Tetragrammaton with Rick Rubin - Alex Spiro
Episode Date: July 16, 2025Alex Spiro is a partner at Quinn Emanuel Urquhart & Sullivan and one of the most prominent trial lawyers in the United States. A Harvard Law School graduate, he serves as Co-Chair of the firm’s Inve...stigations, Government Enforcement & White Collar Defense Practice. Spiro has represented a wide range of high-profile clients—including Elon Musk and New York City Mayor Eric Adams—and has served as lead counsel in over 50 trials across federal and state courts. A former Assistant District Attorney in Manhattan, he has also contributed to legal education as a faculty member of Harvard’s Trial Advocacy Program, a lecturer at Harvard Law School, and Chairman of the Board for the Fair Punishment Project, a Harvard criminal justice initiative. ------ Thank you to the sponsors that fuel our podcast and our team: Squarespace https://squarespace.com/tetra Use code 'TETRA' ------ LMNT Electrolytes https://drinklmnt.com/tetra Use code 'TETRA' ------ Athletic Nicotine https://www.athleticnicotine.com/tetra Use code 'TETRA' ------ Sign up to receive Tetragrammaton Transmissions https://www.tetragrammaton.com/join-newsletter
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Discussion (0)
Tetragrammaton.
In any case or any battle, there's just always a lot of ups and downs. It's like, you know, people say don't watch the stock price.
It's hard to find a clear road all the time.
It's not as if day one, the truth comes out.
It is a battle.
It is a war.
And unless you keep going and going.
But I think ultimately what I believed as I'm graduating law school, which is that the
truth would come out in a courtroom if ever, I think that's right.
Does it?
I think so.
If the system works right and the people at battle are doing it the right way, it does.
Now there's parts of this country and this system that are plagued by maybe all of the
racism and all sorts of other issues that are endemic in the system, maybe in any society.
So I don't want to say that it works perfectly because of course it doesn't.
But if I'm handling a case, there's enough attention on it and I'm locked in, I think
the truth's going to come out. When there's attention on a case and I'm locked in, I think the truth's gonna come out.
When there's attention on a case,
where would it come from?
Natural forces at work, you know,
some people on some issues are more interesting than others
and so people gravitate towards them.
And then over time, you know,
they'll pay more attention to my cases
because they're my cases.
If a case is a highly publicized case,
does it change anything? It changes a lot because everyone is a highly publicized case, does it change anything?
It changes a lot because everyone is a little bit more on edge, especially if they haven't
been there before.
So you'll see, I mean, almost always early on in cases I have when there's a tension
on it, a judge makes the wackiest ruling of the judge's career.
And I don't think they're doing it on purpose.
I tend to...
Just the stress of the judge's career. And I don't think they're doing it on purpose. I tend to describe-
Just the stress of the situation?
The stress, the lights, the not knowing how to deal with it.
Somebody who used to work with me used to say
that anytime I would walk into some random courthouse,
the judges would either be way too deferential
and nice to me or wanting to start a fight with me
the moment I walked in for no apparent reason.
And you would just see a little bit of a dichotomy.
What would cause one versus the other?
Maybe respect and fear at the same point,
and they don't know how to interact or deal with it.
Or maybe the reputation even is one of respect and fear.
I don't even mean that in a positive way,
I just mean they don't know what to expect.
They don't know how I'm going to interact with them
in the system, am I there to throw my weight around,
am I there to, you know, think that I'm just gonna get away
with whatever I'm gonna get away with
because I think I should, and so that tension,
you know, causes them to act in different ways,
makes it interesting.
Is it adversarial in a friendly way in the courtroom
or is it different than that?
It's maybe about as friendly it is on a sports field.
Not quite an actual war where you're
trying to make it so that somebody doesn't leave alive.
But I think it's a sport with higher stakes.
So there's gonna be sharp elbows to some degree
and people, again, react to those situations
in different ways.
Some people don't know how to shake hands after a game.
Yeah.
Can you shake hands after a game? how to shake hands after a game. Yeah. Can you shake hands after a game?
I can shake hands after a game,
but I've had a lucky run, so I haven't had to,
I haven't had to face, you know,
I haven't sat in a courtroom with a friend
and watched them be taken away.
You say lucky, how much of it do you think is luck
versus something else?
I think you make your own luck.
Okay.
So.
How much of the job is storytelling?
A lot of it.
You know, you're a communicator,
you're trying to take information and facts,
distill them into a way that makes sense,
marry them to the law.
I don't get to decide the law, the law is the law.
And then package it in a way
that you can convince a group of people that you're right.
That the truth that you're telling is the correct,
is the answer to the puzzle.
What's coming from the other side,
how often does it feel disingenuous?
I think it depends on the arc of the career.
I mean, you know, when you're a prosecutor
and you're all revved up about whatever the justice is
you were seeking and the other side
is trying to play trickster,
that's how you view a trickster,
not a test on the system.
I see.
That's how you see the world,
or at least I saw the world when I was 25,
a little bit, a little bit.
I think I grew past that phase very quickly
because I think much of my leaning is
that people are more complicated
than the worst thing they've ever done,
that people deserve second chances,
that the system needs checks and balances.
So because I was leaning that way,
that notion of 25 disappeared quickly.
On the other side of it, it has not dissipated as quick.
The sort of prosecutor looking to,
as I say amongst friends,
update their LinkedIn profile or whatnot
by taking somebody out or by bringing a case
that's on the margins of criminal law.
Some lawyers are trying to get rich,
some lawyers are trying to get famous, whatever that.
I'm still more jaded, calmer than I would have been at 25,
in some respects, but I'm still a little cynical
about Poulten.
You think calmer from experience or something else?
Yeah, some of it's experience, some of it's just age.
I've said, if I looked back at 25 cross-examining a witness,
it was very breathless.
I mean, I had so much energy, so high octane.
I used to be able to go 21 straight hours though, but that'd be, now, no.
I mean, how much of that is hopefully developing some grace
and wisdom or whatnot?
Some of it is just biological, I think, that just.
Would you say you're better now than you were at 25,
even though then you had a little more energy.
For sure.
So, it works out.
Exactly.
Yeah.
How much research do you do before a case?
Endless, as much as there is to possibly.
Tell me how that works.
How do you start?
