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February 17, 2026 42 mins

Roberta “Robbie” Kaplan is a renowned civil litigator and trial lawyer with decades of experience in commercial, higher education, government regulation, civil rights, and employment litigation…but is perhaps best known for her recent triumph defending her client E. Jean Carroll against Donald Trump. In both 2023 and 2024, Kaplan took on Trump in court and won both cases, securing two unanimous jury verdicts against him. Kaplan has been described as the kind of “lawyer that you don’t want to see opposing you” and has been consistently ranked as one of the top litigators in the country. Kaplan also famously argued before the Supreme Court of the United States on behalf of LGBT rights activist Edith Windsor in United States v. Windsor - which resulted in a landmark decision that invalidated a section of the 1996 Defense of Marriage Act and required the federal government to recognize same-sex marriages. Kaplan was formerly a partner at Paul, Weiss, Rifkind, Wharton & Garrison before starting her own firm in 2017. In 2018, she co-founded the Time's Up Legal Defense Fund. Kaplan recently started a new firm in 2024 and is currently a partner at her firm Kaplan Martin LLP.

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Speaker 1 (00:01):
This is Alec Baldwin, and you're listening to Here's the
Thing from iHeart Radio. In twenty twenty three and twenty
twenty four, author E. Gene Carroll faced Donald Trump in
court and one both times. My guest today is the
attorney who took on Trump in both cases and secured
two unanimous jury verdicts against him. ROBERTA. Or Robbie Caplan

(00:27):
as a renowned civil litigator and trial lawyer with decades
of experience in commercial, higher education, government regulation, and civil
rights litigation. She has been consistently ranked as one of
the top litigators in the country. Caplin famously woned the
Supreme Court on behalf of LGBTQ rights activist Edith Windsor

(00:48):
in a landmark case that required the federal government to
recognize same sex marriages. Originally from Cleveland, Ohio, Caplin attended
Harvard University and Columbia Law School, But before settling in
New York City, Kaplain studied Russian history and briefly lived
in Moscow. I was curious what it was like living

(01:09):
in Russia.

Speaker 2 (01:11):
In a lot of ways, I think it shaped my
view of the world more than anything else in my life.
It was nineteen seven, I'm very old, and Glossnows had
been announced. Gorbachev was the head of right of the government.
Glassos had been announced, but it was still the old system.
And so I got, you know, a semester of seeing

(01:31):
what it was like to live in a totalitarian, authoritarian regime.
And it was insane. We would go into our classrooms
and there would be these bugs at the ceiling and
sometimes the bugs would break and you'd hear like all
the static coming out, and everyone would just act like
it was normal. The teachers all had to be Communist
Party members, and so they had a class on the

(01:54):
Russian words strata vietnya. I guess it would be like
customs of the country, and they would say things like, oh,
you know, we have the consa male and then one
of the American kids will raise their hands and say, oh,
we have the same thing. It's the girl Scouts and
boy Scouts, and I'd be like, what are you talking about?
Like it was just terrifying to see how if you
put people, even Americans. I guess we're seeing that today,

(02:16):
but if you put Americans in that environment, they kind
of succumb to it. It gave me I'm sorry to say,
a very negative view of human nature, which probably isn't
such a good thing, although it's good for a lawyer.

Speaker 1 (02:26):
I often tell myself that, you know, all these societies
ours included, you can't judge them by their political leadership.
I mean, the people might be completely different. Are the
Russian people very different from their political Well?

Speaker 2 (02:39):
I know, the people I knew and hung out with
were like, I was crazy. They're hung out with all
these dissidents and refused next Jews who had asked to
leave and been refused. And you couldn't tell one group
of friends about the other group of friends because that
would make them paranoid. And it was very kind of
cloak and daggery kgb E. But the people I were
friends with was great, and you would this is actually

(03:00):
and you would hang out all night and drink vodka
and talk about Russian literature. And then when I came
back here, I was like, what's wrong with Americans? Like
were also shallow. I had a little bit of a breakdown.
I was like, what's our society is just so surface
as opposed to the Russians.

Speaker 1 (03:15):
Did you come from like a super legal minded family?

Speaker 2 (03:19):
What do I had a roof coding. Business really didn't
really wear in Cleveland, which was my mom's dad's business.
So I don't going to sound very clean. In Cleveland,
it's proounced roof coding, I under said, New York, it's
roof coding. But he had a factory, and in the
summers I worked there, I would load five gallon pails.

Speaker 1 (03:36):
With Now, do you have any siblings.

Speaker 2 (03:38):
I have a younger brother, and he was in the business. Yeah,
he had to do the fun stuff because he could
like drive the forklift.

Speaker 1 (03:44):
Now, when you decide to go to law school, what what?
What inspired that decision?

Speaker 2 (03:50):
So originally I thought I was so into Russian history
from college. I thought I wanted to be a Russian historian.
But I soon realized that if you're going to be
a professor, you don't really have any control about where
you live. And I knew from the time I was
a very young kid that I wanted to move to
New York. My mom had a subscription New York Magazine
and I would read it, and I would read all

(04:11):
the new journalism and Gale Green's restaurant reviews and Tom Wolfe,
and I was like, ALLEGI, yeah, exact this is for me.
So once I realized that I could end up like
it Wisconsin or wherever an academic, I was like, I
want to do the law. And I went to law school,
still not one hundred percent sure, but then I kind
of fell in love with the not so much the
school part of law school, but the courtroom part, because

(04:32):
I would go and watch trials and stuff.

Speaker 1 (04:35):
And when you are there, what year do you enter
Columbia Law School?

