7 Seasons in Zell

Looking back on his deal to acquire the Tribune Company, Sam Zell told Bloomberg TV in April 2009, "I made a mistake."

It only took the Chicago real estate mogul about two years to realize that fact. This week, news hit that he'll possibly give up his stake in the company, publisher of the Chicago Tribune, the Los Angeles Times, the Baltimore Sun and others, as well as owner of the Chicago Cubs and other assets.

According to the New York Post's Josh Kosman, Zell, "is on the verge of giving up his claims to buy a huge stake in the company and, according to a source familiar with the matter, is ready to walk away from the company."

Maybe he felt like he'd done enough damage.

Zell bought the paper chain two years ago for $8.2 billion with help from the company's own employees' stock holdings. (Ever savvy, he only ponied up $315 million of his own money.) Less than a year later, the company filed for bankruptcy to protect itself from $13 billion in debt, much of it brought on by the sale— before Zell's takeover, the company had about $5 billion in debt.

The bankruptcy filing prompted MarketWatch to ask, "Is there any doubt now that Sam Zell is in over his head as the head of the Tribune Co.?" Probably, but it wasn't all Zell's fault: Newspapers across the country are suffering from an ad slowdown and declining readership. As the nascent newspaperman told Portfolio in November 2008, "the newspaper business and advertising, generally, has gone off a cliff."

Some of the trouble may have also come from Zell's run-and-gun, come-what-may style. In a lengthy New Yorker profile from November 2007, Connie Bruck described Zell's approach to business as follows: "Zell has made much of his fortune by identifying opportunity where others see only trouble. He says that he is constantly trying to 'shut out the noise' of conventional wisdom, because, although it may not always be wrong, it is rarely profitable." (Example: Subprime crisis "manageable": Sam Zell, Reuters, December 12, 2007.)

But a few months later, Zell was calling the purchase of the Tribune company as "the deal from hell," and to judge from the way he's treated employees (you know, the ones who helped bankroll his purchase), it was hell for them, too.

In early 2008, according to the New York Observer's John Koblin, Zell tried to inspire the troops at Long Island Newsday by telling the staff, "Every company I've ever been with is growing. We've got to get off our ass [sic.]." (That was nicer than the time he said "fuck you" to a reporter from the Orlando Sentinel.) Luckily for them, he sold the paper to Cablevision Systems a few months later.

In August 2008, the Chicago Tribune shed 80 employees: 30 from buyouts, the rest from layoffs. Another 90 people lost their jobs at the paper in April 2009.

In Los Angeles, the Times cut 250 jobs in July 2008, then 75 in October 2008, and another 300 in January 2009.

It wasn't all losses: In July 2009, the company agreed to sell the Chicago Cubs to TD Ameritrade founder Joe Ricketts for $900 million.