Kamala Harris for President?

Jamal Simmons spent a year working as the communications director for Vice President Kamala Harris. In his first podcast interview since leaving the job, Jamal talks with Ben and Khalil about everything it takes to be vice president. What is the role of a VP? What challenges has Vice President Harris faced as the first woman of color to have the job? What should we make of criticisms of her from both the left and the right? What are VP Harris's prospects as a likely future presidential candidate?

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Episode Transcript

Speaker 1 (00:14):
Pushing. I have this moment where I'm like, Okay, I'm
on the I'm on air force to briefing the vice
president in her private cabin and I'm about to say,
that's the good stuff, man, that's the story. Away from
the West Side of Detroit, Brothers, it's a long way

(00:35):
from Dexter. I'm Khalil Jabr Muhammad. I'm Ben Austin. We
are two best friends, one black, one white. I'm a
historian and I'm a journalist. And this is some of
my best friends are some of my best friends are like,

(00:55):
I don't hate establishment democrats. Some of my best friends
are establishment democrats. You got it. So in this show,
we wrestle with the challenges and the absurdities of a
deeply divided and unequal country. And today we're going to
consider the future of the US presidency. Joe Biden's getting
up there in age and his vice President, Kamala Harris

(01:18):
is next in line for the presidency. We're going to
talk about who she is with someone who knows her
better than any of our best friends, Jamal Simmons, who
was the communication directors for Kamala Harris, and he happens
to also be an old friend of ours, and listen,
this is his first podcast interview since he left the
White House. This is a scoop, So let's do it.

(01:45):
Last baby's dad, so Khalil, the President of the United States,
our President, Joe Biden, is eighty years old. Yes, yes, eighty,
or I should say old af And my wife Danielle,

(02:07):
was recently in Arizona to visit her uncle and aunt,
and she ended up watching the State of the Union
with all these eighty year olds and because you know,
they're they're they're from Chicago, but they went down there
to kind of like Winter's right, and so she's watching
it with them, and you know, all these eighty year

(02:28):
olds are commenting on his his age and how he looks,
and whether he's had work done on his face, and
like how he's moving with with my cousin who I
was watching it with, whether he had botox or not,
let's just name it, like, you know, look pretty clear
to me, you know. And so the whole question of
his age was was so even more present in that

(02:49):
viewing for her, because um, it wasn't just how young
people view him, it's it's how his actual peers view him.
And you know, man, They're like, I'm not. I'm not.
I'm retired. I'm not. I'm not. I don't have the
biggest job in the world right now. Yeah, they're basically saying,
I don't even think it's a good idea that this

(03:11):
guy is is gearing up to maybe run for a
second term. Yeah. Yeah, that's ah, that is the question, right,
and so much the question that I was watching it
and looking at Kamala Harris the whole time, and it's
been behind him, over his right shoulder as they do,
like that's how it works. Yeah, yeah, you know. I mean,

(03:32):
and I have to say, like watching her in this role,
in this back half of the Biden presidency, these next
two years where the Republicans have now taken majority, and
she's sitting next to the speaker Kevin McCarthy as opposed
to Nancy Pelosi, right, I mean, it did hit me differently.
And I have to say I had a lot more

(03:53):
pride in just seeing her in that role symbolically than
I than I remember having when I watched her next
to Nancy Pelosi. Um and yeah, and it had me
thinking a lot about how Biden's own decision to run
for a second term has huge implications for whether or

(04:14):
not Kamala Harris will be the presumptive nominee in a
twenty twenty eight race, because at that point there'll be
no question she's served two years or two terms in
this vice presidential role. Yeah, I mean, that's what we're
going to try to unpack today. What we're going to
talk about is this attention on Kamala Harris, because when
you do have an eighty year old president man the

(04:35):
vice president, it means something, right in one sense, like yeah, yeah, man,
she could be president next week. That has a lot
of scrutiny on her because of this. That's right, there's
so much scrutiny. By the way that the New York
Times ran a pretty significant story reported by some of
their top political reporters who had access to the high

(04:56):
ranking Democrats in the White House, who expressed some concern
about whether or not she actually would be a liability
for the ticket in twenty twenty four. You're saying, Khalil
that even if she's just on the ticket as vice president,
that's somehow that's a liability for Biden, like it might
mean that a Trump or around the Santas the governor

(05:17):
from Florida, they might win because because she's just even
part of the ticket. Again, well, yes, and I'm saying
that's what the New York Times is reporting, because she
would be that much closer to potentially inheriting the presidency
in light of the fact that Biden might either not
make it through his term or might be incapacitated. I mean,

(05:38):
you know, just as a matter of history, this is
not abstraction. The notion of someone dying in office is
a very real thing, and Democrats are suggesting that she
might be a liability if in fact people start calculating
whether or not Joe Biden can make it through the
end of his term. And so all of this makes
me think, like there's such a need to assess Kamala
Harris and the role she's done as Vice president and

(06:00):
who she is and what her values are, and you know,
maybe how she might govern in a much more like,
you know, in a serious way, and to understand more
about her because you know, so this idea of her
being the VP and being, as you said, like feeling
this kind of pride there's a woman of color there
in this role the first time ever. Yeah, Yeah, she's
a first she's a first Black woman in this role,

(06:22):
and she's a first Asian American woman in this role.
And and you know, I mean that Times article talked
about some of this of sort of that the that
role of her, how her race and gender plays into
some of this, and even as as slights um there's
this one note in there of like when she goes
on these foreign trips and meets dignitaries and you know,
the vice presidents of other countries, they try to introduce

(06:44):
her set up meetings with the first ladies of these
other kinds. That crazy and She's like, Nah, I'm not
doing that. That that's not That's not what I'm about.
That's like yeah, so I want to think more about
about her identity, politics, her actual politics. And also like, man,
you know, what is a vice president? What are they

(07:05):
supposed to do? What are what are we supposed to
expect from them? Are we holding her to a standard
that's unfair or not? And well need to find out
more that's right. And on this point, her former communications
director Jamal Simmons, who only stepped down in the last
few weeks. And guess what, we get to talk to him.