So if there's a subject matter, I have to learn everything about the setting, the subject
matter.
And I do everything. I want to know whether it was hot or cold out. I want to know what
the wind is like. I want to know if it's a movie set, how do people interact on a movie
set? And if it's an old town, how do people interact in that town? Do people tip? Do they
use cash? Do they use credit cards? How do they interact? Does everybody know each other?
Would they have been saying hi to each other. I'm trying to basically visualize like-
The whole world.
The whole world in which the case exists
and how it would have been if I had been there myself.
I remember early when I was a prosecutor,
you know, we used to go for drinks after cases
and I used to sort of say, you know,
unless you've been drinking in a bar and seen a bar fight, you would never be able
to be as good at trying a bar fight case
as if you had been watching a bar fight.
And from early on, I always thought
that some real world experience and the ability
for me to picture what actually happened
was a special ability, if there was one.
And so that's the setting.
And then in terms of everybody, I'm trying to figure out, you know, who they are and
what makes them tick.
And psychology is sort of where it begins for me and the main thrust of it.
So what kind of person is this?
How were they built?
What are they likely, you know, influenced by?
And why would they do or say or think the things they were doing and seeing.
And then as they retell it, what's intentional,
what's motivated, what's unintentional,
and trying to sort of piece that together.
And the more nuanced I can get, the more gray
in terms of the reflection of what I'm watching,
the more special the unraveling
of what really happened is gonna be,
and the harder it is to prepare for.
So if I'm asking somebody questions,
and I'm getting at stuff inside of them
that they have not fully grasped.
Which is probably often,
people don't know themselves very well.
I think that it is, and it's definitely played out that way,
I think, in cases and in some
of the cases that never got that far, frankly.
But that's what I'm trying to do.
It's very hard for a witness to prepare for that or anybody to prepare the witness for
that because the witness wouldn't have even shared that with the lawyer trying to prepare
them for a question that's never been asked in a courtroom since the beginning of time.
Can you think of a time where you took an approach on a case that you're sure no other
lawyer would have taken?
In every case I've ever handled, I think that there are nuances of the psychological approach
that I take that no lawyer ever would have done.
Now I'm not saying that like the macro defense
wouldn't have been whatever the same macro defense,
but they would not have thought about
the way it all fit together the same way.
So if you have two different people
with very different psychological makeups
and they both perform the same action,
that would be different for you because one
of them is doing it for one reason, one's doing it for another reason, so it's a different
story.
Is that right?
Right.
As long as there's a thread between the two.
A person can drop a cup of water and one person could be built one way and be very different
in Freudian terms than the other person, but they both still just, you know, humans drop
glasses of water.
And you have to make sure that you also remember that, that some things are not data points.
Some things are just part of existence.
It just happens.
Do you think that your little bit of time as a prosecutor helped you as an advocate
for your clients?
For sure.
And it's where I got the training wheels off the bike. And so, you know, people
always ask me, you know, well, what should I do? How do you become a trial lawyer? All
these things. And one of the things is you got to learn the ABCs. And if you're really
good at the ABCs, you can spend less time thinking about it like anything else. So when
a great basketball player dribbles basketball, they're not thinking about it. They're not
thinking about anything
other than watching everything else move around.
Being in the moment.
Correct.
Do you feel like that when you're in the courtroom?
Like nowhere else I'll ever be.
In the moment.
Like nothing else, nothing I could even describe to you.
Yeah.
When it's less of a human situation,
less about place, temperature, nature of the town, and if it's more like
a corporate thing where it's on a technical issue, do you have to learn the technical
issue?
Yes.
That's the playing field then.
Right.
But even if it's a technical issue with emails and everything's really emails, emails can
come to life too,
if you understand the personalities and the players.
There's humans behind it all, you know.
Yeah.
Do you ever recommend not to go to court?
Sure.
What would be the situation that would recommend
not going to court?
There's no story here.
And when I say story, there's no tone to that word story.
There's no story here. And when I say story, there's no tone to that word story. There's no version of events here
where I like the way that it packages for you.
Yeah, well you can tell the story
in support of your client.
Correct, and I won't go into court,
I mean people can scoff at this what they want,
but I don't go into court and say things that aren't true.
It has to be true.
It has to be my truth, but it has to be true.
And so if the person comes in and wants to spin up
a story that is just, I wasn't in the town that night,
then that's not gonna work.
And other people have all sorts of other reasons
where there are collateral consequences
for them going all the way
that I just don't think make sense.
And people who come to sit with me and meet with me
sometimes follow your advice and sometimes they don't.
It's just that simple.
Are there any that you work with
that don't follow your advice?
I mean, most don't follow my advice all the time.
And to be honest with you, arrogant or not,
it surprises me.
Because I give them a speech and I tell them,
I'd say pretty much, and there's 200 I can show you
that a lot of people know about.
There's another 2,000 nobody knows about
other than me and the people very close to me.
And I can show you a data set of 2,200
and there should be nothing you follow
other than what I'm about to tell you.
And I know how arrogant it sounds.
But I'm like, how many times have I done this?
How many times have you done this?
And I can be objective and I can play doctor and I'm not as close to it and I'm not, how many times have I done this? How many times have you done this? And I can be objective and I can play doctor
and I'm not as close to it and I'm not emotive about it.
Just trust me.
And even then, some of these people are friends,
great relationships with, brilliant people.
Sometimes they still don't listen.
And if they don't listen, will they find someone else
or will they ask you to do it
even though you wouldn't suggest it?
Some combination and sometimes they will use a straw man
to try to get me to, right, there's one person in particular,
one entity in particular I should say, a company.
Whereas if I give them the correct but not wanted advice,
they will say, well you know what, I'm just gonna,
I'm sure Bob, Susan, and Tony will come in here
and tell me effectively what they're telling me.
I'm saying, okay, go for it.
Because you have to digest so much material for every case,
have you found any helpful techniques
that just make that easier?
Well, everyone's memory works a little bit differently.
And I'm effectively memorizing a bunch of stuff
as I'm preparing.
And I know how to make myself memorize things.
And I use a disorganized
method and an organized method. And I think that disorganization can help memory and organization
can help memory. So I will have posted notes all over. If you walked into my room, just
they're everywhere. And then I can kind of piece them together and people would say,
well, that's disorganized. How do you make sure that you don't? But by having to keep
track of them and seeing how they work together. It works for you.
