WEBVTT

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Welcome to the Deep Dive. Today we're looking

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at Ezra Edelman. He's a... Documentary director,

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but maybe more accurately, a master curator of

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American complexity. That's a good way to put

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it. Yeah. His real gift seems to be taking these

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huge, messy, kind of overwhelming stories, you

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know, high stakes trials, decades of music history

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and shaping them into something you can actually

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grasp, something essential. And deeply layered.

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That's key. Exactly. Edelman's work really embodies

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what we try to do here. This idea of a deep dive.

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Yeah. He's the person you bring in when. Well,

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the story just doesn't fit a standard movie length.

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Right. When it needs, say, eight hours. Precisely.

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Eight hours to unpack decades of context. His

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skill is taking just massive amounts of source

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material and distilling it, making it digestible,

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but still powerful. And that's really our mission

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for you, the listener, too. Absolutely. He's

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a specialist in scale. So today, yeah, we want

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to unpack his path. We'll look at his foundations,

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you know, the family background in law, civil

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rights, these cultural intersections that really

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set him up for this kind of work. And then, of

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course, we have to talk about O .J. Made in America,

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that defining Oscar -winning achievement. Can't

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miss that one. Definitely not. And finally, we'll

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spend some real time on, well, this fascinating

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and pretty high -stakes saga of the Prince documentary,

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The Book of Prince. The one that never came out.

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The very one. Nine hours, five years of work,

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a huge Netflix investment. And it might just

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stay locked away forever. It really highlights

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this clash between creative control and legacy

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protection. OK, so the big takeaway for you right

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at the top. Edelman isn't just filming things.

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He's acting like a historian, maybe assistance

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analyst. He just refuses to treat these big public

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figures or events like they happen in a vacuum.

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Instead, he uses them like like prisms to see

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these bigger systemic issues. That's exactly

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it. That perspective lists his work way beyond

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simple reporting. It makes it foundational viewing.

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So where do we start to understand that perspective,

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the family? I think we have to. You need to understand

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the world that shaped him. So Ezra Benjamin Edelman,

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born in Boston, August 1974, and he inherits

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this family story that's just deeply, deeply

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woven into American civil rights history, legal

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history. Okay. His mother, Marian Wright Edelman,

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I mean, she's a giant in this field. A former

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civil rights leader. She worked as an aide to

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Martin Luther King Jr. Wow. Yeah. And, of course,

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she founded and led the Children's Defense Fund.

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And the CDF, it's not just a charity. It's a

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major advocacy group focused on long -term systemic

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change for kids using law. Right. It's about

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changing the system, not just helping individuals

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with it. Precisely. And you see that focus later

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in his films, don't you? This concern with legal

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advocacy, structural power, historical marginalization.

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It makes sense. He literally grew up in an environment

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where law and policy were seen as the tools for

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change. And his father, Peter Edelman, mirrors

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that commitment. He was an aide to Senator Robert

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F. Kennedy. During a pretty critical time. A

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very critical time. Later served as assistant

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secretary of health and human services. And he's

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a longtime law professor at Georgetown. So you've

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got this pattern, high -level government, law,

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civil rights engagement. But then there's the

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personal context of his parents' marriage. The

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sources mention this specifically. Yeah, and

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it's really significant. They were the third

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interracial couple to marry in Virginia after

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the Loving v. Virginia Supreme Court decision.

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The third. Wow. Think about that timing. Loving

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v. Virginia. That's 1967. The landmark case striking

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down bans on interracial marriage. It wasn't

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just a legal thing. It was a huge social shift.

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So his own family's existence is tied directly

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to this massive civil rights legal victory. Exactly.

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His life is inherently linked to these themes.

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Legal battles, racial integration, how public

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law impacts private lives. It's baked in from

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the start. And that complexity, that sort of

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dual identity, it goes beyond race, too, right?

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Into his religious upbringing. It does. Another

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liar of navigating different worlds. His father

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is Jewish, and the sources note his paternal

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great -grandfather was a Polish rabbi killed

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in the Holocaust. Oh, wow. While on his mother's

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side, his maternal grandfather was a Baptist

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minister. So Edelman was raised in both traditions.

