Trippi, a veteran Democratic campaign strategist, was then helping organize what would soon become a national, if short-lived, political earthquake: the technology-fueled, anti-war end-run around Democratic Party politics as usual by a previously obscure Vermont governor named Howard Dean. Here’s how Klein described his unusual new relationship in the October 2004 issue of The Washington Monthly:

As our correspondence continued, my initial, tentative support gave way to full-blown enthusiasm. . . . Trippi slowly drew me in. Each time I opened my email or checked my messages and found a Dean campaign official inside, my interest intensified. Soon I was selling Howard Dean online, then organizing for him around my Southern California hometown. Finally, I accepted Trippi’s invitation to spend the summer in Vermont, working for the campaign. I had barely noticed, but Trippi had turned me from a nominal supporter of his candidate into a die-hard Deaniac.

Sounds like a Paul Begala or James Carville in the making, right? Think again. The Dean experience actually pushed Klein away from party activism and toward what would become his career. “It turned out I hated working for a campaign,” he says now. “I have strong opinions about American public policy, and the nature of working on a campaign is that you have to sublimate your opinions to somebody else’s. It’s really around that time that I began taking journalism more seriously.”

Klein became part of an emerging “Netroots” phenomenon: left-of-center political junkies, native to the Web, who tilted at windmills during the dark reign of George W. Bush and would eventually help refashion Democratic politics and political media. These young grassroots bloggers were basically functioning as political columnists without a mainstream-media platform: among them, Markos Moulitsas (founder of the innovative and high-trafficked community site Daily Kos), Duncan Black (the dour, acid-penned proprietor of The Eschaton Blog, known by his pen name, Atrios), and Matthew Yglesias (well-known even before graduating from Harvard in 2003).

During President Bush’s second term, the left’s newly energized bloggers developed a wry shorthand to mock the political-media bubble they saw enveloping Washington. Morally pompous Iraq war supporters (especially on The Washington Post op-ed page) were tagged “Very Serious People,” since “un-serious” was a frequent slur on the allegedly ill-informed anti-war left. Above-it-all Beltway paeans to bipartisan comity were dubbed “High Broderism,” in anti-tribute to David Broder, still considered by many to be the dean of the DC journalism establishment. “Even The New Republic” became a favored sardonic phrase. As National Review’s David Frum wrote in May 2007, “If even The New Republic finds more to praise than to blame in the left blogosphere, then the brakes are truly off the Democratic machine.”

The Netroots crowd reserved its harshest critique for what it dubbed “The Village”—that unreal political island in the District of Columbia where absurdly powerful people treat important policy like frivolous sport and pretend to disagree with one another on cable chat shows. Connecticut Senator Joe Lieberman—sanctimoniously pro-war and favorite of The New Republic—always seemed to be the only Village “liberal” allowed in places like NBC’s Meet the Press, where he would wallow in host Tim Russert’s High Broderism and cluck his tongue at the uncivil rabble to his left.

“I think a lot of blogging was founded on a very particular critique of the media,” Klein says. “During this period of the Iraq war, there was a broad feeling that the media hadn’t done its job, that it had been hampered by this requirement to pretend the truth always was in the middle. And I was part of that critique.” (Klein was originally in favor of the Iraq war on liberal-hawk grounds that he would soon repudiate.)

Still an undergraduate, Klein found himself attracted to Matthew Yglesias and the older, left-of-center blogger Kevin Drum, both of whom were more journalistic and amiable than the typical bomb-throwing diarist at Daily Kos. “If you wanted to tell the story of my coming up, Matt Yglesias is the key figure,” Klein says. “Matt’s blog was a major inspiration for me, because he was a college student and he did this kind of data-driven, very careful work that appealed to me.”