It works for me.
And then I will then distill them into my yellow notepad
and more coherent, organized, structural thoughts.
But I have to kind of break things apart
and play with them.
I'm experimenting as I go.
Just sort of say, well, does this all fit together?
And what if the witnesses go in a different order?
Will it still work?
Will the thing come to life the same way?
How much do you know in advance in terms of
who be the witnesses, what order they go in,
how much of it can you control,
how much of it is out of your control?
I mean, a lot of it's out of your control,
but as time goes on, you kind of know certain certainties.
Right, you know of the 15 people
that may come into the movie, you know seven
of them almost certainly. And you know the order, you know, two-thirds of the order more
or less, you could make an educated guess. And then of the other eight, half of them
will come half of the long. So you've got to also make a judgment on the return on your
time of preparing for that which will not come or figuring it out. And then if the movie plays out with these 11 characters versus these nine versus these
13 or in a different order, how is that going to appear?
And that changes things dramatically.
Well, if they call three witnesses in a row that are very eddy steady, very sort of buttoned
up people, then for the first two or three days of the trial, no one's going to think
of this was a wacky crew of misfits.
They're gonna think these are straight up
buttoned up people, right?
Whereas if the first witness they call is flaky or flighty,
then it's like, well, maybe they did lose the paperwork.
I see.
You know, I mean, and so the order of it
will change the way that I'm constructing it.
Does it always go prosecution goes first? Yes, they have the burden of proof.
They go, they lay out their case, then it's the defense case.
And in civil trials, it's pretty much that way too.
Let's talk about that burden of proof because we've grown up with this idea of burden of
proof, innocent until proven guilty.
Yet, with the media today, it seems like that's not how things work.
As soon as somebody gets accused of anything, they're treated as guilty in the public.
Yeah, I'm hopeful that good advocacy
and watching some cases go the way that they went
leaves some imprint in people's mind
that maybe I don't have it the right way.
But if the allegation coupled
with a little bit of corroboration,
boy does the prosecution,
and I'm using prosecution to mean basically prosecution
and a plaintiff's lawyer,
anyone trying to set out to prove something.
Boy, are they 90% of the way there.
Yeah, it seems like that.
It seems unfair, really.
It is unfair.
It seems unfair.
Do you get to see all of the witnesses for the prosecution
in deposition beforehand?
No.
Really?
None of them.
Really?
And this is, I think, a very interesting point that I don't know that everybody knows and
something that I like.
I think it works to my advantage.
But no, in civil cases, you get to depose the witnesses.
In criminal cases, in almost no state in the United States, do you get to depose the other
side?
So the first time you're ever speaking to these people is on the stand.
Right, which some people might think works to a good questioner's advantage.
They've never seen your pitch.
Now they can study, they can try to prepare, but they can't prepare the same way as if
they had spent eight hours in a room with you before.
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How much do people change when they're on the stand
versus in a room or in deposition even?
Like in a podcast times three,
because they know that people are paying attention.
Again, higher profile case, higher stakes.
Witnesses are over-prepared, so they get more rigid,
they start practicing their answers.
People think that it doesn't look like it's practice,
it looks practice to me.
And they're just gonna get tighter.
And when they get tighter, they look less natural.
We arrived at the location at 9.05 AM.
Yeah.
OK.
How do you know?
Would you say how do you know or no?
No, I mean, that's not an important enough.
It just seems ridiculous.
You can't jump on everybody.
No, it sounds like you read that in your memo, not in your mind.
Right.
And so if I harped on every little thing
that I saw with a witness, my cases would take years.
Yeah, yeah.
Okay, so you gotta pick and choose a little bit.
Not everything speaks to some higher, you know,
but if you wanted to make a point out of that,
you know, if I needed to go backwards
a little bit to go forward,
you could go back and just sort of say,
you know, I just wanna talk to you for a second
about what leads you to give your very first answer when you got on the win stand, right?
Yeah, you're not sitting here sort of closing your eyes remembering something and just trying to do your best for this jury
I know. What do you mean?
It's like no no, you reviewed paperwork, right and the paperwork told you nine. Oh five a.m
Right. So all you're doing is you're the guy reading your own paperwork. Isn't that right?
And then if you think that that's going to either
make a point that matters, or rattle them,
how important is it that the jury likes you?
It's important they respect me.
I'm not foolish enough to think everyone's gonna like me
and everyone's gonna take to my personality,
but they have to believe that I am credible.
They can't hate me so much,
they can't believe I'm credible.
Is there ever a fear of going too hard
on someone on the stand?
Yes, you can't be aggressive with a kind of a witness
where I'm gonna look aggressive.
It could turn off the jury,
even if the person is being flaky.
You have to be able to change your speed
and your pitch and your whatever to the witness.
So if there's an 80 year old grandma
who's a lady who is cooking in the kitchen,
you can't go in there and start screaming at them.
Whereas if there's some slick character
that seems like he's trying to deceive everybody,
even when he's ordering coffee,
you can go more aggressively at him.
It doesn't mean that the grandma isn't lying.
But why would she, and what does she have to gain,
and how do you unpeel that, and we have to know
the imprint of the psychology on the person doing it,
which is that we are making knee-jerk assessments of people every single day
and every single way.
And so if that witness is a hero, right,
I mean, I've crossed heroes, you know,
if they're a hero and you start going right at them,
you're trying to beat up a hero.
You can't do that.
How different are juries?
They're very different based on location,
just like, you know, 12 people in New York City
are different from 12 people in Santa Fe with almost no overlap.
I will say that when you have 12, the combination of viewpoints, that's why the diversity of
viewpoints is so important, hopefully forms a reasonable person based on 12 experiences
and 12 viewpoints.
In some way, are you also an advocate for the jury?
Yes, insofar as, again, I want them to know that I want them to know what really happened.
Right?
So if they're there and I'm trying to say, listen, I've been living this movie for nine
months, just come with me.
Yes.
And you're going to learn what happened.
So yeah, I am trying to, which is why I don't,
I don't think I'm very, I'm not objection heavy,
I'm not blocking evidence heavy, I'm not,
I'm sort of like, no, no, no, let it in.