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So from day one, he's navigating these different

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historical legacies, different faiths, trying

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to find common ground. You have to imagine that

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fosters a certain kind of thinking. a comfort

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with complexity, withholding multiple perspectives

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at once. And then educationally, he gets the

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tools for that kind of analysis. Sidwell Friends

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School in D .C., then Yale for his bachelor's.

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Right. Top tier education providing the intellectual

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framework. So let's synthesize this. You've got

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the dual heritage, the deep immersion in civil

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rights and law through his family, this complex

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background. How does that translate to directing?

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Well, I think it means he doesn't just see O

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.J. Simpson as a famous football player who got

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arrested. He sees Simpson as... Maybe the result

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of all these systemic forces, segregated L .A.,

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failures in the justice system, the weird way

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we monetize fame in America. His background gave

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him that critical framework, that ability to

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zoom out. The ability to see the system, not

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just the individual. That's the direct result,

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I think. He was trained in a way by his environment

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to look for those structural narratives, the

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policy angles, not just the personal drama. And

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that understanding is what made the O .J. film

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so much more than just retelling a famous trial.

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OK, let's dive into that then. O .J. Made in

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America. This is what put him on the map for

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a lot of people, right? 2016. Absolutely. He'd

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done strong work before, which we should cover.

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But this was the breakthrough. Commissioned for

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ESPN's 30 for 30. Which is already a prestigious

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series. Very. But this project quickly became

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something else entirely. It blew past the usual

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boundaries of a sports stock. And the key was

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the scale, wasn't it? Getting that eight hour

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runtime. That was the crucial move. He convinced

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them the story needed nearly eight hours. And

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it wasn't just padding. It was essential to his

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argument. Well, think about it. To understand

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why OJ was convicted of domestic abuse by one

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jury and then acquitted of murder by another

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just years later. Yeah. You can't just start

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in 1994 with the Bronco chase. You need the history.

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You need the deep history. Right. The Watts riots.

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Rodney King, the decades of toxicity between

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the LAPD and the black community in L .A. Edelman

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argued you needed all that context first. So

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the structure itself makes the argument. Exactly.

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That eight hour runtime was his brilliance. He

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spends the first two hours basically teaching

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you L .A. history, racial politics, celebrity

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culture, justice system failures before you even

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get close to the night of the murders. So context

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isn't just background. It is the story. That's

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his philosophy in action. The trial is the climax,

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sure, but the history is the engine driving everything.

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And that approach, that scale, it obviously paid

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off, awards -wise. Oh, massively. One of the

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biggest documentary award sweeps in years. It

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validated that need for scope. He won the Academy

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Award for Best Documentary Feature. Which is

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huge, especially for something initially linked

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to a sports network. Incredible. But it wasn't

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just the Oscar. He basically swept the board.

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The Primetime Emmy for directing nonfiction in

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2017. The DGA Award. Critics' Choice Award for

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Best Director in 2016. So the industry recognized

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the achievement in direction and synthesis, not

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just the topic. Right. And importantly, in his

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Oscar speech, he didn't just thank people. He

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used that moment. What did he do? He dedicated

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the award specifically to Nicole Brown Simpson

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and Ron Goldman, the victims. Ah. Bring you back

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to the human cost. Yes. After years of the O

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.J. story being about celebrity, race, the trial

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as spectacle, Edelman in that moment refocused

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it on the tragedy, the lives lost. A powerful

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statement. So the film's impact goes way beyond

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just true crime then. Way beyond. It showed how

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the OJ story was this perfect storm of American

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issues. Celebrity enabling someone to try to

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become colorless. The LAPD's history making accountability

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impossible. The resulting deep skepticism in

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the black community that made that acquittal

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verdict, while shocking to some, feel almost

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inevitable to others. The film basically put

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the whole country on trial in a way. That's a

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good summary. It didn't just explain the events.

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It explained the contest, why it had to unfold

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that way in America at that time. That's why

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it resonated, even with people who thought they

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knew the story inside out and why it needs those

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eight hours. He was documenting decades of social

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history through one figure. OK, so. OJ is the

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peak, but you mentioned he had a strong track

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record before that. He built up to this. Definitely.

