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The New York Times has chosen the occasion of its website redesign to introduce its first batch of native ads. In this photo, a man polishes the sign for The New York Times at the company's headquarters, July 18, 2013 in New York. (Mark Lennihan/AP)

The New York Times has long resembled a Woman of a Certain Age rushing to catch the last train out of Innovation Station … and just missing it.

But that may be changing.

Start with Snow Fall, the paper’s dazzling multimedia piece that detailed an avalanche in the Washington Cascade Mountains last year. The digital extravaganza was quickly hailed as the future of online journalism and fathered subsequent Times mega pieces such as The Jockey.

The lavish praise also led to Snow Fall Ambivalence, Snow Fall Fatigue, and inevitably, Snow Fall Hate. But the Times was inarguably innovative with a capital I.

Next up in the Times catching that train: The paper’s much ballyhooed website redesign introduced on January 8th. (You can see website redesigns since 2001 here.)

The approach by the Times to native advertising has two potentially fatal flaws: honesty and transparency.

The latest incarnation of nytimes.com features a responsive design format that promises (according to this preview video) a cleaner, simpler interface for a more immersive reading experience, stories that scroll instead of click so there are no unwanted page breaks, article pages that load faster, photos that enlarge beautifully, and comments that follow as you read.

In other words the Times has hauled its digital self into the 21st century, finally catching up to what the Boston Globe, its recently offloaded kissin’ cousin, did several years ago.

And the Times has chosen the occasion of its redesign to introduce native advertising, those ads in sheep’s clothing tricked out to look like editorial content.

That initiative started last fall when the Times announced its intention to join the branded content set. The announcement was quickly followed by official reservations from Times executive editor Jill Abramson, who worried about “leaving confusion in readers’ minds” and Times public editor Margaret Sullivan, who cautiously previewed the “delicate balance” between advertising and editorial.

But Times ad execs said don’t worry — it’ll all be on the up-and-up. And native advertising’s debut on the redesigned Times website was just that: clearly labeled and set apart from the editorial stream. 

Click on the homepage ad upper left and you get what’s clearly a traditional ad. But click on the PAID POST box lower right and you get this article: “Will Millennials Ever Completely Shun the Office?”

Other Paid Posts (clearly labeled ”Paid for and Posted by Dell” at the top) include “Reaching Across the Office from Marketing to IT” and “Can the Government Become Entrepreneurial?

Don’t know about the government, but the Times certainly can.

There’s no way of knowing whether the Times redesign “points to [the] future of online publishing,” as one report had it. Heck, it may not even point to the future of New York Times publishing. That’s because the approach by the Times to native advertising has two potentially fatal flaws: honesty and transparency.

Part of native advertising’s appeal to marketers — and effectiveness with consumers — is its dishonesty and opaqueness. (They don’t call it stealth marketing for nothing.) The Times approach short-circuits that.

And so, you can see these possible future scenarios:

1.) Marketers will avoid the Times native advertising because it’s too transparent.

2.) The Times native advertising will become less transparent.

In the end, the average reader might not want to count too much on the assurances of the Times ad execs, considering their largely cavalier attitude this week when CBS Films doctored a Twitter post from Times film critic A.O. Scott and used it in a full-page ad for “Inside Llewyn Davis” in, yes, the Times. The ad side never even checked with Scott, who had denied CBS Films his permission to use the post.

As public editor Margaret Sullivan noted: “This is not native advertising. However, on the very week that native advertising is scheduled to begin in The Times, this episode does give one pause about keeping the lines between editorial content and advertising perfectly clear and well-defined.”

Uh, yeah.

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