That's educational in some way for them.
Correct.
Tell me about when the aha moment comes.
You're doing research and you come to,
okay, I know my approach.
Does that happen early in the process?
Does it happen late in the process?
Does it ever change?
All of the above.
And again, there's like 18 different ahas
that have to come together to make one of these
sort of resounding victories.
The jury's not coming back in 40 minutes.
In a case you shouldn't have any chance at
unless you found like 18 aha moments.
Because the evidence would have been so strong
that in order to separate yourself
from that blinding evidence,
you needed to have many different things.
It wasn't just simple enough that one,
in the one witness case where there's no corroboration,
where there's some, it looks like the guy outside
of the motel, sure, you can have one moment
where you just destroy that witness and the thing falls.
And I could look at the paperwork and say, wait a second.
Right, and there are these cases, I mean,
a lot of the cases, wrongful convictions in this country
was one witness says the guy that they see,
cross-racial identification outside the motel
in 11 seconds in the dark
was the guy sitting there and they go away. But if I see paperwork like that and I see a case like
that, I don't get so lucky with my cases to have a case that falls apart so easily. But then yeah,
then you can have one moment where you say there's no chance that is going to survive.
But those are the cases that to the degree I've had those kinds of cases,
they never even get to the verdict.
What's the most witnesses you've had in a case?
Witnesses, as in people that have been spoken to,
well over 100, witnesses that end up coming
into the court, more like 30.
30's a lot.
Yeah, it's a lot.
Some of them break down into less important,
less controversial, right?
There could be five that are somewhat,
just to get in a piece of evidence,
and there could be five that, you know.
I mean, there are many witnesses
I won't have a single question for.
You can't, unless the theory of your case
is that it's all one big conspiracy.
They can't all be lying,
unless they're all lying for a reason.
So you can't also go at everybody the same speed, right?
It has to be that a lot of these people are just good,
normal, hardworking people, and the jury can compare.
That's what a real witness looks like,
and that's what somebody trying to fool you looks like.
Do you look forward to going to court?
Yes, I mean, I wish I didn't, but I do.
I do love it.
Well, that's great.
I think it's great that you do,
that you found the perfect job.
It seems like a high stress situation,
and if you thrive going into that high stress situation,
that seems like a positive.
It is.
That having too many problems on one's shoulders
at all times for too many decades,
I don't know, is a good thing.
But the actual moment as I'm walking into a courtroom
is one of relaxation, joy, intensity,
all wrapped up together.
Relaxation is in there.
Is in there for sure.
I love that.
I wouldn't have guessed that.
Yeah, it's just like,
cause you're finally there, there's nothing left to do.
I see. But to go.
I see. Right.
And so it's like taking a test where you know that.
You've studied, you know all the answers.
I know, it's well enough thought through in my head
that I think I'm coming out ahead.
Yeah, and in some ways you get to get it over with.
You don't have to keep thinking about it.
Yeah, I think that's part of it too,
and a lot of it's just adrenaline, honestly.
I am just as hopped up as I would be
for like a sporting event, right?
It's just, it's very adrenaline based.
Can you let go of all the information after the case?
Yes, in fact, I don't let go of the adrenaline,
but that takes a few weeks.
But the facts, yes, I mean, I always will remember
some stuff about each case,
but I think I'm intentionally, frankly,
washing my brain of it.
It seems like that would make sense.
There's so much volume of information that you're taking in all the time that if you
don't get rid of some, I don't know how there'd be room for new stuff to come in.
Right.
I'm not doing it brick by brick thinking it through, but I do let it wash away.
How different are judges from case to case?
They're pretty different.
Like I mentioned earlier, I have, or the people around me, I don't want to just put it on
me, have noticed the pattern of some of the dichotomy I described.
So I see some similar things, or even other judges will say to me, oh, so-and-so never
gets like that.
But I think you're making them a little nervous, or they don't know which way you're going
ever.
And some judges, until the third witness comes, they don't know which way you're going ever. And you know, some judges, until the third witness comes,
they don't get into their own.
I mean, I've had trials that started with a judge
interrupting almost every question I asked
because they basically they wanted to know
where I was going before I got there.
Just anxiousness and how do they know
if I'm doing it in a different way
and I'm doing it in a way where I'm not revealing my hand,
how do they, they would say how did they know
I was gonna get to something relevant if I'm asking questions
about 905 and the mama book, why is that relevant?
So if they're very tight and anxious and they haven't seen my pitch before, they start interrupting,
interrupting, interrupting.
By the third witness when they go, whoa, I get it, something is about to happen here,
they will then go back to normal judge school
and be closer to each other than they are different.
Are there any judges who are just adversarial towards you?
You'd have to ask them.
That you believe there are any?
No. I don't harbor such. I hope that if any of them were ever asked about, when I'm done
doing this, they would all say, you know, more positive things than negative.
How often is the trial about the actual case versus an excuse to target someone?
I mean, again, just in my view that everything is pretty gray out there.
They're not picking people off the street like a rendition and then coming
up with a crime.
But some combination of forces allows on the outskirts of criminal law, a lot of people
would come into the vacuum of it.
In certain circumstances and situations, make somebody a shinier target, then if they're
a little shinier, then the crime can be a little less bad and still cause them to get caught up in the vacuum.
And so I think some of these things are combinations
where it takes a bit of a perfect storm
to cause it to happen and a perfect unraveling
for it to unravel.
Do business competitors ever go after their competitors
who are extremely successful
just to try to take out the competition?
Every hour of every day, every minute of every day.
Yeah.
So...
That's not about the law.
That's about trying to get this guy,
finding a way to get this guy.
Listen, jealousy is one of these driving psychological motivations
that we probably don't talk about enough.
And just greed or whatever that is
to take out the competitor, of course.
That is, now the competitor who is doing the action
would say, but he's a bad actor.
And the answer then could be,
well maybe from your lens he's a bad actor,
but you want him to be a bad actor.
Tell me about the positions.
I don't like them as much
because I don't want to show my hand,
but obviously as I'm pouring through the history of the case
and the history of the people, I read every word.
But I almost wish that the deposition
is not a good deposition
because then they won't know what's coming.
They knew perfectly what was coming
and you can sit in a room with a bunch of lawyers and suits on
and try to pivot around it, right?