(07:26):
That's who we have on today Jamal Simmons, who's been
a longtime friend of ours. He worked as Kamala Harris's
communications director for all of twenty twenty two. He held
this position for a year. He is our friend, and
he is going to be our Kamala Harris explainer. That's right,
we're gonna learn a lot more about her from someone
who's one of our best friends who can give us

(07:48):
the inside scoop. Let's do it. Jamal, what's up, my man.
It's great to see you. It's good to see you guys. First,
I want to say that we've known each other since college.
You know, you were in Morehouse and you were friends
with Danielle who is now my wife, and she and
I were dating then, and she was going to school

(08:10):
in Atlanta too, and so yeah, we've actually been friends
since then. I mean, that's been been a little bit.
And the first thing I want to say, is you
getting this job as the communications director for the vice
president of the United States. I was just I just
I just felt immense pride. So I just felt pride.

(08:30):
I appreciate that it was a it was a good
time and honor and a privilege, you know, to be there,
and uh, I felt the moral support that I was
getting even though I was exhausted all of the time.
We can only imagine that we want to hear it.
We want to hear exactly what makes one exhausted in

(08:52):
the White House. So listen, um, I mean, I'm a historian,
Ben's a journalist, but neither one of us are political junkies,
certainly not in the way you are. And while we
pay close attention to what's happening in the country nationally obviously,
but but here you are coming off of being the
man in charge of the messaging of the vice President
of the United States of America. So tell us exactly

(09:14):
what you did. Yeah, I mean, I gotta. I actually
I'm proud of him, but I don't I don't have
no clue what he actually was it where you're just
are proving emails to send out under her name, I mean,
that's that's probably what it was. I would say all
of the above, right, So I'll just tell you this.
My first day in the office was January tenth of
two thousand and twenty two, and I got about four

(09:37):
hundred and eighty seven emails that day I count it,
and some of them you can kind of get rid
of immediately because they don't believe I mean that they matter,
But it's just like somebody sending you a press release
about an announcement somewhere. Some of them, though, are conversations
that are happening between people. But ultimately the communications director's
job is to figure out all the ways the vice

(09:58):
president is engaging in the public through media speeches. In
my office, I had the director's speech writing, the press secretary,
the digital director um and then a communication staff and
so all those people reported to me, and the idea
was that we should all be saying the same thing
on the same day, okay, And so that was the

(10:21):
job was to figure out, you know, with my colleagues
and the other departments and the Vice President, what is
it that we want to talk about on Tuesday, and
how is it that we're going to communicate that message
to as many people as possible, and what venues are
we going to do it? And then we present that
to the Vice President and then she crosses off fifty
percent of what it is, we say, add in a
bunch of more, and then you know, she goes out

(10:43):
and said and and and tell us a story of
like a time that that you came up with a
message and it went south or something where it was
like really tricky. Um, well we're luckily, I will say
I didn't have any experiences where things went south. There
were some experiences I think people had before I got there.
Um And and as you know, I would just say,
all these success was hers, all the mistakes were mine.

(11:05):
Uma that next job look a no. But you know,
the big thing is she actually knows a lot about
what she wants to say. The thing that I remember
about Kamala Harris is that she's been her entire early
part of her career as a prosecutor. So like many

(11:27):
of us when we start learning our jobs, those lessons
that we learned very early to stick with us throughout
the rest of our careers. So for her, words have
a lot of meaning because, as she would say, when
she would get up in front of the public and
talk to the press, it was usually about somebody's freedom,
right because if she was going to prosecute somebody, they

(11:47):
may go to jail. Or was about a family that
was in pain because something had occurred to them and
she felt some responsibility to them. So that always informed
what the word choices. She would make the way she
wanted to communicate. Sometimes I would say she could have
been a little bit more rhetorical. I wanted her to

(12:08):
sometimes be a little bit more um, you know, a
little more political flourish or kind of a you know,
a bigger story. But I think her response to say
that she was not that funny is that sounds like
she just because I was serious. Yeah, she could just
I don't think of I don't I don't think of

(12:28):
a single prosecutor who I've ever heard actually told a
joke that anybody was interested in laughing. She needed to
loosen up. She would never tell jokes, you know, in
that environment, right, because it's usually a very serious environment.
So I think the thing that I always hope that
she would do more of, which was which was be

(12:49):
a little more funny, be a little more personally revealing,
um and uh, you know, talk more about the bigger picture.
But she always wants to take the bigger picture and
then figure out, like what way to make it real
to people in very concrete ways. Uh. And that's kind
of her brand, is like you know, what does this mean.
We're gonna we passed this huge bill. We're gonna spend

(13:12):
a bunch of money on infrastructure. I'm in Chicago today.
Tell me about the stretch on Wabash, you know, Avenue
or whatever. Tell me about that. That's the that's the original,
that's the original, coldish pronunciation. He's got he's got more
roots than we do. He's like, he researched this. I

(13:34):
love its right. So and then we're looking for jokes
wherever we could find. I love it. I'll take it.
I'll take it. The White House. It's like a joke
free environment. So I'll get my joke game back up,
and and and and what about you, Like, what's the
moment of this year, of this intense work where you

(13:56):
probably didn't see your family, you didn't see your young children.
What's the moment that you're most proud of, like your
own your own work that you did. You know, there
are some things that I'm proud of that have really,
really very little to do with me. So, for instance,
when the tragedy happened in Buffalo, the shooting, we went
to Buffalo and the Vice President was just going to
go to attend a funeral. She was sitting in the

