Six years ago, Joe Trippi was heralded as the man who was reinventing campaigning for the Internet era on behalf of the outsider who nearly became the Democratic standard-bearer. 

In the 2010 cycle, he’s becoming known as the man throwing bombs at the establishment working for a string of primary challenges, most notably Jeff Greene in Florida, at a time when Democrats are fighting hard to avoid them.

He pushes back hard against the label, but Democratic establishment types are now calling the strategist a “mischief-maker” as he takes aim at the party’s powers-that-be in a cycle where anti-incumbent sentiment is running high.

But this isn’t about being “anti-Democratic establishment, that’s crap,” Trippi said, arguing that the same Democrats criticizing him now were fearful in 2008 that he was harming the "inevitable'" nominee Hillary Clinton.

“It’s anti-status quo….I think a lot of the energy on the Democratic side is diminished and that most of the energy right now is on the right.”

While Trippi agreed to an interview, he added that he would “rather be doing almost anything else.”

“Let’s just get the hatchet job done,” he said before talking for 40 minutes in response to about a dozen questions, then calling back three times with more to say.

Trippi has worked on top presidential runs in the past two cycles, and many other campaigns big and small over the years. This time around, he has a patchwork of primary challengers to candidates who the Democratic Senatorial Campaign Committee and White House had hoped would proceed unscathed to the general election.

Trippi’s current clients include Colorado Senate hopeful Andrew Romanoff (of White House “Jobgate” fame), who is challenging Michael Bennett, who was appointed to the seat; Jerry Brown, the longtime California pol; and Florida billionaire Jeff Greene, who is challenging Rep. Kendrick Meek and who has made headlines for not being able to say whether he voted for Jimmy Carter or Ronald Reagan in 1980.

Bill Romjue, Romanoff’s campaign manager, called Trippi “one of the most innovative thinkers in the party,” adding that a story looking at him as a flamethrower would be “carrying water” for someone’s agenda.

“I’m really lucky because I can work for who I want to work for” instead of having to hustle clients, Trippi said, insisting his career has been a healthy mix of politics and business, so that he’s not hustling clients constantly. He points to his work on Jerry Brown’s 2006 attorney general campaign in California (the two have an on-and-off relationship spanning three decades), and in helping to elect Rep. John Hall in NY-19 out of nowhere.

His many rivals, critics and detractors within the party say something different.

“These are the clients he’s taking because he can’t get work on the top races,” groused one Democratic strategist, arguing that Trippi’s significance in politics has been overstated, and that he has actually had relatively little involvement with races over the years. The strategist added that Trippi has cast himself a rebel because the A-list crew doesn’t tend to use him.

Another strategist agreed, saying, “He’s doing the clients he’s doing to make money. As much as everyone likes to act like what we do is a cause, we’re in this business to earn a living.”

Bob Shrum, the veteran Democratic strategist who worked on John Kerry’s 2004 race and was in practice with Trippi for years, said that’s an unfair assessment.

“If you achieve a certain amount of notoriety in this business people try to put you in a box, and the new box for Joe, I guess, is the mischief-maker,” he said. “I think it’s not so much a box as that this guy is unorthodox. He’s not bound by the parameters of orthodoxy on who the DSCC thinks should be the nominee, or who the press thinks is a [serious] candidate.”

The Florida race has been perhaps the key piece of evidence in his critics in the party’s indictment of him. Trippi has questioned Rep. Kendrick Meek’s ethics and suggested he is too much of a “Washington insider” to shake up the establishment.

Meek, a four-term incumbent, is struggling mightily, and a recent poll showed Greene pulling even with him as Republican-turned independent Charlie Crist is threatening to surge past either potential Democratic foe.

Greene’s presence has infuriated Democrats, with one telling POLITICO’s Jonathan Martin that the potential $40 million effort by the candidate who collects erotic art, cashed in betting on the housing market collapse and had Mike Tyson in his wedding party is “obnoxious.”

But Trippi brushed off criticism of Greene’s run, saying, “I don't think Meek has a chance to win,” and that the billionaire didn’t bet on the housing crisis, but having lost his fortune in the last recession saw the housing crisis coming and steered his way through it.

