Podcast Summary: The Daily – "The Origins of Jeffrey Epstein"
Host: Rachel Abrams (The New York Times)
Guest: David Enrich
Date: December 23, 2025
Overview
In this episode, Rachel Abrams speaks with investigative journalist David Enrich about the early life and rise of Jeffrey Epstein, focusing on how he amassed wealth, social connections, and influence that later facilitated his infamous sex-trafficking crimes. This discussion is prompted by a new, but ultimately uninformative, Justice Department release of files about Epstein. The episode explores how Epstein used manipulation, deceit, and relationships to rise to power, emphasizing the broad complicity and impunity of those in his orbit, and probes long-standing questions—especially around figures like Donald Trump—that remain unanswered.
Key Discussion Points & Insights
1. Justice Department File Release: What’s In—and Not In—the Files
[01:23]
- Recent release of Justice Department files failed to greatly advance public understanding of Epstein, his crimes, or his network.
- “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.” (David Enrich, 01:48)
- Files contained some new photos, e.g., Bill Clinton with Epstein, and evidence that an Epstein victim reported him to the FBI as early as 1996—far earlier than prior federal investigations.
2. The Political Context of File Releases
[02:48]
- The release was forced by political pressure, especially legislative action under Trump.
- Files were heavily redacted, with the DOJ claiming the need for more time for review.
3. Pivotal Unanswered Questions
[03:36]
- Central questions: Who enabled Epstein? Did others participate in his crimes? How did he rise from obscurity to vast wealth?
- Enrich and colleagues are investigating Epstein’s financial “origin story,” noting that official files have not illuminated this.
4. Epstein’s Early Life and Social Ascent
[05:17]
- Focus: How did Epstein obtain the resources and connections to enable a global sex trafficking operation?
- He grew up working class in Coney Island, child of a New York City parks worker, and barely scraping by.
Memorable Quote
"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."
—David Enrich, [06:28]
5. Career Launch: Teaching, Opportunity, and Bear Stearns
[06:47]
- Epstein was a math teacher at Dalton School in Manhattan (1976), where a parent introduced him to Ace Greenberg, then-executive at Bear Stearns.
- Bear Stearns valued “psds”—“poor, smart, and deeply desirous of being rich.”
- Epstein’s path: Hired at Bear Stearns, becomes Greenberg’s protege, even dates Greenberg’s daughter.
Remarkable Manipulative Skill
"[Epstein] gets caught lying on his resume about graduating college... Instead, Epstein says: ‘You’re right, it’s true, I did lie...if I didn’t lie, there is no way a firm like Bear Stearns… would take me.’"
—David Enrich, [08:26]
- His candid admission, turning his disadvantage into a plea for a second chance, impresses his boss.
Insight:
"He understood 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."
—David Enrich, [09:37]
6. Early Patterns: Expanding Wealth Through Manipulation
[09:58]
- Rapid ascent at Bear Stearns, named a limited partner—huge income.
- Caught abusing expense accounts, violating company rules—yet resigns instead of being penalized, learning more about evading real consequences.
Learning to Act Wealthy
"[He learns] how to dress appropriately, how to introduce yourself… but also to have the confidence that he belongs in these settings, in these rooms with rich and powerful people."
—David Enrich, [11:38]
7. The First Major Scam: Michael Stroll and the Illusory Oil Deal
[11:56]
- Uses connections to defraud Michael Stroll, video game executive, out of $450,000 in a fake oil investment. Sends a pint of crude oil to maintain the ruse. Stroll loses nearly all his money, but Epstein escapes consequences.
Pattern of Impunity
- Lawsuit goes nowhere; “He’s 2 for 2—cheated and lied at Bear Stearns, then with Stroll, and got away with it both times.”
—David Enrich, [13:12]
8. Self-Styled “Financial Bounty Hunter” and the Obregón Windfall
[13:55]
- Early 1980s: Hired by actress Anna Obregón’s family to recover lost millions—successfully retrieves assets from Cayman Islands with a partner, becomes a millionaire.
