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History Unplugged Podcast

Clarence Dillon: The Roaring 20s Wall Street Baron Who Wrote the Rules for Corporate Takeovers, Junk Bonds, and Bankruptcy

History Unplugged Podcast

History Unplugged

Society & Culture, History

4.23.7K Ratings

🗓️ 25 November 2025

⏱️ 49 minutes

🧾️ Download transcript

Summary

J.P. Morgan, John D. Rockefeller, and Charles E. Mitchell are names that come to mind when thinking of the most prominent icons of wealth and influence during the Roaring Twenties. Yet the one figure who has escaped notice is an enigmatic banker by the name of Clarence Dillon. In the 1920s, as he rose in wealth and influence, Dillon became one of the original behind-the-scenes players in Hollywood, and his contact list included everyone from Thomas Edison to Charlie Chaplin and Joseph P. Kennedy to FDR.

A revolutionary in finance, Clarence Dillon single-handedly created modern bankruptcy law, pioneered leveraged buyouts, invented junk bonds, and engineered some of the biggest mergers and acquisitions ever seen. His firm engineered the 1925 buyout of Dodge Brothers Company for $146 million in cash, then the largest such industrial transaction in history, which resulted in the company's merger with Chrysler Corporation in 1927

Today’s guest is William Loomis, author of “The Baron of Wall Street.” We look at Dillon and his life, which fills a void in how we view the wild excesses of the Roaring Twenties, and how we understand the increasingly complex nexus between Wall Street and political power in our own time.

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Transcript

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0:00.0

Scott here with another episode of the History on Plug Podcast. When it comes to finance,

0:09.0

whether personal finance or corporate finance, we live in the world of Clarence Dylan. Dylan was

0:14.5

an investment banker who rose a prominence in the 1920s, and he pioneered leverage buyouts,

0:19.1

created modern bankruptcy law, invented junk bonds,

0:21.8

and engineered some of the biggest mergers and acquisitions ever. Before Dylan, if a company

0:25.6

experienced corporate failure, it was liquidated and sold for scraps and parts. After Dylan,

0:30.6

leverage buyouts became normal. A company with valuable assets could be repackaged and resold.

0:35.5

He did this with Goodyear tires. He engineered the buyout of

0:38.1

Dodge Motors in 1925 and sold it to Chrysler and created our modern system of creative

0:43.1

destruction in the American business world. Dylan also pioneered investment trust, which allowed

0:48.0

retail investors to pool money and access diversified portfolios of securities. This led to

0:53.1

modern mutual funds and index funds, which affects nearly every American

0:56.6

salaried worker because your retirement could now be in a 401k.

1:00.0

And even if you work on Main Street, you can invest in Wall Street, and you don't have to rely on getting family farmlands and inheritance or a company pension.

1:07.5

Today's guest is William Loomis, author of The Baron of Wall Street.

1:10.5

We look at Dylan

1:11.3

in his life, how he invented techniques during the roaring 20s that weren't really allowed after

1:16.6

the Great Depression when commercial and investment banking were separated, but then became in vogue

1:20.6

again in the 1980s, and Dylan was sort of a patron saint of Motorola, brick phone-era Wall Street,

1:26.4

and the good and the bad of the growing

1:28.5

codependency of Wall Street and political power in our own time.

1:31.8

Hope we enjoyed this discussion with William Loomis.

...

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