(14:18):
front row of a pew and they invited her to
come up and speak, and she got up and spoke
and gave one of her most compelling addresses. We didn't
write it. She you know, just got up and gave
it off the cuff. But then she also went and
met with some of the families in like the church
gymnasium and just watching her walk, you know, family and
the family shaking hands, hugging people, talking about their loved ones,

(14:40):
talking about the tragedy that had occurred. And I said
to her, like, wow, this is like, you know, you
were really you know, you were really kind of good
in there, Like she said, you know, I spent my
entire career talking to people in pain, and she had
a really you know way of talking to people who
were experiencing like a profound moment of grief. And I

(15:01):
think those families felt comfort, you know, having her there.
That was a big day for me. Yeah. Yeah, I
do have a follow up question though. It's like, you know,
I'm thinking about about what you said about her skills
right as a prosecutor, in the way in which she
was very careful and deliberate in addressing these very serious
topics before the public, and I'm thinking about like a

(15:22):
pastor who has to do a lot of eulogies, Like
there's a certain kind of rhetorical structure that you're accustomed
to because people are always in pain when you are
addressing them, and you just have this natural way of
deliberately walking that line between the kind of you know,
acknowledgement of that grief as well as the aspiration that

(15:44):
people want to believe, you know, in in where this
person is going next. You know, they're heavenly afterlife and
the family's going to move on. So we just learned
a little bit more about her gifts. She could be
a prosecutor, or she could be a pastor, giving you well,
you know, what's the other thing I'll say. There was

(16:05):
another big moment which we all know you all sign
the news when the Supreme Court who started to rule
on Roe v. Way, the Dabb's decision. The first thing
that happened was the case leaked before it was supposed
to come out, right, So the case leaked. We go
into her office. She's supposed to speak at Emily's List

(16:25):
that night, which is a pro choice women's political organization.
She's supposed to speak at Emily's List that night. We're
sitting in her office around around the table and she
starts talking about the what's come out in the League
of the decision. She said, if this is true, that
means they're going to go after privacy rights. That's our freedom,
that's liberty. She starts like going through this whole list,
and she starts saying, you know, I mean, who are
these guys? How dare they do this to American? How

(16:49):
dare that? And she starts going to this and so
I'm sitting there and I look at the speech writer
and I'm like, and so he's you know, they're typing.
He's typing and she's talking. And so that ended up
in the speech she gave that night at Emily's List,
which was one of the most quoted moments for her. Well,
we say, how dare they? How dare they tell a

(17:09):
woman what she can do and cannot do with her
own body? How dare they? How dare they? Is right? Wow,
what a powerful voice in that moment for Kamala. We're
gonna take a quick break, and when we come back,
Jamala is gonna make the case for his former boss,
Vice President Kamala Harris. We are back with Jamal Simmons,

(17:42):
the former now communications director for the Vice President of
the United States, Kamala Harris, and he is on Some
of my best friends are and while most people are clony,
hear us. We can actually see you, Jamal. And I'm
seeing these like folders on your desk and some of
them are more classified, I think in top secret. You

(18:04):
have all these these documents there, what are those? And
so for the for the security services that are listening
to this, these are jokes. These are all just um,
you know what's funny. What's funny is I was listening
to this quote unquote scandal. It has been unfolding for
the last few weeks, and I was thinking about my

(18:26):
exit from the White House and the briefing that I got.
Don't get it. Basically, this belongs to you nothing. You
take the pictures of your kids and you know the
cards that were given to you. Everything else belongs to
the government. So you should leave it in this white
box and good luck. All right, So so listen, we

(18:49):
we are. We are expectant, like so many people, that
at minimum, the current Vice President, Kamala Harris, will likely
be a presidential candidate in twenty twenty four. She was
once already so this won't be the first time that
she at least runs in a primary. So we don't
know Biden's going to do. But let's just say that

(19:11):
she's in the cards. But before we figure out like
how to evaluate her as a future presidential candidate, we
want to have a clearer sense of how to judge
her as a vice president. So let's just start off
with a really basic question, what the hell does a
vice president do? Anyway? Okay, I just want to say
this one thing. Joe Biden is running for president in

(19:33):
twenty twenty four. So everybody, we just we just broke
We just broke the news. Ben. This is that we've
been waiting for this moment for two seasons. We just
broke news. All right, expectations He's running for president. She
will be his vice president, vice presidential running mate. You
may see her, I think in twenty twenty eight. Listen,
here's the thing about Comma Herr. She's fifty eight years old. Ye,

(19:55):
she's going to be too old in twenty twenty eight.
Joe Biden is one hundred and twenty three. Like I
was joking, best line ever you can president forever? Um? No,
So I think. So that said, the likelihood is one

(20:18):
day you will see her name on the ballot again,
um by itself or at the top of the ticket,
whether there's twenty four or twenty eight. Um. So what
does the vice president do? The vice president has two responsibilities.
One is to cast votes and tie tie breaking tie
breaking votes in the United States Senate, there's a fifty

(20:40):
fifty split, all right. She did more of that than
any friends and any vice president since like John Quincy
Adams happened to me fifty fifty those twenty six times,
twenty six times, and by one hundred and seventeenth Congress.
You just had that in your back pocket, Khalil Or
did you come on, man? You know I'm just playing.
I'm possum here. I'm already. I'm just playing. He's a
well resoarsed man. Um uh. And so so that's number

(21:05):
one job is to cast tie breaking votes. Number two
job is to be in case you have to become president.
That's it. Everything else is like made up. So I
had this, I had this approach when I took the job,
and I talked to my staff about this. That what
the idea of something being vice presidential is built upon

