7. Chicago Sun-Times
Circulation: 313,176 (.2% increase since 2007)
Sunday Circ: 255,905 (3% increase since 2007)
Parent Company: Sun-Times Media Group
Parent Co.'s 2008 Revenue: $372 milion
Parent Co.'s Current Stock Price: $0.05
While much of the news is centered on the crosstown Tribune's troubles - its eponymous parent company filed for bankruptcy in December - the Sun-Times is actually doing worse. Its worthless stocks were booted off the NYSE big board in mid-2008 and they're now trading at about a nickel a share. The paper's financial liabilities are fast approaching $1 billion. And while the Tribune Co. has the Chicago Cubs and Wrigley Field to sell to raise cash, all the Sun-Times can do is cut cost.