Ivan Boesky: The Wall Street Legend Who Crashed and Burned (with Rory Scovel)

Summary

SNAFU with Ed Helms

Season 4, Episode 24: Rory Scovel and Arbitrage on Wall Street

Release Date: March 18, 2026
Host: Ed Helms
Guest: Rory Scovel

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Episode Overview

This episode of SNAFU dives into one of Wall Street’s most infamous screw-ups: the rise and fall of Ivan Boesky, the real-life inspiration for Gordon Gekko in Wall Street. Host Ed Helms and comedian Rory Scovel unravel the high-stakes world of 1980s financial arbitrage, the greed and hubris that fueled a wave of insider trading scandals, and the lasting impact of Boesky’s downfall on American business culture. The conversation is equal parts history lesson, comedic banter, and sobering reflection on power, ambition, and accountability.

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Key Discussion Points & Insights

1. Personal Catch-up & Comedy Tributes (02:40–07:56)

• Warm banter opens the episode, with Rory Scovel lauding Ed Helms’s film Vacation.
  • Rory: “Vacation is potentially one of the funniest movies that I have seen... I have not seen a comedy where literally every five minutes, I sort of need to pause the movie to collect myself.” (03:57)
• Name pronunciation jokes lead to Southern accents and Scovel’s SC roots.
• Rory plugs his new podcast, Crimeless, which focuses on stories of inept criminals (07:16).

2. Setting the Stage: Wall Street’s Greed Era (08:09–12:21)

• Ed sets up the real-life inspiration for “Wall Street” and Michael Douglas’ “Gordon Gekko”: Ivan Boesky—a rags-to-riches Wall Street legend.
• Boesky’s notorious daily uniform and rigid habits introduced:
  • “He said, I have enough big decisions to make every day. This is one I can just take off the list.” (09:36)
• The pair recall the “Greed is good” speech, noting its cultural impact and how it encapsulates the 1980s’ business ethos.
  • Ed: “Greed, for lack of a better word, is good. Greed is right. Greed works...” (10:36)
  • Rory: “Yeah, yeah, yeah. I think we know now... it’s going great. It’s going so good.” (11:06)

3. Ivan Boesky’s Backstory & Early Ambition (12:44–18:26)

• Boesky’s upbringing: son of a Russian immigrant, Detroit bar owner, went to the now-famous Mumford High School (from Beverly Hills Cop trivia).
• Early signs of intensity:
  • Cited as “single minded... he drove himself mercilessly—as far as exercise goes” (13:18), drawing comparison to today’s Elon Musk.
• Marriage to Seema Silberstein, daughter of a wealthy tycoon, and motivations shaped by his ambitious, sometimes condescending father-in-law (“Ivan the Bum”).
  • Ed: “How much of a person’s identity or ambition gets shaped by all the people shouting at them that they’re a failure?” (18:26)

4. Psyche of Ambition & Failure (18:26–20:10)

• Conversation tackles the psychological impact of being underestimated, and how vengeance or external validation can drive people to succeed—or self-destruct.
  • Rory: “Criticism like that starts to become your reality... it’s vengeful fuel.” (19:13)
• Boesky, heavily backed by his father-in-law, enters Wall Street with a major chip on his shoulder (20:10).

5. Life on Wall Street: The Rise (20:10–31:19)

• Boesky’s workaholism and odd personal habits: 20-hour days, barely eating, relentless exercise.
  • Ed (on Boesky’s sleep): “He was like, as we mentioned before, relentlessly working out. Just like a very intense guy. And also never slept.” (21:14)
• Arbitrage explained:
  • Not conventional investing (buy and hold), but exploiting tiny windows for profit, often during company takeover rumors—high risk, high reward.
  • Boesky favored massive, risky bets where others played it safe.
  • Ed: “It has nothing—there’s no loyalty… You’re just trying to spot the moment when the price is about to change and be there first.” (24:44)
• Rory reflects on how arcane and alien Wall Street can seem to those outside (“to me it’s just a circus I can’t understand”). (32:18)

6. Peak Fame, Greed, and the 80s Wealth Culture (31:19–36:57)

• Boesky achieves meteoric wealth ($280 million in 1985, $840 million in today’s dollars).
• Discussion of wealth gaps:
  • Ed: “$840 million...is not considered crazy wealthy [today]... you have to be a billionaire to be crazy wealthy… The wealth gap has just exploded since the ‘80s.” (29:51)
• Boesky actively cultivated his image, publishing Merger Mania: Arbitrage, Wall Street’s Best Kept Money Making Secret.
• Ed and Rory lampoon the appeal and accessibility of such a book (“anybody at the post office, you read this? Money Mania?”) (32:00)

7. The “Greed is Good” Speech—Reality vs. Fiction (35:59–37:20)

• Boesky delivers the infamous UC Berkeley speech:
  • Quote: “Greed is all right… I want you to know that I think greed is healthy. You can be greedy and still feel good about yourself.” (36:02)
• Rory compares this to cultish or right-wing trends in modern America (“empathy is bad”), and Ed draws parallels to Ayn Rand and Christian nationalist influences. (36:48)

8. The Fall: Insider Trading Scandal (37:30–54:29)

• Collapse begins in 1982 with major losses, spiraling into illegal insider trading.
  • Ed: “Is there anything more human than trying to recover from a humiliating loss by just immediately making a series of worse decisions?” (43:11)
• Simple but sharp explanation of insider trading—distinguishing between diligent research and illegal tip-offs. (44:11–44:45)
• Regulatory crackdown:
  • SEC investigation uncovers a network stretching from Merrill Lynch in Venezuela to Dennis Levine and Boesky.
  • Rudy Giuliani, then U.S. Attorney, is pivotal in the case (pre-mayoral fame).
• Boesky cooperates with authorities for a reduced sentence but is branded “a rat.”
  • Ed: “He narked, he ratted, he turned, he did bad things and then tried to get off the hook by doing bad things to other bad guys, I guess.” (47:59)
  • Rory: “You should have been a criminal to begin with… But now that you are one, leave the other criminals alone.” (48:31)
• His book, grants, and social positions are all stripped away; faces a $100 million fine and a (reduced) prison sentence.
  • Boesky is permanently banned from the finance industry.
  • Ed (on the personal impact): “What if you got banned from comedy?” (50:57)
    • Rory jokes about running a coffee shop or coaching college soccer in its place.