(21:26):
a notion created by every other person who had ever
been vice president. So whatever Kamala Harris does will become
vice presidential because she is the vice president, and therefore
she will set the tone for her for whatever the
future of this office is. And so we should take
advantage of that, and we shouldn't feel imprisoned by what

(21:47):
other people chose to to do or chose not to do.
And if you think about her versus our most recent
vice president, I mean, like the guy she's the vice
president for exactly like a Joe Biden type. So we
have this notion, we have this notion of these vice
presidents who are people who are more experienced in the
ways of Washington and politics, national politics and the president. Right,

(22:09):
Joe Biden the Washington tutor for Barack Obama, you know,
George H. W. Bush was the you know, the tutor
for Ronald Reagan. Um, Dick Cheney was the hold on.
But Dick Chaney was the actual president, right, Like he
wasn't tutoring George Walker Bush, he was actually the president. Okay, sorry,

(22:33):
sorry about that, so right, so mean, so you see
you see the pattern. You see the pattern here, uh,
and Cheney being the most extreme case. Um, that's not
true for kamal Aaris right, like Joe Biden, has got
the most Washington experience. So in her world, I always
looked at it like this. She is the face of
the America we're becoming, not the America that we used
to be. Right, it's more educated, it is more centered

(22:57):
in the Sun Belt, the West and southern states of
the United States. Um and frankly a little more progressive.
So um, So she should not be thinking about how
a conservative white guy used to do this job. Conservative
white guy who've been in Washington his whole life, his
whole career, you should do this job. She should do

(23:18):
the job based on who she is and bringing something new.
So we spent most of our time traveling around the
country three days a week, meeting people who are out
in the country, bringing people from other parts of the
country to Washington to meet with her in her office,
because I believe that her power lie out in the
country with the people who were looking for her to lead,

(23:39):
not sidered in marble hallways inside Washington, DC or the
White House. So don't play the game of Joe Biden
or Al Gore. Make a new game where you go
out to the country, not one where you go out
to the Senate. So this is like her basically going
around meeting with all the AKA branches, the alfacap alf
branches around the country to break with tradition as a

(24:02):
part of in fact of maybe what you did, so
you called you called it the Ski week, right, I
will say I will say this, there were more Divine
nine meetings, not just akas, but there were more Divine
nine meetings in the last year of my life than
probably in the last thirty five years of my life.

(24:23):
All right, So Ben Ben Ben is in this conversation,
and while he's cool, he you know, I just have
to tell you, Ben, Divine nine are the historically black
fraternitys and sororities. It's it's the umbrella way to define
all of them together. Just I thought i'd let you man.
Thank you SAMs. All right, all right, all right, I
was I was five Beta Kappa. He is married to

(24:46):
an AKA, so I'm sure he's heard some of this before.
That's true. So Jamal, you came into this job. It's
a communications director at a time when when Kamala Harris
was getting criticized for a dysfunction in her office, and
she's often criticized and I want to hear from you, like,
can we talk about the criticisms of her? Could you
tell us maybe to start, like, like, what are the

(25:07):
invalid ones? What are the ones that you think are
trumped up? Maybe we can't say trumped up anymore. What
are the ones that you think? Yeah, yeah, yeah, if
you we can yeah. Um uh So I'll start here,
which is that racism and sexism misogyny are real. Um.
And it is not that she is flawless. It's not

(25:29):
that she doesn't make mistakes. It is, however, true. Two
things are true. One, when she makes mistakes, um, they
are magnified and people look to them as more of
an indicator of some innate ability or disability or lack
of ability. Um. Then if somebody else makes a mistake.
I mean, Joe Biden says things all the time, you know,
and turn out to be wrong or I'm a fucker

(25:50):
as president. If you looked at the things he said
over time, I mean it's crazy, Like if you just
if those if you just took the list of his
his malaproprisms or like screw ups or like, you know,
funky things he said just about like Barack Obama. I
mean somebody asked me the other day. They were like, yeah,
so what you know, where's commonly hair has been. I'm like,
what do you believe? Remember about Joe Biden? You remember
a couple of things about Joe Biden. One healthcare bill passes,

(26:14):
big fucking deal, right, it says into the microphone, and
Barack Obama's like patting him on the shoulder like come on,
bro stop um uh. And then two to the beer summit,
yess to. And then the third one, I would say
is when he came out in favor of marriage quality
before the before me. Yeah, right, yeah, that's kind of

(26:35):
which was a gaff which was kind of a gaff
in and of itself. Right, So from a communication standpoint,
I mean, just very briefly describe how that was a
communications a crisis in a way. So if the president
the number one okay, the number three job of the
vice president after vote, stay alive and take the job.
The number three job is don't upstage the president. Exactly

(26:59):
is it is one of the cardinal problems. And I'll
tell you people always said, well, you know about the
filibuster or one of the other issues. You know, the
vice president vice president here should should She should just
say what she wants to say. You know, Joe Biden
bucked Barack Obama marriage quality. She should say something about
voting rights or criminal justice or something else, even if
Joe Biden doesn't believe it. Well, I think you get

(27:21):
one bite at that apple, right, You sort of get
to do that at one time, and you better hope
you're on the right side of history, because you could
end up spending the rest of your time going to
funerals in the South Pacific, you know, South Pacific islands
for American allies, you know, around the world, instead of
she was just out there anyway? Is that right? She did?

