The Los Angeles Times provoked gasps last April when it took the once-controversial idea of front page advertising one misstep further. The financially strapped paper ran an ad thinly disguised as a news story in the body of its front page—an “innovative” concept it had pitched to NBC for the TV drama Southland.

Yesterday, the even more beleaguered Detroit Free Press apparently took an even more dramatic leap toward shrinking the gap between news and commerce.

At the suggestion of health insurer and advertiser Humana Inc. the paper prepared and ran a package of stories centered on senior health and the upcoming Medicare open enrollment period, according to The Wall Street Journal. Ads in the section also were sold to other advertisers.

Moreover, the Journal reports, in late September the Free Press allowed advertiser Target to choose the dates on which education articles and their adjacent school-related Target ads appeared in the paper’s front section.

So, where do the actions of the Detroit Free Press fall in the ethical spectrum?

Neither Humana nor Target had any say in the content of the stories, topics the paper already planned to cover anyway, according to Paul Anger, editor and publisher of the Free Press.

“One of the things I think newsrooms have to realize,” Anger told the Journal, “is we’re here to cover the news in an unvarnished way, but we’re also here to facilitate commerce.”

The Freep is only the latest in a long line of papers—hurting and hunting hard for new sources of revenue—that are resorting to “creative” ways to stay funded. Many of these strategies (seminars with journalists on topics of public interest, for example, or subscription wine clubs started by The New York Times, USA Today, and The Wall Street Journal) raise no ethical red flags.

Others, however, have crossed the line that divides “savvy money-making strategy” from “totally improper behavior for a respected newspaper.” And they’ve often been quickly—and harshly—reprimanded for their transgressions. The Washington Post’s “salons,” planned to be staged chez publisher Katharine Weymouth, drowned in a sea of embarrassment before the first shrimp cocktail was served. When Chicago Tribune reporters rebelled against the paper’s practice of conducting focus groups on story ideas before publication—and when the Associated Press turned that practice into a story—Tribune Editor Gerould Kern swiftly pulled the plug on an approach he said “compromises the reporting process.” (Disclosure: I worked for the Chicago Tribune for twenty-five years before taking a buyout last December.)

As for the Freep, the propriety of its actions remains an open question. Getting an idea from an advertiser may sound unseemly, just as scheduling stories at the convenience of an advertiser may sound sleazy. But if in this case there truly was no involvement by the advertisers in the journalism itself—if the stories in question would have been done anyway—is there any ethical problem at all?

Back in the good old days of 2007—just before the relentless storms of circulation declines, revenue plunges, layoffs, buyouts, dwindling news holes, and shrinking news pages made such a consideration an unaffordable luxury—one of the most agonizing questions facing many newspapers was whether to put display ads on their front pages.

By early 2009, the agonizing question for most papers had become whether there would continue to be a front page at all. And with that change came another shift: Most major American newspapers, including The New York Times, by that time had offered front page ads. Despite much handwringing over the sanctity of the front page—an idea that didn’t take hold until the 20th century—none of the papers’ reputations, today, seem much the worse for it.

No longer are such ethical issues matters simply of conflict-or-cleanliness; increasingly, the choice facing papers is between compromising and being compromised. Concepts that would have been dismissed airily out of hand in rosier times must be boldly reexamined in the harsh light of the industry’s current crisis.

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Lisa Anderson is a 2009-2010 Encore Fellow at CJR. She was the the New York bureau chief and a national correspondent for the Chicago Tribune until December 2008.