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It wasn't out of nowhere. He honed this skill,

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telling big, complex stories, often using sports

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to talk about bigger things like law, justice,

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society, mostly at HBO Sports. Right. So what

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were some of those earlier key projects? Well,

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there was Magic and Bird, A Courtship of Rivals,

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great film. Explore that defining NBA rivalry

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in the 80s. Huge rivalry. Changed the league.

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Totally. But Edelman wasn't just interested in

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the dunks and passes. He looked at how that rivalry

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played out nationally. Often along racial lines,

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geographic lines, how it mirrored a changing

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America. Interesting. Using sports as a lens

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again. Always. Then, maybe even more pointedly,

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in 2011, he did The Curious Case of Kurt Flood.

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Kurt Flood, the baseball player. Right. And this

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is where you really see his background in law

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and justice come through. Flood challenged baseball's

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reserve clause. Okay, reserve clause. Remind

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us what that was exactly. It sounds technical.

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It was. But it was huge for labor rights. Basically,

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it bound a player to one team forever, even after

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their contract ended. The team owned the players'

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rights, could trade them, sell them, whatever.

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Sludd argued it was like modern -day slavery,

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a total restriction on freedom. So Edelman's

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film wasn't just a sports bio. Not at all. It

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was about labor law, civil rights, corporate

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power, all colliding in the world of baseball,

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using a sports figure to spotlight a systemic

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legal injustice. You see the direct line to O

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.J. there, right? Right. Another story that became

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about the justice system itself. Yeah, absolutely.

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What else? He also did Brooklyn Dodgers, Ghosts

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of Flatbush. Yeah. Want to name me for that one.

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That's less about policy, more about cultural

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memory, identity, what happens when a team leaves

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a city. The loss felt by Brooklyn shows he understands

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the emotional weight of institutions too. Capturing

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that sense of place and history. Right. And he

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stayed a 30 for 32. wrote and directed Requiem

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for the Big East about that college basketball

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conference. Another institutional story. Yeah.

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What's consistent is his range biography, labor

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law, institutional history, but always digging

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into the underlying structures, the forces shaping

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things. And that focus on structure, that led

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him into producing series too, not just directing

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features. Exactly. He produced Wyatt Cenac's

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Problem Areas for HBO. Two seasons. That showed

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him moving into more current, kind of satirical

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social commentary, but in that longer, serialized

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format. Comfortable with big, multi -part stories.

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And more recently, is he still working across

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different areas? Definitely. The range continues.

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In 2024, he produced Stax. Soulsville, USA for

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HBO. A deep dive into Stax Records. The legendary

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soul label. Legendary. And again, notice the

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theme. Stax was huge musically, but its story

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involves integration, race in the music business,

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financial collapse, legal issues. It's system

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building and system failure through art. Makes

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sense. Also in 2024, produced Vow of Silence.

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The assassination of Annie Mae for Onyx Collective

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and Hulu. About the indigenous activist, Anna

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Maya Quash. Another tough subject. Very. Confirms

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his commitment to using his platform for these

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complex, often overlooked stories involving systemic

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violence and justice for marginalized groups.

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And there is talk of a Roberto Clemente biopic,

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too. Yeah, that was reported back in 2018 in

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development with writer Rowan Ricardo Phillips.

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Clemente's life baseball, Latino identity, humanitarian

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work. Tragedy feels like another perfect multi

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-layered Edelman subject. So clearly he juggles

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these huge ambitious projects that take years.

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Which brings us to the big one that got away.

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The Mount Everest he climbed only to find the

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summit blocked. The Book of Prince. Nine hours.

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Nine hours. Six parts. He spent five years developing

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this documentary series on Prince. How did that

00:12:24.470 --> 00:12:26.830
even start? Prince was notoriously private. It

00:12:26.830 --> 00:12:29.409
started big. He was recruited back in 2019 by

00:12:29.409 --> 00:12:32.009
Lisa Nishimura at Netflix. She was a major force

00:12:32.009 --> 00:12:34.789
there, VP of indie film and docs. And the project

00:12:34.789 --> 00:12:37.830
ended on this incredible promise. Access. Access

00:12:37.830 --> 00:12:41.210
to what? Access to the vault. Prince's legendary,

00:12:41.509 --> 00:12:44.490
almost mythical archive of unreleased music,

00:12:44.789 --> 00:12:48.929
footage, writings, everything. Whoa. That's like

00:12:48.929 --> 00:12:51.169
the Holy Grail for music documentarians. It really

00:12:51.169 --> 00:12:53.529
is. And Netflix paid accordingly, reportedly,

00:12:53.769 --> 00:12:56.070
tens of millions of dollars for that access.

