Pinned

Why a 100-Year Bond Hooked My Curiosity

In November, I read a book that’s stuck with me. Dangerous Dreamers was a historical recounting of the events that set the stage for the junk-bond and LBO explosion in the 1980s. I was intrigued by how an obscure book and an insight that fast-growing companies couldn’t borrow money in the bond markets at the time sparked Michael Milken’s idea to create (and control) the market for high-yield—junk—bonds.

Ever since then, I’ve been interested in learning more about bonds of publicly traded companies (and governments) and the public market for them. I’ve bought several books and started tracking down people who work in these markets to talk with. Lots to learn, but I think it’ll be a fun multiyear project. I suspect it will complement what I’ve learned from analyzing and investing in public stocks.

Today I read an article (see here) that made me want to begin this project sooner rather than later. It was reported that Alphabet (Google’s parent company) is thinking about issuing a 100-year bond. From what I can gather, a bond with a 100-year duration is very rare and hasn’t been issued by a technology company since 1997 or so.

Reading that article highlighted that I don’t know what I don’t know about the bond market, and it made me more curious and more eager to fill my knowledge gaps. Hopefully I’ll be able to carve out time soon to start reading my new bond books.

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Connected Books
Dangerous Dreamers

1993

Biography

by

Robert Sobel

1993

November 2025

A historical narrative about the people and events that set the stage for the junk-bond boom, LBO wave, and eventual S&L turmoil of the 1980s. It traces how early innovators like Louis “The Junkman” Wolfson, Charles Merrill, and conglomerate builder James Ling introduced concepts that later figures—Michael Milken, T. Boone Pickens, Carl Icahn, and others—would scale dramatically. The book explains how an obscure book on bond analysis sparked Milken’s insight into high-yield bonds, laying the groundwork for the junk-bond market, modern private equity, and the LBO era. It also highlights how the Great Inflation of the 1970s depressed stock prices, creating fertile conditions for takeover artists and financial engineers to use leverage to acquire companies trading below intrinsic value.