I also believe the source of the problem is that the Sun-Times has a conservative editorial POV, which doesn't float well in Chicago, a liberal bastion.
The problem with the Sun Times (other than it being a tabloid), is like 99.999% of all periodical publishing in the world, they essentially give their content away for free, or close to free, or even if they limited the amount of stories you can read, enough people do, repost them and you get the news and features anyway.
I truly don't understand a business model where you give your content away for free and expect to turn a profit. Even less, a business model where the content is produced by amateurs, comments from the man on the street and cell phone imagery.
I also don't understand a business model where you cut the talent, the equity out of your product and expect anyone to want to pay for it.
Publishing wants to keep one foot in the creek and one on shore with the expectation of staying dry. It makes no sense.
If you don't digitize it, or if you digitize and it takes a full subscription to use any of it, then the links die down and your content will become yours and yours alone to actually sell and make a profit.http://online.wsj.com/article/SB10001424127887323830404578141561687144972.html#articleTabs%3Dvideo
Music, traditional TV, publishing have all rushed to enable a world of for "free" or reduced priced content for the web, thinking that someday somebody might pay them serious money.
That's not a business model for growth.
The advertising world knows that analog dollars once into the digital domain equates to pennies.
I think the only traditional "network" head that understands how to turn a profit today is Les Moonves of CBS.
A long time ago he changed the thought that CBS was an old line network, moved to a content provider and he's dead set on not making a profit from his content.http://online.wsj.com/article/SB10001424127887323830404578141561687144972.html#articleTabs%3Dvideo
(view the two interviews, revenue streams, and not embracing the I-pad)