By David Crisp

Lee Enterprises, Montana’s media behemoth, has purchased a share of Okanjo, a native commerce company in Milwaukee, Wisconsin.

Native commerce has nothing to do with business on the reservation. It’s a technique for presenting ads on web pages so they blend seamlessly with news content.

Lee’s investment in Okanjo was announced in May, but the two companies had been working together for a year, according to an article in the August issue of Editor & Publisher. The size of Lee’s investment and its stake in the company were not disclosed. As part of the deal, Lee’s vice president of digital, James Green, is joining Okanjo’s board of directors.

For Lee, which owns the Missoulian and Billings Gazette, it’s a way to try to ramp up online ads as print revenues continue to decline. Digital revenues at the company grew 16 percent a year over the last decade, but still made up only 24 percent of total revenues in the quarter that ended in June. Overall revenues were down nearly 5 percent in the quarter.

Lee has been in an uphill battle since acquiring a couple of other newspaper companies in 2002 and 2005. It still owes $640 million, but its stock price has rebounded to $2.55 a share.

Okanjo is working on three advertising platforms: one that automatically places ads near relevant stories, one that amounts to an online auction, eBay style, and one that will allow customers to purchase products directly from display ads.

The company hopes to have parts of the program in place at all Lee papers by the end of September. It promises not to collect information about individual consumers.

Okanjo’s website says it uses keywords and “sentiment” to place ads with stories. The exact definition of “sentiment” is imprecise, but Bethany Grabher, vice president of business development for Okanjo, gives this example: Suppose the Green Bay Packers beat the Minnesota Vikings. Online readers of the Wisconsin State Journal will automatically start getting ads for Packer products.

Others have suggested examples of “sentiment” that are less, shall we say, sentimental. Delta Airlines presumably would not want its ads showing up next to a story about an airplane crash—or about massive flight cancellations.

Okanjo says it won’t take ads for children’s underwear, for reasons I would prefer not to think about, nor will it take ads for guns. I get that: You wouldn’t want a story about the latest mass murder accompanied by an ad for assault rifles.

None of this is exactly new, but it still feels a bit creepy. Back in the days when tobacco companies were running national newspaper ads, they insisted that their ads not run on the obituary page, apparently out of concern that someone might suspect a relationship between smoking and death.

Still, those decisions always have been made on a case-by-case basis by actual human beings. So-called “advertorials” may not have been a hallmark of great journalism, but their very nature required that editors think about what they were doing.

As newspapers become increasingly desperate for money, finding new ways to blur the line between ads and content has become a top priority, not an anomaly.

Tying ads automatically to stories seems to raise the game to a new level. How long before the news quits determining what ads run, and the ads start determining what news runs? And will there be anybody left in the office to even notice?

This article originally appeared on Last Best News.

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