Against the Rules: The Big Short Companion
Episode: The Short Sellers
Date: October 21, 2025
Overview
In this commemorative episode, Michael Lewis and co-host Lidia Jean Cott revisit The Big Short 15 years after the book and ten years after the Oscar-winning film. They analyze the enduring impact of the 2008 financial crisis, the book, and the movie by catching up with the real-life figures behind its characters as well as discussing the deeper legacy of “short sellers” in finance and society. Through candid conversations with Greg Lippman (the inspiration for Ryan Gosling’s character) and Steve Eisman (portrayed by Steve Carell as Mark Baum), Michael Lewis pulls the curtain back on Wall Street’s culture, the fundamental human dynamics that fueled the meltdown, and the unresolved fallout of systemic fraud.
Key Discussion Points & Insights
1. Revisiting The Big Short and the People Behind It
- Early Scene in the Movie ([00:51])
- The podcast opens with a reenactment of an iconic scene—Greg Lippman (Ryan Gosling) pitching a “too good to be true” deal to the skeptical FrontPoint Partners team.
- Michael Lewis reflects:
“Even Greg Lippman thinks he’s Greg Lippman when he’s watching it...he was the only honest man on Wall Street at that moment.” ([01:14])
Tone of Wall Street
- Lippman was seen as a “used car salesman,” which made him both compelling and mistrusted.
- Steve Eisman was “designed to mistrust Wall Street,” making their partnership unlikely but inevitable, which Michael describes as a “match made in heaven.” ([01:39])
2. Greg Lippman: The Outsider With the Truth ([05:58]–[11:45])
Diagnosing the Crisis
- Lippman succinctly lays out the path to the crisis:
“Human nature vacillates between fear and greed...Institutions were taking on greater and greater risks in order to generate the same returns as interest rates kept going lower...As long as we make new loans to pay off the old loans, they’ll never be a problem.” ([06:18–07:07])
Selling the “Trade of the Century”
- Lippman pitched the idea to 250 hedge funds; only about 75 took it up. The ones who listened were often outsiders, not “prom kings.”
“People who felt a little bit more like outsiders, were either more willing or more able...some of your characters even were hoping to see it more than others.” ([07:56])
The "Wrong Number"
- The famous meeting between Lippman and FrontPoint was, in part, a “wrong number,” but also desperation:
“I was trying to find anyone that was willing to listen to my idea and pay this week’s, you know, bar tab.” ([09:52])
Views on Wealth and the Investment World
- Lippman observed that many wealthy people he encountered seemed unhappy:
“Most of those people seemed unhappy, which is interesting in and of itself.” ([11:26])
3. Steve Eisman: Cynicism, Honesty, and Aftermath ([14:47]–[26:33])
Character Dynamics and Trust
- Despite initial mistrust, Eisman says of Lippman:
“He was always honest with us, but he comes across as a bit like a used car salesman. … There is not one thing that Lippman ever did that wasn’t completely above board with me.” ([15:46])
“Dog Shit Wrapped in Cat Shit”
- Iconic metaphor from the film and confirmed by Eisman for subprime products:
“So mortgage bonds are dog shit? CDOs are dog shit wrapped in cat shit.” – Movie quote, confirmed ([15:15]) “Yeah, that’s right.” ([15:21])
Living Through the Crisis: Scenes & Memories
- Eisman recalls the week Lehman Brothers collapsed and the anxiety in the market:
“In the morning it looked like Planet Earth was burning. … I remember turning to one of the guys and I said something like, these poor people, they have absolutely no idea what's about to hit them.” ([17:05]–[18:40])
Government Response and Moral Failure
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Acknowledges government action prevented a depression, but:
“The biggest mistake the Obama administration made was that nobody went to jail. That was a terrible, terrible policy error. … This is the biggest fraud in human history.” ([19:01]–[21:01])
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Explains the due diligence fraud in mortgage securitization—a critical and under-discussed mechanism of the collapse.