9. Consequences and Reflections (52:26–57:01)

• Boesky, despite the penalty, retains “enough money to just go and coast”—a happy retirement, in Rory’s cynical view.
• Ed corrects the notion of victimless crime:
  • Ed: “These deals… demolished companies and put thousands of people out of work… these are not victimless crimes… there’s a massive price to be paid, and it’s being paid by working-class people.” (52:44–54:14)

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Notable Quotes & Memorable Moments

• On the 1980s:
  Ed: "I'm just going to say a word that I associate with the '80s. Cocaine." (12:21)
  Rory: "That's where the art community and Wall Street found common ground." (12:28)

• On Greed:
  Ed (reciting Boesky's speech): “Greed is all right… I think greed is healthy. You can be greedy and still feel good about yourself.” (36:02) Rory: “It has echoes of this… empathy is bad…” (36:48)

• On Downfalls and Accountability:
  Ed: “Absolute power corrupts absolutely… it’s very disheartening.” (40:00–41:04) Rory: “That’s why I like the brass rail bars… just keep me in that pocket where I can just go get a beer in a pint glass. I don’t want to run the world.” (41:51)

• On Justice in White-Collar Crime:
  Ed: “Maybe that’s not fair. Maybe that’s not enough, you know?” (54:14)
  Rory: “Now it doesn’t even like two years almost seems insane to get any kind of a penalty whatsoever. And you’re right, it’s the blue collar working class that pays for it.” (54:29)

• On Modern Parallels:
  Ed: “The playbook hasn’t changed since then… Boesky believed winning proved he was right. And once you convince yourself of that, the rules feel optional, which is very much the energy of this Trump administration.” (55:11–55:34)

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Timestamps: Segment Highlights

• [02:40–05:05] — Rory’s comedy tribute to Ed, Vacation
• [08:09–12:21] — Wall Street, Gordon Gekko, and the “greed is good” ethos
• [13:16–18:26] — Boesky’s Detroit roots, father-in-law conflicts, “Ivan the Bum”
• [20:10–21:14] — The quirks, intensity, and sleep deprivation of Boesky
• [24:44–27:00] — Arbitrage explained; how Boesky disrupted the field
• [29:51–31:19] — Wealth gaps—a then-versus-now perspective
• [35:59–37:20] — The real “greed is good” speech and its modern echoes
• [43:11–44:45] — Insider trading, both legal and illegal
• [44:57–47:56] — The SEC investigation, Giuliani, and Boesky’s cooperation
• [52:44–54:14] — “Victimless” crimes and their very real human costs
• [55:34–56:31] — The “winning is everything” mindset and Trumpian parallels
• [56:31–57:01] — The rarity of true accountability

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Tone & Style

• Warm, bantering, self-deprecating tone from both Ed and Rory; serious topics are dealt with humor and candor
• Accessible explanations of Wall Street mechanics, blending history with pop culture
• Honest reflection on modern power, consequences, and corruption.

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Final Takeaway

Through the lens of Ivan Boesky’s wild ride from “bum” to billionaire to convicted criminal, Ed Helms and Rory Scovel illuminate the contagious allure—and enormous human cost—of greed without guardrails. The episode closes with both hosts reflecting on the persistent lack of meaningful accountability for high-level white-collar misdeeds, and how history’s SNAFUs remain urgent cautionary tales for our own era.

“Having done tons of these stories about major snafus… the one thing that rarely happens is accountability of any kind. And in this case, even two years of prison is like, thank God he got something… it feels like a little small morsel of justice, not like full justice.” — Ed Helms (56:31)

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Missed the episode? This summary covers all the major beats, memorable moments, and key reflections for your water cooler or podcast club conversations.

Transcript

[Rory Scovel]

It's very seldom I run into someone who I really think is just kind of a piece of shit. I go for the most part, everybody's just at their job, whether they're wildly famous or not, and they're just trying to do the job and then go home and hang out with their family. It's just kind of our universal situation.

[Ed Helms]

Well, you know what that means, Rory. That's me. You're the piece of shit.

[Rory Scovel]

Oh my God. Foreign.

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[Ed Helms]

Hello and welcome to Snafu your favorite podcast about history's greatest screw ups, or if we're being completely honest, a show about the spectacular hubris of humanity, the epic disasters it creates, and the lessons we like to pretend we can learn from them. I'm your host, Ed Helms, and my guest today is a very funny comedian, actor, writer, and podcast host. He released his first comedy album, Dilation, in 2011 and pumped out not one, not three, but six different standup specials, the most recent of which Religion, Sex, and A Few Things in Between you can find on HBO Max. He's appeared in a variety of film and television programs with a particularly standout performance opposite Rose byrne in Apple TV's physical, which is a fucking awesome show, by the way.

[Rory Scovel]

Nice.

[Ed Helms]

Yes, indeed. And he's set to appear in a new ABC show called do youo Want Kids? And I think I also just saw a trailer that had you in it for my buddy Steve Carell's new show, Rooster. That's right. So please welcome to the pod, the amazing Rory Scovell.

[Rory Scovel]

Thank you very much for having me. I've gotta say, Ed, I have waited to see you face to face because this was the only way to tell you this, but Vacation is potentially one of the funniest movies that I have seen in. I do not. I don't know how long, but I have not seen a comedy where literally every five minutes, I sort of need to pause the movie to collect myself. And I have shown so many people that movie, and I tell them, you will cry laughing, and it's so true. I loved that movie so much.

[Ed Helms]

You are this. You're gonna make me cry right now.

[Rory Scovel]

You're really touching me.

[Ed Helms]

And I'll tell you why. Because I and the writer directors of that movie have long felt that that movie, like, we are so proud of it. It is. It's a movie we loved making. We love the product, and it just didn't capture the audience that we. That we hoped for. And so when I get these little nuggets of affirmation like that, I really appreciate it. That really means a lot.

[Rory Scovel]

You guys should absolutely be proud of it. Just given the fact that it's not comedically predictable, it's not hacky, it's not like the cringy comedy that you can find out there, which is fine. The fact that it actually is just so. Moments of that car is so stupid.

[Ed Helms]

The car is so funny. There's a key fob with a million buttons on it. And Christina Applegate goes, is that a swastika? And I Just say, yeah, we won't use that. What is that?

[Podcast Announcer]

What is that?

[Ed Helms]

What?

[Rory Scovel]

It's great.

[Ed Helms]

All right, well, enough about me. We're here to talk about you. First of all, I've actually known you a long time. Not. Well, we've bumped into each other over the years. But I have a very borderline offensive question for you, which is, do you say your last name Scovel or Scovel?

[Rory Scovel]

I say Scoville, which I'm going to go and say is correct, but that's my. So many versions of it.

[Ed Helms]

Right, Scovel.

[Rory Scovel]

Yeah.

[Ed Helms]

Good. Because I am Southern, so I have all these little, like, contractions. I say things like my friend Eleanor. I say Eleanor and Scoville and that sort of thing, but I'm always conscious that I'm probably doing it wrong as well. Where are you from originally?

[Rory Scovel]

The South. From South Carolina. Greenville.

[Ed Helms]

Oh, right on.

[Rory Scovel]

Eleanor is exactly right.

[Ed Helms]

Even though it's spelled with an oh Y pronounced with an I or even an apostrophe. An apostrophe R. Eleanor. Eleanor.