But that can work out too,
because then they pivot themselves right back into a wall.
Tell me about law school.
Feels like a very long time ago.
Good experience, loved it?
Yeah, I did love it.
You know, I was always curious
and I sort of showed up there a little out of the blue in my own mind.
I didn't intend to go to law school
and it kinda happened quick.
You just go take a test and you're there,
you're thinking, wow, I'm here.
But it wasn't natural for me to go be a entry level person
on Wall Street or whatever I could have done
in an alternative world.
How did you pick law school
if that was not the track you were on?
People suggested it.
People suggested it.
I loved a few good men and my cousin Vinnie, right?
I was gonna ask you about your favorite courtroom movies.
Well, there has been very, I mean, no offense to those
who have made them or been in them in the last 20 years,
but I actually think that they very much trailed off
or I understood how it all worked.
But a few good men in my cousin Vinnie, I think, and so I think that they predisposed
me.
And I was always a little bit of a justice seeker, underdog, or you know, injustice perceiver.
And so the combination of those tendencies, you know, I was working in a hospital at the
time and they were like, I mean, you're no scientist and you're very impatient.
You're really gonna go seven years ago to medical school, right?
And again, the entry-level job isn't because I'm too proud to do an entry-level job.
Those are some of the most important jobs at the hospital for sure and in many fields.
It's just impatience probably.
I don't know that that would have been the perfect role for me, frankly.
So I mean, it's easy to say now, but if you go from law school to 24, 25, and you're a prosecutor, when you're a prosecutor, sure, you've bosses,
but you're very much in charge of your own cases. It is extreme autonomy, extreme. You're
always then pushing the curve of what you're doing from the beginning. And if that excites
you and the more important, but some could say mundane roles of an entry-level
person in any profession would not have excited you, it allows you to push the gas further.
Do you think law school now is the same as it was when you went?
I really have no idea.
At the time, it was very Socratic, at least Harvard was.
And so I liked that.
I liked the debating.
I enjoyed that. I liked the debating. I enjoyed class. I enjoyed, you know, super smart
fellow students and professors, you know, batting around and thinking through ideas. And,
you know, I liked it and it was fun. I mean, we were all together living in the dorm room and
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How do you think doing this job has changed you as a person?
That's a complicated question.
The parts of the sort of justice seeking,
the time in the courtroom have made me evolve and deeper
and given me something important to do
and principled to do that I'm happy that I am doing,
I think is important, I think is somewhat unique,
maybe fully unique. And that's given me purpose,
and purpose is one of the most important things.
And I've been thinking about this a lot,
because you get older, and so it causes you
to reflect a little bit, and I just think
there's a cost to everything.
There's just a cost to everything.
Time, really?
It's time, it's stress, it's battle scars,
it's you know, if you wanna fly high,
your wings will constantly be shot at
or singed or whatever and you're less on the ground
smelling the roses if you're always up there
in the mountains and I think there's been a cost
to that with me and for me.
How would you say the stress affects you?
You know, it doesn't, as I described walking into a courtroom, it doesn't affect me in
the spirit of the moment.
I just think that it is, it just can wear you down over time.
Yeah.
And it sounds corny, but I don't know that it's corny.
It's just, I don't like separate my problems from their problems.
I'm not going to say that I am quite at the level of trying to find a way to solve something
as the person whose life or business is on the line, but it is too close for comfort.
And so I have basically been through, right, if you watch somebody on trial, I actually
tried a case of a very close friend and I got to watch him and his extended family,
his grandmother and everybody come to court every single day. And I watched for six weeks as they got older,
the way a president would.
And if I am that tied to their fate,
physically, psychologically, I mean, even just,
I am waiting in the waiting room as if it was
my family member.
I understand.
And I would say one trial changes somebody's DNA
and complexion forever, and I've had 100.
And so, yeah, I just think it's scar tissue.
Does the story change in the courtroom?
You mean from what I expected to be going in?
Yeah, you go in with a Lot I mean
You know, we don't go from the the halls of the hospital the outer space
But when something turns differently or witness appears differently, I mean I will
Have a plan to go after witness and watch them appear and appear differently
Or watch the other side, you know
I don't know what they're planning watch the other side pull or change a door or whatever and being able to Or watch the other side, you know, I don't know what they're planning. Watch the other side pull or change a door or whatever.
And being able to adjust on the fly
is one of the most important.
Can you give me an example of an extreme unexpected
something that happened on the stand
that led you to change direction?
Well, I mean, I remember one trial was a corporate dispute
where they intentionally called the first witness who was a 70-year-old female,
small in personality, small in frame,
who was just there, who was the,
they called first intentionally
so that I would skip over them.
So they would get their story out
without having to deal with me for the first date.
Okay.
Very interesting. But they coached the witness too much,
and I picked up on patterns an hour in.
So what would have been, in this particular case,
what they expected to be a 30-minute cross-examination,
which I would have frankly expected to be a 30-minute,
went on for three days,
to the point that by the end of the second day,
a trial that we should have never been able
to even have a chance of winning was already won.
Because the amount of coaching and it just unraveled.
They were vulnerable to that very cross because they were never prepared for that cross and
because they were such a nice person, they were able to feed information through them.
And so it just kind of exploded on them.
Because the person was overly scripted.
When you went off script, they didn't know what to do.
Not only did they not know what to do,
they were readily available to me to tell the jury
that they had been told exactly what to say.
That none of it was true,
but that they were putting their finger on the scale.
Basically, and then by the time that was done,
you start looking over at the table of lawyers that put this witness
up to this
Case was over you start with an opening statement. Yep
How scripted is it?
Is it an outline or a script?
It's closer to a script than an outline
Because an outline suggests like I'm trying to hit these eight points and be done.
And it's a very short script
because the jury can't follow too much, okay?
And I don't want to show too much.
Is the shorter the better, would you say?
All things equal.
Yeah.
Do you memorize it?
If I didn't have my notebook, it's memorized,
but I'm glancing down.
Okay.
It's not full memorized.
It's memorized to the extent that I could do it without notes, but it wouldn't come
out the same way.
Is there ever improvisation added?
Definitely.
In the opening, there hasn't been that much action.
Splashes here and there.
