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The latest release of files related to the sex offender Jeffrey Epstein left key questions about his rise to power and his connections to the president unanswered.
Today, my colleague, David Enrich explains how he and a team of reporters worked to fill in those mysteries and reveal the truth about Jeffrey Epstein's origins.
It's Tuesday, December 23rd.
David Enrich, welcome to the show.
Thanks for having me.
David, I think this is probably your fourth or fifth appearance on the show this year to talk about Jeffrey Epstein.
And this time we're having you back because on Friday there was obviously this massive file released from the Justice Department that, as far as I understand it, did not really advance our understanding of Jeffrey Epstein or his crimes or the people in his orbit.
Can you tell us what you think the biggest takeaways were?
It's a hard question because there were not huge takeaways.
And we got lots of bits of incremental color and detail that reinforced the deep depravity of Epstein's crimes and the horrible things he was doing.
We also got some new tidbits.
We saw, for example, Bill Clinton In numerous photos with Epstein and his associates, including in a swimming pool.
We saw that one of Epstein's victims back in 1996 had reported him to the FBI for having child sexual abuse material.
And that's a decade before we know the federal prosecutors actually started investigating Epstein.
So that was definitely a new development.
But for the most part there was nothing here that fundamentally altered our understanding of Epstein and his network, and notably also very little about Donald Trump, whose name was barely mentioned in these files.
And it was Trump's relationship with Epstein that triggered a lot of the political interest in this investigation to begin with.
Right.
Just to remind people, this whole file release is coming about because of a massive pressure campaign, mostly from Democrats, but also from some within the MAGA orbit, for Donald Trump and his administration to release the so-called Epstein files.
Right.
And that basically forced Trump to sign legislation authorizing these files to be released from the Justice Department.
Yeah, it's worth noting that the Justice Department did not do what it was legally required to do, which was release all of the files.
And those files that were released were in many cases so heavily redacted that you couldn't make any sense of them.
And why didn't they release them?
The Justice Department has said that they will release the rest of the files on kind of a rolling basis over the next few weeks and that they need this additional time to be able to properly review and redact these huge quantities of materials.
OK, so knowing that there would be this sort of staggered release, what were you expecting to get?
Or, maybe more importantly, what questions were you hoping that this batch of files would actually answer?
I mean it depends on your perspective and what your interest is in this.
I mean, I think one of the biggest questions that many victims have and many people who have been focusing on Epstein for a while are there other men who were enabling him or participating in sex crimes with him?
And for me and my colleagues.
I've been working with Matt Goldstein, Jessica Silver Greenberg and Steve Eder for months now to really understand Epstein's financial web that he wove and looking at his origins and how he went from kind of this rags to riches story, where he managed to transform himself from a working class family into an extraordinarily rich and well-connected person.
And so we were wondering if there would be any revelations in these files about that.
And we're just completely disappointed in that regard.
Well, that reporting that you mentioned is what I want to talk to you about, because everybody's been eagerly awaiting the release of these files, right?
Like hoping perhaps, that the files would address some of these enduring questions about Epstein and his crimes.
And obviously that did not happen on Friday.
You and our colleagues have been digging into a different period of Epstein's life, one that preceded the era of his most flagrant criminal activity that he became known for, that he was arrested for.
Why was that period your focus?
Why was it important in your estimation to understand the early period of Epstein's life?
Well, Epstein built an extensive sex trafficking operation all over the world and that was really expensive and it required the support of a lot of powerful people.
And so the question for us has been how did he get in a position where he had the money and the power and the connections to do that?
This was a guy who came from a really working class background.
He grew up in Coney Island in Brooklyn.
His dad was an employee of the New York City Parks Department.
He was really kind of scraping by growing up and then somehow starts to climb this ladder.
And I think the absence of information about Epstein and his early years has given rise to just a vast number of conspiracy theories, ranging from that Epstein was running the super sophisticated blackmail operation.
Right. to that he was affiliated with intelligence services.
And the period from basically the mid-1970s to the early 1990s for the most part has been just a complete black box.
And so our goal when we started reporting on this months ago was to try and get inside that black box and figure out how Epstein got his start.
And the bottom line of how he did that was that he was an extremely successful con man.
He stole, he deceived, He manipulated and he learned over and over again that he could do so basically with impunity.
So where does the story begin?