[Rory Scovel]

Yeah, that R comes in quick.

[Ed Helms]

You're rapidly becoming an American treasure. And, yeah, I. I love.

[Rory Scovel]

This is the best podcast I've ever been on. We should just do this.

[Ed Helms]

This is called Butter Us Up. We just. We just compliment each other, Boys with Edward. Butter Boys. How great are you? That's what this is called. No, but it's fun when I have people on that I think are awesome like you. So you have a new podcast also. You're getting into this space. Starting to horn in on MySpace.

[Rory Scovel]

That's right.

[Ed Helms]

A little bit. What is it? Tell me more.

[Rory Scovel]

It's a show called Crimeless. I do it with journalist Josh Dean. And yeah, he basically not so unlike this show. Just in the world of crime stories and stupid criminals throughout history and throughout the world, Josh kind of reads me a story about, can you believe this bonehead, you know, criminal story? And I'm just hearing it for the first time and commenting on it, and I love it. I'm shocked every time that. I mean, I'm not shocked, and I am shocked that 95% of the stories are from Florida, but that's just the reality of it. But, yeah, it's out now, and it's been super fun to do, and Josh is a great co host.

[Ed Helms]

Cool. I am psyched to check that out. And it's also a perfect segue into what we're about to do. I'm about to talk to you about this snafu. And in this particular case, it is also A crime.

[Rory Scovel]

Perfect.

[Ed Helms]

Have you seen the movie Wall Street?

[Rory Scovel]

I've seen the movie Wall Street.

[Ed Helms]

Okay. With Michael Douglas and Charlie Sheen, Daryl Hannah. It's Oliver Stone movie. It's phenomenal. So the guy that Michael Douglas plays in that movie, who's like a corporate raider and like a Wall street tycoon, he's based loosely, but he is based on a real guy. Is this. Does this ring any bells for you?

[Rory Scovel]

No, I. I don't think I. I don't think I was aware of this. No.

[Ed Helms]

Okay, so this is a Wall street legend of sorts. It's just one of those really epic stories about a man who rose from rags to riches and then plummeted from riches to an orange jumpsuit. Our man of the hour is Ivan Boeski, and he was considered widely thought to be the direct inspiration for Michael Douglas. Very slippery 80s villain, Gordon Gekko. We have a photo of Mr. Boesky here.

[Rory Scovel]

It just seems like.

[Ed Helms]

I think that I've seen other pictures of him where his eyes look normal. So I'm just gonna guess that's a weird. He's either winking or it's just one of those weird, weird moments that cameras get. But there's a slickness to this guy.

[Rory Scovel]

And look at his skin.

[Ed Helms]

Yeah, he's got game show host vibes. He does. He kind of looks like he'd be

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fun to hang out, have a beer with.

[Ed Helms]

I'll be honest. That's right. Well, we're going to learn why he might not be somebody that you wanted to hang out with. Also, funny footnote, he's wearing a black suit and a white shirt in this picture. And that was his go to every single day. And someone asked him at one point, why do you wear the same suit and shirt every day? And he said, I have enough big decisions to make every day. This is one I can just take off the list. Which is funny because Einstein is also famous for that. Albert Einstein always wore the same suit and shirt for the same reason. It's just like, take it off your plate. Right.

[Rory Scovel]

It makes sense. It makes. I don't know if you do that. I don't do it for those reasons. When I wear the same clothes, it's clearly like a lazy sort of.

[Ed Helms]

When I wear the same clothes every day, it's problematic. It's a bit of a red flag.

[Rory Scovel]

There's stains.

[Ed Helms]

It happens that you have to explain.

[Rory Scovel]

Right.

[Ed Helms]

Here is Michael Douglas famous piece of dialogue from Wall Street. He's giving a big speech to stockholders meeting for a big company, and he's, he's walking the aisle with a microphone and he's, he's tons of gravitas and he's just saying greed, for lack of a better word, is good. Greed is right. Greed works. Greed clarifies, cuts through and captures the essence of the evolutionary spirit.

[Rory Scovel]

Yeah, yeah, yeah. I think we know now the state of our politics that he was right. It's going great. It's going so good.

[Ed Helms]

He's all right. What he left out is. And all of that sucks. And that the consequences of all of this is not good.

[Rory Scovel]

The end game of this is devastating. Exactly.

[Ed Helms]

So today we will find out what that spirit conjured throughout the 80s. Of course, your show Physical takes place in the 80s. That's right. How do you, how would you capture the spirit of the 80s? How would you describe it?

[Rory Scovel]

I don't know. I feel like it's almost a good. I feel like that that's why there's something to his speech in that movie. Because it's almost like the 80s was like you can get up and you can create your own future and greed and wanting to do it and having to step over people to pull it off is a great way, is a great start. And then the other side of it feels like Cyndi Lauper and Madonna, which I feel like I identify with more in my, in my spirit of what I like to envision of the 80s. But as far as business. Yeah, I think it was like that also.

[Ed Helms]

I'm just going to say a word that I associate with the 80s. Cocaine. Yeah, lots of it. Yeah.

[Rory Scovel]

And that's, and that's what crossed the aisles. That's where the art community and the Wall street found common ground. Am.

[Ed Helms]

All right, well, let's get into Ivan Boeski a little bit. He starts out modestly, born in 1937. He grew up in post war Detroit, the son of a Russian immigrant who ran delis and old school brass rail bars, which is those blue collar taverns fueled by rye bread, cigarettes and cheap liquor and a little fun Detroit footnote. Boesky attended Mumford High School. Does that mean anything to you? No. Mumford High School later achieved pop culture immortality thanks to Eddie Murphy's gray sweatshirt in Beverly Hills Cop.

[Rory Scovel]

Oh yeah, okay.

[Ed Helms]

He has a Mumford sweatshirt. I love that. Yeah, well, so Boesky actually went there. From the sounds of it, Ivan strove for more. There's a peculiar quote from his second cousin found in a Time magazine article. He had this capacity for single mindedness. He drove himself mercilessly as Far as

[Rory Scovel]

exercise goes, that's the most unfair, unrelatable sentence I've ever heard.

[Ed Helms]

Yeah. He goes on to talk about how he does hundreds of push ups, which is odd, but I guess speaks to a driven sort of character as a young man. Have you ever watched someone with incredible focus and drive and just thought, that's really impressive before realizing that's the energy that also is wrecking everything? Yes.

[Rory Scovel]

But also they almost seemed. You can't picture them laughing or saying something originally funny, or you just. They almost feel like carbon copies of carbon copies of people. Yeah, I know what you mean. I don't understand that drive.

[Ed Helms]

It's a little bit Elon Musk's arc, right?

[Rory Scovel]

Yeah.

[Ed Helms]

It feels like he was this incredibly inspiring, kind of relentless innovator. And then. Whoa, whoa. It just went so.

[Rory Scovel]

Yeah.

