Dec. 9, 2008 -- Sam Zell might have never become a billionaire real estate magnate without the help of "grave dancing" -- a term he coined for making money off distressed properties.
"Grave dancing is an art form that has many potential benefits," Zell wrote in 1976. "But one must be careful while prancing around not to fall into the open pit and join the cadaver."
Some 30 years later, the pit is calling.
Zell's foray into the media business, the Tribune Co., filed for Chapter 11 bankruptcy protection Monday. The company owns 10 major newspapers, including the Los Angeles Times and the Chicago Tribune, as well as more than 20 television stations and the Chicago Cubs baseball team. Tribune will continue to operate its media businesses during its bankruptcy restructuring while the profitable Cubs franchise -- which was put up for sale last year -- is not a part of the filing, the company said.
In a statement issued by Tribune Monday afternoon, Zell blamed the company's decline on "a precipitous decline in revenue and a tough economy coupled with a credit crisis that makes it extremely difficult to support our debt."
But critics argue that it was more than that -- Zell himself, some say, is also largely to blame.
"We know that he was a real estate person and I think he's demonstrated that in his short ownership of the Tribune Company," said Bernie Lunzer, the president of the Newspaper Guild of the Communications Workers of America. "I just don't think he really fully understands what he got into. ... I think a lot of us predicted that the Tribune Company would get to this point."
A Tribune spokesman did not respond to a request by ABCNews.com to interview Zell.
The company's bankruptcy filing comes after a stormy year under Zell's leadership. In December 2007, Zell engineered a private takeover of the ailing, once publicly held company. He invested $315 million of his own money into Tribune, secured billions more in financing for the takeover and installed himself as the company's president and chief executive officer.
Known for brash, aggressive tactics and colorful language -- he has been caught on videotape saying "f--- you" to a reporter during a speech before newspaper employees in Florida -- Zell's take-no-prisoners style initially proved exciting to some but ultimately angered many in the media business, including his own employees, some of whom eventually sued Zell.
Zell's Employee Relations
His takeover of the Tribune Co., a group of Los Angeles Times employees argued in a lawsuit filed in September, was a deal "designed to benefit corporate insiders at the employees' expense."
In a statement after the suit was filed, Zell dismissed the employees' claims as "frivolous" and "unfounded."
The infamy brought on by 2007 Tribune deal followed what had been more than four decades of deal-making glory in the real estate business, starting in his college days. His business savvy dates back even further.
Zell's parents were Polish-Jewish immigrants who fled their home country on the eve of the 1939 Nazi invasion. They settled in Chicago, where Zell was born in 1941.
"My father made a life-and-death decision at age 34, and he was right," Zell told Dividend, a University of Michigan business school alumni magazine, in 2006. "My dad was very, very strong and very confident. I had to be very confident and strong to succeed in his shadow."
His first taste of business success came at age 12 from an unlikely source: Playboy magazines. After discovering a newsstand that sold the adult magazines, Zell began buying them and reselling them to classmates for $3 -- six times more than he'd originally paid for each, according to Dividend.
By the time Zell entered college at the University of Michigan in Ann Arbor, he had turned his sights to real estate and took jobs managing different apartment buildings while still in school.
Eventually, he would join real estate developer Don Chisholm in buying properties in the college town.
Chisholm remembered how Zell once convinced a reluctant seller, a woman who lived with her brother. She worried that her brother wouldn't be able to find his way to their new home after a night of drinking if they moved.
Zell made her a deal: If she sold, Zell would find her a new house close to a bar and would install a ramp and a handrail just for her brother. It worked.
"He was so smart and had so much drive," Chisholm told ABCNews.com. "The perseverance and the attention to detail was remarkable at that point -- he was just 21 or 22."
Real Estate Empire to Media Takeover
What Zell began in Ann Arbor he eventually built into a real estate empire. In 2006, while the real estate market was still strong, he sold part of that empire for $39 billion.
"He's a gambler, he's a smart guy and he made a lot of money in real estate by guessing where these trends were going with commercial properties," said Christopher Mackin, the president of the strategy consulting firm Ownership Associates in Cambridge, Mass.
But, Mackin said, Zell's "judgment of what was going on with the [media] industry was wrong."
It wasn't just Zell's timing that was off, critics say. Zell's deal to take over Tribune saddled the corporation with more than $8 billion in new debt that it is now struggling to pay off.
"He certainly took out a substantial amount of debt made on certain assumptions that have not come true," said Lunzer of the Newspaper Guild.
The deal also relied heavily on an employee stock ownership program that scuttled the company's practice of matching employee 401(k) contributions with cash to matching it with Tribune stock.
As a result, "many employees will have a retirement fund that is heavily invested in a company that is overly encumbered with debt," according to the lawsuit filed against Zell in September. (An automated recording on the Tribune's employee benefits hotline number said that employees' 401(k) accounts are not affected by the bankruptcy filing.)
But there was more that raised Tribune employees' ire about their new boss: After initially saying he didn't support the idea that layoffs at newspapers were the way to address drops in revenue -- a statement that employees met with applause during a meeting at the Tribune-owned Hartford Courant in Connecticut -- Zell ultimately slashed more than a thousand Tribune Co. jobs.
"The reality is, what's my choice?" Zell asked during a conference call with reporters, the Hartford Courant reported in July. "Do I try and create a business that can be viable and preserve two-thirds of the jobs? Or do I let all 100 percent of them go by the wayside because I'm not willing to confront the realities of the environment?"
In an interview with Conde Nast Portfolio Magazine at a media conference last month, Zell said that these days, newspapers could no longer afford to operate as "charitable trusts."
"If you don't want to be a charitable trust, then you've got to focus on producing a return for investors' capital," he said, "and it's just that simple."
It's that outlook that prompts criticism from journalists and media watchers like Ken Auletta, a columnist for the New Yorker magazine.
The problem with Zell, he said, is that he just doesn't appreciate journalism.
"One had a sense in listening to him that he didn't think he was in the news business. He could have been in the cattle futures biz or the manufacturing of beds," said Auletta, who sat in on the Portfolio interview.
"Journalism is not an endeavor just to maximize profit," he said. "It is an endeavor that is protected by the First Amendment in order to provide information to the public that they need to make decisions in a democracy."
Zell, meanwhile, appears resolute in the face of both criticism and strong financial headwinds.
The bankruptcy filing, he said in Monday's Tribune statement, "will take pressure off our operations, so we can continue to work toward our vision of creating a sustainable, cutting-edge media company that is valued by our readers, viewers and advertisers, and plays a vital role in the communities we serve."
ABC News' Brad Martin contributed to this report.