Speaker 2 (04:39):
So I entered Columbia Law School eighty a graduate college,
in eighty eight. They used to call me straight through.
I should have taken time off. I didn't take your
time off.

Speaker 1 (04:47):
So you go. You start Columbia Law School in eighty eight.

Speaker 2 (04:50):
Up by Columbia Crime was incredible.

Speaker 1 (04:52):
Well, the reason I asked that is because what was
law school like for a woman back then? Did you
find it was different than it is now?

Speaker 2 (04:59):
And now I teach the I just taught my class yesterday. Yeah,
I mean it was. There were much many fewer women
in the firms, for sure. In New York there were
a lot. You know, when I went to Paul Weiss,
there was one woman litigation partner who's now a judge.
And they made me partner a year early with another
woman because they didn't have anyone, partly because they didn't

(05:20):
they need to get someone partners quick, and there weren't
a lot of role models out there, that's for sure.

Speaker 1 (05:27):
I read, well, you had your classes with people in
the firms you worked in. Was it a situation where
it's like, with men do it, it's fine, but if
women do it, they're apparently it.

Speaker 2 (05:36):
Was that for sure. He's passed away. So I can
say this. I had the former head of my firm
tell me one day that I was a bulldog, and
first of all, I felt like saying, well, maybe you
meant bull dyke, Like I'm not sure what you mentioned
with bulldog wethink that I said? But second of all, like,
I'm a litigator, Like what are you saying? That's what
we do? So there that was definitely an issue throughout
the profession. It's it's gotten better, for sure.

Speaker 1 (05:58):
When you decided to go to law school. When you
were done, was it worth it? Did it turn out
to be satisfy this thing you wanted about dwelling in courtrooms?

Speaker 2 (06:07):
Yeah, I mean I think the idea, I mean, the
great gift of being a lawyer and having the kind
of career of had and being able to work at
firms with all their problems. But who taught me so
many things is the ability to actually change things in
our society in a way that very few people can.
I mean, you can really make a difference not only
to your clients but to causes in the United States

(06:29):
if you bring the right case at the right time
and rage equality. Yeah, when there's the perfect example. So
you know, in Paul Weiss where I started, really that
culture was so strong in the litigation department. Arthur Lyman
and Marty London were great heads of the departments, and
that's how they practice, and that's how they taught me
how to practice.

Speaker 1 (06:48):
When you take a case, what just makes you decide
you're going to take the case? What do you look for?

Speaker 2 (06:54):
So if it's a case where I think it's very
likely to go all the way to trial, I mean,
it's probably not that different than what you look at
very much thinking about how is this witness going to appear,
how is she going to this person going to appears
a witness? How credible is their story? What do they
have that corroborates their story, What are the weaknesses of
the story, and I kind of put it all together

(07:16):
in some weird Yeah.

Speaker 1 (07:19):
Well, I mean Egene did this show, and she would
be as I've heard referred to in like movies of
the thirties and forties, she would be a flibberty gibbet.
She's a very kinetic woman.

Speaker 2 (07:29):
You can say that again.

Speaker 1 (07:30):
Yeah, she's like a bird out of the cage and
she's all over the place. What were your concerns about
that in terms of her as a witness.

Speaker 2 (07:37):
So she came into There were two things that immediately
I thought that they were. On the plus, I won
I don't have to tell you. I mean, she's this
beautiful woman, so when you're having a woman who's alleging
that someone assaulted her, I mean it was totally credible
that Donald Trump would find her attractive. So that was good.
And she was very articulate, and I thought she'd be
able to be charming in the courtroom, which she ultimately was.

(07:59):
The other thing that's me was that the story was
so kooky, like the details of it that she went
in to Berndurf Goodman and he said, let's go shopping,
and they went up to the lingerie department in the evening.
No one was the stories. If you wanted to make
up a story about Donald Trump sexually assaulting you, that
would not be the story you would make up. And then,
of course she told her two close friends within the

(08:20):
next forty eight hours. The donald sides, of course, were A.
It was Donald Trump. B. It's generally very very hard
for women to prove sexual assaults, especially one that took
place pretty sure it was the spring of nineteen ninety six,
those many years ago. She she is a very kinetic
human being, and we had to work I mean, I

(08:40):
thought she was great in the courtroom, but we had
to talk and work with her about kind of how
to testify as opposed to how to kind of talk
as a journalist. She has a tendency to become a
journalist all the time and to ask people questions, and
we had to keep saying, oh, no, no, you have to
answer questions. Now you can't ask the questions. I think
she doesn't want talk about herself, so she'd rather be

(09:01):
a drunk. I have to say, my colleagues at the time,
no one thought it was a good case. Other than me,
they were very well, what was their logic so long
ago there wasn't any physical evidence. I mean, she'd have
this dress, but the likelihood that there was anything.

Speaker 1 (09:15):
That was going to do it wasn't the black dress, like
Monica Lewinsky.

Speaker 2 (09:18):
Well, she actually said, well it wasn't. It wasn't. She
saved her dress, but not to prove anything. She saved
it because it was a Donna Karen Black, very expensive dress,
and she was like, this is too good of a dress.
I'm not getting rid of it. So she put it
in the back of her closet. She never wore again.

Speaker 1 (09:33):
Now, of course, I'm of the school having done this
whole Trump stick on SNL for quite a while, for
four years, that first four years. For me, everything that
could be possibly said about Trump has already been said.
And anybody talking about Trump anymore other than in actual
facts and journalism is a waste of time. When you're

(09:53):
in there. He was in the courtroom and you got
to examine him.