[Ed Helms]

So far over the. The line.

[Rory Scovel]

Yeah.

[Ed Helms]

At some point.

[Rory Scovel]

Yeah. The ambition gets taken away or just takes off way too far. I also think some kids. Speaking of the 80s, I think you watched movies. I think there's a lot of us that saw something like the Karate Kid and wanted to be Daniel LaRusso. And then some people were like, no, I want to be Johnny. I want to be the blonde headed dude who's clearly a bad guy. And it's. You see that in their lives.

[Ed Helms]

That's so interesting. I mean, I definitely. When I saw those guys jumping motorcycles around in their skeleton Halloween costumes, I was like, I definitely want to be that.

[Rory Scovel]

Right.

[Ed Helms]

But when Daniel LaRusso, like, kicks him in the face with the. The swan kick, I'm like, yeah, that's who I want to be.

[Rory Scovel]

You're like, that's the guy.

[Ed Helms]

Yeah.

[Rory Scovel]

Yeah.

[Ed Helms]

While in school, Boesky married seema Silberstein in 1962, daughter of real estate lawyer and hotel tycoon Ben Silberstein. We could probably actually do a whole story on Silberstein. He is fascinating in and of himself. Himself. But here's a quick anecdote. Allegedly, when he was younger, he was turned away from the Beverly Hills Hotel. On a subsequent visit with his youngest daughter, Muriel, she exclaimed that he thought he should simply buy the place. And so he did. Yeah, I guess it's kind of a fuck you. He just bought the hotel for $5.5 million in 1954.

[Rory Scovel]

Oh, my God.

[Ed Helms]

That's. That's just over 66 million today. And I think it's worth a lot more than that. Safe to say Boesky was well aware of this class differential he was marrying into and really wanted to prove Himself. After graduating from the Detroit College of Law, he drifted through a series of soul suck gigs. Law clerk, accountant, kind of rinse and repeat. None of it sticking, none of it's satisfying. Then his father died. In 1964, Boesky took over the family's last Brass Rail bar and rebranded it

[Rory Scovel]

Le Club a Go Go no.

[Ed Helms]

And brought in like topless dancers and all. Made it a kind of tawdry, salacious affair. And of course it was bankrupt within two years.

[Rory Scovel]

God, the Brass Rail bar is so fun. Every time I like hear that, I think of Rudy when his dad threw him and his brother out of the bar. When all the guys were off work at the mill and they were just drinking at the bar. And then Rudy was, Sean Astin was doing something and his dad told the owner to throw them out. It lives in my mind forever because I thought, why don't you just tell your son to leave the bar? Why does the owner have to now get involved in throwing your kid out of the bar? But I always picture that, that 5pm blue collar guys in their, their, you know, destroyed clothing from working at the mill, just having beers and it just seems so cozy.

[Ed Helms]

Now introduce like, like a, like a burlesque dancer to that vibe. Yeah. And it was not successful this wi it. It went bankrupt in two years. Bosi at the time was not exactly happy. His father in law would constantly let him know how unhappy he was with his daughter's choices. He nicknamed Ivan Boeski Ivan the Bum and openly referred to him as a ne' er do well who would amount to nothing. Which is kind of, kind of a brutal way to talk to your son in law.

[Rory Scovel]

I feel like Ivan Brokski was right there for the taking and he went with the bum.

[Ed Helms]

Yeah. Oh gosh, you're going to be a tough father in law.

[Rory Scovel]

I'm excited with that kind of nicknaming. Yeah. Love it for the nicknames.

[Ed Helms]

This is an interesting one. How much of a person's identity or ambition gets shaped by all the people shouting at them that they're a failure?

[Rory Scovel]

Of course. Oh my God, absolutely. I mean, that's the core of representation in entertainment and how you're represented in entertainment and who you are that you, you know, when you start to identify with people who look like you or you feel like you relate to, like that's what inspires the idea that you think, well, I'm just meant to be a failure or I can be a success, you know, for sure. But you're right, like criticism like that it starts to become your reality.

[Ed Helms]

Yeah. It can either. It can either destroy someone or, like, give them, like, very intense fuel.

[Rory Scovel]

Yeah. And.

[Ed Helms]

And I would. I would also say that's probably not, like, good fuel, healthy fuel, vengeful.

[Rory Scovel]

Vengeful fuel. Right. Yeah.

[Ed Helms]

It's like, I want to be a success not because I want to, like, have nice vacations with my family. It's because I want to make this other person feel like, yeah, a hotel

[Rory Scovel]

when they refuse service. That really puts me in my place. I couldn't do that at a gas station or a. If I went to a fast food place and they disrespected me, I'd be like, you just wait, I'm gonna buy this place. I'm gonna need about 20 years just to kind of get the green together, but I'll show you.

[Ed Helms]

Well, needless to say, Boesky was extremely motivated, in part probably to best his father in law. He and Seema moved to the Big Apple. Now, Rory, that is a Wall street term for New York City.

[Rory Scovel]

Okay. You said we were going to learn today. You said that.

[Ed Helms]

The Big Apple. Make a note of it.

[Rory Scovel]

Yeah.

[Ed Helms]

Now, I guess father in law Silberstein was at least kind enough to put them up in a Park Avenue apartment. He even bankrolled Boesky's first company with $700,000. This was 1975, and Ivan had found his passion and promise on Wall Street. He was an incredibly hard worker, allegedly clocking 20 hour work days. This is an interesting thing that sort of emerges in a lot of biographical material about him. He never ate. He would go to these big functions and meals or host big things. Dinner and this, that, and like, no one ever saw him eat. He would have, like, a grape or, like, little nibbles of things. And he was like, as we mentioned before, relentlessly working out. Just like a very intense guy. And also never slept. It's just one of those weird vampire dudes who can like, like, I have my sleep tracker. And if it's like, less than eight hours, I'm just like, oh, God, this is gonna be a hard day.

[Rory Scovel]

Yeah, your day's ruined my day.

[Ed Helms]

Sorry. I go into the day already like, I'm half a tank, guys.

[Rory Scovel]

And you're like, if I could just get three pastries in my body, I bet I could find some fuel in there.

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[Ed Helms]

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[Redfin Advertiser]

Let's talk about modern home shopping. It's sort of become a fun side hobby, right? Scrolling listings at night, dreaming about kitchens you've never seen or backyards you haven't even stepped foot in. All from the comfort of pretty much anywhere. Redfin knows a lot of people like you want to own but are stuck in this browsing mode loop. That's where Redfin flips the script. With listings that update within minutes and tours you can book right from the Redfin app, you can see your dream home the moment it appears. Now, liking a listing is easy, but actually landing it? That's where Redfin comes in. Redfin has over 2200 agents with local expertise, and Redfin agents close twice as many deals as other agents. That means they want to help you win. Not just window shop. Redfin is built to help you go from just looking to wait. This could actually be home. So become the newest neighbor on the block. Visit redfin.com to start finding and start owning. That's redfin.com Wasn't that delicious?