9. Questioning the “Financial Genius” Narrative
[15:08]
- Despite reputation, little evidence Epstein was brilliant; possibly his only undeniable value-added moment.
- Bear Stearns now seeks Epstein as a client, eager for his business and revenue.
10. Weaponizing Women and Social Leverage
[16:27]
- Bear Stearns staff directed young female assistants to Epstein, often resulting in sexual relationships—pattern later echoed at larger scale.
- "Epstein had discovered that he could use attractive young women as a potent form of currency."
—David Enrich, [17:42] - Began using women as vehicles for personal gain: giving tours, attending dinners, leveraging for business contacts.
Critical Take
"[Schmidt] was very clear eyed about her role in this and that she was being used. The way she described it to me was, ‘I was his plaything.’"
—David Enrich, [17:53]
11. Ascent into Elite Circles
[18:24]
- By the late ’80s and ’90s, Epstein’s developed a compounding network of wealth and influence, extending to David Rockefeller, Les Wexner, JP Morgan, and other powerful figures.
12. Where Is the Accountability? (Return from Break)
[21:12]
- Discussion shifts to accountability, with focus on absence of information in official files about Trump and other enablers.
On Trump’s Role
"Epstein and Trump were operating in very similar social circles… at times, apparently very close friends… competing for young women. They were one another’s wingmen."
—David Enrich, [21:51]
- But concrete evidence or business dealings remain elusive, with speculation about why files remain hidden.
On The DOJ’s Reluctance and Systemic Protection
"…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."
—David Enrich, [24:48]
13. The Broader Lesson and Public Takeaway
"[Epstein] didn’t need to be a secret spy or whatever these other conspiracy theories… 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."
—Rachel Abrams, [25:52]
Impunity as Central Theme:
"…the story of Epstein is really one of impunity. …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."
—David Enrich, [28:08]
"The reason that people remain obsessed about Epstein… is that there are so many people out there who have not had a similar public reckoning."
—David Enrich, [28:36]
Notable Quotes & Memorable Moments
- "He was an extremely successful con man. He stole, he deceived, he manipulated, and he learned… he could do so basically with impunity." —David Enrich, [06:28]
- "He understood human dynamics so well …that would be something likely to get him a second chance. And sure enough, it worked." —David Enrich, [09:37]
- "Epstein had discovered that he could use attractive young women as a potent form of currency." —David Enrich, [17:42]
- "It just doesn’t feel right that only two people… have really been held to account for this so far." —David Enrich, [27:00]
- "The story of Epstein is really one of impunity… for people with a lot of money and power and connections, they really can act with impunity." —David Enrich, [28:08]
Important Timestamps
- 00:31: Episode setup – new Epstein files released, but key questions remain
- 06:45: Exploring Epstein’s origins and early scams
- 09:09: Epstein’s manipulation at Bear Stearns
- 13:33: Epstein refines his skills as a con artist
- 15:08: The “financial bounty hunter” phase and early windfall
- 17:42: Epstein learns to leverage women as currency
- 21:51: Discussion of Epstein’s relationship to Donald Trump and elite circles
- 26:08: Thoughts on the Rorschach nature of Epstein’s story & public perceptions
- 28:08: Takeaway: the culture of impunity around Epstein and his enablers
Overall Takeaways
- The newly released files from the DOJ reveal little that fundamentally changes public understanding of Epstein’s crimes and network, with notable absences about Trump and other powerful men.
- David Enrich’s reporting reveals the blueprint of Epstein’s rise: leveraging charm, lying, social advantage, and learning repeatedly that wealth and connections can shield from meaningful consequence.
- Epstein’s story is less about shadowy conspiracies and more about the systemic impunity afforded to the rich and well-connected—a reality that continues to enrage and fascinate the public as many figures remain unaccountable.
For more information, listen to the full episode of The Daily: “The Origins of Jeffrey Epstein.”