00:12:56.269 --> 00:12:58.570
Tens of millions just for the access. Just for

00:12:58.570 --> 00:13:01.509
the access. And critically, the sources are clear.

00:13:01.649 --> 00:13:04.740
Yeah. The deal they struck. with the bank managing

00:13:04.740 --> 00:13:06.960
the estate at that time specifically guaranteed

00:13:06.960 --> 00:13:09.720
Edelman and Netflix editorial control. Okay,

00:13:09.740 --> 00:13:12.019
that's huge. They paid for the right to tell

00:13:12.019 --> 00:13:13.779
the story their way. They paid for the right

00:13:13.779 --> 00:13:17.059
to apply that same critical, nuanced, systemic

00:13:17.059 --> 00:13:20.100
analysis Edelman used on O .J. to Prince's incredibly

00:13:20.100 --> 00:13:22.840
complex life and career. The brilliance, the

00:13:22.840 --> 00:13:24.559
contradictions, all of it. You thought they'd

00:13:24.559 --> 00:13:26.980
protected that right. But this is where Edelman's

00:13:26.980 --> 00:13:29.320
mastery of narrative runs smack into the realities

00:13:29.320 --> 00:13:33.129
of Hollywood power shifts and... Intense legacy

00:13:33.129 --> 00:13:34.830
protection. Things started to go wrong. What

00:13:34.830 --> 00:13:37.169
happened? First, an internal blow at Netflix.

00:13:37.450 --> 00:13:39.389
Lisa Nishimura, the executive who championed

00:13:39.389 --> 00:13:42.250
the project, got laid off. Ah, the project loses

00:13:42.250 --> 00:13:45.009
its internal protector. Exactly. That happens

00:13:45.009 --> 00:13:47.929
all the time. A new regime comes in, sees this

00:13:47.929 --> 00:13:51.269
super expensive, maybe sensitive project inherited

00:13:51.269 --> 00:13:53.889
from the old guard. Suddenly it looks like a

00:13:53.889 --> 00:13:56.549
liability, not an asset. Especially with a subject

00:13:56.549 --> 00:13:59.720
as complex as Prince. Right. But the bigger problem,

00:13:59.860 --> 00:14:02.980
the fatal blow, came from the estate side. The

00:14:02.980 --> 00:14:05.620
management of the Prince estate changed. And

00:14:05.620 --> 00:14:08.659
a key figure emerged, L. Lundell McMillan. A

00:14:08.659 --> 00:14:11.299
former lawyer for Prince. Correct. And he became

00:14:11.299 --> 00:14:14.000
very influential in the new estate setup. And

00:14:14.000 --> 00:14:16.320
according to reports, McMillan led the charge

00:14:16.320 --> 00:14:18.620
against the documentary, objecting strongly,

00:14:18.799 --> 00:14:21.019
trying to block its release. Why? Was it the

00:14:21.019 --> 00:14:23.659
quality? Doesn't seem like it was about craftsmanship.

00:14:23.799 --> 00:14:26.490
The reporting suggests it was the content. Edelman,

00:14:26.549 --> 00:14:29.190
being Edelman, likely presented a full, nuanced

00:14:29.190 --> 00:14:31.029
picture, the good, the bad, the complicated.

00:14:31.289 --> 00:14:34.029
The same way he did with OJ. Precisely. And that

00:14:34.029 --> 00:14:36.090
clashed with what the estate seemingly wanted.

00:14:36.730 --> 00:14:40.389
A more celebratory, maybe sanitized legacy piece.

00:14:40.549 --> 00:14:42.769
Something commercially safe. So it's a classic

00:14:42.769 --> 00:14:45.529
battle. Historical truth versus brand management.

