, certain meme lords trying to hit her on that.But I don't think it goes anywhere, ultimately.

Harris Runs for U.S. Seanate

You talked about the Senate race, and about why she ended up taking it, and how sort of Gavin Newsom boxed her out.When you saw her arrive in Washington, had she changed?Did she seem to be the same person you had worked for?What were your impressions of her time in the Senate?

Well, the Senate is a good place to be, because it's a safe place for a politician.You get six years.There's not a lot—There's not a lot demanded of you in the Senate, because you're one vote out of 100.And you're not responsible for the state of the state, or the budget, and all these other things.So I think it was a good place for her to learn the ropes of Washington.

And so, but of course, it puts you one step away from the White House.And so in the end, it was an interesting and fateful move.And I'm sure Gavin Newsom now wishes he had ended up in the Senate instead of in the governor's office.

I mean, it's also fateful that she arrives right at the same time as Donald Trump.

Yeah.

And she's a prosecutor, former prosecutor.And that sort of becomes her identity in the Senate, is you see those hearings of her grilling people.I mean, how important was it for her to arrive at that moment in Washington, as Donald Trump was coming in?

It's clearly fate that she gets there at the same time.Because I think that the rise of Donald Trump has really galvanized Democratic party's fear of the Republican party's sort of increasingly extreme agenda.And so I think to be in the middle of that, everybody who is there in this generation, even if you're not in Washington, realizes the stakes are very, very high.And I think that it's not an accident that they get there at the same time.And that here we are, in 2024, and they're going to go head-to-head with two very different visions of what the country should be.

So I think it's—it's not a coincidence.I think it's, again, Kamala Harris' destiny is to face off with Donald Trump in this very consequential battle.And I'm sure that, you know, it was a hard time for Democrats to be there, and to see this happen, and to have just come out of the Obama era, where so much hope had been generated.And the idea, I remember, I was there at the inauguration of Obama, and feeling that there had been a paradigm shift.And we would never go back.And everything would be moving forward from now on.That was literally his campaign slogan.And that we had beaten the darkness of history and of the Republican party in the years of Bush.And so to have to go back to Donald Trump winning, and to slide even further back than anybody thought was possible, in terms of the behavior of the president, and the policies he pursued, I think was really radicalizing for many Democrats, in terms of, everybody has to do their part, right now, to stand up and find a way to get the country back.

And so, although I've been a critic of Harris, I have a tremendous amount of empathy for her, that she has so much of this burden on her shoulders now.Because I know it must be a tremendous pressure.And it's not just about her personal advancement.For all of her flaws, Kamala Harris' heart is in the right place.What she wants to see this country become is a better version of itself that includes everyone.And if she loses this election, she will go down in history as the person who couldn't pull it off against Donald Trump.

And so, I think she realizes the weight of the task ahead of her, and has been there since the very beginning of Trump, in 2016.And so I don't think the stakes could be much higher.And I think no one understands that better than Kamala Harris.

Harris’ 2019 Run for President

I mean, she thought that in 2019 and 2020, it was also her moment.And you've talked about you were watching that from the editorial board.And I mean, help me understand that, as you see her walk out, and announce that she's running for president, the woman you worked for, and that campaign, which is going to not end successfully for her.Help me understand what you saw.

Well, I was here in Oakland that day when she announced.I wasn't at the rally.But it was amazing, the amount of energy and enthusiasm and momentum that rally seemed to generate her announcement.And then it kind of fizzled over time.And the campaign, again, was caught up in debates over whether she should be this prosecutor type who's tough on crime, and a different kind of Democrat, and we're quasi moderate, maybe some little appeal to Republican voters there, or whether she should be a progressive, almost to the left of Bernie Sanders on some issues, and appealing to younger people, and certain people of color, pockets of it.Because there's a lot of people of color who were actually more conservative.So there was a debate over that in her campaign.And it doesn't seem like it was resolved, and that it became a real dysfunction.

And it ends up with her staff leaking stories about the dysfunction in the campaign to the New York Times and Politico and Washington Post.And when I saw those stories, they had a familiar ring.And I knew that that was the beginning of the end for her campaign.And because any time that your staff is out there leaking this stuff to the press, it's pretty much in a terminal phase.At the same time, as her campaign fell apart, which led me to write a column that ended with, “You can't run a country if you can't run your campaign,” which became very viral and is very popular among Republicans and the Fox News type these days.²

Santa Maria Times: Kamala Harris wants to run the country. Can she run her campaign?