It begins in 1976.
Epstein is a teacher at the Dalton School in Manhattan and he gets invited to a reception at an art gallery.
And he goes kind of grudgingly in his tongue.
And at the reception he bumps into the parent of one of his students who is impressed with his math chops.
Mm-hmm.
And the parent suggests that maybe he is wasting his time being a teacher and instead should consider a career in Wall Street.
And the parent then introduces Epstein to a guy named Ace Greenberg.
Very big name.
Yeah, who at the time was a top executive at Bear Stearns, which is this scrappy Wall Street investment bank?
And Epstein goes in to meet Greenberg for a job interview.
And Epstein fits the bill.
Greenberg is bowled over by the guy's charisma and charm and apparent math prowess and offers him a job.
So he arrives at Bear Stearns and he quickly becomes the protege to some of the firm's top executives.
One is Greenberg, the guy who hired him, who is so taken with Epstein that he introduces him to his own 20-year-old daughter and they start dating, which affords Epstein something akin to protected status at the firm.
And that really quickly comes in handy because within a couple of months of his arrival at Bear Stearns, Epstein's boss, a guy named Michael Tenenbaum, learns from the HR department that that Epstein had lied on his resume about having graduated from college.
And so Tenenbaum summons Epstein into his office, is not really sure what to do about this, because you know this is a very serious infraction.
On the other hand, the guy is dating the boss's daughter.
And confronts Epstein with this, expecting Epstein to lie and dissemble and deny, which in that case would allow Tenenbaum to easily fire him.
Instead, Epstein says, you're right.
It's true.
I did lie.
And the reason he lied, Epstein goes on to say, is that if he didn't lie, there is no way a firm like Bear Stearns or anyone else is going to give him a chance without having a college diploma.
And Tenenbaum is so taken aback and disarmed by this honesty that he decides to give Epstein a second chance.
And this is a pattern we'll see repeating over and over and over again.
It's sort of remarkable because, first of all, he gets this job because in a way, Ace Greenberg is like fetishizing his lower middle class background right.
Something that would have been a disadvantage to somebody else is an advantage to Epstein.
He gets his foot in the door.
And then when he gets caught, he doesn't just make himself sympathetic.
He actually makes himself a victim of the institution where he's working, right?
Like I had no choice but to lie.
Otherwise, you big, powerful, mean Wall Street bank would never have taken a chance on me.
Yeah.
And to Tenenbaum.
You know this is now what.
40 or 45 years later, when I spoke to him, he was still kind of marveling at Epstein's knack for understanding human dynamics so well that just on the spur of the moment, he understood that that would be something that was likely to get him a second chance.
And sure enough, it worked.
So what happens next?
Well, he keeps his job and he starts very quickly climbing through the ranks at Bear Stearns.
Within a few years, he has been named a limited partner, which means that he is getting paid boatloads of money at that point, something like 800000 in today's dollars.
And yet the problems still keep bubbling up.
And Epstein was found to abuse his expense account.
He took a work trip to the Caribbean and charged Bear Stearns something like 10000 on jewelry and clothing for his girlfriend.
So this is after he was dating the boss's daughter.
Mm-hmm.
Another thing is that it turns out that he has been helping his girlfriend get early access to lucrative investment deals at Bear Stearns, which is a violation certainly of the company's rules, if not the law.
And he's helping his high school friend get a loan to buy securities at Bear Stearns, which is also a violation of company policies, if not the law.
And eventually Bear Stearns gets wind of this and starts investigating.
And Epstein is kind of headed for a slap on the wrist.
He's likely to pay a financial penalty and also be suspended for a couple of months.
And instead of suffering that indignity, he decides to resign, saying that he's been deeply offended by the fact that he was even being investigated.
So one of the many things he learned at Bear Stearns, through this network of acquaintances and colleagues that he built up, was basically how to act and behave as a really rich person.
Is this like which fork to use, or is this about acting comfortable or giving off an air of ease in the face of?
It's both.
It is what fork to use.
It's how to dress appropriately, how to introduce yourself to a member of royalty or to a senior politician.
But it's also to have the confidence that he belongs in these settings, in these rooms, with rich and powerful people.
And that immediately pays dividends for him.
A former Bear Stearns colleague introduces him to a guy named Michael Stroll who is a video game executive.
