Welcome to the Deep Dive. Today we're looking
at Ezra Edelman. He's a... Documentary director,
but maybe more accurately, a master curator of
American complexity. That's a good way to put
it. Yeah. His real gift seems to be taking these
huge, messy, kind of overwhelming stories, you
know, high stakes trials, decades of music history
and shaping them into something you can actually
grasp, something essential. And deeply layered.
That's key. Exactly. Edelman's work really embodies
what we try to do here. This idea of a deep dive.
Yeah. He's the person you bring in when. Well,
the story just doesn't fit a standard movie length.
Right. When it needs, say, eight hours. Precisely.
Eight hours to unpack decades of context. His
skill is taking just massive amounts of source
material and distilling it, making it digestible,
but still powerful. And that's really our mission
for you, the listener, too. Absolutely. He's
a specialist in scale. So today, yeah, we want
to unpack his path. We'll look at his foundations,
you know, the family background in law, civil
rights, these cultural intersections that really
set him up for this kind of work. And then, of
course, we have to talk about O .J. Made in America,
that defining Oscar -winning achievement. Can't
miss that one. Definitely not. And finally, we'll
spend some real time on, well, this fascinating
and pretty high -stakes saga of the Prince documentary,
The Book of Prince. The one that never came out.
The very one. Nine hours, five years of work,
a huge Netflix investment. And it might just
stay locked away forever. It really highlights
this clash between creative control and legacy
protection. OK, so the big takeaway for you right
at the top. Edelman isn't just filming things.
He's acting like a historian, maybe assistance
analyst. He just refuses to treat these big public
figures or events like they happen in a vacuum.
Instead, he uses them like like prisms to see
these bigger systemic issues. That's exactly
it. That perspective lists his work way beyond
simple reporting. It makes it foundational viewing.
So where do we start to understand that perspective,
the family? I think we have to. You need to understand
the world that shaped him. So Ezra Benjamin Edelman,
born in Boston, August 1974, and he inherits
this family story that's just deeply, deeply
woven into American civil rights history, legal
history. Okay. His mother, Marian Wright Edelman,
I mean, she's a giant in this field. A former
civil rights leader. She worked as an aide to
Martin Luther King Jr. Wow. Yeah. And, of course,
she founded and led the Children's Defense Fund.
And the CDF, it's not just a charity. It's a
major advocacy group focused on long -term systemic
change for kids using law. Right. It's about
changing the system, not just helping individuals
with it. Precisely. And you see that focus later
in his films, don't you? This concern with legal
advocacy, structural power, historical marginalization.
It makes sense. He literally grew up in an environment
where law and policy were seen as the tools for
change. And his father, Peter Edelman, mirrors
that commitment. He was an aide to Senator Robert
F. Kennedy. During a pretty critical time. A
very critical time. Later served as assistant
secretary of health and human services. And he's
a longtime law professor at Georgetown. So you've
got this pattern, high -level government, law,
civil rights engagement. But then there's the
personal context of his parents' marriage. The
sources mention this specifically. Yeah, and
it's really significant. They were the third
interracial couple to marry in Virginia after
the Loving v. Virginia Supreme Court decision.
The third. Wow. Think about that timing. Loving
v. Virginia. That's 1967. The landmark case striking
down bans on interracial marriage. It wasn't
just a legal thing. It was a huge social shift.
So his own family's existence is tied directly
to this massive civil rights legal victory. Exactly.
His life is inherently linked to these themes.
Legal battles, racial integration, how public
law impacts private lives. It's baked in from
the start. And that complexity, that sort of
dual identity, it goes beyond race, too, right?
Into his religious upbringing. It does. Another
liar of navigating different worlds. His father
is Jewish, and the sources note his paternal
great -grandfather was a Polish rabbi killed
in the Holocaust. Oh, wow. While on his mother's
side, his maternal grandfather was a Baptist
minister. So Edelman was raised in both traditions.
So from day one, he's navigating these different
historical legacies, different faiths, trying
to find common ground. You have to imagine that
fosters a certain kind of thinking. a comfort
with complexity, withholding multiple perspectives
at once. And then educationally, he gets the
tools for that kind of analysis. Sidwell Friends
School in D .C., then Yale for his bachelor's.