“How many Wall Street firms then ordered [Clayton Mortgage] to do due diligence on the remaining 90%?”
“Zero.” ([21:39])
Two Systems of Justice & Political Fallout
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On the failure to prosecute fraud:
“Prior to the crisis, everybody’s sitting there’s suspecting there are two systems of justice, one for rich or one for poor. Now we know there definitely is.” ([23:15])
“That created the Tea Party. … And the anger is still there.” ([23:31])
4. After the Big Short: Life, Legacy, and Looming Risks ([23:47]–[26:33])
The Effect of Fame
- Eisman laughs off his notoriety:
“Sometimes it’s kind of funny, I take the bus cross-town and somebody looks at me and says, ‘Hey, aren’t you Steve Eisman?’” ([23:54])
Where’s the Next Big Risk?
- Cautions the private equity industry is a potential blind spot:
“The only thing that might worry me is...the private equity world...nobody really knows what’s going on there. … It has not been stress-tested like the banks at all.” ([24:20])
On Being the “End of the World” Guy
- Eisman’s current reputation amuses him:
“The position of Steve Eisman is taken.” ([25:55])
- He’s bullish on markets, despite his past as a crisis prophet.
Teaching and Explaining
- Michael Lewis remarks on Eisman’s clarity:
“You have an unbelievable ability to clearly explain things. And it’s refreshing to be back in its presence.” ([26:33])
- Eisman jokes about an alternate career as a high school history teacher.
Notable Quotes & Memorable Moments
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Michael Lewis on Greg Lippman:
“Greg Lippman was the only honest man on Wall Street at that moment. … He seemed like a used car salesman, so nobody trusted him.” ([01:39])
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Greg Lippman on pitching the trade:
“I was on a mission. I had to find people to cover this week’s bill. … I was giving people an amazing thing, and they just weren’t gonna make all the money, but they were gonna make tons of money.” ([09:44])
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Steve Eisman on short selling ban:
“We were sitting on the steps of St. Patrick’s Cathedral, and it was a gorgeous day. … These poor people, they have absolutely no idea what’s about to hit them.” ([18:36])
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On Wall Street’s fraud and lack of accountability:
“Nobody investigated. Now why? I don’t know. And to this day, I do not understand it.” ([22:14])
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On lasting political consequences:
“That created the Tea Party. I’m convinced. … The anger is still there.” – Eisman ([23:31])
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On his legacy:
“All these people want to be me. They want to be the person who predicts the end of the world. And I got news for all of them. The position of Steve Eisman is taken.” ([25:55])
Important Segment Timestamps
- Opening breakdown of the Big Short’s legacy: [00:13–01:39]
- Early scene and characterization in the film/book: [00:50–01:39]
- Greg Lippman Interview: Diagnosing the crisis and pitching the trade: [05:58–11:45]
- Steve Eisman Interview: Working with Lippman, living through the collapse: [14:47–23:47]
- Explaining due diligence failure and fraud: [19:01–22:41]
- On two systems of justice and political aftermath: [23:15–23:43]
- Post-crisis reflections, private equity as blind spot: [24:20–24:49]
- The “end of the world guy” joke and Eisman’s new outlook: [24:49–26:06]
Episode Tone and Style
Maintaining Michael Lewis’s trademark mix of wry observation, narrative clarity, and respect for character complexity, the podcast is reflective yet urgent—combining humor with a deep sense of injustice and unresolved risk.
Conclusion
This episode smartly blends nostalgia for The Big Short with a critical reassessment of what we’ve (not) learned since. It delivers rare self-reflection from industry insiders, untangles the social psychology of the crisis, and warns that the risks that caused 2008 may still lurk, just in new forms. The enduring anger and lack of accountability, as Eisman notes, still shapes U.S. politics and trust in institutions.
Next Week Tease:
Michael Lewis will catch up with other FrontPoint traders—Vinnie Daniel, Porter Collins, and Danny Moses—to continue exploring the crisis’ aftershocks.