(27:44):
But okay, but I do think that this is this
is like a thing. It's a very hard thing to do. Uh,
it's to buck the president. That is actually like your
job is to do the you work for the president
of the United States. Um. So you know it is
very hard for the vice president to make news. And
so um I shouted off here she won racism, sexism

(28:07):
a real It doesn't mean she doesn't make mistakes, just
means they get magnified. Two people think she might run
for president one day. So there is a concerted effort
on the right to attack her, go after her, you know,
and blow up any small mistakes she may make and
turn that into a bigger deal. Alternate may otherwise be Okay, Well,
you've already said she was very deliberate, so I might

(28:30):
already know the answer this question. But you know, Obama
was very circumspect and very reserved stoic, even in the
face of the same kinds of attacks, at least because
of his race as opposed to his gender and certainly
caricature lampooned in the most racist ways imaginable, and for

(28:51):
the most part, he kept us cool. I mean, with
the exception of Michael Key and his version of Obama's
alternative ego Luther, instead of giving voice to this, is
there an alternate ego for Kamala Harris. She have her
own version of Luther that she's playing out either in

(29:13):
her head that you could tell or in private inside
of the White House. She actually really is cool as
a cucumber. You know, I think these things happen. I'm
not saying they don't annoy her, but they I think
they happen, and she does let them kind of blow off. Um.
She also, by the way, likes to use the F bomb.
It is, oh all right, the way she's in good

(29:33):
company with Ben. It is by far the best swear
word in the in the American language because because it
is it is there's an adjective, verb and a now
right depending on usage. I kind of love that. So
I should tell you this funny story. So an episode
we did you Know a few few episodes back, Ben's

(29:54):
mom listened to it, and she regularly listens to our show,
and Ben sent her a note asking her something, and
she answered the note back She's like, Yeah, I'm gonna
fucking do this when you fucking tell me to do it.
And and by the way, you fucking curse too much
on your show. So according to succeeded, I changed her

(30:14):
language to use this fantastic word. Yeah. Absolutely, I like hearing.
That was a good question. Khalil um jamal. Are they're
valid criticisms? Can you talk about about sort of things
that she has slipped up or could do better? Like
was the dysfunction real? Like we heard all these stories
of dysfunction in her office, and that she's, you know,
a manager that wasn't able to retain people. So, um,

(30:38):
here's what I'll say about that. Every day that I
was with her, I saw some little black or brown
girl look at her like she was wonder woman right,
like she was there on their own personal superhero. I
saw older women of all races, black, white, and others
grab her by the hand and say, I never thought

(30:59):
I would see the day right how a woman that
would be in this office would be in the White House,
even a vice president, And I want you to be
president one day. A lot of people would say that,
even if people felt some kind of way, A lot
of people would say like, I hope you get to
be president. With that, I think she feels very acutely
the responsibility to all of those people who are looking

(31:20):
at her with this, with this expectation and this um,
this pride in her assent um. And she would say
like she's not that this is not the first job.
She was the first black woman ag in California. Now
she's the first black woman vice president. So she's had
this expectation on her for a long time. And I
think some of that is part of the reason why
she's probably more reserved that somebody would like me, would

(31:43):
want her to be because the idea of making mistakes,
every mistake she made that got blown up in public.
I think she didn't just feel it as a personal problem,
but she felt Perhaps she never told me this, but
I'm supposing that if she was letting down all these
people who looked at her and said, I'm so proud
of you, right, I want somebody I want my daughter

(32:05):
to be like you. Um So I think, um. I
think that I created like a reservedness about her that
I think does not always suit her and does not always,
you know, do her well. And I think she could
stand to get outside of that. And I think it's
rooted though, and something that's very legitimate. It's also rooted
in talk about the staff thing, that responsibility she feels acutely.

(32:26):
She holds herself to a high standard. She holds her
staff to a high standard, and she can be tough.
She could be a tough boss. But I think it
comes from a place that is rooted in I've got
to perform because these there are millions of people who
want and need me to perform, and I can't afford
to let them down to get this job. Jamal, did

(32:47):
you have to tell them that you voted for Kamala
Harris and the primary? The Democratic primary nobody asked. And
I mean, that's I'm thinking out a loud here because
Khalil and I I'm pretty sure Khalil didn't. I know
I didn't, And you know, sort of that to even
hear us talk about why, and then maybe you can
sort of like, you know, try to tell us what differently,

(33:10):
you know, why you didn't. Don't tell me she didn't
make it. She didn't make it. She wasn't actually on
the ballot in the Democratic primary. That is a good
even Yeah, you know, you know, from from jump as
you're sort of picking who your who your people would be,
you know, I mean, I think for me, part of it,
part of it was her background as a prosecutor and
the attorney general in California and some of her her
stances on criminal justice and not looking for criminal justice reforms. Um.

(33:35):
Some of it was that I felt, you know, I'm
more progressive, I think than than some of her policies.
But and then in a way that the sort of
symbolic things that you said of being the first, of
being a woman, of being a woman of color, those
are really important to me, and still policy things felt
like they superseded them. You know what's interesting she actually

(33:56):
used to be regarded she was kind of the progressive
prosecutor right, So in San Francisco she led the way
on prosecutors actually waiting into criminal justice reform. So in
San Francisco she started this first step program where she
would get people who had been in their first conviction
and tried to deal with recidivism and reform and get
them into like, you know, track them into other occupations,

(34:19):
maybe away from the thing that got them in trouble
in the first place. So she was ahead of her
time on that. And one of the ways she first
became known is because in San Francisco there was a
cop killing in her first year as DA, and she
and everybody wanted the killer to be prosecuted under the
death penalty, and she refused to go after the death
penalty for this cop killer, and the police in California

(34:41):
and all came out against her because of this, and
people were protesting her. So in early two thousand she
was really at the forefront of prosecutorial criminal justice reform.
I think what happened is the movement, you know, sort
of passed by this leader, which happens to a lot
of people in leadership where you know, they start down
to place and they get you know, vilified by the