And Epstein persuades Stroll to hand him 450000, which is about 10 of Stroll's net worth, to invest in what Epstein claims is an oil deal.
Hmm.
There's no evidence that any oil deal existed.
And Stroll loses virtually all of his money and keeps pestering Epstein saying, where is my money?
You promised me we would get this kind of payout.
Epstein rebuffs him over and over again.
At one point sends him a pint of crude oil to convince him that the oil deal actually does exist.
But the money is just gone ultimately.
And so this is one of Epstein's huge first killings.
He walks away with what appears to be several hundred thousand dollars of money that he just stole from this guy.
And nothing really happens.
And Stroll files a lawsuit against him.
It bounces around the federal court system for years.
Ultimately, Epstein prevails on technical grounds.
And so –
Epstein is now two for two.
He cheated and lied at Bear Stearns and essentially got away with it.
Now he's cheating and lying with this video game executive and walking away with his money once again with impunity.
And for someone like Epstein, the message there is very clear, which is that if you lie and cheat well enough and often enough and are sufficiently manipulative, you can make a real living doing this.
So he's not only learning that he can get away with it, but it sounds like he's learning that he's getting away with it at a larger level and with people who are arguably within his social network.
Yeah, that's right.
And Epstein is nothing if not a very good student of fraud and thievery.
And you can see him progressing from one stage of this to the next and getting more ambitious and bolder and bolder the more times he pulls this off and the more times he gets away with it.
So where does he go from here?
So Epstein, around this time, has been referring to himself as a financial bounty hunter, basically someone who like, tracks down hidden assets all over the world.
And as it happens, we're in the early 1980s at this point.
He is dating a Spanish actress named Ana Obregón.
And it turns out that her family has just realized that they have lost millions of dollars in the implosion of a securities firm in New York.
And so they hire Epstein to track down their missing money.
And he pairs up with a friend of his who's a former federal prosecutor.
And together they spend the next couple of years trying to track down these missing assets.
And lo and behold, they find them.
They're in a bank in the Cayman Islands.
And Epstein and his buddy charter a jet, go down to Cayman.
And somehow walk away with millions of dollars of these securities.
They recover it and get paid a certain portion of that as a fee.
And so Epstein, by this point, is almost certainly a millionaire, which is really – it's quite an extraordinary turnaround for a guy who, just a few years earlier, was this working class guy trying to make a living as a high school teacher.
The story of the recovered money though, is also so interesting because one of the narratives about Epstein in recent years, in recent memory, is that this guy was not actually a financial genius.
That's the thing you hear over and over again.
People are like, why Epstein?
Would these billionaires hand him millions of dollars to manage when he wasn't proving himself as singular in any particular way?
But this is the only story I think I am familiar with where he really provides tangible value to people in a way that does seem quite singular.
Right.
And, to be frank, it's one of the things I've struggled with a little bit in reporting the story and in understanding the story, because Epstein, he likes to present himself as this financial genius.
We have not seen evidence to support that claim.
We do see here some glimmer of cleverness that does set him apart.
And so around this time, Epstein has amassed enough money that he has gone from having been kind of chased out of Bear Stearns with his tail between his legs to now he returns to Bear Stearns, this time as a valued client.
He's doing lots of trading through the firm, which produces revenue for Bear Stearns, which makes Bear Stearns very eager to keep him in its good graces.
And so they start extending some favors to him.
Favors like what?
Well, one of Epstein's former managers at the firm, who is now helping to run him as a client, has a very attractive young assistant named Patricia Schmidt.
And one night in 1987 the manager asks Schmidt to deliver some papers to Epstein's apartment at night.
And Schmidt goes over to the apartment.
Epstein makes her tea, gives her a tour of his very nice apartment building and invites her to come back whenever she wants to use the building's swimming pool.
And Schmidt takes him up on that offer and thus begins a year-long sexual relationship between Schmidt and Epstein.
And one of the things we found in our reporting is that the same Bear Stearns manager on multiple other occasions also sent young female assistants over to Epstein's apartment.
And that ended up leading to sexual relationships.
And Epstein seems to realize that if Bear Stearns can use women as a source of leverage, so can he.
And Schmidt.
When I spoke with her, she was very clear-eyed about her role in this and that she was being used.
And the way she described it to me was that I was his plaything.
And Epstein perceived her as someone that's going to help him get where he wants to go.
