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It’s hard for me to imagine two sites more different than Gawker and Craigslist. Nor can I imagine two people more diametrically opposed than the founder of Gawker, Nick Denton, and the creator of Craigslist, Craig Newmark.

But each, in their own way, have shaped the journalism of today. And, both have made the news of late. Denton, because Gawker was brought down by the Hulk Hogan lawsuit. That court proceeding, and others, were secretly funded by billionaire Peter Thiel. Back in 2007, as Gawker outed Thiel as gay, much to the chagrin (to put it mildly) of Theil, a founder of PayPal and the first outside investor in Facebook. In June, Gawker filed for bankruptcy, as did Denton, a short time later. Gawker has now been purchased by the publisher Ziff Davis.

Meanwhile, Newmark was the subject of a recent Q-and-A by the magazine version of Inc. In it he discusses his approach to philanthropy and to his management of Craigslist, a remarkable classified ad site that is now in 700 cities worldwide. The site was started in 1995 as an email Newmark sent to a dozen friends. By 1997 it was getting a million page views a month.

Craigslist, along with eBay, had a huge impact on local newspapers, back when the World Wide Web was still a curiosity to newspapers. Those publications saw their vital classified revenue wither in the face of free or cheap ads on Newmark’s site. It’s estimated Newmark’s plain text site alone cost papers at least $5 billion in revenue between 2000 and 2007. In other words, print publishers were totally blindsided by a site one guy built. 

Gawker has had its own influence on media. Stories like the Hulk Hogan sex video are more prurient than prudent and have no journalistic value. But, it’s easy to forget that it was Gawker, not the Toronto Star, that first published the Rob Ford smoking crack story. And it was Gawker that brought the underground marketplace Silk Road to public attention.

Gawker’s site Deadspin revealed not only that U.S. pro footballer Greg Hardy had assaulted his girlfriend but that the NFL did nothing until the story broke.

And the site challenged the comfortable, polite and legacy journalism that was way too slow to adopt the etiquette (or lack of it) and expectations of a new social media.

In fact Gawker published what I think is the seminal article about why Gawker matters. The piece, “On Smarm,” points out why calling out bullshit and being “the asshole in the room” is a vital part of being a journalist.

And, even critics of Gawker are quick to point out how dangerous it is for a billionaire to be able to kill a media outlet. Many news organizations, especially smaller, alternative ones, know all too well that they are a lawsuit away from Gawker’s fate.

It’s also interesting to point out that Nick Denton and Craig Newmark are two entirely different personality types. Denton is a brash, extroverted entrepreneur with a penchant for thumbing his nose at the rich and powerful.

Newmark is a quiet, thoughtful philanthropist who has given to Kiva, Wikipedia, and the Global Fund for Women.

He’s also worth $400 million. Nick Denton is broke. 

I don’t know if that says anything about either man. But I do know that it proves that changing the face of journalism doesn’t necessarily make you rich. And that maybe every now and then, nice guys finish first.

Listen to an audio version of this column, read by the author.

Wayne MacPhail has been a print and online journalist for 25 years, and is a long-time writer for on technology and the Internet.

Photo: Andrew Mager/flickr

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Wayne MacPhail

Wayne MacPhail has been a print and online journalist for 25 years. He was the managing editor of Hamilton Magazine and was a reporter and editor at The Hamilton Spectator until he founded Southam InfoLab,...