And I'm also, if I'm playing defense in this, I'm hearing a few new things as they give
their opening. So there'll be splashes, tweaks, read the room kind of stuff.
It's not a wholesale kind of change. Unlikely to wholesale change at that time.
And closing statements.
I think about that as soon as I figure out what happened.
Really? From the beginning?
And work backwards.
Before the trial?
Way before the trial and way before the opening.
Wow.
Everything else is a pawn leading towards the summation.
That's really interesting.
Yeah, so I'm thinking this is how it's gonna end
because this is what really happened.
Yes.
How do I get myself there?
Yeah, yeah.
That's the first thing I'm thinking about
once I figure out what happened.
Did they teach that in law school?
No.
Tell me about the element of surprise.
The greatest gift against a competitor.
What are your thoughts on free speech?
I'm a proponent of it.
It means different things to different people.
But the founders of the United States made it the very first part of the Constitution
because it was so important to them.
And as you watch society evolve and even think about all the things that we once thought
were true that then debate taught us were not true, I think it's very dangerous for
governments to begin to police it because where does that end and how does that work?
And it becomes untenable.
And so it's a bit cliched to say I'm a believer in free speech, but I think
this is a topic unto itself, something I'm going to write about at some point because,
you know, misinformation, my views on what happened on college campuses.
I have a lot of views on a lot of these topics that I would like to, like a trial lawyer,
lay out and people can hopefully think about them differently
and maybe think about them in a better way.
I would love to read that book.
I'll send it to you.
Great.
Please.
Tell me about criminal justice reform.
It's never been successful anywhere.
You know, since the dawn of time and you can go back, you know, forget hundreds of years, thousands
of years, every society pretty much has a minority population that has been incarcerated
at a larger extent.
And if that's the case, you've got to ask yourself, isn't the society using the weapon
of the justice system in a negative way?
Next thing you have to realize is that the law works backwards.
So you don't get to go, okay, what do we want the law to be? The law is an imprint, like a geological imprint of what happened before.
So a case comes down and says XYZ. The next case can't say something too different.
It has to say, well, we're interpreting XYZ to be XYZQ.
And so it can't evolve that quickly. It has to say, well, we're interpreting XYZ to be XYZQ.
And so it can't evolve that quickly.
And because so much of the population has been incarcerated or disenfranchised, the
people that are in charge of the legislature, the judiciary, the people on the mountaintop
are not from the population being as most harmed.
So they're not as likely to be speaking to that constituency.
They may want to emotively,
they may see what I'm describing,
but it can't possibly, you know,
I say I can get almost so close to the person
who's gonna be incarcerated as their own mother,
but I can't get as close.
I'm not their mother.
And so, you know, unless the legislature
and the judiciary all had someone who had gone through the system
falsely accused, how can they ever get
to that same point of reflection?
Yeah.
And so, you know, there have been things done
around the edges, but it's still historically based.
And so if you want to use America as an example
and the original sin of the Constitution
and the incarceration of black and brown people
in the country, even if we change the laws, a lot of these folks, their great-great-great-grandparents
were slaves.
And their great-great-grandparents finally got the chance to even go to a school.
And their great-grandparents got to go to a school that looked at least a little bit
like the schools I got to go to. And so that obviously ebbs through the entire lineage and affects everything.
Their dads may not have been around.
Their moms may have had to work two jobs.
They weren't buying extra flashcards.
And so the kid has a harder time getting a job.
He's going to be more likely to steal a loaf of bread. And so what to say other than it's a messed up world
and until unless you gave somebody
the same opportunity at the start,
you could never even it out.
And I'm not a socialist, that is the truth.
And so okay, so then what do you do about that?
I mean, we have made some reforms.
Bail reform was something that I fought for.
Very very large prison sentences other than in the worst crimes don't make a lot of sense.
People are different at 30 than they are at 13.
In most societies, you don't have 40, 50, 60 year sentences for drugs or childhood burglaries
and things like this.
If a kid is picked up in the suburbs in some state in the United States, they get a ticket
and they go home.
They call that a burglary in other parts of the country.
And depending on the color of your skin, you go away for 10 years.
So another long and complicated topic that has gone on for hundreds and thousands of
years.
How is the system different in different parts of the world?
Do you know?
I mean, I know I'm not an expert per se.
In some ways, they're similar.
In some ways, not every country has jury trials.
Most westernized or civilized societies have shorter jail sentences.
The United States incarcerates a higher proportion of people basically by any metric than any
country in the history of the universe.
And then there are parts that are the same.
The facts are the facts.
The laws, frankly, tend to be somewhat uniform, right?
You're not allowed to do things to other people
you wouldn't want them to do to you.
And again, they're similar from the way I started,
which is that we often pick on the minority, right?
And we pick on the person that can't defend themselves.
So when you
say that even watching at some level the cases I've handled or whatnot, the system doesn't
seem fair, imagine the person that doesn't even have a legal team effectively. So it's
a complicated, messed up part of our world and a sad part of our world.
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Tell me about the first time you met Elon.
First meeting.
I was told he had considered calling me into a meeting on a couple of cases that they had,
that he had been told that there was a kid in New York that liked to try cases and was
okay at it.
And I would hear, oh, he was going to call me in and then he didn't, or who the hell
knows what happens.
And eventually he called me to San Francisco.
I went, checked into my hotel, went to Tesla factory, kept me waiting for nine hours or
some ridiculous amount of time.
It was not four hours, I'll tell you that much.
And eventually he came out and he sort of said, I have got to go to LA, just get in
the car basically.
And we flew from San Francisco to LA.
And the punchline of the story, I guess, is not that he kept me waiting for so long, or
that I was such a kid, but that my stuff was in the San Francisco hotel room.
So that's what happened.
And what did you make of the meeting?
Was it interesting?
It's very interesting.
Yeah.
I find meeting pretty much all people that are very unique interesting.
And there are only so many people that are effectively one of one. And if you
have a chance to meet those people, like them, love them, I know people are polarizing, especially
when they're one of one. But whether it's listening to Paul Simon in a concert or it's
watching somebody that you say to yourself, is there ever going to be another? And that
makes it interesting in its own right.
Does every case come down to a simple principle
everyone can understand?
