Scamfluencers – ENCORE: Mike Milken: When Junk Was King | Episode 187 Date: November 10, 2025 | Hosts: Sarah Hagi & Sachi Koul | Wondery

Episode Overview

This episode revisits the infamous story of Michael Milken, known as the "King of Junk Bonds." Through sharp, irreverent commentary, co-hosts Sarah Hagi and Sachi Koul trace Milken’s rise to power in 1980s finance, the disruptive impact of junk bonds, and his apocalyptic fall amid scandal and federal charges. The conversation unpacks how Milken rewired Wall Street, changed markets (for better and—especially—worse), and later rebranded himself as a philanthropist. The hosts dig into personality, motives, victims, and the lasting legacy of a complex scamfluencer who altered American capitalism.

Key Discussion Points & Insights

The Rise of Michael Milken and Junk Bonds

• [02:32] Milken the Visionary... or Rigging the System:
  Sarah outlines Milken’s unique approach: he exploited a niche in high-yield, high-risk "junk bonds", allowing companies spurned by banks to access capital—but with huge strings attached.
  "Michael made a mint and left behind the financial hellscape we’re all living in today." (Sarah, 03:16)

• Case Study: Steve Wynn & Golden Nugget Casino ([03:33–07:00])

  • Wynn wanted to expand into Atlantic City. Traditional banks wouldn’t back casinos.
  • Milken’s firm Drexel Burnham (then not a Wall Street giant) stepped in, raising $160 million through junk bonds, revolutionizing casino financing.
  • "The house always wins. Michael has been rigging the global financial system..." (Sarah, 06:51)
  • Wynn later credits Milken for making his empire possible.

• Milken’s Early Life: Driven Outsider ([08:10–11:00])

  • Math savant, workaholic, always the underdog among finance’s Old Guard.
  • At Wharton, feels like an outsider in a sea of WASPs; vows to outdo everyone.
  • "He only cared about bringing the truth. If Mike hadn’t gone into securities, he could have led a religious revival." ([15:20] – former Drexel executive, quoted by Sachi)

Shaking Up Wall Street: The Method & the Madness

• Drexel, Disruption & Cult of Milken ([11:55–14:56])

  • Drexel Burnham takes Milken’s bet. He runs his division as a grueling, insular shop—traders working New York hours in LA, slave wages but immense returns.
  • "It's a slave ship out there. High-priced slavery." ([21:31] – former trader)
  • Staff idolize Milken: "Michael is the most important individual who has lived in this century." ([22:11])

• Junk Bond Conferences & The Predator's Ball ([22:40–28:30])

  • Annual gatherings become legends for excess, power-playing, and conspicuous wealth.
  • Shift from bringing up-and-comers to empowering “corporate raiders” and hostile takeovers—transforming how companies are bought, sold, and gutted.
  • "[Drexel's strategy] levels the playing field. The small can go after the big." (Fred Joseph, read by Sachi at [27:09])
  • "The shift … is so big, it earns the conference a new nickname—from here on, people call it The Predator’s Ball." (Sarah [27:23])

The Deals: How Milken and Drexel Changed Everything (for the Worse)

• Ted Turner, MGM, and the Spiderweb of Conflicts ([31:18–35:35])

  • Milken arranges convoluted deals—secret stock purchases, hiding conflicts, making fees at every stage.
  • He bankrolls some of the 1980s’ most aggressive takeovers—including Turner’s MGM purchase, Revlon, Northwest Industries, and more.
  • "In addition to being a talented creative genius, Michael is among the most avaricious, ruthless, venal people on the face of the earth." ([35:35] – Drexel colleague, read by Sachi)

• The Real-World Fallout ([36:12–38:13])

  • Hostile takeovers create a corporate culture of fear, perpetual cost-cutting, layoffs, R&D neglect.
  • Average workers become collateral damage as markets turn volatile and inequality rises.
  • "A volatile market … restructuring, overhead cutting, layoffs ... All while Michael and his rich buddies get even richer. Does that sound familiar to you?" (Sarah, [38:13])
  • Sachi: "This sounds like everything that has ever happened in our entire lives." ([38:17])

Exposure: Investigations & Media

• Investigative Journalist Connie Bruck & "The Predator’s Ball" ([39:03–41:13])
  • Connie Bruck senses “something there” due to Drexel’s extraordinary profits. She’s offered hush money by Milken—twice.
  • "He just hadn't offered a big enough price …" "What would I do for integrity for the rest of my life?" (Connie Bruck on Fresh Air, read by Sachi [40:41])
  • Connie presses on, exposing Drexel’s rot. The book eventually becomes a bestseller as the scandal explodes.

Downfall: Insider Trading, Betrayal, and Collapse

• Ivan Boesky, Snitches, and the SEC Raid ([43:03–49:26])

  • Drexel execs and raider Ivan Boesky are swept up in federal investigations and snitch on each other.
  • Tension and paranoia dominate Wall Street.
  • "There will be no honor among these thieves." (Sarah, [49:28])

• Public Relations Meltdown & Desperate Rebranding ([51:19–53:44])

  • Drexel flails with music videos and ad campaigns (e.g., “Junk Bonds Keep America Fit”), trying to save face as scandals mount.
  • They tout Milken as a "national treasure" and push philanthropic gestures, but the narrative turns hostile.

