Zell dubbed himself "grave dancer" more than 20 years ago for the kind of business deals he did. The description "conjures up images of the short, bearded 49-year-old financier merrily jigging over the remains of some over-leveraged, imploded corporation," the L.A. Times wrote in a 1991 profile of him, explaining, "Buying cheap and selling dear has always been Sam Zell's stock and trade."
By the mid-2000s, Zell owned significant Chicago real estate holdings and television and radio stations. He purchased Tribune, the L.A. Times parent company, in 2007, later calling it "the deal from hell."
Zell's purchase of Tribune saddled the company with a reported $8 billion to $13 billion in debt; the company filed for Chapter 11 bankruptcy less than a year later. Zell put only $315 million of his own at risk purchasing Tribune, according to the Wall Street Journal. He currently has an estimated net worth of $4.9 billion.