Yahoo is investing in content again, launching a new tech site with New York Times columnist David Pogue. But the company has tried and failed to make money in journalism before.

With David Pogue Hire, Yahoo Joins the Journalism Investment Boom

David Pogue. Photo: Ed Schipul/Flickr

Following in the footsteps of eBay founder Pierre Omidyar, Amazon CEO Jeff Bezos, and venture capital firm Accel Partners, Yahoo has pumped new money into original journalism, launching a website with prominent tech reviewer David Pogue.

Pogue says he’s leaving the New York Times after 13 years as the paper’s highly visible tech reviewer to lead the forthcoming Yahoo site, where he’ll contribute videos and blog posts. Yahoo CEO Marissa Mayer called the venture “a major expansion of consumer tech coverage on Yahoo.”

At the starchy Times, Pogue has been dogged by ethics questions revolving around his paid outside engagements. But Yahoo — based in freewheeling, deal-loving Silicon Valley — will presumably be less concerned about such issues.

Yahoo’s Mayer joins a crush of tech-heads rushing in recent months to bring innovation to online journalism. EBay’s Omidyar has committed $250 million to a joint venture with Guardian investigative journalist Glenn Greenwald. Amazon’s Bezos spent as much to buy the Washington Post. And Verge publisher Vox Media recently raised $34 million in a round led by Accel.

It’s a remarkable infusion of cash for such an ailing industry. But history is not encouraging. Yahoo, for one, went down this road three years ago, before Mayer’s arrival, hiring a slew of seasoned journalists from Newsweek, USA Today, Congressional Quarterly, Politico, and Gawker. But the web giant had trouble meshing its Silicon Valley sensibilities with the hard-driving style of East Coast journalists.

Content was also briefly king during the tech boom of the late 1990s, when Microsoft invested a reported $20 million in the unprofitable Slate and Adobe co-founder John Warnock began subsidizing Salon.com, whose losses now total $116.5 million. Even the Huffington Post, a relative success story, spent five years in the red, only to fold into struggling internet conglomerate AOL.

So it makes sense that Mayer praised Pogue for being one of the “most positive people I’ve met.” If anyone is going to reverse the trend lines in web journalism, he or she must certainly be an optimist.