8. St. Paul Pioneer Press
St. Paul Pioneer Press
Circulation: 184,973 (3% decrease since 2007)
Sunday Circulation: 246,431 (2% decrease since 2007)
Parent Company: MediaNews Group
Parent Co.'s 2008 Revenue: N/A (privately held)
parent Co.'s Current Stock Price: N/A (privately held)
Its Twin Cities rival Minneapolis Star Tribune filed for bankruptcy in January, but the smaller Pioneer Press may go belly-up first. Owned by Dean Singleton's Media News Group, the Pioneer Press is suffering the same financial crisis that's plaguing the entire company - heavily leveraged, with loans from Hearst, Gannett and even Bill Gates, and short on cash. And while the Star Trib is trying to get its act together under bankruptcy protection, the Pioneer Press is sinking deeper. This sets the trend of the smaller papers struggling to survive in what's left of two-newspaper towns.