Right. Top tier education providing the intellectual
framework. So let's synthesize this. You've got
the dual heritage, the deep immersion in civil
rights and law through his family, this complex
background. How does that translate to directing?
Well, I think it means he doesn't just see O
.J. Simpson as a famous football player who got
arrested. He sees Simpson as... Maybe the result
of all these systemic forces, segregated L .A.,
failures in the justice system, the weird way
we monetize fame in America. His background gave
him that critical framework, that ability to
zoom out. The ability to see the system, not
just the individual. That's the direct result,
I think. He was trained in a way by his environment
to look for those structural narratives, the
policy angles, not just the personal drama. And
that understanding is what made the O .J. film
so much more than just retelling a famous trial.
OK, let's dive into that then. O .J. Made in
America. This is what put him on the map for
a lot of people, right? 2016. Absolutely. He'd
done strong work before, which we should cover.
But this was the breakthrough. Commissioned for
ESPN's 30 for 30. Which is already a prestigious
series. Very. But this project quickly became
something else entirely. It blew past the usual
boundaries of a sports stock. And the key was
the scale, wasn't it? Getting that eight hour
runtime. That was the crucial move. He convinced
them the story needed nearly eight hours. And
it wasn't just padding. It was essential to his
argument. Well, think about it. To understand
why OJ was convicted of domestic abuse by one
jury and then acquitted of murder by another
just years later. Yeah. You can't just start
in 1994 with the Bronco chase. You need the history.
You need the deep history. Right. The Watts riots.
Rodney King, the decades of toxicity between
the LAPD and the black community in L .A. Edelman
argued you needed all that context first. So
the structure itself makes the argument. Exactly.
That eight hour runtime was his brilliance. He
spends the first two hours basically teaching
you L .A. history, racial politics, celebrity
culture, justice system failures before you even
get close to the night of the murders. So context
isn't just background. It is the story. That's
his philosophy in action. The trial is the climax,
sure, but the history is the engine driving everything.
And that approach, that scale, it obviously paid
off, awards -wise. Oh, massively. One of the
biggest documentary award sweeps in years. It
validated that need for scope. He won the Academy
Award for Best Documentary Feature. Which is
huge, especially for something initially linked
to a sports network. Incredible. But it wasn't
just the Oscar. He basically swept the board.
The Primetime Emmy for directing nonfiction in
2017. The DGA Award. Critics' Choice Award for
Best Director in 2016. So the industry recognized
the achievement in direction and synthesis, not
just the topic. Right. And importantly, in his
Oscar speech, he didn't just thank people. He
used that moment. What did he do? He dedicated
the award specifically to Nicole Brown Simpson
and Ron Goldman, the victims. Ah. Bring you back
to the human cost. Yes. After years of the O
.J. story being about celebrity, race, the trial
as spectacle, Edelman in that moment refocused
it on the tragedy, the lives lost. A powerful
statement. So the film's impact goes way beyond
just true crime then. Way beyond. It showed how
the OJ story was this perfect storm of American
issues. Celebrity enabling someone to try to
become colorless. The LAPD's history making accountability
impossible. The resulting deep skepticism in
the black community that made that acquittal
verdict, while shocking to some, feel almost
inevitable to others. The film basically put
the whole country on trial in a way. That's a
good summary. It didn't just explain the events.
It explained the contest, why it had to unfold
that way in America at that time. That's why
it resonated, even with people who thought they
knew the story inside out and why it needs those
eight hours. He was documenting decades of social
history through one figure. OK, so. OJ is the
peak, but you mentioned he had a strong track
record before that. He built up to this. Definitely.
It wasn't out of nowhere. He honed this skill,
telling big, complex stories, often using sports
to talk about bigger things like law, justice,
society, mostly at HBO Sports. Right. So what
were some of those earlier key projects? Well,
there was Magic and Bird, A Courtship of Rivals,
great film. Explore that defining NBA rivalry
in the 80s. Huge rivalry. Changed the league.
Totally. But Edelman wasn't just interested in
the dunks and passes. He looked at how that rivalry
played out nationally. Often along racial lines,
geographic lines, how it mirrored a changing
America. Interesting. Using sports as a lens
again. Always. Then, maybe even more pointedly,
in 2011, he did The Curious Case of Kurt Flood.
Kurt Flood, the baseball player. Right. And this
is where you really see his background in law
and justice come through. Flood challenged baseball's
reserve clause. Okay, reserve clause. Remind
us what that was exactly. It sounds technical.