Speaker 2 (09:57):
None in the courtroom examined him.

Speaker 1 (09:58):
At Marlago, you did, You did deposition with him, yeah,
which it was depicitioning. So he never testified in a trial.

Speaker 2 (10:04):
He had the option to. The judge gave him until
to just change his mind, until five o'clock first, the
judge said ten o'clock on Sunday.

Speaker 1 (10:11):
But you can't make them testify. I thought in civil
cases you could. I'm gonna talk to him, right.

Speaker 2 (10:17):
I was able to use the deposition video though, because
he didn't testify, we were able to play some of
the most telling I would say, excerpts of the deposition
for the jury. Who saw them and.

Speaker 1 (10:27):
When you had and you questioned him for how long
in mar a Lago?

Speaker 2 (10:31):
Probably seven hours.

Speaker 1 (10:33):
In one session or a couple sessions one session once.

Speaker 2 (10:35):
I did it twice one it was another case I
had against him, a fraud case that ultimately didn't survive.

Speaker 1 (10:41):
And then in the case with her, how did you
find him in terms of because he's obviously very cagy,
He's a guy that has sidestepped a lot of serious
problems with his wits and his guts and his madness perhaps,
but how did you find him?

Speaker 2 (10:58):
So? I had a strategy I learned actually as a
young lawyer, kind of being in a minority and having
people think about you differently as a woman, which I
call the spider strategy. What I mean by that is
I kind of act like I don't know what I'm
doing and then for a long time and then I'll
finet the end, I'll kind of pounce. And so with him,
I was very polite. I spent the first two hours
asking him questions that he could brag about. So, for example,

(11:22):
we know it was a Thursday night. It happened for
two reasons. One that's when Berdruf Gribbin stayed late one
night a week back then. And two that's when the
writer's table met at Elaine's. And the truth of it
is Egene was going to go to dinner there afterwards,
and I know the whole thing began. She's admitted this
because she thought it would be a great story. Oh,
I'll tell my friends this joke, a story about how
I helped Trump shop for a gift. And so I

(11:44):
got him to say, I said, oh, you used to
like going to Elaine's. Yes, you went there and with
Havana very often. Yes, And you must have sat at
the Writer's table, didn't you. And He's like, oh, yes,
sat there many times. Like you could get him to
say same thing that he'd been at a Saturay Night Live.
She you know, Egene wrote for season you were Night
Live a lot. Yes, you could kind of get him
to admit, I don't think you understod I was doing,

(12:06):
but that he was. He had every reason to know
who Egene was. Like you, they overlapped in certain ways
in New York society and ways that he definitely knew
who she was. And I kind of just loaned him
into it.

Speaker 1 (12:17):
And she was a woman in terms of her physical
composition that certainly he's she would he would make it
his business to meet someone like that.

Speaker 2 (12:26):
And as he said it, the thing he identified her
as Marvel Maples, they did look a lot alike. The
truth is, back then.

Speaker 1 (12:32):
When you have a contingency case. In my cases, my
civil cases we've had, there are support expenses, photo copying,
all this stuff. Paralegals, I mean, they're they're the people
say again it's a fortune. Well, the person who was
my attorney, we had a contingency arrangement, but not for

(12:52):
those expenses. So they're handing you, even though you're not
paying the major bill, you're getting handed hundreds of thousands
of dollars of this this stuff. Now with you, did
you do that? Did you have to pass on to her? No?

Speaker 2 (13:05):
We had very long all. No, don to Eddy, there
has become very controversial. Trump is obsessed with this. Reied
Hoffman stepped in and agreed to pay the outside expenses.
And he was he's the guy started linked in a
technic and he did why. He thought it was a
good case and he thought it would be you know,
important for people to see what happened, and so he agreed.

(13:27):
He had a foundation that was doing kind of Trump
stuff and they funded almost all that's the cost the
most expensive which were security of course, right, because when
every time we went to court, we needed bodyguard and
all that stuff.

Speaker 1 (13:39):
For her for her Wow. So it's to be assumed
because you've got five million in one judgment in eighty
three whatever, and the other one.

Speaker 2 (13:48):
She's about I think she's I'm going to knock on wood.
I think we're going to get the first five right,
and we've waived our contingency on that, so she will
get the whole entire five million.

Speaker 1 (13:55):
Right, and then it's down the road where they're going
to get the eighty front.

Speaker 2 (13:58):
That's a little bit of a bigger bet.

Speaker 1 (13:59):
You do a contingency, Is it assumed that there are
times you don't win, Yeah, and you have to eat
that call those months and months of trial.

Speaker 2 (14:10):
And a lot of these firms that take on these
huge continuencies that last years and years, they have to
fund it all that, and sometimes they have this thing
called litigation finance.

Speaker 1 (14:18):
Where right people invest in the case and they buy
a piece.

Speaker 2 (14:21):
I've never done that, but.

Speaker 1 (14:22):
You never have. What do you what's your opinion of that?

Speaker 2 (14:24):
I think it can be very helpful. I just I
would rather get the whole thing at the end. So
I'm willing to bet on my own risk.

Speaker 1 (14:29):
Right, I'm going to pivot to me two times up.
You know, if Trump weren't president, if you weren't someone
who was empowered politically by so many people, he'd probably
be in jail right now, don't you think.

