Most of the company's debt comes from the complex transaction in which the company was taken private, with employee ownership, by real estate mogul Sam Zell last year. Although Tribune's next major debt payment isn't due until June, the company has been in danger of missing financial targets set by its lenders.

Other newspaper companies have also struggled with their debts, but many have successfully negotiated with lenders to ease their targets in exchange for higher interest rates.

"Tribune's debt was so outsized and so disproportional to its cash flow compared to these other companies that it can be the sore thumb sticking out rather than an example of the industry," said Ken Doctor, media analyst with Outsell Inc.

The Tribune owns the Chicago Cubs baseball franchise, as well as the Los Angeles Times, Chicago Tribune, The Sun of Baltimore, The Hartford (Conn.) Courant, six other daily newspapers and 23 television stations.

The company's lending agreements require the company to keep its debt at a certain point relative to its cash flow. Those deals become harder to meet as revenue declines, even if the debt itself doesn't increase.

And while Tribune had planned on meeting its obligations with lenders by reaping income from its various properties, the recession has led consumers and advertisers to severely cut spending this year, exacerbating pressures the industry already was facing because of the migration of readers to the Internet.

To make a debt payment this year, Tribune sold the Long Island daily Newsday to Cablevision Systems Corp. for $650 million.

Chicago Cubs News News » Tribune media company seeks bankruptcy protection
Tribune media company seeks bankruptcy protection
NEW YORK (AP) - Media conglomerate Tribune Co., smothered by $13 billion in debt and weak prospects for generating cash through advertising, on Monday became the first major newspaper publisher to seek bankruptcy protection since the Internet began siphoning readers from traditional outlets. MLB Hot Stove