It was. But it was huge for labor rights. Basically,
it bound a player to one team forever, even after
their contract ended. The team owned the players'
rights, could trade them, sell them, whatever.
Sludd argued it was like modern -day slavery,
a total restriction on freedom. So Edelman's
film wasn't just a sports bio. Not at all. It
was about labor law, civil rights, corporate
power, all colliding in the world of baseball,
using a sports figure to spotlight a systemic
legal injustice. You see the direct line to O
.J. there, right? Right. Another story that became
about the justice system itself. Yeah, absolutely.
What else? He also did Brooklyn Dodgers, Ghosts
of Flatbush. Yeah. Want to name me for that one.
That's less about policy, more about cultural
memory, identity, what happens when a team leaves
a city. The loss felt by Brooklyn shows he understands
the emotional weight of institutions too. Capturing
that sense of place and history. Right. And he
stayed a 30 for 32. wrote and directed Requiem
for the Big East about that college basketball
conference. Another institutional story. Yeah.
What's consistent is his range biography, labor
law, institutional history, but always digging
into the underlying structures, the forces shaping
things. And that focus on structure, that led
him into producing series too, not just directing
features. Exactly. He produced Wyatt Cenac's
Problem Areas for HBO. Two seasons. That showed
him moving into more current, kind of satirical
social commentary, but in that longer, serialized
format. Comfortable with big, multi -part stories.
And more recently, is he still working across
different areas? Definitely. The range continues.
In 2024, he produced Stax. Soulsville, USA for
HBO. A deep dive into Stax Records. The legendary
soul label. Legendary. And again, notice the
theme. Stax was huge musically, but its story
involves integration, race in the music business,
financial collapse, legal issues. It's system
building and system failure through art. Makes
sense. Also in 2024, produced Vow of Silence.
The assassination of Annie Mae for Onyx Collective
and Hulu. About the indigenous activist, Anna
Maya Quash. Another tough subject. Very. Confirms
his commitment to using his platform for these
complex, often overlooked stories involving systemic
violence and justice for marginalized groups.
And there is talk of a Roberto Clemente biopic,
too. Yeah, that was reported back in 2018 in
development with writer Rowan Ricardo Phillips.
Clemente's life baseball, Latino identity, humanitarian
work. Tragedy feels like another perfect multi
-layered Edelman subject. So clearly he juggles
these huge ambitious projects that take years.
Which brings us to the big one that got away.
The Mount Everest he climbed only to find the
summit blocked. The Book of Prince. Nine hours.
Nine hours. Six parts. He spent five years developing
this documentary series on Prince. How did that
even start? Prince was notoriously private. It
started big. He was recruited back in 2019 by
Lisa Nishimura at Netflix. She was a major force
there, VP of indie film and docs. And the project
ended on this incredible promise. Access. Access
to what? Access to the vault. Prince's legendary,
almost mythical archive of unreleased music,
footage, writings, everything. Whoa. That's like
the Holy Grail for music documentarians. It really
is. And Netflix paid accordingly, reportedly,
tens of millions of dollars for that access.
Tens of millions just for the access. Just for
the access. And critically, the sources are clear.
Yeah. The deal they struck. with the bank managing
the estate at that time specifically guaranteed
Edelman and Netflix editorial control. Okay,
that's huge. They paid for the right to tell
the story their way. They paid for the right
to apply that same critical, nuanced, systemic
analysis Edelman used on O .J. to Prince's incredibly
complex life and career. The brilliance, the
contradictions, all of it. You thought they'd
protected that right. But this is where Edelman's
mastery of narrative runs smack into the realities
of Hollywood power shifts and... Intense legacy
protection. Things started to go wrong. What
happened? First, an internal blow at Netflix.
Lisa Nishimura, the executive who championed
the project, got laid off. Ah, the project loses
its internal protector. Exactly. That happens
all the time. A new regime comes in, sees this
super expensive, maybe sensitive project inherited
from the old guard. Suddenly it looks like a
liability, not an asset. Especially with a subject
as complex as Prince. Right. But the bigger problem,
the fatal blow, came from the estate side. The
management of the Prince estate changed. And
a key figure emerged, L. Lundell McMillan. A
former lawyer for Prince. Correct. And he became
very influential in the new estate setup. And
according to reports, McMillan led the charge
against the documentary, objecting strongly,
trying to block its release. Why? Was it the
quality? Doesn't seem like it was about craftsmanship.