And sure enough, we see him start to use Schmidt for other things, such as he would have Schmidt give his clients and acquaintances tours around Wall Street, bringing them into Bear Stearns, maybe take them out to a nice dinner.
And so Epstein had discovered that he could use Schmidt.
Attractive young women was a potent form of currency as he sought to impress and cultivate relationships with rich and powerful people whom he wanted to do business with.
He's taking advantage of the fact that other people are motivated by sex and they might do something for him.
If he does something for them, ie send this woman out to meetings with them.
As far as we can tell, this is probably the first time that Epstein has really fully discovered his ability to use women to really advance his own agenda.
And at the same time around now Epstein has also really cultivated enough connections and built enough wealth that those things start compounding upon each other.
And we will see over the ensuing decade that Epstein really takes that to the next level and starts building connections with kind of the creme de la creme of American finance and society.
And so he'll build and exploit relationships with people like David Rockefeller.
Like Les Wexner, the retail tycoon, ultimately with big institutions and big banks like JP Morgan.
And this is the Epstein who we all now know, right?
As someone who has built this huge network not only of young women and girls whom he's abusing, but also this cast of rich powerful, famous men who have supported him and enabled him along the way.
We'll be right back.
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So David, you've described a lot of the lessons that Epstein learned in his early years, that allowed him to climb his way up the social ladder, that allowed him to amass great wealth and, of course, enabled his criminal activity over many, many years.
But one name that you have not mentioned is Donald Trump.
And pressure on the president is what led to the disclosure of these files, because people want to understand what evidence the government has about Jeffrey Epstein and his criminal behavior and the network in which he operated.
And so I wonder, then, how are we to think about where Donald Trump fits into Epstein's early years?
Well, Epstein and Trump were operating in very similar social circles for a number of years, basically from the late 1980s into the early 2000s.
They were at times apparently very close friends.
And our colleague Nick Confessori has just spent months digging into this.
And one of the findings in his investigation was that not only were they close friends for years—
But they were also competing with each other for young women.
And Nick in his story described Epstein and Trump as being one another's wingmen.
That being said, there's still...
A lot of unanswered questions about the exact nature of that relationship, if there were business dealings between the two of them, for example.
And it is not clear to me whether there are answers that are lurking in these as yet undisclosed Epstein files that the Trump administration is sitting on.
And one way to think about this is that, at the outset, what the Justice Department has been told and is required under law to release are files related to the federal investigations of Epstein over the years.
And it is not clear to me that federal investigators were doing a whole lot of investigating into the men with whom Epstein was associated, whether that's Trump or men like Leon Black or Les Wexner or people like that.
And so to the extent that those were not subjects of investigation—
We're not likely to see a tremendous amount about them in these files.
But at the same time, there's also a question of why exactly Trump and his administration have been so reluctant to come clean about what is in these files to begin with, and if they had just released this stuff when they said they would back early in this year, we might not be talking about this anymore anymore.
And the fact that they have been fighting so hard against full transparency here, it does suggest that there is something in there that they want to hide.
But at the same time, one of the things I've never quite understood about the Epstein files, as we have been calling them, is if there was evidence of criminal behavior on the part of Trump or any of these other notable figures that has been in the possession of the DOJ across multiple administrations for years.
And so I don't mean to come off as naive and say like if the DOJ had evidence of crimes, why would they not investigate it?
But I just don't quite understand why exactly we believe that it wouldn't have come out before now.
It's not self-evident that this would have already come out for at least two reasons.
One reason is that it's become, I think, accepted conventional wisdom that if an administration has damaging information about its political enemies, that that will immediately be released.
That is not the way justice departments have historically operated.
And so it's entirely possible that a previous administration's Justice Department might have had damaging information about its opponents that it kept under wraps because it was supposed to do so.
That's thing one.
Thing two is that it is also entirely possible that there could have been reports or suspicions or investigative trails that were followed that did lead to powerful men and powerful institutions.
And those investigations went nowhere, maybe because there wasn't evidence, but also it could be because there's a long history of federal investigators not aggressively pursuing cases that involve white-collar defendants.
When you have some of the richest, most powerful people in the world, it is not surprising, and it's not a conspiracy to think that those people might get away with it.
I guess the reason why I'm sort of lingering on this is that it feels like everybody is waiting for another shoe to drop.