Speaker 2 (14:43):
Yeah, I mean it's not one hundred. I mean, first,
certainly the special prosecutor would have put him in jail
for sure had that happened, because I mean, he's been
testifying today and it's incredibly powerful. Jack Smith, Look, I
think eaching it would be surprised to me. Let me
put this way, that Egene were that Egene was the
only one. I mean, other women have said that he

(15:04):
assaulted them. I assume it's true. I assume there are
women out there who are just too afraid for good
reason to come forward. I was actually down at the
Manhattan DA last night until ten o'clock with a client
terrible story domestic violence, and I was talking to the
young prosecutors and I said to them, you know, Egene
was right not to go to you guys in nineteen
ninety six, like they won't have done it. And he

(15:25):
was like, no, you're right, they won't have done anything
in nineteen ninety six, But sooner or later I would
have caught up to him.

Speaker 1 (15:31):
Apropos of Me two times Up, there are tremendous successes,
in my opinion, and overdue justice on behalf of people
in terms of the ME two times which you know
Harvey is the ault obviously, but how do you wait?
What what the time ME two times up campaign has

(15:51):
a complied?

Speaker 2 (15:52):
So I've spent a lot of time thinking about this
and how it crashed and burned at the end, and
why it crashed and burned at the end, and really
and then kind of the bad publicity that I got
and others involved got. Look, on the one hand, there
were people like Harveing others who deserved everything they got.
But I do believe, and it actually goes all the

(16:13):
way back to Russia that we reached a kind of
Robespierre period and it actually helped reelect Trump where it
was just after collecting heads rather than exercising judgment, seeing
like the differences understanding nuance, etc. There definitely was a
kind of guillotine aspect to it at its height, and

(16:37):
that was a mistake. There's no question that people were hurt.
There's no question that people who were guilty again, as
I said, got their just desserts. I've thought a lot
about what we could have done to change that. Part
of me thinks that's human nature when these things happen.
But it's terrible, and it's terrible because people who were
hurt bright. It's terrible because again I think it had

(16:58):
a huge impact on reelect in Trump the second time.
The other thing I think about a lot is that
at times up we were dependent on celebrities for our power.
And that was great. It gave us great power. But
we failed to realize is that, and this is understandable,
celebrities don't have a lot of tolerance for controversy, right,
So the minute things started to get a little iffy,

(17:21):
you know, people started fleeing the ship very very quickly,
and it was hard to hold it together.

Speaker 1 (17:25):
I remember seeing people individual people meeting with them, meeting
them with in studios, very much like this Keeler Charlie Rose.
Not everybody was pressing a button to lock the door
of their office at NBC to prevent you from getting out.
There were gradations of this, and I felt that a
lot of people got washed up in the sweep there unfairly.

(17:47):
Look there people who didn't deserve to be canceled. I
they need some counseling.

Speaker 2 (17:52):
The Times tried to cancel me. So two summers ago,
there was a reporter at the Times who spent ten months,
literally ten months, calling everyone who's ever worked with me,
everyone I know, saying what's the dirt on Robbie Kaplan,
which is pretty insane because I'm kind of boring. There's
like not a lot of dirt on me. And she
wrote this very nasty piece and it really gave me.
I have to say, it was a very painful period,

(18:14):
but it really gave me an understanding of the damage
that could be done. I mean it was at the
second Trump trial. I'm standing there closing to the jury.
I have Trump seven feet to my left, and I
have this New York Times reporter seven feet to my right,
and I was like, I don't even just wait wait
to look. I was like, this is insane. So it

(18:35):
gave me a lot more sympathy and empathy for how
damaging that can be. Again, I think we've moved away
from it. But the problem with social media is it
just it encourages it.

Speaker 1 (18:49):
Lawyer Robbie Kaplan. If you enjoy conversations with lawyers representing
controversial clients, check out my episode with Dean Strang the
defense Attorney Fee to the documentary Making a Murderer.

Speaker 3 (19:03):
This happens a client comes in, potential client comes in,
You meet with him, he lays it all out, and
you know, my reaction is, look, you're cooked. They've got you,
and they're gonna want you to cooperate against others, and
you probably should. That's probably your best option right at
this point.

Speaker 1 (19:22):
And I don't do that. I'm not the right lawyer
for that. To hear more of my conversation with attorney
Dean Strang, go to Here's the Thing dot org. After
the break, Robbie Kaplan tells the story of taking her
seven year old son to the White House and his
interaction with Justice Ruth Bader Ginsburg. I'm Alec Baldwin, and

(19:56):
this is here's the thing. Robbie Kaplan received her graduate
degree from Columbia Law School and went on to join
the law firm Paul Weiss. While at the firm, Kaplan
would eventually take on her alma mater as a client. Today,
Caplin teaches a yearly seminar at Columbia University's Law School

(20:17):
as an adjunct professor. I was curious how her experience
with Columbia has changed over the years and how she
would describe law students today.

Speaker 2 (20:28):
Well, it just certain my new class yesterday.

Speaker 1 (20:30):
What do you teach?

Speaker 2 (20:31):
It's a very sexy topic, advanced civil procedure. I'll have
a question for someone actually signs up for that. I
think they're more serious than we were, for sure.

Speaker 1 (20:41):
Really why because the world saw.

Speaker 2 (20:44):
Grim Really that's a sense.

Speaker 1 (20:46):
Do they express that to you in some ways.

Speaker 2 (20:48):
A little bit? I mean, it was just the first
class yesterday, But last year I taught it too, and
they seem, I mean, we had some interesting discussions about it,
but they seem there's not a lot of hope for them.
About it's sad they can achieve. Even talking about courts
and cases and kind of how the system has changed
over time is a little bit depressant. You want to
hear my best White House story?

Speaker 1 (21:08):
Go right ahead.