He also said that of the four candidates in Florida, Greene is the only one who's not tied in some way to "some kind of criminal investigation."

And Trippi took umbrage at the notion that he’s taking on clients that others won’t. A source close to Trippi said that at least one other well-known ad-making firm interviewed for the job with the Greene campaign, and didn’t get the gig.

“One of the really strange things that's been going on this year is this orders from on high that you're not allowed to have a primary,” Trippi says derisively about the White House.

“Where the hell did that start? We can’t spend our resources, our precious resources, because we might lose the general….does anybody remember this stuff or was I the only one alive two years ago? Obama didn’t listen to this stuff [in his 2008 primary run against Hillary Clinton].”

Trippi also had a slow-rollout last year advising Rep. Carolyn Maloney as she was gearing up for a possible run again Sen. Kirsten Gillibrand, widely seen as vulnerable after her appointment by an unelected governor to the seat vacated when Hillary Clinton left the Senate to join the administration. At first he was cited as “supporting” her, before it came out that he was on her pay roll, a nondisclosure he publicly apologized for twice.

Trippi at times seemed to want a fight more than his candidate, issuing tough statements even as Maloney’s words telegraphed reservations about risking her House seat to take on a race that was far from a sure thing. She ultimately decided not to pull the trigger.

Earlier this year, Trippi also supported Merrick Alpert, the businessman and former military man who ran an uphill battle against Connecticut Attorney General Richard Blumenthal for the Democratic nod in the race for the open seat to replace retiring Sen. Christopher Dodd (D).

Alpert made a huge stink leading into the opening of the state’s Democratic nominating convention about not being able to address the delegates from the stage – only to decide, as the voting began and it became clear he couldn’t secure a ballot berth, to take to the stage and announce that he would be withdrawing his nomination and supporting Blumenthal.

“Merrick was a friend, I didn’t get paid,” Trippi said, adding that he pushed him to throw in the towel.

Trippi has bounced around politics for decades, having worked for Los Angeles Mayor Tom Bradley’s campaign and Gary Hart’s presidential run, among other bids for office.

After partnering with Shrum and ad-maker David Doak for much of the 80s, Trippi said he got disillusioned with politics after the 1988 presidential race, and was re-engaged in a new way by Dean’s campaign.

“You have to read my book and memos to Dean to understand any of this,” he said, referring to his tome “The Revolution Will Not Be Televised.” In the book, he describes the importance of Dean’s race in often-grand strokes, calling the candidate’s surge from second-tier candidate to front-runner “a dot-com miracle. In fact, it was a stunning victory that will resonate long after the election of 2004 is forgotten. In fact, it was the opening salvo in a revolution, the sound of hundreds of thousands of Americans turning off their televisions and embracing the only form of technology that has allowed them to be involved again.”

But while the Dean campaign used the Internet as an effective organizing and fundraising tool and surged in the polls, it didn’t find a way to translate that enthusiasm to the ballot box in Iowa, where the Vermont governor, never the establishment pick, came in a dismal third despite the passion he tapped into on the left.
Trippi’s strategy was derided at the time, but his model for using the web was successfully melded into nearly every campaign in the last presidential cycle.

In 2008, Trippi went to work for the John Edwards campaign, where he took a less central role but helped to steer the candidate toward his raw populist “Two Americans” message – which often hit stumbling blocks as details about the trial lawyer’s lavish personal lifestyle were made public.

A Democratic strategist who has worked with Trippi before cracked: "When you read Joe Trippi, Chapter 1 and Chapter 2, it's fine. But when you read Chapter 17, you start to realize it's all the same thing."

Despite such criticisms, Trippi sees himself as one of the honest brokers in politics.

He hammered the White House for trying to "puff [Meek] up with hot air" after the incumbent gained no traction after a year and a half of campaigning.

"If all these [candidates] are so flawed, why bother? And if I'm so bad, if I can't consult my way out of a paper bag, then why do [they] care?" he asked.

Shrum put it this way: “Joe is fantastically talented and creative and sometimes exasperating, and I always found the exasperating worth it.”