The reporting suggests it was the content. Edelman,
being Edelman, likely presented a full, nuanced
picture, the good, the bad, the complicated.
The same way he did with OJ. Precisely. And that
clashed with what the estate seemingly wanted.
A more celebratory, maybe sanitized legacy piece.
Something commercially safe. So it's a classic
battle. Historical truth versus brand management.
Perfectly put. You've got millions spent, five
years of work, guaranteed editorial control.
all hitting a wall built by the estate's desire
to control Prince's image posthumously. Where
did that leave the project? By September 2024,
things looked grim. The New York Times Magazine
flat out reported there was no indication that
the film will ever come out. Just think about
that nine hours of synthesized knowledge. Unseen
archival stuff just locked away. And then came
the final nail in the coffin. Pretty much. February
2025, the estate makes it official. Edelman's
documentary will never be released. And, adding
insult to injury, they announced a new print
stock would be made, without Edelman. Presumably
one they have more control over. So Edelman's
five years, Netflix's millions. Just gone. Gone.
Nullified. It seems the threat of a lawsuit from
the estate challenging the content was enough
to kill it, regardless of any contract about
editorial control. So what does Edelman himself
say about all this? His take is, well, brutally
honest and kind of sad. In an interview around
March 2025, when asked why this epic nine -hour
film isn't being released, he reportedly just
said he doesn't feel like getting sued. Wow.
That says it all, doesn't it? It really does.
It's chilling. Even with Netflix money and a
contract guaranteeing control, the threat of
a long, expensive legal fight from a powerful
estate was enough to effectively shelve the whole
thing. The legal threat trumped the creative
freedom, and we, the public, lose out. Okay,
so we've traced his path, the foundation, the
OJ triumph, the diverse filmography, and now
this, this major roadblock with Prince. What's
the synthesis here? What does it all mean? Well,
if you connect the dots, you see him tackling
these huge narratives differently. With O .J.,
it was a public story, historical events. Charged,
yes, but ultimately open to his critical interpretation.
Yeah. He had the freedom to make his argument.
Right. With Prince, it was intensely private,
deeply personal, commercially sensitive for the
estate. The stakes felt different, more controlled
by the legacy holders. So his method requires
deep access and critical thinking. Always. But
the Prince story shows that access, even when
you pay millions and get it in writing, isn't
truly guaranteed if the resulting story doesn't
align with the estate's preferred narrative.
And that's relevant for us, for you, the listener,
Hal. Well, Edelman's whole process shows the
value of going deep. Yeah. The eight hours on
OJ, the five years trying with Prince. That level
of contextual exploration is what gives you real
understanding beyond headlines. But the Prince
outcome. is a warning sign. It's a huge warning
sign. It shows that even when you do everything
right, get the access, secure the funding, have
the creative vision, powerful legal forces driven
by legacy concerns can still shut it down. The
knowledge gets locked away. The whole effort
gets torpedoed. Completely. Yeah. It makes you
realize these deep dives aren't just costly in
time and money. They carry enormous legal risks
now. Risks that can lead to permanent loss of
cultural knowledge. Which brings us right to
our final thought for you to chew on. We know
the stories Edelman did tell, Kurt Flood's fight,
the Big East's history, the whole complex tapestry
of O .J. Simpson. But that print stock, five
years, the vault access, nine hours of insight
we might just never get. So the question it leaves
hanging is. How much vital cultural knowledge,
how much deep understanding are we losing when
creative freedom gets tangled up in legal battles
or estate disputes? Even when the doors were
supposedly open, the contracts signed. It's a
frustrating question. It really is. The loss
isn't just about money for Netflix or a setback
for Edelman. It feels like a permanent gap in
understanding one of the most fascinating, most
enigmatic artists of our time. It really sticks
with you, doesn't it? The cost of trying to tell
the deepest truth. It absolutely does. Shelving
that project. Despite everything. Yeah. It really
shows the tension between historical inquiry
and, well, legacy management. That's the frontier
right now. Sobering thought to end on. That's
it for this deep dive. We hope you feel informed,
maybe a little bit frustrated by the mystery
still locked in the vault. We'll see you next
time.