Speaker 2 (21:09):
So after Windsor, we get invited to the White House
for it was the Honka party, I think, and I
said to my our son was about seven or eight,
And I said to my wife, like, should we bring him?
He was pretty hyperactive as a kid. I said, well,
bring him. I said, we'll probably never get invited to
the White House again, so let's bring him. And so
I said to him, my name is Jacob, said Jacob, listen,

(21:30):
we're gonna go. You're gonna have to go through all
the security. If it gets to be too much for you,
I promise you we can leave. So he was like fine.
We went and he did fine. He had a little
tie on. He was adorable. He did fine for about
the first hour, and then it did start to get
super crowded, and he said, okay, you told me we
could go, and I said fine. So as we're walking out,
Justice Ginsburg is walking in and I said to Jacob,

(21:54):
I said, okay, let's go over and say hello to
Justice Ginsburg, and I am not exaggerating. Jacob had a
temper tantrum on the buckles of her Faeragama shoes. He's
literally on the floor on her feet having a snappertentrum.
I have a look on my face like I'd rather
this happened to anyone else on the planet other than you,
Justice s Kinsburth, And she looked at me. It was

(22:15):
the kindest thing on the one She said. Listen, She said,
I have a son. He's exactly your age his childhood
was Was he acted like that when he was a kid,
she said, But he's now professor at Chicago and he's
married with kids, and don't worry at all. Be fun.

Speaker 1 (22:30):
My kids are in a face now where we went
shopping for ski coats and buying them, and I say, well,
I think this one looks good on Newarthi and my kids.
One of my sons turned to me, he goes, what
do you know you're from Long Islands?

Speaker 2 (22:41):
Oh, my god, they're all born.

Speaker 1 (22:42):
And raised in the city. He goes, what do you
know you're.

Speaker 2 (22:44):
From my sonset My son's version of that as you're
from the last century. Oh that happened in the last century.

Speaker 1 (22:49):
Yeah, yeah, yeah, Now civil procedure in terms of the
type of civil law you would attend to, don't you
think there's some need for some reform to streamline that process.
And I'll allow judges to sit there and go, hey, mister,
you're full of shit, get out of here. Why can't
we streamline that process.

Speaker 2 (23:06):
Exactly what we talked about yesterday actually in the first
class of my seminar. And I do think that, you know,
what happens is we keep making procedural rules to kind
of screen out the bad cases and then their unintended
consequences to those rules, and they don't end up achieving
what we want them to achieve. Good judges, and there
are many good judges, especially in New York, especially federal

(23:28):
judges in New York, kind of do it on their own,
you know. They, especially if they've been on the bench
a long time, they have a very good sense of
what's a good case and what's not a good case,
and what are the weaknesses in a case, and they
will kind of maneuver the case, I think appropriately if
it's a bad case to get it dismissed, and if
it's a good case, to push it along. People have
debated different ways to do this. Should we have different

(23:49):
courts for different kind of cases? Different judges only do
one kind of case? Should we have different courts based
on how much money is at stake? In federal courts?
All you need is seventy five thousand dollars hasn't changed
for decades and probably is way too low.

Speaker 1 (24:03):
Seventy five thousand dollars for what to bring.

Speaker 2 (24:05):
A diversity case in federal court. There's people from different states.
You have to be from different states, and you have
to seek more than seventy five thousand dollars. When that
was first past, seventy five thousand dollars was a lot
of money. Today it's not. And there's been no kind
of way to update that, or Congress hasn't. But sure,
I mean it's something that needs to be thought of.
We have a lot of other legal problems to deal
with and that Congress has to look at, but that

(24:26):
would be one on my agenda as well. And the
courts are overwhelmed.

Speaker 1 (24:29):
Do you find you have a talent for reading juries?

Speaker 2 (24:33):
I think I've gotten good at it. Yeah, it's hard,
and the minutes before a jury, like a you know
when they say they've come in with a verdict when
you're waiting. Every time it happens, I think I'm going
to have a heart attack right there.

Speaker 1 (24:43):
I can't stand it.

Speaker 2 (24:44):
We had I did this big case against the guys
who were responsible for the violence in Charlottesville the rally
in August twenty seventeen. It was during COVID and it
was very hard to read the jury in that case
because they everyone had to wear masks. The juries were
sitting kind of where the audience would sit, like two
jurors to a bench. But there was one guy in

(25:04):
the back. There were very strict rules about wearing a mask,
and he constantly his masks would constantly go down, and
I would say the judge found him there, like, the
guy's not following the rules, And then the guy must
have figured it out because he would kind of give
me nasty looks. And the best thing that ever happened
is the morning we were driving over the court to
find out for them to start deliberating, the judge said,

(25:26):
it turns out a kid at this guy's school got COVID.
The guy wasn't vaccinated, and the judge said, I'm letting
you go. And I was like, oh, thank god. So
things like that really matter. Actually, whether people are vaccinated
is a great indicator of whether the Yeah, well, in
New York you are well. I don't know if you
are now, but you were for the last several years, and.

Speaker 1 (25:47):
And proof that they were vaccinating indicates what to.

Speaker 2 (25:49):
You, rationality.

Speaker 1 (25:53):
I'm going to remember that, honestly, I'm going to remember
that when I got to New Mexico in a couple
of years.

Speaker 2 (25:57):
You don't want to vaccinated jurors, trust.

Speaker 1 (25:58):
Me, I don't want to. Okay, Often these cases settle,
and preferably this vast majority cases, the vast majority. I'm
to show how many of the settlements are spurred by
the judges of themselves or by your opposing counsel or both.
Did the judge ever say to you, hey, let's cut
the shit. You settle this now.