I predicted that she would make an interesting pick for vice president.And that there was a case to be made that she would be a good counterbalance to Joe Biden.And I wrote a piece about that, which surprised some people.But again, my columns are never rooted in my personal feelings.It's a cold-eyed assessment of what the facts are, and what the possibilities are.And I was actually a little surprised when he did pick her.

And so, in a weird way, by running and failing, by going really hard at Biden in that debate, where she said, “That little girl was me,” and accused him of siding with the segregationists on busing, which was seen as a bit of a ruthless play, and a flop at the time, that's kind of what got her to where she is, you know.In a weird way, with Kamala, there's a degree to which her mistakes and her defeats end up being also the keys to her later victories.And that's a good talent for a politician to have.And that's why I kind of hedge on assuming that she will fail, right.I assume that she can do it, but she's got to dig deeper and find that greatness in order to do it.

So while she did fail as a presidential candidate in 2020, she succeeded in getting to where she is now.So she must be doing something right.

Does she struggle to define herself?I mean this goes back to when you were—you were talking about where you're going to take a stand on this, you're not going to take a stand on this.And here we are, in 2020.And as you're describing that campaign.I mean, is this a challenge for Kamala Harris?

I think she currently is doing a much better job at that.I think once you reach this level, you've got to make your choice, and you've got to roll with it.And I think that the contrast between the two candidates couldn't be more clear.And I do think I've seen, even in her speeches recently, a certain confidence and energy that is somewhat new, you know.This is the moment.It has arrived.You know, they say nothing sharpens the mind like a deadline in journalism.Yeah, nothing sharpens a politician's mind like a possibility of defeat that could be the most consequential defeat in political history.

And I think that hopefully, this will bring out the best in her.And that the short timeline we have here, 100 and some-odd days before the election, will work in her favor.There's not a lot of time for anybody to do anything except be really focused on the goals.She already has a template for the campaign, because she's been a part of the administration and its successes for the past nearly four years.

And so, I think that these elements work in her favor.I think largely, what she has to do, is be that symbol, and be that avatar of freedom and hope and possibility and of the preservation of American democracy.I think it's a really high level communications job at this point.And there will be policies, and there will be an agenda.But that's not what people are going to be deciding on now.

If Kamala Harris can bring out the best in people, and make them see hope, and make the case that the only choice for freedom and democracy is to vote for a Democratic candidate in this election, she has a really good chance of winning.If it devolves into a debate over policy, and other things, then it's going to get dangerous.

Was part of the problem that she was, you know, in that race, who she was as a prosecutor, and the problem was, is that how she's going to present herself?And if she's not going to present herself as a prosecutor, then who is she?You know, in the midst of Black Lives Matter, and more skepticism towards prosecutors, was that a big problem for her that year?

Oh definitely.It turned out to be a year that was really bad to be perceived as being in law enforcement.The nickname for the attorney general is the “top cop.” And suddenly, being perceived as a cop became a very bad thing.And that was the drama in her campaign, was whether to lean into that, or to go off to the left, and try to be a part of the zeitgeist and where it was.

And I think it was very hard for her.She also had, as her advisor, her sister, a member of her family.And so that makes it really hard when you have a member of your family advising you to see things with the cold-eyed clarity that you need sometimes.And so you know, I think that was kind of a built-in problem in that campaign.A good political advisor is going to lose if they have to fight against your family member.And that seems to be how the sort happened in that campaign.So hopefully she'll avoid that mistake this time, and keep it only to the campaign team, and just pick a side, and then roll with it.

And I think it's pretty easy in this one.There's not a lot to debate.It's mostly about the perception.And if there's a gift Kamala has, is that she is an amazing symbol, that really taps into the hopes of many people, and the aspirations of many people.I mean, look at Donald Trump.He's kind of the opposite of that.He's a symbol that taps into the hates of many people, and the anger of many people.And just being that, alone, not a policy genius, not a guy with a track record of caring about people, or trying to do good things in the world, that's enough to get him elected.

Sadly, a lot of what happens in politics tends to happen on a level that is superficial in terms of language and images, but taps into deeper things in our brains, in our hearts, in our beliefs.And so she really has to use that role she has as a symbol for hope and opportunity and equality and freedom and justice, and sell that story.Sell that version of herself.

The prosecutor thing will be there.But it's more about defense right now.It's about defending this country and what it stands for.Her campaign slogan in 2020 was “Kamala Harris for the People.” And I think that that's kind of what she's saying now, you know.It's about freedom.It's about “for the people.” And it's about preserving what is good about America, while expanding beyond the definition of what's been possible in the past.In many ways, like Obama was able to do.

