Traditional print media: "Quick, Matthias, hand me the ff ligature."

It may seem incredible, but with the Wall Street bailout, the frenzy over the Palin-Biden debate, and the Cubs’ annual collapse in the playoffs, there was enough room in the newsosphere this week for other events to occur. Three, in particular, bear ominous portents for the future of print media:

Minneapolis Star Tribune skips debt payment: Minnesota’s largest circulation newspaper, the Minneapolis Star Tribune, announced on September 30 that it would stop making payments to its senior creditors. This means that the Star Tribune will attempt to restructure its debt and negotiate with its lenders for more breathing room as it tries to find a formula for making money in an increasingly difficult environment for big city newspapers.

What this really means: the Star Tribune, for all practical purposes, is bankrupt. Regular folks don’t get to tell the gas company or the dog groomer that they’re “suspending debt payments to senior creditors.” They just skip their bills and hope for the best, which is what the Star Tribune has done. That’s not a terribly good way of handling one’s finances, but then most folks don’t have $432 million in debt. It is the Star Tribune’s good fortune, however, that it does have $432 million in debt, which means that it still has some leverage here. As the saying goes: “if I default on a $10,000 loan, that’s my problem: if I default on a $10 million loan, that’s the bank’s problem.” Right now, with the Star Tribune defaulting on its senior debt, there are a number of senior creditors who are wondering why they loaned money to the newspaper in the first place.

The New York Sun sets for the last time: The New York Sun announced on Septermber 29 that it would cease publishing after its September 30 issue. The Sun, founded six years ago as a conservative alternative to the New York Times, was unable to find a profitable niche in a market already dominated by four huge daily newspapers.

What this really means: The Sun boldly claimed to have a daily circulation of 150,000, despite a subscriber base of less than ten percent of that figure. Tossing the newspaper gratis on the front porch of non-subscribers, it seems, merely accustomed people to view the Sun as a free-drop newspaper, sort of like the PennySaver edited by William Kristol.

Alt-weekly publisher Creative Loafing files for bankruptcy: Creative Loafing, Inc., the publisher of the Chicago Reader, the Washington City Paper, and four other alternative urban weeklies, filed for Chapter 11 bankruptcy on September 29. The step means that the company will attempt to negotiate its debt and restructure its operations. The newspapers will continue to publish during the restructuring.

What this really means: Creative Loafing went on a buying spree with its purchase of the Reader and the City Paper, incurring sizable debt that it couldn’t match with staff cuts and other cost-saving measures on the expense side of the ledger. The company said that “[t]his filing has little to do with the acquisition,” which, of course, means that it had everything to do with the acquisition of those papers.

Now, before pronouncing the inevitable valedictories on the American newspaper, it should be acknowledged that the recent Wall Street meltdown had a large part to play in all of these events. With a tightening of credit, these media companies discovered that it was a pretty bad time to hit up their bankers for a ten-spot until payday. Of course, that also means that the creditors that had previously loaned money to these companies are the ones looking like the suckers here. Nevertheless, it’s hardly a coincidence that newspaper companies would be some of the first victims of the financial collapse.

Despite the similarities of these stories, however, there are some significant differences. The Star Tribune is the victim of the same forces that have affected all large urban dailies: a decline in readership that goes back to the 1950s and an accompanying drop in advertising revenue. That trend is endemic in the newspaper industry as a whole, and the Star Tribune was no more immune to it than other late, lamented bastions of journalism like the Houston Post or the Nashville Banner.

For the New York Sun, the problem wasn’t in attempting to run a print newspaper in an internet world, it was in starting a newspaper in an internet world. Really, starting up an urban daily these days is like being the last passenger rushing to board the Titanic. Perhaps the innate conservatism of the Sun’s owners inclined them to invest in an eighteenth-century technology in the twenty-first century, but it proved about as successful as introducing a revolutionary new buggy whip into the market. The Sun tried to make up for its over-reliance on press service news stories by the depth of its feature articles as a means of competing with its far more well-established daily rivals. Its news commentary and coverage of the arts, in particular, were highly regarded. What it failed to consider, however, was that its target audience had already decided that it had adequate alternatives to the “liberal” main stream media. The Post and Daily News had superior coverage of local news and more strident, albeit less cerebral right-wing editorial stances, while the Times always had better features. The Sun tried, in effect, to be the National Review of daily papers, failing to recognize, too late, that readers already had something that fit that niche: i.e. the National Review.

The announcement of Creative Loafing’s bankruptcy proved, I suppose, that free-drop newspapers aren’t immune to the same economic forces that doomed the Sun and threaten the Star Tribune. The alt weeklies, however, have always been more dependent on classified advertising than the daily papers, which means that they have been particularly susceptible to competition from free internet services like Craig’s List. The Reader, for instance, was long the place to find an apartment in Chicago, but the listings have dwindled recently as those ad buyers have migrated to the web. As readers are increasingly able to find a “2 BR/1 BATH” or a “hardly used” 1969 Chevy Camaro on the net, however, the kind of news stories in which the alt weeklies specialized are in danger of disappearing as well. It’s unlikely, for instance, that Craig’s List will publish an investigative series on police torture in Chicago like the Reader did.

This week’s news isn’t entirely grim, it’s just mostly grim. The Star Tribune is clearly in trouble, but there’s always the possibility that it could arrange to enter into a joint-operating agreement with its cross-town rival Pioneer-Press and keep the Twin Cities a two-paper town. But the Star Tribune‘s massive debt may rule out such arrangement, and JOA’s are, in any event, merely the business equivalent of writing up the obituary before the public figure has perished, as the prolonged death rattle of the Detroit Free Press demonstrates. Creative Loafing’s main problem was in taking on too much debt in connection with its rapid expansion, and other alternative weeklies seem to be doing all right. The alt weeklies, however, still need to find an economic model that works in the internet age: featuring Dan Savage columns just won’t cut it any more. As for the New York Sun, the good news is that we now have proof that there’s not much of a market for a print version of Fox News.