Now the Chicago company moves to consider its next big asset sales -- potentially the Chicago Cubs baseball team and Wrigley Field -- to meet its obligations to creditors in 2009.

The deal announced Monday puts Newsday, one of Tribune's largest newspapers, into the hands of cable operator Cablevision Systems. Like Newsday, the cable company is based on New York's Long Island.

Investors have been skeptical that Cablevision would reap benefits in the deal, because that it hasn't operated a newspaper before, and the newspaper industry is struggling as readers and advertisers move to the Internet.

"It's incredibly hard to fathom why they want to expand into the newspaper business," said media analyst Richard Greenfield of Pali Capital. "Why are they putting dollars towards newspapers rather than buying their own stock?"

For Tribune, there's no doubt why the deal make sense: The company needs cash. In December, Tribune bought out its public shareholders in an $8.2 billion deal orchestrated by real estate mogul Sam Zell, and now it's struggling to service that debt.

Zell had originally hoped to keep Tribune's newspaper and broadcasting businesses intact, but he changed course and considered options for Newsday after a rapid deterioration in the newspaper business this year.

Tribune last week reported an 11 percent decline in first-quarter newspaper revenues, which have been hit hard by the slumping economy and online competition.

Tribune now seems to be covered on a $650 million lump-sum debt payment due in December, as well as other near-term obligations. However, analysts say it needs to get moving on other asset sales so it can deliver on an additional $750 million debt payment in June 2009.

Mike Simonton of bond ratings agency Fitch Ratings cautioned that the deal "does not get them out of the woods necessarily."

Up next: Cubs, Wrigley

The next step for Tribune would be selling the Chicago Cubs and Wrigley Field. Together, the two could fetch as much as $1 billion, which would get the company past the 2009 payment.

Once those sales are behind it, Simonton said, there would be a better indication of whether Tribune would face pressure to sell more assets.

Much would depend on whether the company's new management is able to stabilize Tribune's newspapers. "A year and a half from now, it will be more clear if further asset sales are necessary," Simonton said.

Tribune is still marketing the Cubs, and it's in talks with an Illinois state agency about Wrigley Field. Those talks are complicated by the fact that the agency, which also owns U.S. Cellular Field, where the Chicago White Sox play, wants laws that restrict changes to Wrigley Field loosened.

Another option for Tribune would be selling its roughly 30 percent stake in Food Network back to E.W. Scripps, which owns the rest of the rapidly growing cable TV channel. Analysts estimate that stake could be worth more than $500 million.

Scripps, however, is going through changes of its own as it splits into two separate companies, one with the cable networks and another with a group of newspaper and TV stations. That split is expected to be complete by the end of the second quarter.

To get favorable tax treatment, Tribune will retain a 3 percent stake in a joint venture to be formed containing Newsday as well as several related assets, including Newsday.com, some regional magazines and the free New York City daily newspaper amNewYork. Cablevision will hold the remaining 97 percent.

Cablevision, which is controlled by the Dolan family, has about 3.1 million subscribers in the New York metro area and owns Madison Square Garden, the NBA's New York Knicks and the NHL's New York Rangers.

Company shares fell 45 cents to $24.52 Monday.

Newsday is the 11th largest newspaper in the country, according to the latest figures from the Audit Bureau of Circulations, with 379,613 average paid weekday copies in the six-month period that ended in March.