Everyone is waiting with bated breath to see what's in these files, and maybe these files will finally answer our persistent questions about Epstein's orbit and Donald Trump.
But it feels like the picture that's emerging, at least from your reporting, is that we already kind of know the answer about how Epstein became Epstein in some way, which is that he didn't need to be a secret spy or whatever these other conspiracy theories that have popped up in intervening years would suggest.
He just needed to be a remarkably savvy guy who learned very early on that he could manipulate people, he could commit crimes and he could basically get away with anything he wanted as he climbed up the ladder.
Yeah, I think that's right.
And I think there's been a lot of really good reporting that has peeled back a lot of layers of the Epstein story.
I do think that there are still a bunch of layers left to unpeel and I'm not holding out a huge degree of confidence that these files, as they get released, are going to do much of that peeling.
But I do think there are still a ton of important questions that have not been answered.
And I think the Epstein saga for years now has been kind of a political Rorschach test and that people on the left, or many people on the left, view it as a weapon with which to go after Donald Trump.
I think on the right a lot of people view this as a vehicle to attack kind of liberal globalist institutions and individuals.
And I think the truth is probably somewhere in the middle, right?
That there are a lot of very rich, powerful men who enabled Epstein and may have participated in some of his crimes.
I do not think that there has been very much accountability for those men yet.
And I don't think that we have a full sense of what information may or may not be in these government files pertaining to those men.
But I think the reason people think that there may be more shoes to drop It's partly that their dreams of having their political enemies crushed by the Epstein scandal remain unfulfilled.
But it's also partly a recognition that there were so many people involved in supporting Epstein and allowing his criminal network to prosper that it just doesn't feel right that only two people, Jeffrey Epstein and his associate Ghislaine Maxwell, have really been held to account for this so far.
Okay, but speaking of being held accountable, I do wonder if that's the takeaway here.
Because on the one hand, obviously, Jeffrey Epstein died in a jail cell.
On the other hand, he got away with horrific crimes and amassed so much money and power over the years.
We've been talking this whole conversation about the lessons that Epstein learned in order to do that.
But I do wonder what lessons we, as the public, should learn looking at Epstein's story and how he came to an end.
Well, look, dying in a jail cell is no one's idea of a happy ending.
That said, the story of Epstein is really one of impunity.
And he, as you said, got away with this for years, despite repeated red flags, despite many warnings, despite many victims coming forward and trying to blow the whistle on him.
And to me it's also a broader story of impunity, not just about Jeffrey Epstein, but the people around him many of whom – really have not had a public reckoning about the roles they play in this.
The reason that people remain obsessed about Epstein to a large degree, I think is that there are so many people out there who have not had a similar public reckoning.
And so to me that's the great takeaway that for people with a lot of money and power and connections, they really can act with impunity.
David Enrich, thank you so much.
Thanks for having me.
Late on Monday night the Department of Justice released more files related to the investigation of Jeffrey Epstein.
The documents contained hundreds of references to President Trump, although most of them are from media reports, unverified tips and discussions among investigators, including a mention that Trump was a passenger on Epstein's private jet eight times between 1993 and 1996.
None of the mentions appear to be evidence of wrongdoing.
We'll be right back.
Here's what else you need to know today.
President Trump announced on Monday that the Navy would build two new quote with the eventual goal of acquiring 25.
The move was the latest example of the president rebranding an aspect of the federal government in his image.
The announcement also comes as the US has ratcheted up its threats against Venezuela's President, Nicolas Maduro, and intercepted tankers that serve the country's oil industry.
In a move that prompted criticism from a veteran correspondent, CBS News abruptly removed a segment about El Salvador's notorious Seacott prison from an episode of 60 Minutes after the network's new chief, Barry Weiss, said the segment needed additional reporting.
The decision drew condemnation inside and outside the network, where critics of Weiss saw the move as evidence that the network was more interested in kowtowing to the Trump administration than preserving its journalistic integrity.
Today's episode was produced by Claire Tennis-Getter, Olivia Nat, and Mary Wilson.
It was edited by Devin Taylor and Lexi Diao.
Contains music by Leah Shaw Demeron, Alicia Baitube, and Marian Lozano.
And was engineered by Alyssa Moxley.
That's it for The Daily.
I'm Rachel Abrams.
See you tomorrow.
