Lehman Brothers Holdings Inc. (defunct)

Henry Lehman, a German immigrant, opened a dry goods store in Montgomery, Alabama in 1844. His brothers Emanuel and Mayer joined him, and the firm began accepting raw cotton as payment from farmers — effectively becoming commodity traders. When Henry died of yellow fever in 1855, Emanuel and Mayer moved the business to New York. The firm survived the Civil War, the Panic of 1873, the Great Depression, two World Wars, and multiple financial crises over 158 years.

Lehman Brothers transformed itself from a commodities firm into an investment bank over the course of the twentieth century, eventually becoming the fourth largest investment bank in the United States. The firm built a particular expertise in fixed income — bonds, mortgages, and structured credit products. This expertise would eventually be both its greatest strength and the instrument of its destruction.

Under CEO Dick Fuld — nicknamed "the Gorilla" for his aggressive management style — Lehman became one of the most aggressive buyers and packagers of subprime mortgage securities in the 2000s. The firm borrowed $30 for every $1 of its own capital to buy mortgage-backed securities, betting that U.S. house prices would never fall nationally. When house prices began declining in 2006, Lehman's position became increasingly precarious. Fuld reportedly dismissed early warnings from risk managers.

Over the weekend of September 13-14, 2008, U.S. Treasury Secretary Hank Paulson and Federal Reserve Chairman Ben Bernanke held emergency meetings with the heads of America's major banks to arrange a rescue of Lehman Brothers. Unlike Bear Stearns six months earlier, no buyer could be found and no government guarantee was offered. On September 15, 2008, Lehman Brothers filed for bankruptcy with $639 billion in assets — the largest bankruptcy filing in U.S. history. Global credit markets froze. The Dow Jones fell 504 points. The 2008 financial crisis had begun.

Lehman's bankruptcy trustee spent years unwinding the firm's positions, eventually recovering approximately $130 billion for creditors — far more than initially expected. But the damage to the global economy was incalculable. An estimated 8.7 million Americans lost their jobs in the recession that followed. Dick Fuld was never criminally charged. He later said: "I wake up every single night wondering what I could have done differently."