[Podcast Announcer]

So good.

[Wells Fargo Advertiser]

Your bill, ladies.

[Redfin Advertiser]

I got it.

[Podcast Announcer]

No, I got it. Seriously, I insist.

[Rory Scovel]

I insisted first.

[Podcast Announcer]

Don't be silly. You know me, silly.

[Wells Fargo Advertiser]

People with The Wells Fargo ActiveCash credit card prefer to pay because they earn unlimited 2% cash rewards on purchases.

[Redfin Advertiser]

Okay.

[Podcast Announcer]

Rock, paper, scissors for it. Rock, paper, scissors.

[Rory Scovel]

Shoot. No.

[Wells Fargo Advertiser]

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[TurboTax Advertiser]

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[Ed Helms]

Ivan Boesky was very dedicated to sort of carving out his place on Wall Street. He was not a traditional investor. He, he worked in a space known as arbitrage. So traditional investing is like planting a tree. You buy a stock and you believe in the company and you hold it for a long time believing that this company will grow. Stockbrokers will research companies in order to sort of know which companies have the best chances of growing and accumulating value. Arbitrage is a different kind of investing. It's all about timing. It's fast in and fast out. So you buy something that you think is temporarily underpriced and then sell it the minute the, the price correct. So it kind of works like this. You would find a small company, something that has like a, a sort of special or obscure value. Maybe it's a product or a service or an expertise of some kind and it, but it's something that a bigger company would want. Then you figure out that a takeover by this bigger company or, or any number of bigger companies is likely before the public catches onto this. And you buy a ton of shares of this small company while the stock price is relatively low. Then when this takeover happens and is announced, the stock price jumps and you immediately sell. Yeah, it has nothing. There's no loyalty. You're not, there's no belief in the company. You're just trying to spot the moment when the price is about to change and be there first. It's one of the most risky kinds of investing. And at the time, most arbitrage players were very cautious. Small bets, careful math, lots of hedging. But Boesky was not built this way. He just went big. He pushed harder, he took huge risks that others wouldn't touch. And as the 70s sort of turned into the 80s, this, all of his bullheaded bluster turned him into a force of nature. He was also incredibly smart and gifted at, you know, market analysis. And somehow Ivan Boeski just kept crushing it.

[Rory Scovel]

Every time you say Boesky, I only picture Michael Douglas. Anyways, eating. Honestly, just eating the raw meat that he gets at that restaurant.

[Ed Helms]

That movie was so good. I need to rewatch that.

[Rory Scovel]

I mean, when he stands on the balcony at the apartment and Charlie Sheen just yells out to the city, who am I?

[Ed Helms]

Yeah.

[Rory Scovel]

It's like we've all been there.

[Ed Helms]

Been there. Did you live in New York City at any point?

[Rory Scovel]

I lived there for four years. And then what?

[Ed Helms]

When was that?

[Rory Scovel]

I was there. 07 to 2011.

[Ed Helms]

Ah, right after me. I, I was there 96 to 2007.

[Rory Scovel]

Basically I was there when I lived there. I was at all those Del Close marathons watching you guys. That, that, those that won that venue was incredible. But those are some of my happiest memories from comedy. Just going and watching.

[Ed Helms]

Amen.

[Rory Scovel]

Insane improv at the Del Close marathon.

[Ed Helms]

Yes.

[Rory Scovel]

Like three in the morning.

[Ed Helms]

Yes. It was so, it felt so punk rock 100. Right. And that was like. That's what I loved about it is like there were, there were a lot of like, like, I've always been pretty nerdy and like clean cut. But like, I value punk rock. I value the weirdos and the people on the margins. I just think that they're such a marvelous part of our culture and society. And then you have an institution like the Upright Citizens Brigade that just brings it all together somehow. And you have buttoned up comedians performing next to just the wildest performance art wackadoos.

[Rory Scovel]

Yeah.

[Ed Helms]

And it's just pure joy.

[Rory Scovel]

Ah, I love it. 100 agree.

[Ed Helms]

We're now in the midst of the mid-80s. We're talking Lycra leggings, Tom Selleck's mustache, and everyone's asking, where's the beef? Because of the Wendy's commercial. Yeah, it was Wendy's.

[Rory Scovel]

Oh, I don't know. Is that where it came from?

[Ed Helms]

Where's the beef? Yeah. Like a little old lady opening up her hamburger and it's like a tiny little meat patty.

[Rory Scovel]

Yeah.

[Ed Helms]

In 1981, the Ivan F. Boesky Corp. Was rolling in it, making more than $150 million in profits from short runs on CBS, Gulf Oil and Conoco. According to Vanity Fair, $150 million was more money than Ivan's father in law ever had.

[Rory Scovel]

Perfect.

[Ed Helms]

So I guess some, some nice warm com.

[Rory Scovel]

The evolution of the human spirit right there.

[Ed Helms]

Yeah, exactly.

[Rory Scovel]

Just gotta get above that number.

[Ed Helms]

Oh, just gotta win. I just gotta win.

[Rory Scovel]

Yeah.

[Ed Helms]

At whatever cost to my soul. It's fine. So Ivan is raking it in. By the spring of 1985, he was reportedly the highest paid broker on Wall street with a net worth of over $280 million, which is nearly 840 million in today's dollars, which I just want to point out. $840 million like in today's money is not considered, you know, the, the crazy wealthy. The crazy. You have to be a billionaire to be crazy wealthy. And that's a comment on like in the 80s, as much money and excess as, as these guys are engaging in, we're still not in a culture with the wealth gap that we have today. Yeah, right. The wealth gap has just like exploded. It's exploded since the 80s. But it's just interesting to me that we're talking about these guys as if they're Jeff Bezos or, or Elon Musk or Zuckerberg, but they're not even close to that by comparison.

[Rory Scovel]

And yet still titans in their own

[Ed Helms]

time of the day. They were that.

[Rory Scovel]

And I think it's that trickle down economics of the 80s where people are like now give all this money, give it up here and you'll get it back. It'll come back to you. Yeah, I know what you mean. Like that wealth gap is massive now. And I think there's something to the 80s of like yeah, this is what really lit the, lit the fire.

[Ed Helms]

Yeah. Boesky held a spot on the Forbes 400 list of America's wealthiest people. He ran his firm with real intensity, ferocity, orchestrating like a real high pressure operation of roughly 100 employees. His self promotion was legendary. He hired his own PR firm to help promote himself. His, his self promotion tour included press for his his own book written with the aid of journalist Jeffrey G. Madrick called Merger Mania Arbitrage. Wall Street's best kept money making secret. And yeah, you know that big old shit eating grin right on the front.

[Rory Scovel]

It's so funny like a book like that. You're like, just like, just considering where I grew up in like South Carolina. Like my dad worked at the post office. Like is anybody the post office? You read this? Money Mania. Arm. Yeah.