00:14:45.970 --> 00:14:48.570
Perfectly put. You've got millions spent, five

00:14:48.570 --> 00:14:51.070
years of work, guaranteed editorial control.

00:14:52.049 --> 00:14:54.809
all hitting a wall built by the estate's desire

00:14:54.809 --> 00:14:57.409
to control Prince's image posthumously. Where

00:14:57.409 --> 00:14:59.970
did that leave the project? By September 2024,

00:15:00.429 --> 00:15:02.529
things looked grim. The New York Times Magazine

00:15:02.529 --> 00:15:05.389
flat out reported there was no indication that

00:15:05.389 --> 00:15:07.450
the film will ever come out. Just think about

00:15:07.450 --> 00:15:10.190
that nine hours of synthesized knowledge. Unseen

00:15:10.190 --> 00:15:13.889
archival stuff just locked away. And then came

00:15:13.889 --> 00:15:16.610
the final nail in the coffin. Pretty much. February

00:15:16.610 --> 00:15:19.610
2025, the estate makes it official. Edelman's

00:15:19.610 --> 00:15:22.529
documentary will never be released. And, adding

00:15:22.529 --> 00:15:24.570
insult to injury, they announced a new print

00:15:24.570 --> 00:15:27.289
stock would be made, without Edelman. Presumably

00:15:27.289 --> 00:15:29.230
one they have more control over. So Edelman's

00:15:29.230 --> 00:15:33.029
five years, Netflix's millions. Just gone. Gone.

00:15:33.269 --> 00:15:35.850
Nullified. It seems the threat of a lawsuit from

00:15:35.850 --> 00:15:37.789
the estate challenging the content was enough

00:15:37.789 --> 00:15:39.929
to kill it, regardless of any contract about

00:15:39.929 --> 00:15:41.950
editorial control. So what does Edelman himself

00:15:41.950 --> 00:15:45.169
say about all this? His take is, well, brutally

00:15:45.169 --> 00:15:47.980
honest and kind of sad. In an interview around

00:15:47.980 --> 00:15:51.460
March 2025, when asked why this epic nine -hour

00:15:51.460 --> 00:15:53.820
film isn't being released, he reportedly just

00:15:53.820 --> 00:15:56.240
said he doesn't feel like getting sued. Wow.

00:15:56.820 --> 00:15:59.059
That says it all, doesn't it? It really does.

00:15:59.139 --> 00:16:01.519
It's chilling. Even with Netflix money and a

00:16:01.519 --> 00:16:04.279
contract guaranteeing control, the threat of

00:16:04.279 --> 00:16:06.840
a long, expensive legal fight from a powerful

00:16:06.840 --> 00:16:09.200
estate was enough to effectively shelve the whole

00:16:09.200 --> 00:16:11.799
thing. The legal threat trumped the creative

00:16:11.799 --> 00:16:15.379
freedom, and we, the public, lose out. Okay,

00:16:15.419 --> 00:16:18.000
so we've traced his path, the foundation, the

00:16:18.000 --> 00:16:20.460
OJ triumph, the diverse filmography, and now

00:16:20.460 --> 00:16:23.919
this, this major roadblock with Prince. What's

00:16:23.919 --> 00:16:25.919
the synthesis here? What does it all mean? Well,

00:16:26.039 --> 00:16:28.019
if you connect the dots, you see him tackling

00:16:28.019 --> 00:16:30.100
these huge narratives differently. With O .J.,

00:16:30.100 --> 00:16:32.940
it was a public story, historical events. Charged,

00:16:32.940 --> 00:16:35.759
yes, but ultimately open to his critical interpretation.

00:16:36.120 --> 00:16:37.759
Yeah. He had the freedom to make his argument.

00:16:37.840 --> 00:16:39.720
Right. With Prince, it was intensely private,

00:16:39.940 --> 00:16:41.980
deeply personal, commercially sensitive for the

00:16:41.980 --> 00:16:44.279
estate. The stakes felt different, more controlled

00:16:44.279 --> 00:16:46.480
by the legacy holders. So his method requires

00:16:46.480 --> 00:16:50.240
deep access and critical thinking. Always. But

00:16:50.240 --> 00:16:52.639
the Prince story shows that access, even when

00:16:52.639 --> 00:16:55.220
you pay millions and get it in writing, isn't

00:16:55.220 --> 00:16:58.059
truly guaranteed if the resulting story doesn't

00:16:58.059 --> 00:16:59.820
align with the estate's preferred narrative.

