The Kindness of Strangers: Drexel Burnham, Chesapeake Energy and OpenAI

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Relying on the kindness of strangers has never been a good business or investment strategy, but it doesn’t mean that people don’t wish that it worked. The main issue with this hope is that it’s foolish to believe that other people’s grace and money will always be there.

This idea should look similar to going to a teller window. If you have ever watched the movie, It’s a Wonderful Life, you are able to visualize this. At one point in the movie, everyone lines up at the teller window because the other banks have closed. Everyone begins to ask for the money they need. George uses his life savings to get the bank through that time, but we all know that not everyone is as benevolent and selfless as George. The open teller window for funding can and will close in different assets and business models, often at inopportune times.

I was born in 1983. Three years prior, my father was hired as a retail stockbroker at Drexel Burnham Lambert, a private, enterprising investment bank. Their claim to fame was that Michael Milken had cracked the code on the value of the junk bond market. Companies that needed to raise capital came to him. Investors who wanted high returns on fixed income came to him. Wall Street stood on the outside looking on as Drexel became the most profitable private enterprise in America in 1986.

People on the outside of Drexel, other investment banks, had a different view. They so badly wanted a meaningful piece of junk bond issuance and bookrunning. These other investment banks were left with crumbs. Ivan Boesky, a major Drexel customer, was indicted in 1986. This was so problematic for Drexel because the investment bank, as a private company, was heavily funded by the deal flow from its customers. Savings and loans (SNLs) were raising brokered certificates of deposits (CDs) so that those same banks could turn around to buy the junk bonds that Drexel was offering to its institutional customers.

If something caused this chain to break down, Drexel was going to be subject to the kindness of strangers. In the end, there was no kindness from regulators and competing banks. The ultimate dagger was when Executive Life Insurance of California was seized by its state insurance regulator in 1991. Milken and Drexel’s thesis was proven true. Junk bonds were good for investors, but unfortunately the kindness of strangers was nowhere to be found in the late 1980s, and because of that, Drexel is no more.

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