[Ed Helms]

Merger. Merger Mania.

[Rory Scovel]

Merger Mania. Yeah. Book about Wall Street.

[Ed Helms]

Yeah.

[Rory Scovel]

I feel like you just explaining investing in companies, getting in and getting out is probably the biggest lesson I've gotten in my life. What it even is to me it's just a circus that I can't understand.

[Ed Helms]

Yes, I agree. I find it all very like brain mangling. Using Venmo without cash back is like

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[Ed Helms]

of brands every 30 days.

[Venmo Advertiser]

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[Redfin Advertiser]

Let's talk about modern home shopping. It's sort of become a fun side hobby, right? Scrolling listings at night, dreaming about kitchens you've never seen or backyards you haven't even stepped foot in. All from the comfort of pretty much anywhere. Redfin knows a lot of people like you want to own but are stuck in this browsing mode loop. That's where Redfin flips the script. With listings that update within minutes and tours you can book right from the Redfin app, you can see your dream home the moment it appears. Now, liking a listing is easy, but actually landing it? That's where Redfin comes in. Redfin has over 2200 agents with local expertise, and Redfin agents close twice as many deals as other agents. That means they want to help you win. Not just window shop. Redfin is built to help you go from just looking to to wait. This could actually be home. So become the newest neighbor on the block. Visit redfin.com to start finding and start owning. That's redfin.com Wasn't that delicious?

[Podcast Announcer]

So good.

[Wells Fargo Advertiser]

Your bill, ladies.

[Redfin Advertiser]

I got it.

[Podcast Announcer]

No, I got it. Seriously, I insist.

[Rory Scovel]

I insisted first.

[Podcast Announcer]

Don't be silly. You don't be silly.

[Wells Fargo Advertiser]

People with the Wells Fargo Active Cash Credit card prefer to pay because they are earn unlimited 2% cash rewards on purchases.

[Redfin Advertiser]

Okay.

[Podcast Announcer]

Rock, paper scissors for it. Rock, paper, scissors. Shoot.

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No the Wells Fargo Active Cash credit card. Visit Wells Fargo.com ActiveCash Terms apply.

[TurboTax Advertiser]

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[Ed Helms]

In 1986, Boesky was invited to provide a commencement speech at the University of California at Berkeley, Haas School of Business. And this is where that speech that was the inspiration for Gordon Gekko's infamous framing was derived. But it's not exactly the same as Gordon Gekko's. What he said is, greed is all right. By the way, I want you to know that I think greed is healthy. You can be greedy and still feel good about yourself. This sounds like a cult leader. It's weird. You know what? It has echoes of this. This. This. All this stuff emerging from both the Christian nationalist movement and Elon Musk, where it's like, empathy is bad, right?

[Rory Scovel]

Yeah, yeah, yeah.

[Ed Helms]

This is saying the same thing. In the sort of inverse, greed is good. Self interest is good. It's very and randy in that way. Like, it's just.

[Rory Scovel]

It's very. Discard the seven deadly sins and move on. Greed is okay. It's fine.

[Ed Helms]

Right?

[Rory Scovel]

It's fine. Right, Right. Y.

[Ed Helms]

The Bible literally tells you that this is a deadly sin. Yeah, it's one of them.

[Rory Scovel]

I'm saying this. This is destructive to you personally and to all of people, but if you want to have an elevator in your house, you gotta have a little bit of it.

[Ed Helms]

Yeah, this is. I love the last sentence. You can be greedy and still feel good about yourself. That's awesome.

[Rory Scovel]

Yeah.

[Ed Helms]

Okay, so all of this is going on, and all of a sudden, record scratch. Just months after riding high, it all unraveled. On November 14, 1986, Ivan Boesky pleaded guilty to conspiring to file false trading records, which is a complicated way of saying insider trading. Basically, Time magazine put his grinning face on the COVID and dubbed him Ivan the Terrible, which is a little derivative, but okay.

[Rory Scovel]

It's still better than Ivan the Bum from the Father.

[Ed Helms]

Sure not. And not as good as Ivan Brokski.

[Rory Scovel]

Right? That's right.

[Ed Helms]

One minute this guy is Wall street royalty, the next, he's a cautionary tale. And the high roller era was over, he is headed to prison. Do you think that repeated success always turns people into egomaniacs or, like, just disasters? Is it possible to remain humble?

[Rory Scovel]

I think it's possible to remain humble based on, I think, how much you've acquired as a person before you've reached that success. For instance, I think a lot of people in our industry who find fame or fortune later in their careers tend to be so much more. A little more chill and fully aware that life is fickled and it can go away. And yesterday I was doing this job, and today I'm grateful I've got this one. But I think when you have it at a young age, and nothing against those people that get it at a young age because they are missing that. That sort of educational step, I think a lot of times they can come off as. As awful people, and maybe it's. Something happens and they turn a corner and they change. But you definitely see it in people who come from a certain background. I think it's just learning the value of. Of things, for sure. But I think people can remain humble. I tell people all the time that, like, friends back home or people who ask me if I've worked with someone, they always want to know if someone's a jerk. I go, I gotta be honest. It's very seldom I run into someone who I really think is just kind of a piece of. Yeah, for the most part, everybody's just at their job, whether they're wildly famous or not, and they're just trying to do the job and then go home and hang out with their family. It's just kind of our universal situation.

[Ed Helms]

Well, you know what that means, Rory?

[Rory Scovel]

What?

[Ed Helms]

That means you're the piece of shit.

[Rory Scovel]

Oh, my God. Shit.

[Ed Helms]

If you can't actually see how much other people are a piece of shit, it means you're a giant piece of shit.

[Rory Scovel]

Oh, fuck. I just thought they were so fun. I looked up to all of them.

[Ed Helms]

I mean, our industry, obviously, is a very hot crucible of all of this stuff. But I think also, just looking into the business world and seeing especially these modern tech titans and your Jeff Bezos and so forth, it's really amazing. You can chart their values and their appearance, their physical appearance, how it changes over time with their power and wealth. And it's very disheartening, the notion that absolute power corrupts absolutely. Really. Seems to hold a lot of water.

[Rory Scovel]

Yes, 100%. And also, you do wonder in the origin story, right, of these billionaires or tech titans, you do wonder, are they coming from a Place of sort of like, Ivan. Like, was it vengeance? Were they like, oh, I'll show this world I have value, and I'll become this. Because I think the world has treated me this way. There's such an irony to then becoming a billionaire who kind of, in many ways, runs the world and not having compassion for who might also be what you once were, but instead being like, no, those people are trash.

[Ed Helms]

Like, what? Well, that's what you. Right. We have pictures of you. Yeah, we have. We have pictures of Jeff Bezos as the sweetest little nerd.

[Rory Scovel]

Yeah.