00:17:00.039 --> 00:17:02.200
And that's relevant for us, for you, the listener,

00:17:02.279 --> 00:17:04.339
Hal. Well, Edelman's whole process shows the

00:17:04.339 --> 00:17:06.700
value of going deep. Yeah. The eight hours on

00:17:06.700 --> 00:17:10.720
OJ, the five years trying with Prince. That level

00:17:10.720 --> 00:17:13.339
of contextual exploration is what gives you real

00:17:13.339 --> 00:17:16.099
understanding beyond headlines. But the Prince

00:17:16.099 --> 00:17:19.059
outcome. is a warning sign. It's a huge warning

00:17:19.059 --> 00:17:21.859
sign. It shows that even when you do everything

00:17:21.859 --> 00:17:25.299
right, get the access, secure the funding, have

00:17:25.299 --> 00:17:28.200
the creative vision, powerful legal forces driven

00:17:28.200 --> 00:17:31.400
by legacy concerns can still shut it down. The

00:17:31.400 --> 00:17:33.039
knowledge gets locked away. The whole effort

00:17:33.039 --> 00:17:35.160
gets torpedoed. Completely. Yeah. It makes you

00:17:35.160 --> 00:17:37.220
realize these deep dives aren't just costly in

00:17:37.220 --> 00:17:39.799
time and money. They carry enormous legal risks

00:17:39.799 --> 00:17:42.180
now. Risks that can lead to permanent loss of

00:17:42.180 --> 00:17:44.359
cultural knowledge. Which brings us right to

00:17:44.359 --> 00:17:47.160
our final thought for you to chew on. We know

00:17:47.160 --> 00:17:49.559
the stories Edelman did tell, Kurt Flood's fight,

00:17:49.799 --> 00:17:52.680
the Big East's history, the whole complex tapestry

00:17:52.680 --> 00:17:55.900
of O .J. Simpson. But that print stock, five

00:17:55.900 --> 00:17:58.799
years, the vault access, nine hours of insight

00:17:58.799 --> 00:18:01.960
we might just never get. So the question it leaves

00:18:01.960 --> 00:18:05.250
hanging is. How much vital cultural knowledge,

00:18:05.349 --> 00:18:07.509
how much deep understanding are we losing when

00:18:07.509 --> 00:18:09.869
creative freedom gets tangled up in legal battles

00:18:09.869 --> 00:18:12.589
or estate disputes? Even when the doors were

00:18:12.589 --> 00:18:15.670
supposedly open, the contracts signed. It's a

00:18:15.670 --> 00:18:17.690
frustrating question. It really is. The loss

00:18:17.690 --> 00:18:19.930
isn't just about money for Netflix or a setback

00:18:19.930 --> 00:18:22.390
for Edelman. It feels like a permanent gap in

00:18:22.390 --> 00:18:24.490
understanding one of the most fascinating, most

00:18:24.490 --> 00:18:27.329
enigmatic artists of our time. It really sticks

00:18:27.329 --> 00:18:29.150
with you, doesn't it? The cost of trying to tell

00:18:29.150 --> 00:18:31.130
the deepest truth. It absolutely does. Shelving

00:18:31.130 --> 00:18:33.890
that project. Despite everything. Yeah. It really

00:18:33.890 --> 00:18:35.750
shows the tension between historical inquiry

00:18:35.750 --> 00:18:39.410
and, well, legacy management. That's the frontier

00:18:39.410 --> 00:18:42.829
right now. Sobering thought to end on. That's

00:18:42.829 --> 00:18:45.109
it for this deep dive. We hope you feel informed,

00:18:45.309 --> 00:18:47.849
maybe a little bit frustrated by the mystery

00:18:47.849 --> 00:18:49.309
still locked in the vault. We'll see you next

00:18:49.309 --> 00:18:49.529
time.