Speaker 2 (26:16):
Yeah. A lot of judges do that, and I think
that's a good thing. I think judges should be.

Speaker 1 (26:19):
Doing that now when you are in settlements, what's the strategy? Meaning,
how did you get to eighty three million with the
Trump Well it was a jury verdict.

Speaker 2 (26:29):
That was a jury verdict. But that's all his fault.
I mean, he sat in that course. So the first
trial he didn't show up at all. He was in
Scotland at his golf course. So the second trial he
did show up because that one was about money. But
he acted like a fourteen year old delinquent the whole trial,
and the jury saw it. And then every day he
would leave the courtroom go to I think we was

(26:50):
going to some office downtown at some trumplone building. It
he would give a press conference and he would defeye
Egen again. So I would walk in next morning, I'd say,
he did it again, Judge.

Speaker 1 (26:59):
Here's the video, and it's just who was that judge?

Speaker 2 (27:02):
His name is Kaplin, no relation, but he really every
penny of the Lewis Kaplan is his name.

Speaker 1 (27:09):
Not the one that adjudicated the Steve Donziger case with.

Speaker 2 (27:12):
The same judge. Same judge.

Speaker 1 (27:16):
Donz is a friend of mine who's on this show.
Yeah anyway, okay, no comment there. He was.

Speaker 2 (27:22):
I'm a big fan of Judge Kaplin.

Speaker 1 (27:24):
I wish I could say the same, but the I
find people. I was at a dinner party and at
the table with us was this guy that was a
judge of federal judge and I tried and I did.
I've arrested myself from asking him a lot of questions
like don't you feel just a suffocating burden to judge
people and to make decisions they're going to change their lives?

(27:47):
What's the psychological training? What's the emotional or behavioral training
they give you in school to master that where you're
gonna go in and say you're gonna go none zero.
So I wonder if some people must drive them.

Speaker 2 (28:00):
So one of our young associates just put in. We
asked for their comments and they said, look, I think
there should be some training on this, and I was like,
you know, she has a good idea. So we're actually
bringing in a psychologist, I think in the next couple
of months to talk to our people about dealing with
these cases where the people have experienced great trauma and
that itself is hard to do.

Speaker 1 (28:18):
I have a job I created for myself, and I'm
only half kidding, but I'll watch TV and they'll show
a segment of a trial and I'll go, you got
to be kidding me. You went to law school and
you study the law, and that's how you present your
case in court. I want to be the acting coach
for your period of the litigators. I'm not kidding. I
want to say to them, I want to take their speeches.
I want to take their summations and say, okay, you

(28:39):
want to motor through this, to only take the earned pause,
you go, you go. The audience is way ahead of it.
But boom, boom boom is like a horse stop. And
then you lay this line out real slow, you squeeze it.
Because I see people who speak in court and they're horrible.
Their acting skills are dreadful, and it is a bit
of acting, so.

Speaker 2 (29:00):
As I get to be great. So in the Carol case,
she told these two people right away, one her friend,
Lisa Burnbock, and a couple days later another friend, remember
Carol Martin the old newscast took her friend. Yeah, so
Carol had some texts that she had to produce where
Egene was getting on her nerves and she's talking to
her daughter about how Egene's getting her nurs and they
thought these were great the other side, and so during

(29:22):
my closing I raised the issue of the text and
I said, I looked at the women jerors, I said,
you know, sometimes it's just the way we talk about
our friends, and they got it. Like they got it immediately.
That's just how people act sometimes.

Speaker 1 (29:36):
Lawyer Robbie Kaplan, if you're enjoying this conversation, tell a
friend and be sure to follow. Here's the thing on
the iHeartRadio app, Spotify or wherever you get your podcasts.
When we come back, Robbie Caplan tells us how being
too honest on a form prevented her from becoming a prosecutor.

(30:08):
I'm Alec Baldwin and this is here's the thing. Robbie
Kaplan was a partner at the law firm Paul Weiss Rifkin,
Wharton and Garrison for eighteen years. At the firm, she
represented clients ranging from JP Morgan Chase to Edith Windsor
in the landmark Defensive Marriage Act Supreme Court case. I

(30:28):
was curious why, after eighteen years and much success, Kaplin
decided to leave Paul Weiss and start her own firm,
and if this was always her plan.

Speaker 2 (30:39):
So I had an early date with my wife. We
just met each other and we're having dinner at some
QB strow in the village, and I start telling her that, oh,
you know, when they were people get it to be
a certain agent. Paul Weiss. They moved their offices to
like smaller offices, but I think that would be okay.
I'm thirty telling her this, and my wife looks at me, like,
have you lost your mind? Like you're thirty years old,

(30:59):
you're thinking about what office you're going to be in
when you retire. Paul Weiss, I thought I'd spent my
life there. What changed the business of law firms like
Paul Weis and such as Paul White. All the big
firms got bigger and bigger. The corporate departments got bigger
and bigger. Paul weize, that's been quite dramatic. And what
that meant for the legation department is the kinds of

(31:20):
cases they were able to do got narrow and narrower.
So it got to the point where the only cases
that Paul Weiss was really wanted to or able to do,
are these huge cases with five partners and thirty associates.
And I could do those cases. I did plenty of them,
but I wanted to be able to do more, have
more diversity, both in the size of case and in

(31:41):
the kind of case. I told this guy, my mentor,
Marty London, who was an old partner, that my goal
is to have his practice, and I think I've finally
gotten It's taken me a long time.