[Ed Helms]

So. So bizarre.

[Rory Scovel]

I think that's why I like the brass rail bars. Just keep me in that pocket where I can just go get a beer in a pint glass. I don't want to run the world.

[Ed Helms]

Don't limit yourself, Rory. You can't. We want you to run the world.

[Rory Scovel]

I mean, it'd be more fun. Yeah. I'll tell you, that Burning man wouldn't be just a week. It wouldn't be just one week in one location. I'll tell you that.

[Ed Helms]

Welcome to Rory's world. All right, so how did we get here? How did this epic crumble of a. Of a Wall street titan occur? It starts in 1982, when Eboski took a brutal hit, losing $60 million on a bad deal. Again, that. That's a lot of money. But it was way more back then. Suddenly, this guy who always seemed to be one step ahead was underwater. And that's when the line started to blur. The pressure mounted, the bets got darker, and Boesky crossed into insider trading. Is there anything more human than trying to recover from a humiliating loss by just immediately making a series of worse decisions?

[Rory Scovel]

It is true. It's our common bond.

[Ed Helms]

It's such. It's what makes us all human.

[Rory Scovel]

Yeah.

[Ed Helms]

Even on a small scale. I just feel like if you spill something in your lap and then your panic makes you spill, like, so much more shit. God. So now it's 1985, and Boeski's having an amazing year, and so were a lot of other savvy traders, all raking in millions. In fact, they were winning so hard that it was beginning to feel an awful lot like somebody knew something somewhere that somehow was tipping off those someones with some slick insider gravy. Basically, regulators began to suspect that the stench of insider information was bubbling up from the sewage of these multimillion dollar deals. Quick Wall street check in. Do you understand what insider trading is? Conceptually?

[Rory Scovel]

I think so. For instance, your example earlier about a business Being acquired by another business and finding that out and deciding, all right, let's buy low so we can sell high, because we know it's coming.

[Ed Helms]

Right. So the, the honest way to do that is to, like, just do your research and your homework and try to figure out which companies are going to get bought.

[Rory Scovel]

Yeah.

[Ed Helms]

The illegal insider trading is for someone who knows a company is about to be bought to like whisper it to you. So you can then go and buy those shares and then as soon as the company's bought, the value of those shares just like, rockets up.

[Rory Scovel]

Yeah. It seems like it's very legal now because it seems to occur quite often, including the White House directly.

[Ed Helms]

Well, it is. It's so ironic. And of course, within Congress, so many Congress people, people have so much access to what is considered inside information.

[Rory Scovel]

Yes.

[Ed Helms]

Because they know about laws that are coming that will dramatically affect these various companies and industries, and they can invest accordingly. And they do. And it is so dark. And the irony is that the securities and Exchange Commission, which is tasked with catching these people and bringing them to justice, they now have incredible analytics and tools to catch people doing this stuff and to catch sort of suspicious activity and then be able to research massive amounts of data more quickly. Like, the tools to catch these people are better than ever. And yet it feels like we're just swimming in it more than ever, which is insane.

[Rory Scovel]

All the time.

[Ed Helms]

Yeah, yeah, yeah. So these investigators back in the day, they, they, they thought they smelled something. And they were exactly right. According to Fortune, it was in 1985 that the SEC began to unravel a tangled web. Beginning with two Merrill lynch employees in Venezuela. The SEC managed to connect them to high profile investment banker Dennis Levine, among others. And it was Levine who then? Levine gave up the gossip on Gordon Gecko. I mean, Ivan Boesky. Levine had struck a deal to cooperate with the U.S. attorney of the Southern District of New York, who was. Wait for it. Rudy Giuliani.

[Rory Scovel]

Oh, wow.

[Ed Helms]

This, of course, is pre mayoral, pre disbarred, pre Four Seasons total landscaping. Giuliani.

[Rory Scovel]

The Four Seasons thing will live forever.

[Ed Helms]

Oh, my God. Just.

[Rory Scovel]

Yeah. But to then act like you meant

[Ed Helms]

to do it, the abject stupidity of it all. And the. It's so shocking.

[Rory Scovel]

Yeah.

[Ed Helms]

And shocking to think there was a time when he was actually on the right side of things like this was he was actually doing good work as the attorney for the Southern District of New York and was beloved.

[Rory Scovel]

Yeah. Yeah.

[Ed Helms]

So Levine admitted to providing Boesky with non public information about pending deals. And this was Enough to bring Boesky in, and they caught him red handed. Then, interestingly, Boesky would make a deal of his own with the Department of Justice, and this would lower his prison sentence from five years to three. Not only did he wind up paying $100 million, which at the time was a record high penalty for such criminal activity, he also agreed to tattle on other traitors by secretly recording them and turning them over to authorities.

[Rory Scovel]

He's one of those guys. He narked.

[Ed Helms]

He narked, he ratted, he turned, he did bad things and then tried to get off the hook by doing

[Rory Scovel]

bad

[Ed Helms]

things to other bad guys, I guess.

[Rory Scovel]

Yeah, yeah.

[Ed Helms]

And it's very morally ambiguous.

[Rory Scovel]

You don't know how to feel about it.

[Ed Helms]

Yeah. Because you don't like rats. Rats are like, they're the worst. They're turncoats. But, like, oftentimes they're on the morally and ethically correct side of things.

[Rory Scovel]

Yeah. You should. You actually should admire them, but you're

[Ed Helms]

like, no, no, now I respect you even less.

[Rory Scovel]

Yeah. You should have been a criminal to begin with. Yeah. But now that you are one, leave the other criminals alone.

[Ed Helms]

I think it's the cynicism of it. Right. It's like, it's not coming from a good place.

[Rory Scovel]

Right? Yeah.

[Ed Helms]

Yeah. There you go. The fall from grace was swift and merciless. In the 1986 Times article, an unidentified friend of Boesky's is quoted. He wanted so much to be accepted, and he thought money was the only way. That's kind of poignant, actually.

[Rory Scovel]

Sad.

[Ed Helms]

Another investment banker, also unidentified, is quoted as saying, I always knew he was a rat. That's in Time magazine. I always knew he was a rat. It's like, so Shakespearean for to see

[Rory Scovel]

money in your future. The other guy being so poignant and so intelligent and deep. Money isn't the path. Oh, all right. Well, you're also a trader. You're also at investments.

[Ed Helms]

A few quick hits on his swift downfall. His book, Merger Mania, was immediately dropped by the publisher, Henry Holt and Company. He was forced to scrap a plan to remodel his Westchester county family home to mirror that of Thomas Jefferson's Monticello.

[Rory Scovel]

A common goal for all of us. Yeah, sure.

[Ed Helms]

I mean, we all want to get there. We all want. We all want our homes to look like Monticello.

[Rory Scovel]

Yeah.