I think so, but in order to pull off the ultimate ability
to see that, you have to get a lot of other things
done along the way to get to that point of clarity
It's a lot of work
Yeah
And it could be two or three points of clarity that you need to layer upon oneself to reach the ultimate conclusion
Not every accident is a horrific criminal accident
not every bad person did something bad in that moment and
criminal accident, not every bad person did something bad in that moment. And the truth ultimately is X.
But if you don't get past one and two, the blinders and the fog is so great, no one can
ever see the third point.
That's interesting, the idea that this guy's maybe done bad things in their lives, but
he didn't do this.
That's a lot of the people I've represented
go into a trial very unpopular.
Wild.
Is the law static or does it change?
It changes, but it moves slow.
It's glacial.
It relies upon what happened yesterday,
and very rarely are there pronouncements
that change it in wholesale ways.
If a case is controversial,
is it negative to you or it doesn't matter?
That is a question that people would have
differing views on.
For you?
Well, it doesn't become negative for me,
meaning if I didn't feel principled
and comfortable doing what I was doing,
I wouldn't do it.
But boy is it complicated,
because if everybody goes in thinking,
wow, what a horrible thing.
And if the person's even accused of that, they're a horrible person.
And what kind of monster would be their lawyer?
You know, you're talking in terms of a complicated deck to start things with.
But I like to think that because I believe that I've had a principled career,
if I do take on a case that is extra controversial,
I'm hoping that the reasonable person at least,
the sophisticated reasonable person sees it and says,
there's a reason he's taking this on.
He sees something in this case that makes him think
that he has to get this truth out
or he has to fight against whatever's wrong with the system.
And if as long as I have a breath,
I just need a little bit of space to operate.
But listen, a lot of these cases can start
between the anxious judiciary,
the opponent who has unlimited resources
and has spent six months working up to the moment
of trying to kill you and the client,
complicated clients, complicated subject matter.
You can start, you know, six touchdowns behind
and the first, you know, two quarters of the game,
you know, wear your pads and you wouldn't want to watch it live.
Wow. Has a client ever let you down?
Not unforgivably. You know, I try to get them to listen,
you try to get them to not repeat mistakes,
try to get them to do the right thing. But you know, some have tried to put me in positions
I wasn't comfortable in.
Yeah.
I mean, and I'm not let down because I didn't do it.
And I don't sit in judgment of people like that.
Meaning I see them for what they are,
which is complicated and flawed,
and they made a mistake in that moment,
and they shouldn't have done that.
But I'm not stewing or unforgiving of any of them.
Have you ever let a client down?
You'd have to ask that.
I mean, I'm taking very few cases.
I have been for quite some time taking
a very small percentage of cases that one could take
if you had unlimited time.
So 25 people call in a three day period,
which is not an unusual situation.
And I'm talking real substantive,
person knows one person in common with me.
I take one out of 25, 24.
And then there's other people who,
they may not see it the way I see it,
but wanted to push an envelope in a way
or present in a way that I just don't have enough time.
I don't have enough will, I don't have enough will.
I don't have enough fight in me
to take on every fight on the earth.
Would you ever recommend something specific
based on something you see that you don't wanna do
but you feel like this other guy
would be the right person to do this?
Yeah, I refer, yeah, I send cases all the time to people.
Right?
The way I go at these situations is so intense
that you can't do it.
It's like some glow that every time I use it it burns off
Yeah, it's limited resources. There's only so much time. It's only so much time, but it's also like I don't know how
That zone that I'm talking about. I
Don't know how many times I can get here is not unlimited. I understand. What is a plea deal?
It's a negotiated less than what they were going to get if they lost a trial,
and worse than they would get if this situation ever came about.
So, you know, you were going to get five months after trial, you can have one month.
It's a risk-adjusted bargain.
How did it come about?
I mean, in some levels, it's natural to bargain in this way.
In some ways, it creates the wrong incentives on the system
because the truth will come out at a trough,
the truth doesn't come out in a plea agreement.
So if there's too many cases on the docket,
they start playing them out and playing them out.
And a lawyer who has too many cases
or not enough inclination to fight
is gonna tell their client to take a lot of pleas.
And that then becomes complicated
because sometimes clients should take deals.
But it's hard to hear that.
It's hard to hear that because it's hard to admit
to wrongdoing in the first place.
It's hard to hear that because you know
that we live in a system where if you take a deal,
that other person has more time back
because they don't have to have the trial.
So it's a necessary part of the system,
but it has become too ever-present
and if it monopolizes the system,
it's not a real justice system, it's a system of please.
Do you have any opinions on high-profile trials
that you weren't part of?
Johnny Depp, Amber Heard, Sam Bankman Fried,
Elizabeth Holmes, Harvey Weinstein, O.J.
What's it like watching a public trial,
knowing what you know?
Well, I mean, I try to not have opinions
on the ultimate reality of what happened
because I don't know enough.
And I'm trying to tell everybody my entire life,
in fact, it's the one time somebody will hear me pipe up
a little bit at a dinner party about anything substantive
is when I wanna remind everybody,
you don't know what happened.
Don't jump to conclusions.
So since that's the one time you see me pipe up,
I don't really wanna be in the position
where I'm sitting around going,
you know what, that person was guilty, that person was not.
Not to be an arrogant prick,
but it's usually pretty painful to watch
other than F. Lee Bailey.
And the only one of those cases you're talking about
that I actually saw any part of,
of any substance was OJ, and that was 20 years before,
you know, I was a full grown lawyer.
So, I don't have, you know, much in the way
of opinions on them.
Tell me about Tiger King.
I don't know if you know Eric Good.
Do you know Eric?
I do.
Yeah. I just remember when he was an animal lover first.
Yeah.
And you know, he had the turtle ball
and he would talk about animals.
And so he went at this with a different lens,
but I was this prosecutor
who had prosecuted murder cases that he knew.
And so, you know, I might ask him questions
about turtle conservancies
that I don't know anything about.
He would ask me questions about the criminal justice system.
So eventually they and Netflix asked me
would I look into it and the family wanted me
to look into it and so they reached out to me
and I reinvestigated and put it together my way.
I'm not gonna remember every detail.
I do remember though one of the first things that I did
was there was one anecdote or part
of it which was that she was outside, she meaning Carol Baskin, in the middle of the
night, the night he went missing, effectively.