(35:04):
establishment for being too pushing, too far, and then the
activists sort of keep pushing and maybe pushed past where
they were when they started. So she kind of got
she kind of got caught in between both of those, um,
both of those polls of being both a progressive and
being a prosecutor. I love that you are complicating our impressions.
I mean, the truth is, you know, you know her

(35:25):
up close better than most people. Certainly having these conversations.
I will say that you know her leaning into the
role as a top cop writing a book about smart
own crime. You know, this was this was progressive light
right by the standards of where the conversation moved. You know,
I think it's fair to say she was, well, it's

(35:46):
progressive light today. But I mean, your history made your history.
A historian, you kind of have to look at people
in the context their times as well as in the
context of what we think may may or may not be.
Like the ultimate what years did she Lets let's run
this down real quick. What years was she in the
office progressive prosecutors? Then it wasn't yet a thing, So yeah,

(36:07):
she invented the concept. By two thousand and three, the
Sentencing Project had for more than a decade pointed out
the rash of sentencing laws under mandatory minimums and drug
sentencing that had wreaked havoc on justice in this country.
The footprint of racial disparity data by that time was

(36:29):
already a mountain. And even I mean, you know, you
know this as well as anybody. I was showing Boys
in the Hood, which was like a foil for John
Singleton to give life to this notion of mass incarceration
and the relationship between concentrated disadvantage and a system of
brutality from policing, you know, to caging black people as

(36:51):
a death sentence back in nineteen ninety one when that
film was released. So while I will accept that within
the construct of what prosecutors saw themselves capable of doing,
Kamala Harris can claim a role as a pioneer, but
there was a politics that was more to the left

(37:11):
of where she was, and that's important. Now I'm going
to also say one more thing, so without saying too much,
you know, I know her sister Maya Harris because of
my time as a fundraiser at Schaumberg when her sister
was VP at the Ford Foundation, and through a series
of relationships, I got to ask a little bit about

(37:31):
Kamala Harris, and you know what I got, What my
little birdie told me was that, you know, she wasn't
her sister, that her sister was more progressive. Her sister
had been worked at the ACOU And so I think
it's fair to say that Kamala Harris was more centrist.
Not just that she was kind of on the cutting edge,
but she was fundamentally more centrist on some of these

(37:52):
really tough issues than a lot of people even at
that time. Listen, I think that maybe true. I wouldn't
dispute that. I think what is true also is that
you have different jobs. Right. So if Maya is a

(38:12):
social justice ACLU for foundation, you know, NGEO leader that
has a different job than being a prosecutor who is
charged with enforcing the laws on the books of their community,
right and then trying to do what you can creatively
to try to prevent people from being on the wrong
end of your prosecutorial stick. Right. So I think it's

(38:37):
the same thing is true about being a US senator
or being a president being a president is not being
an activist. So I just think you have to look
at people in the role that they are in. And
then the role of the activist and the community outside
of politics is to push the politicians in the direction
that it is we want them to go. But if
the people are not there, it is very difficult for

(38:59):
someone who is elected to go to a place where
the people do not support him or her to be
And I think we, you know, the adults, adults in
us kind of have to recognize that that's that's just
sort of what the world works. All right, Well, this
is good. We're gonna we're gonna keep it moving. From

(39:20):
that point, I did, I did. I did learn something though,
that is that, um, if she can be funnier and
more personable, then she has a really good shot at
running for president in twenty twenty eight and winning. So
she's the most likely, most likely next nominee, most likely

(39:41):
next nominee. So so here's a good question, then, jamal
Or like something for us to think about and discuss,
Like you described all the things that she does as
vice president, and you know, those three big roles and
then these other sort of tasks and part that you
even shaped over the last year of going out and
meeting people. How should we judge her as a presidential candidate, say,

(40:01):
in twenty twenty eight, on what basis? Oh, I think
people should judge her based on the way we judge
every candidate, which is, what do they want to do
for my future? Right? I don't think elections are about
the past. Elections are always about the future, and it's
about and it also comparative, you know, they're also they're
always between candidate A and candidate B, not candidate A

(40:21):
and my sense of who the perfect human being ought
to be in the world, who could sit and sit
in an office. Um. But I think we always make
judgments about what somebody's going to do in the future
and then we decide with not you know, it makes sense. Um.
We also personal qualities matter a lot. Just just to
push you, you know further, like, um, okay, we get

(40:43):
that it's about the future, So tell us just just
give us like her top three values. Like you know,
here we are, we've gone through the resurgence of white
nationalism and white supremacy. We've had every kind of existential
democratic or a democracy threat unfold before us. Um. So
She's not going to have the country that Obama inherits
the first black president. She's going to be the second

(41:05):
black president and the first woman if she wins. So
what is her vision of the future. So, first of all,
I don't work for her anymore, So I don't I
can't speak directly for her, but what I will say
is that she believes a lot in inclusiveness and making
sure that people who are not at the table are
at the table. She believes in standing up to bad

(41:27):
actors and making and holding them accountable. Right, So if
you look at like the Corinthian student loan scandal, like
she went out for them when she was Attorney general
and then as vice president and president. They helped get
people get restitution for some of the people who were
taking advantage of by these predatory companies that had gone
after people who are trying to get educations. So she

(41:50):
believes in standing up against people who are trying to
take advantage. She believes in making sure people who are
not in the picture are at the table in order
to be included. And what it is we're talking about
as a country and how we're going to govern, and
so I think we'll judge you will judge her at
the time on what it is that she really wants
to be, what it is she really wants to say
and offer the country, and people will decide whether or

(42:12):
not they think she's, you know, a good enough candidate. Man.
I love that question, Khalil, what are her values? And
Jamala love that answer? Like you. You were up close
and personal with her. Um, You're right, you don't work
for her anymore, but you you do know her really well,
and so you saw these in practice, and so hearing
them from you is meaningful and if not yet persuasive,