[Ed Helms]

I mean, what. This is the hubris. Like, Jesus, he was forced to withdraw as a trustee at the American Ballet Theater. You know, that hurt. Yeah. He had to cancel and rescind a one and a Half million dollar grant to Princeton, where his son was attending. That's going to be hard on the son.

[Rory Scovel]

Yep.

[Ed Helms]

One crazy aside. John Mulheron Jr. One of Boesky's proteges, feared he himself was about to be implicated in the scandal and allegedly loaded an assault rifle with the intent of killing Boesky and his former head trader. But he was stopped en route, according to police.

[Rory Scovel]

Oh, wow.

[Ed Helms]

Boesky pissed some people off. Of course, he got prison time and this massive fine. This is also interesting. Boesky was permanently banned from work in the financial sector, never to touch stocks, bonds, any kind of securities again. Rory, what if you got banned from comedy?

[Rory Scovel]

I was just literally going, what would I do? What's my plan B? I don't know. I think I'd open a coffee shop or I'd try to coach college soccer.

[Ed Helms]

That's cool.

[Rory Scovel]

All right.

[Ed Helms]

That's actually, those are both nice. You could do both.

[Rory Scovel]

I try to do both of those. I'd actually try to have both of those things.

[Ed Helms]

A soccer cafe?

[Rory Scovel]

A college soccer coffee place. Yeah, sure. For the team. Like the peach pit in 90210.

[Ed Helms]

Well, so even having to. To pay this exorbitant penalty, Boesky was fine. He still had a ton of money. And after he was kicked off Wall Street, a lot more regulations and rules were set up in the world of finance to keep insider trading under control. Most notably was the addition of the Inside Trading and securities Fraud enforcement act of 1988. This act increased penalties for insider trading, required firms to improve internal controls, and introduced a bounty for informants. In April 1990, Boesky was released for cooperating with the feds, serving only two of his three year sentence. Boesky would recede from public view and live out his days in relative peace, having passed away in May 2024. Forever a reminder. Yeah. He just passed away a couple years ago.

[Rory Scovel]

Yeah. Oh, wow.

[Ed Helms]

Yeah.

[Rory Scovel]

I gotta say, like, if he's getting out of it with all that money, it's kind of like, what a great retirement. Sure, you don't want to do two years in prison, but now you're out of the game and you still have enough money to just go and coast. You just coast until it's over.

[Ed Helms]

Yeah, yeah. And he was sure he was in, like, a relatively pleasant white collar prison, too. It wasn't like that. But here's what's interesting. A lot of people look at things like this, and whatever side you're on, you might just be like, well, these are relatively victimless crimes. Right. It's just numbers. It's just financial finagling. Like, is anyone getting hurt? But the truth is, these deals that were happening in the 80s on Wall street, both the raider, the sort of corporate raider culture, and all of this short buying and selling that was going on, these moves demolished companies and put thousands of people out of work. That's part of the great story in Wall street, is that Charlie Sheen's dad, played by his real dad, Martin Sheen, is a mechanic at this company that Gordon Gekko is about to, you know, break apart and he's gonna lose his job. Which is a very sort of personal, poignant depiction of what I'm talking about. These are not victimless crimes. There's a massive price to be paid, and it's being paid by working class people. And so, you know, one could argue that a two year prison sentence, oh, that feels fine. Cuz all he was doing is like, pushing pencils around and like, you know, changing numbers. Maybe that's not fair. Maybe that's not enough, you know?

[Rory Scovel]

Yeah, and I were just talking about earlier about how what it. How rampant it is now as a thing. You're like, oh, God, now it doesn't even like two years. Almost seems insane to get any kind of a penalty whatsoever. And you're right, it's the blue collar working class that pays for it.

[Ed Helms]

That's our story. Rory Scovel, Any final thoughts? Reflections? Did it teach you anything about humanity?

[Rory Scovel]

Well, I feel like I always knew there was this evil out there, this greedy, but you having quoted that speech, does make me feel like, what's the harm in getting my hands a little dirty for just a couple months even? You know what I mean? You can do it, Okay? I got a little cash on the side.

[Ed Helms]

You can be greedy and still feel good about yourself. That is the lesson here.

[Rory Scovel]

Yes, that's what I want.

[Ed Helms]

To your point, though, I really like that you're connecting it to this moment, because the playbook hasn't changed since then. Right. Boesky believed winning proved he was right. And once you convince yourself of that, the rules feel optional, which is very much the energy of this Trump administration.

[Rory Scovel]

It's so much of it.

[Ed Helms]

If you win, if you're just winning, if you're just making libs cry, then you don't actually have to adhere to any standards or rules or frameworks or even the fucking Constitution.

[Rory Scovel]

I know, I know. It's certainly a lesson in how critical these institutions to a degree are. Not that they can't all be improved. But we're learning that if you demolish any of these institutions, you're up against a whole new, a whole new beast of rebuild. If you get the chance. If you get the chance to rebuild.

[Ed Helms]

Yeah, if we're lucky enough to come back in some way and build it

[Rory Scovel]

back better, stronger, more rules, more regulations, more accountability. But yeah, I think as individuals, if we don't have, if we don't care about accountability, then none of it can hold up. Up.

[Ed Helms]

I'll tell you what's interesting. Having done tons of these stories about major snafus, and so many of them are the result of darker forces in human nature, the one thing that rarely happens is accountability of any kind. And in this case, even two years of prison is like, thank God he got something. Like, it's just, it feels like, like a little small morsel of justice, not like full justice.

[Rory Scovel]

Slap on the wrist.

[Ed Helms]

Roy Scoville, this has been an absolute delight and a pleasure.

[Rory Scovel]

Oh my God. Thanks for inviting me. I appreciate it. That was a fun road to go down.

[Ed Helms]

All right, we'll see you out there. SNAFU is a production of iHeart podcasts and snafu Media, a partnership between Film Nation Entertainment and Pacific Electric Picture Company. Post production and creation support from Good Egg Audio. Our executive producers are me, Ed Helms,

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Mike Falbow, Glenn Basner, Andy Kim and Dylan Fagan.

[Ed Helms]

This episode was produced by Alyssa Martino and Tori Smith. Our managing producer is Carl Nellis. Our video editor is Jared Smith. Technical direction and engineering from Nick Dooley. Additional story editing from Carl Nellis. Our creative executive is Brett Harris.

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Logo and branding by Matt Gossen and

[Ed Helms]

the Collected Works Legal review from Dan Welsh, Megan Halson and Caroline Johnson. Special thanks to Isaac Dunham, Adam Horn, Lane Klein and everyone at iHeart podcasts, but especially Will Pearson, Carrie Lieberman and Nikki Ator. While I have you, don't forget to pick up a copy of my book SNAFU the Definitive Guide to History's Greatest Screw Ups. It's available now from from any book retailer. Just go to snafu-book.com thanks for listening and see you next week. Using Venmo without cash back is like

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[Ed Helms]

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