The Tribune's Chicago newsroom has already gone through a series of painful layoffs and faces the strong likelihood of more. The editorial staff of the Tribune-owned Los Angeles Times is half of what it was seven years ago.
Ad revenue for the Tribune Company -- and for all media -- is in a tailspin. That has become a greater problem for The Tribune, which has a huge debt load after going private in a sale to billionaire real estate mogul Sam Zell.
"When you have debt, in good times it's fine: you pay back your lenders, your employees and you have a little left over for yourself. But when advertising revenue fell much more steeply than anyone had anticipated this year, it meant we went into a recession exactly when The Tribune was taken private," said Ann Saphir, Crain's Chicago Business.
The Tribune Company, with its many print and broadcast outlets, has not said that it will file for bankruptcy, only that economic necessity means it must be prepared to file.
With credit markets stingy, the Tribune's efforts to sell the Cubs have taken on the slows. A timely sale is critical, but the sale price for the ballclub most probably will not fetch what the Tribune Company had hoped for.
"It's taking quite a long time to get it done, so that's the problem. So I don't know whether the bankers are willing to cut them that slack. But if they are able to convince them, look, just wait a couple of weeks, wait a couple of months until we get that done, that will be enough -- a big enough chunk of cash that could satisfy the lenders," said Saphir.
Short of bankruptcy, the Tribune will attempt to restructure its debt with its major lenders, all of whom are having their own financial migraines.
The Tribune reportedly has a $500 million debt payment due in June, which is why the Cubs sale is so significant.