(42:33):
it's at least influential. There's a lot of Listen, there's
so much ground between here and twenty twenty four or
twenty twenty eight. Yeah, there's a lot of that point.
But that point, you would the three of us will
be thinking about our social security. Do we want to
go early retirement or we're gonna make it all the
way to sixty five? Man? But I do want to

(42:53):
take this and Khalil, I'm gonna I'm gonna put you
in this camp. I think we've talked about this before.
I just gonna take a personal moment of pride that
the first black president Nited States was named Barack and
the first black woman vice president was named Kamala. They
were not named uh Brian and Camille and Leroy. I'm sorry,

(43:15):
Like you know we have I mean, you know, those
of us who've had names that are you know, rooted
in Africa or our you know, our other cultures, um
have always had this sort of shadow of people saying, oh,
your your opportunities are going to be diminished because you
have these names that's sound Anglo and you know that
quote unquote black sounding names that Bill Cosby, before his

(43:39):
his own self destruction, used to lampoon and make fun
of and tell Black people they were their own worst
enemies because they named their children these made up names.
What an asshole. But here we are, we've all proved
them wrong. Yeah, exactly three of the two of the
three of us here have those black on the names.
We're doing. Okay, that's right, We're doing the damn thing.

(44:02):
All right. We're gonna take a quick break before we
wrap things up with Jamal Simmons. We are back on

(44:25):
Some of my best friends are with Jamal Simmons. Jamal,
I actually want to go back earlier in your career
because you worked in the Clinton administration as well. Yeah,
and I'm thinking about when I first met you, you
gave off this vibe of somebody who wanted to go
into politics, like you had that about you. And I mean, actually, Khalil,
I want to you said that about me. I want

(44:47):
to throw that. I want to throw this at you, actually, Khalil,
because like, like I think everybody who knew Jamal then
was like that fool's going into politics in some way.
And but you know, Khalil, you had you had some
of these ambitions, I guess, but you never went into politics.
You didn't. You didn't look in that way. Did you
think that was something you want to do? Why or
why not? Like what? Oh, that's that's really that's funny

(45:08):
you should ask. Because I actually thought by fifty ben
that I would go into politics. It was the Obama
era that made me change my mind in the opposite direction,
as you know, as opposed to like actually living up
to the ambition. I actually figured I'd do the history
thing for about fifteen good years and I'd go into politics.
But yeah, Obama era kind of turned me off. Yeah, well,

(45:32):
I thought, like, you know, if if if a guy
this brilliant and this committed to uh political ambition. UM
can get into a position of power like this and
have such a hard time UM sort of reconciling his
own biography around racial justice and his own governance strategy.

(45:54):
It just seemed it was a little depressing. Um. You know,
I spent a lot of time frustrating with his first
term and very hopeful for his second term, and the
two together left me UM kind of disenchanted. You know,
even to this day. I think there's like a pill
that you get when you become elected to these uh

(46:15):
senior leadership roles, whether it's in Congress or in a
state house or in the White House, and you know,
you come in and you're like, all right, let's get
this shit done. Let's get let's let's do it. And
then someone like slips you a mickey, and you're like, Okay,
we have to follow the rules just as they have
been followed, and we're going to do these few disabuse

(46:35):
him of his notions educated I'm not. I'm actually gonna
put it in maybe at the context that is familiar.
I think about the president of a university, right, Um,
the president of a university kind of has power but
maybe the deans have more power than the president does.
Right in some ways the dean of in my school.

(46:58):
But don't the deans, I mean in some ways. So
you're the president, but you kind of you have all
these people who have their own little fiefdoms, right like
all of you know, journalism, the liberal or the school
of you know law. They have their own budgets, they
have their own little like worlds that they that they govern. Um.
And so you can kind of get them to do things,
but you just you're not the dictator, you know, like

(47:20):
you have to. So the president's not a dictator. The
president is sort of the one who can try to
cajole the people and the and the people who are
in charge, whether it's a congressional committee or it's a
governor or you know, whatever it is, they have a
say on what the president gets to do. Um. Now,
some people don't care about the rules. We had a
president like that from twenty seventeen. We've had a few

(47:43):
of those, but what one very recently, they don't care.
They do whatever they think, whatever they want. That tends
to not end well, um for those people, because you know,
you sort of have you have to. It's the consent
of the government. And I think if the if the
if the population is split about what it wants, it

(48:04):
is very hard for the president to muscle through big
ideas against the will of say fifty percent of the people.
You can do that maybe once, maybe twice, and one
might argue healthcare could have been one of those times
for the president President Obama. It's very hard to do
that insistently. Yeah, yeah, well, you know, I think that

(48:28):
I'm curious since you were part of the Clinton administration
and you were a young buck like you know, like
we all were back when we were in our twenties.
I mean, you know, that was a consequential presidency. A
lot of big things happened, and of course in hindsight,
from the crime bill to the Welfare reform bill, which
you know, gut it a lot of the social safety
net to the poorest Americans. You know, how did you

(48:51):
experience that period working in the Clinton administration? What what
what is your sense of how you experienced that then
as compared to what you've just been through. So those
things happened, The crime bill happened, the Welfare reform bill happened.
I will say the welfare reform bill happened, and both
of those happened with a lot of support from unlikely places. Today,

(49:12):
there are a lot of people today who were complaining
about those bills, who were in favor of them at
the time. So you know, but the history is that
but including members of the Congressional Black Hawks, absolutely, a
lot of mayors of big cities, a lot of members
of Congressional Black Caukis. But at the same time, during
that era, you also saw a profound amount of growth
in black wealth. You saw more black homeownership, you saw

(49:34):
the lowest black unemployment, you saw more black kids going
to college, you saw higher incomes among African Americans beginning
to go up. The debt of the government was sort
of going down. So the economic prospects for black people
actually were improving, while of course, you had these social
costs on the other side that we all look back

(49:56):
and say they probably we went to far and some
of those social things, the crime bill being the big one.
But you can also look at the crime bill not
to make excuses for it. This is just the politics
of sausage making. While there were these horror punitive laws
that put people in jail for a long period of time.
There also was the Violence Against Women Act. There also

(50:17):
was an assault weapons band that was in that bill.
We haven't been able to get an assault weapons band
passed since that bill was done. So there are things
sometimes in politics that you feel like you have to
do something you don't like in order to get something
done that you think will actually be something you like
and you want to see done. You can shut down
the bad stuff before it gets to be too bad.