This is as I recall the allegation.
It occurred to me that that's interesting because there was no debate about it.
What are the facts that I know for sure?
She was out in the middle of the night,
the night that he went missing.
And so I said, I just remember specifically,
this was the first instinct I had,
was I called somebody that knew her
for a decade plus and sort of said,
is this the kind of person who went out past midnight?
And the response was never, ever, ever.
And you know, make of that what you will.
Yeah.
You work with mental illness before becoming a lawyer.
How thin-
I work with mental illness as well, I am a lawyer.
How thin is the line between what we label normal
and what we label mentally ill?
There is no line.
There is no line. There is no life.
We're all psychological beings.
We are all very complicated.
Some of the most successful people that you know
are the most tortured.
Some of the most stable looking are the most unstable.
I think the DSM would say that the way that you can figure
out if somebody's personality issues or a disorder or not
is whether it has a profound impact on their everyday life.
Does everybody that work with them quit?
Does everybody that spends a night alone with them leave?
Are they unable to function?
Can they not hold down a job?
Unable to function would be the disorder of the DSM.
But ultimately, it's far, far more complicated than that
and people's psychology is a continuum
far more
Profound that goes up and down far more than a person's growth and height and weight and physical traits far more complicated
Describe the home you grew up in I
Grew up in a
Small house in a suburb of Boston on a cul-de-sac.
Brothers and sisters?
Yeah, three siblings.
Old or younger?
All younger.
You know, at one point we shared rooms, then, you know, we kind of made me as I got it,
became a teenager, my own little, you know, small room. And you know, we ran around riding bikes
and playing with football and causing trouble.
Do you guys still get along?
Yeah, we're very close.
Great.
What do you believe now that you didn't believe
when you were young?
Depends what young means,
but I remember thinking the world wasn't a just place when
I was 16, right?
And thinking and believing in second chances and thinking people had to fight for other
people and everybody deserved a shot.
So a lot of that core stuff that I think led to, you know, this chapter of my career has
been very constant throughout. I was more achievement-oriented when I was
a younger adult than I am now.
At some level, I just don't give a shit.
At some level, I realized there's a cost.
That is definitely a change because I don't look at things,
and it's a recent change, has a scoreboard.
Yeah. You still want to win though.
You're damn right. I do.
Yeah.
Was there something that happened at 16 that allowed that revelation of
fighting for the underdog, let's say.
I don't know that there was one revelation.
I grew up in a liberal home.
I grew up in a home with a single mom at that point.
I myself would cause trouble and think it's no big deal.
Yeah.
You know.
Kids, you were a kid.
That, well, sure, easy for you and I to say,
not everybody looks at it that way.
Yeah.
I remember my mom taking me to the hospital
where she worked.
I remember seeing kids
with every possible disadvantage you could say.
I remember thinking that it wasn't really fair
the way that so-and-so got X, Y, and Z,
this person got nothing.
And how could you ever expect that person
to end up in the same place?
And I just felt that you got to even out
the score a little bit.
And-
That sounds like the answer. The fact that your mom worked with you did,
and you got to have that experience played a big role.
It definitely played a big role.
It's hard to know, right,
which of these things was like an imprint then, right?
And my own, like, listen,
I wish people would stand up for me more, right?
And so as I'm growing up
and nobody wants to stand up for me, I And so as I'm growing up and nobody wants to stand up
for me, I'm harboring some of that inside going,
if somebody ever tried to do that to somebody,
I'm watching over good luck.
I still always remark when I'm alone,
how much harder I fight for other people
than any of these people would ever fight for.
Maybe that sounds like a pity party.
I just.
No, it's just your nature.
It's just my nature.
It's just my nature where other people will be like,
well, we'll put up a little resistance,
but they come and take him.
It was fall and won't last it.
Would you say you have good days and bad days
or you're pretty even keeled?
Good days and bad days.
How does that impact things or does it?
Good days and bad days. How does that impact things or does it?
It's also a question of when and in continuums
in terms of when that question is being reflected.
I've definitely gone through periods where
the intensity of what I do has weighed on me.
The loneliness of what I do has weighed on me
to the degree that one you know, one day people
will think I was good at this, creating loneliness at the top weighs on me. And, you know, whatever
little bit of success I have now, you know, too many people asking for too many things
weighs on you. It creates loneliness. And so, yeah, I mean, that stuff,
but you pop back out of it,
and you pop back out of it quickly,
and you just remember,
I mean, and I think this is something
that comes from age.
There's a Kipling poem,
if, that nothing is as good or as bad
as it may seem in the moment,
and boy is that true about life, right?
That what is the point of sweating the small stuff? Mm-hmm.
And so yeah, you remind yourself of those things,
you find your purpose, resettle yourself,
realize that the whole fucking thing is probably stupid,
and you pop back up and you go fight.
You mentioned F. Lee Bailey earlier.
What was it about him that was impressive?
There's only a couple of lawyers that I've seen
that had the ability to really trap a witness
on cross-examination, right?
I mean, I don't want to say that anybody,
but a good trial lawyer, which is like nothing,
nothing to write home about, can take a witness
and look at an index card and say,
well, you were 18 feet away and the lighting wasn't good.
And there was something obstructing your view.
Or, you know, my cousin Vinnie cross-examination
about that, right?
You know, what's that on the window?
Is that silt?
You know, whatever that.
I love that movie.
Yeah, I haven't seen it in a long time.
That's not sort of higher level trial work.
And I thought at least a couple of things
that I saw Bailey do were at another
point of complexity. And also like, listen, being a trial lawyer, you have to have a personality.
He had a personality. I hear good, bad, and ugly, but he had a personality of me. So it
makes it makes a little bit more interesting.
Yeah. What do you think about most outside of work?
What I'm going to do next?
Meaning work wise or in general? I think it's a little bit of work. What I'm going to do next? Meaning work-wise or in general?
I think it's a little bit of both.
Are all cases different or are there common themes or archetypes that you've come to
realize over time that they fit in certain categories?
All cases are definitely different, but all cases have some of the same threads, which
is it's always about people,
people doing things that upset other people, people fallible, people suffering from their own psychologies and their own mistakes. Tetragrammaton is a website. Tetragrammaton is a website.
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