Speaker 1 (31:49):
But you had your own firm for how long?

Speaker 2 (31:51):
Well, I've had two versions of my own firms, so
since twenty seventeen.

Speaker 1 (31:55):
Well, the first one you started when you left Paul White, Yeah,
which you then left that as well. Correct, why got
too big? So again you had created a firm. So
was that an inevitability in the business.

Speaker 2 (32:05):
No, I was just like, focus on my work and
really honestly not paying attention to the firm itself that much.
And it also became too big and too white collar,
and I don't do white collar work, so it didn't
make a lot of sense.

Speaker 1 (32:17):
So you then then then the third iteration was you
started another.

Speaker 2 (32:20):
Firm with a bunch of people from the second firms.

Speaker 1 (32:23):
Second firm, how's that going?

Speaker 2 (32:24):
It's fun because everyone I know known a very long time,
all the partners. We have these incredible group of young
lawyers working for us. They're amazing, our cases are amazing.
We're having a lot of fun.

Speaker 1 (32:36):
When you're in court. This is relates to the question
about the jury. Can you read a judge too? Oh?

Speaker 2 (32:43):
Definitely, Well, you.

Speaker 1 (32:44):
Probably have had a history with them, you know them from.

Speaker 2 (32:45):
The important thing in any case is that who the judges.
I hate to say if this is true, and you know,
if there it's a judge, you know, you know how
they are approach to things, how they practice, what their
attitude is going to be. It's incredibly important. It's not
even that important what it is. It's just important knowing
what it is, right, because then you could advise the
client as to how things are likely to progress.

Speaker 1 (33:04):
And without naming names. Obviously, are there judges where you're
like slightly terrified they have to go into that courtroom
or concerned, let's.

Speaker 2 (33:11):
Say in New York, not that many. We have really
good judges in New York. I was, this is crazy.
So during this second trial, Alina Habba, who was the
lead lawyer who was the USA Traine for New Jersey
for like seven minutes, stood up in court I think
it was the second day, and held her arms like
this and said, Judge Kaplan, I just want you to
know I really don't appreciate the way you're speaking to me.

(33:33):
And I literally almost how a heart attack the idea
that you would say that to it. Yeah, I mean
if I had said he would put He would say,
you're getting put out.

Speaker 1 (33:42):
Why do you think there's all that decorum with the judge?
Why do you stand and call him your honor? We're
not in eighteenth century England here.

Speaker 2 (33:51):
I think it's a good thing because on the surface
you're showing respect to that judge, but fundamentally you're showing
respect for the rule of law. And I wish we
had a little bit more back for the rural law right.

Speaker 1 (34:01):
Now, dwindle in your time.

Speaker 2 (34:03):
Yeah, I mean it's terrible right now. I mean the
DOJ used to be this great costation, right that always
told the truth and always took the right position, and
always cared about consistency, And none of that's true anymore.

Speaker 1 (34:15):
Well, when Trump got into office, I know made note
of the fact that to a degree or in some metric,
I wasn't prepared for how many other bad people would
come with him. I didn't realize this time the well,
the second term, forget it. But in the first term
even I remember saying to myself, I didn't know there
were that many bad people out there who were on
some political operatives rolodex. And now when the second term,

(34:38):
it's like, I.

Speaker 2 (34:39):
Mean, how many prosecutors have quit and dj because they've
been asked to do things that they know are wrong.
I mean, it's it's terrible. I wanted to be a prosecutor.
Want he still a funny story. So I got an
internship when I was in law school to be prosecutor
Southern District of New York. And this was Bush one
and you had to fill out a form for security
and the forum had a pot question. So I go

(34:59):
to see the professor Columbian and I said, so give
me advice. What should I do? And he said, you're
supposed to say experimentally. So the first question was have
you smoked pot? I wrote yes, semi cola and experimentally.
The next question was how many times? And I wrote
twelve plus and the government said, sorry, we're withdrawing your offer.
And I went to the professor to tell the story.

(35:20):
He's like, what in the world were you thinking? Right,
experiment I said, I want to lie, I said.

Speaker 1 (35:25):
My continuing experimentation. I was very You didn't want to lie,
but you realized that if the question is silly, like
you say yes, experiment how many times twice, you should
have lied. You should have lied in that appl because
you're too bunch of a girl scout to do.

Speaker 2 (35:40):
I want to get my hands on that form somehow,
I'm going to try to foid it.

Speaker 1 (35:43):
Well, cut, yeah you should. What kind of work does
your wife do?

Speaker 2 (35:46):
So she's been in Democratic politics part she was is
the Democratic State Committee person for Downtown Manhattan for twenty
some years and has worked down a whole bunch of
anti fracking, a whole bunch of policy stuff. Starting to
think that maybe it's time for a change, but that's
what she's devoted for. She was an activist when I
met her, and then she kind of did a lot

(36:07):
of policy throughout our marriage.

Speaker 1 (36:08):
A lot of facting going on in New York.

Speaker 2 (36:10):
No, she stopped it right. Oh well, with Governor Cuoma.

Speaker 1 (36:13):
I was in Trump was elected. I went to do
that crazy and silly Trump stick those four years in
SNL from twenty sixteen to twenty twenty.

Speaker 2 (36:21):
You may say it's crazy and silly, but it gave
a lot of people.

Speaker 1 (36:24):
Well, people would say that to me, not.

Speaker 2 (36:26):
Just pleasure from watching, but a lot of comfort.