(50:39):
If it's if you start, you are doing your job.
You are modeling your job right now giving us. You
are a schooling us on how to sell the communic Listen,
this was such a great conversation, was so great talking
to you. We are just so happy that you made

(51:00):
time for us. We appreciate the you sharing sensitive government
secrets with us. We appreciate you helping to make sense
of the conflictated things that happened behind the scenes of
the White House, and we look forward to what comes
next for you and for Vice President Kamala Harris. Well,
thank you, and this is my first podcast interview since
leaving the White House, so I am excited to do it.

(51:22):
I appreciate you guys having me, and I'm looking forward
to more episodes to find out who some of your
best friends right on, Jamal, right on, Jamal, You got it?
Thanks man, all right, thanks guys, Khalil. We broke some

(51:46):
news on this episode on Some of my best friends
are today we are. This is amazing and so by
my account, I think we broke three things three story. One,
Joe Biden is running in twenty twenty four. Two. Kamala Harris,
despite all the criticism, is going to be his running
mate in twenty twenty four. We heard it here first,

(52:07):
some of my best friends are number three. The next
time there's an opening, Kamala Harris is gonna run. She's
going to be at the top of the ticket. Yeah. Man,
that's that's really, that's such important news. We did this, man,
we did this together. Listen. Awesome, but no, seriously, man,
I mean listen, this is high stakes politics, right. We
really are talking about a country on the precipice, and

(52:30):
the fact that that's where we've come at this moment
in terms of national politics means that this next presidential
race is probably more important than the last two we've had.
And I mean for real, So in light of that,
I mean, I took a lot of inspiration from Jamal's
insights about Kamala Harris, I have, you know, much better

(52:52):
sense of who she is as a person, and amazing,
amazing to get to speak with him. I mean, he
really gave us an an insider's view, that's right. But
there's one thing that I just want to sort of
think about because I think it matters. You know. He
talked about how leaders lead and active do their thing,
and often the activists have to push the leaders in

(53:12):
order for them to be effective. And while I think
maybe on paper that's generally true, it's not always true
in practice. And I'm thinking about when in the middle
of Black Lives Matter during the Obama administration. I know
people like Deray McKesson actually know him as a personal friend,
and he talked about being at the White House and

(53:32):
talking to Obama and he basically said like they weren't listening,
and they were basically saying, like, you guys are messing
it up, because we got this. And so I just
want to say for the record that we have to
not take for granted that our leaders are actually going
to respond when activists are doing their work, and that

(53:55):
that way, Kamala potentially will have an amazing presidency if
everybody keeps their eyes focused on the issues that will
save this democracy. That's interesting because I'm thinking about that
what you just said, and I'm thinking about all we
learned from Jamal, because I certainly have a better understanding
of what a vice president does and all the limitations

(54:16):
on her, and that when he was talking about how
you can't outshine the president or necessarily disagree, he said,
you have one bite of that apple, you maybe you
can do it once. And so so that sense of
being of being limited by this role, which is largely
symbolic and political, and so what you were just describing

(54:37):
of in the VP role for Kamala Harris, how you
could how you could then sort of push policy beyond
where it is. One of the things I've been thinking
about in from this talk is like that she the
moments when she has shined are in these symbolic spaces
when she's spoken to the issues that you're talking about,

(54:59):
And I'm wondering, you know, I haven't felt like I
haven't seen her around and do the kind of things
you're just describing, and I mean, maybe there's even more
she can do in those spaces. Is that feel symbolic,
but also feel like they're they're touching the most critical
issues of the country at the same time. Right, Well,
I'll just say, I mean, we learn from Jamal that

(55:19):
vice president's job is primarily to stay alive in case
they're they need to become president and to break votes
in Congress. My suggestion is really about if she does
become president, I mean, yeah, whenever that happens, and what
we hope will be her ability to literally save the democracy,

(55:40):
to pursue a scale of equity and justice in this
country that we've not yet seen, and deliver on the
promise that being a black woman, or a black Asian
or any kind of first means more than just the
symbolic and representational pride that comes with it. Yeah, I
mean I think a lot about sharing her identity politics
and not say sharing her politics her policies. But I

(56:05):
appreciated what Jamal said about that we don't really know
her yet and that a presidential campaign is also a
process of getting to know somebody, and we're going to
learn more about her and she's also going to continue
to fill this role. So this was really a valuable
talk and I appreciate you. All Right, Love You Man,

(56:25):
Love You Too. Some of My Best Friends Are is
a production of Pushkin Industries. The show is written and
hosted by me Khalil, Jibron Mohammed and my best friend
Ben Austin. This show is produced by Lucy Sullivan. Our
editor is Sarah Knicks, our engineer is Amanda Kawang, and

(56:49):
our managing producer is Cottonstanza Gallardo. At Pushkin thanks to
Leita Mulad, Julia Barton, Heather Faine, Carly Migliori, John Schnars,
Gretta Kone and Jacob Weisberg. Our theme song, Little Lily,
is by fellow chicagoan the Brilliant A. R. Young from

(57:10):
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(57:31):
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