• Legal Consequences & the End of Drexel ([54:03–57:11])

  • Drexel’s own lawyers become convinced of criminality ("the world of sleaze" tapes).
  • Drexel pleads guilty to six felonies and pays the largest securities fraud fine at the time ($650 million).
  • Michael Milken is indicted on 98 criminal counts.

• Michael's Courtroom Drama: Confession & Sentencing ([59:09–62:49])

  • Milken eventually pleads guilty to six violations, is fined $600 million, and is sentenced to 10 years in prison (serves less than 2).
  • "I realize that by my acts I have hurt those who are closest to me. I am truly sorry." (Milken’s courtroom confession [60:30])
  • Sachi: "This guy's kinda pitiful when he gets in trouble, huh?" (61:54)

The Aftermath: Rebranding, Reputation, and Enduring Influence

• Philanthropy as Reputation Laundering ([62:49–66:38])

  • After serving his time, Milken pivots into philanthropy, notably cancer fundraising, and becomes a Washington darling.
  • "Here is one of the most successful men … What that says is, no matter what your success, financially or otherwise, no money, no power can prevent a deadly disease." (Tony Coelho, read by Sachi, [64:09])
  • Hosts discuss how illness and charity enable Milken to rewrite his public image.

• Continued Influence Despite a Lifetime Ban ([66:38–68:00])

  • Milken keeps working as a financial power broker behind the scenes, makes millions as a “consultant,” is partially rehabilitated, and eventually pardoned by Trump in 2020.
  • His Beverly Hills "Milken Institute Global Conference" becomes a new hub for global movers and shakers, headlined recently by Elon Musk.

Notable Quotes & Memorable Moments

• On Milken’s Propaganda:
  “They want to change things, but they also want to get rich doing it.” (Sarah, [13:27])

• On Corporate Worship:
  “Someone like Mike comes along once every 500 years.” (Sarah, quoting ex-employee, [22:11]) Sachi: “I would be embarrassed to say these things out loud about anybody…” ([22:43])

• On Greed as Virtue:
  “Greed is all right … I think greed is healthy. You can be greedy and still feel good about yourself.” (Ivan Boesky at Berkeley [44:15])

  • This line inspired Gordon Gekko’s "Greed is good" speech in Wall Street.

• On Milken’s Downfall:
  “There will be no honor among these thieves.” (Sarah, [49:28]) “It's just like podcasting.” (Sarah, [55:31])

• On Public Image (and Overwrought Sympathy):
  “This guy's kinda pitiful when he gets in trouble, huh?” (Sachi, [61:54]) “He has always been in control … and I think this is the first time his life had been derailed.” (Sarah, [69:02]) “His actions were so quietly sinister that most people don’t even know they are to pin the blame on someone like him.” (Sarah, [69:26])

Timestamps for Key Segments

• [02:15] – Intro: Setting the stage for Milken’s impact on Wall Street and ordinary Americans.
• [03:33–07:00] – Steve Wynn and the creation of the casino/junk bond pipeline.
• [08:10] – Milken’s early life as an outsider and relentless overachiever at Wharton.
• [11:55–14:56] – Milken’s quirks, work ethic, and cult-like office environment.
• [22:40–28:30] – The evolution of junk bond conferences into “The Predator’s Ball” and the emergence of corporate raiders.
• [31:18–35:35] – The Ted Turner/MGM deal: conflicts, scams, and the machinery of self-dealing.
• [36:12–38:13] – Real-world fallout: the rise of precarity for American workers.
• [43:03–49:26] – Ivan Boesky, the SEC investigation, and paranoia on Wall Street.
• [59:09–62:49] – Milken’s sentencing, emotional breakdown, and prison term.
• [62:49–66:38] – Reputation laundering via philanthropy and ongoing behind-the-scenes influence.
• [67:53–68:28] – Reflection: Milken as the blueprint for modern white-collar scams.

Tone, Style, and Key Takeaways

• Tone: Witty, acerbic, and critical, but loaded with relevant pop culture context and modern analogies.
• Language: Irreverent, conversational, occasionally darkly humorous (“It’s just like podcasting. I’d slit your throat in a heartbeat.”).
• Perspective: The hosts don’t just describe crime—they repeatedly return to the ripple effects on ordinary people, the structural legacy, and the cyclical nature of financial scams.
• Cultural Legacy: Milken is recognized as the grandfather of process-dense, opaque scams that make Wall Street “feel like it’s full of shit.”
• Milken Today: Continues to influence finance and policy despite a criminal record, using philanthropy and networking to launder his image and maintain power.

Closing Thoughts

The episode uses Michael Milken’s story as both a wild true crime narrative and a lens on the roots of our present-day financial order. It’s a cautionary tale about unchecked ambition, the seductions and dangers of “disruption,” and the people who write the rules while the public is left paying the price.

“He claimed to be so hell bent on changing the system, but it actually was just changed to work in his favor… It’s scary to feel like somebody is writing rules you don't understand for a game that you barely knew you were playing—but you are playing no matter what.”
—Sarah Hagi, [69:26–69:38]

Further Reading Cited:

• Connie Bruck’s “The Predator’s Ball”
• James B. Stewart’s “Den of Thieves”
• Edward J. Epstein’s LA Times profile of Milken

Summary compiled for Scamfluencers fans and newcomers. For the full drama (and the contagious hosts’ chemistry), listen to the original episode on Wondery.