Speaker 1 (36:28):
Right. They wanted to have some laughs about what do
you think, let's say we win the mid terms, and
to me that gives me hope, yes, that we can
come back to some degree. It's never going to be
the same. Like they were saying. You saw the guy
from Canada said that they the Americans as the leader
of the free world is over. It's that damage, it's fractured,

(36:52):
it's over. And I thought, wow, what a disturbing I mean,
I didn't necessarily need the United States to be the
leader of the free world, but I thought I'd like
the United States to have the option to be the
leader of the free world if it was necessary, and
then if we could keep things together. And do you
think we're ever going to be able to put it
back together to We just don't know.

Speaker 2 (37:11):
I've been thinking about that a lot since Davos. Obviously. Look,
I think first of all, we have to put things
back together domestically, so we have to kind of redo
all the Watergate reforms, but in a way that works.
All the rules about independence and stopping corruption and disclosures
like we had them, but they're they were too easy

(37:32):
to get around. So I think all of that has
to change. And I have great respect for President Biden.
I think you did a good thing, but I don't
think he was tough enough on that stuff, and then
I think, once we fix our own house, which is
going to take time, we also obviously have to repair
our relationships with our allies. I mean, one thing I
know from the time I was in Russia is that
you know, the Russian government then and now is not

(37:54):
It's not a good thing. And what they're doing in
Ukraine is tragic and we need to have kind that
can work together to fight against that. We can't have
them go take Ukraine and then beyellow Russia and then Poland.
That would be horrific. We're not going to relive, as
my son would say, the last century.

Speaker 1 (38:11):
Without getting into details. What's the case you're working on now?

Speaker 2 (38:15):
Oh, so this is interesting. I can tell you this
is public, So this is not it's all about everything
we talked about roll up into one. So we have
a client. I have a client for many years. His
name is Imron Achmed. He runs it a not for
profit called the Center for Countering Digital Hate, and he's
a big critic of tech and he's written a lot
about problems on big tech and failure to moderate content, etc.

(38:38):
Elon Musk does not like him very much. He sued
him four years ago. I represented Elon in that case.
We got it dismissed. It's still on appeal and AX
recently got sanctioned by the EU for not for failing
to comply with their digital privacy law. And Elon got
very angry and got the State Department we believe to

(39:00):
say that my client screen card should be revoked. They
announced this on December twenty third. In the afternoon. We
go I see to my client, get your toush to
New York. We file papers on five o'clock on Christmas Eve,
saying you can't do this. This is about his speech. The
guy hasn't done it. You're not allowed to just kick
people out of the country because you don't like what

(39:20):
they say. And he's not criticised the American company. Since
when is that a problem? Like people criticize America companies
all the time. And we got an injunction twelve thirty
am on Christmas Day, So my team didn't have the
easiest holiday. But it's a great case. It's ongoing right now.
They can't do anything to him, but I'm going to
see you to litigated.

Speaker 1 (39:39):
What do you think about that judge that smuggle the
presumed terrorists out of the courtroom and just got conviction.

Speaker 2 (39:45):
She got convicted.

Speaker 1 (39:46):
She got convicted. Boy boy, that seems like a tough
thing to do for judge to sit in judgement of
another judge who they believe has made a poor decision.
It was a poor.

Speaker 2 (39:55):
Decision probably, if that's those are the facts it was.
I mean, that's why our client is so different. There
are We do have rights to revoke visus for people
who support terrorists things like that, But criticizing X like
that makes no sense.

Speaker 1 (40:08):
I've been saying the same thing. I'm likely that people
who are the faithful in this issue of campaign finance reform,
the ones I've worked with over the years, for many years.
This is my issue, other than plastics pollution and wanting
to ban single use plastics around the country, Campaign finance
reform is the lynchpin of all of our problems in
this country. What passes for leadership now that is able

(40:30):
to get bought and sold by the local business community.
If cash is speech, then he with the most cast
speaks the loudest. Was the line of us.

Speaker 2 (40:38):
It's true.

Speaker 1 (40:39):
If we don't change this, citizens united and get that overturn,
I doubt we'll ever be able to get off the path.
We're wrong with that, and.

Speaker 2 (40:48):
Which leads to the Supreme Court, which is a whole
other head.

Speaker 1 (40:50):
We want to know what then let's ask let's go
out on that question. Look, I mean sixty.

Speaker 2 (40:55):
Three, as someone who really believed in the system and
the role of law, the idea of Supreme Court reform
was hard for me to kind of get my arms around.
But I'm now at the point. I mean, we'll see
what they do on tariffs, We'll see what they do
on the FED. I think I think he's going to
lose both of those. But this idea that they just,
you know, so easily overturned precedence not Roe v. Wade

(41:18):
and others that have existed for decades, is not good.
It doesn't give it's there's no faith in the system.

Speaker 1 (41:23):
It's law. What do they say, what do they say
when they change it? What is it?

Speaker 2 (41:29):
Basically said, it was wrong a lyough, it was wrong
when it was decided, and reliance doesn't matter, essentially, is
what he said. But it can't be that people have
so little faith in the Supreme Court. I know, I'm
assuming the Chief Justice is worried about this. I think
he needs to be more worried about it. I think
we have to restore that faith as well.

Speaker 1 (41:51):
My thanks to lawyer Robbie Kaplan. This episode was recorded
at CDM Studios in New York City. We're produced by
Kathleen Soo, Zach MacNeice, and Victoria de Martin. Our engineer
is Isaac Kaplan Woolner. Our social media manager is Danielle Gingrich.
I'm Alec Baldwin. Here's the thing is brought to you

(42:11):
by iHeart Radio
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Alec Baldwin

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