Harris as Vice President

I read in one of your columns.And you said that, when she was offered—or when there was talk that she was potentially going to be a VP nominee, that Willie Brown wrote a column in the San Francisco Chronicle saying that she shouldn't take it, that there was no power there.That she should hold out for a more powerful position.And it's sort of, it's both ironic because of her relationship with Brown, because it's also a little bit of a warning about the office that she's about to walk into, as she becomes vice president.Do you remember that, writing about that, what Willie Brown's warning was?And could you just tell me about that?

Yeah.I believe that Willie Brown had wrote a column when Harris was being considered for the vice presidency, telling her not to take it.You'll be second banana.Vice presidents rarely go very far.And you'll be frustrated.There won't be much of a portfolio.If it is, it'll—it'll not be a great one.And you should ask for something like attorney general or some other office, where you have a bit more independent power and profile.

It seemed like good advice, maybe at the time, especially as stories came out saying she wasn't really enjoying the vice presidency, and was sort of squabbling with Biden's people, and feeling a bit left out, and unfairly treated.And I wrote a column that quoted Brown, and gave some advice for how to get things back on track.

It would turn out though, again, as with the Senate race, where people thought, “Oops, now she's not going to be governor, and Gavin is going to be most important person in California politics,” that actually being vice president under Joe Biden was the ticket straight to the top of the ticket.And it's not under the best of circumstances, right.This is a pretty dismal situation, the predicament where the president has to tap out after weeks of saying he won't, and Harris is thrust into the role with 110 days to go in the election.This is a pretty unprecedented situation, a pretty horrifying situation.

It would have seemed like a smart prediction that the vice presidency was a bad choice for her.But in the end, once again, she defies the conventional wisdom, and it ends up being the exact role for her, to be in position to take on Donald Trump.She missed that chance the first time.It's clear why people chose Biden.And unfortunately, because of his age and his performance, he isn't able to go up against Trump the second time.And now, Harris is there, in a strange way, her 2020 campaign was not in vain.It got her here.And the vice presidency was not in vain.It got her here.And now we're going to see where that all goes.

What do you make about that first year, and about the reports of turmoil, and about her unpopularity?I mean does it reveal something about her as a learning experience, and walking into that job?What do you see when you see that, in those first years?

When I read those stories, my assumption was, growing pains for one, a new office, a new atmosphere.Now you're in Washington, the belly of the beast.But also, some of the old habits coming back, you know, the sort of inability to corral the staff, or at least not keep those stories out of the press, you know.And that's been written about a lot.And, you know, when I wrote—I wrote a column about those troubles when those stories came out, and gave some pretty frank advice about the need to get that under control.You can't be in a position where people are constantly telling me stories about your office.And you know, you either have to change the way you handle it, or you have to find a team that's willing to be there, and to deal with it.You have to find a situation that works.You can't have a situation that's constantly not working.

And I gave that advice.People were mad at me about it.It was my most well-read column, I think, that I've ever written.

And have you seen anything that indicates she's a different person, that she has learned from her mistakes, you know, as she went through the vice presidency, as she's gone through this moment?

Well, the last year or so, I've been telling people, she's been really good on the stump.She's been talking about freedom.She's been talking about women's right to their reproductive freedom, abortion rights.And she's been very strong on that issue, which is a crucial issue.There's also been no stories in the past year, year and a half, about staff stuff.That all seems to have quieted down, maybe two years now.So there does seem to have been some kind of realignment, where some of those issues seem to have disappeared.

And I fully assumed that Joe Biden would run, and hopefully win, and then she'd have four more years as vice president.That's not the case now.But I'm happy to see that—I'm happy to see that there has been a change in narrative, where we aren't seeing those stories anymore.Couldn't have happened sooner.It's good timing that it appears to have not been a public issue, at the very least.And I think that's really important.

So I always, you know, people are better than their worst time, their worst day, their worst deed.And none of us are perfect.We're all very flawed.And what's important, in the end, is whether we fulfill our role in the world.And I think that's going to be the test here.And, like I said, I'm not really sure, not just because of her.I think any Democrat, it would have been close, you know.I felt that the panic to push Biden out was a little risky, you know.This is a risky, high-risk maneuver here.And I think, no matter who it was, Gavin, or Kamala, or you name it, I think it would be a close race.And so it's not particular to her that I think it's going to be close.I think that it's just going to be a real hard campaign, and was going to be a hard campaign, no matter who the nominee was.

So our last—the last question we ask everybody, what is the choice that voters are facing in November?What was the choice on the ballot?

This is a choice between democracy and dictatorship.And the choice is pretty clear.And Kamala Harris has a lot of weight on her shoulder.But ultimately, it's up to the voters to decide which vision of the country they want.And I will be rooting for her success.

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