You are using an outdated browser.
Please upgrade your browser
and improve your visit to our site.
Skip Navigation

Double Enmity

If they didn’t hate each other so much, David Sirota and Dan Gerstein might be friends. They certainly have a lot in common. Both are in their thirties. Both are Jewish. And both are Democratic operatives. But their greatest similarity is their shared love of vicious political combat. Sirota, a lanky 30-year-old who has worked on campaigns for Philadelphia mayor and Montana governor, once branded a political opponent a “No Talent Ass Clown.” Gerstein, a thick-necked 39-year-old communications consultant and veteran Joe Lieberman aide, has been known to accuse those who disagree with him of being anti-Semites. Which is why, even by the no-holds-barred standards of a blog feud, the Gerstein v. Sirota smackdown was unusually nasty.

The online flame-throwing started in July, when Gerstein accused Sirota, a vocal Lieberman detractor, of something unthinkable to his left-wing fan base—almost going to work for the Connecticut senator. “Yes, that’s right,” Gerstein taunted on a pro-Lieberman blog, “[t]he same guy who is viciously attacking Joe Lieberman as the great Satan of the Democratic Party actually sought not one but two jobs from the target of his hatred. ... The polite term for that would be chutzpah. Some one less charitable might call Sirota a fraud.” Sirota immediately shot back. On his eponymous blog, he pointed out that his dalliance with the Lieberman staff took place three years ago; that they solicited him; and that, after the interview, he told them he wasn’t interested. The experience, he revealed, was so odious that he “held [his] nose for a meeting with the notoriously arrogant Gerstein.” Perhaps concerned that he wasn’t making his real feelings clear, Sirota added that Gerstein is a “classic, haughty, self-important, professional election loser.” And the fight only got uglier from there, as the operatives lobbed charges at each other ranging from “rank hypocrisy” to being “an unabashed liar.”

The Gerstein-Sirota feud should have been just another rumble in the blogosphere, notable only for its combatants’ particular brand of mean- spiritedness. But recently the melee spilled over into the non-virtual world. That’s because in August, after Lieberman lost the Democratic primary to Ned Lamont, Gerstein was hired to serve as the communications director for Lieberman’s independent bid; and on Labor Day, after the Lamont campaign realized it needed some more political pros for the general election, Sirota was brought on board to help with its research and rapid response. Which means that the Lieberman-Lamont race—a race that is already plenty nasty—is likely to get only nastier, as the Gerstein-Sirota fight graduates to a larger ring.

ALTHOUGH HE IS nearly a decade younger than his rival, Sirota has a reputation for ruthlessness that would seem to make him the odds-on favorite. In 1999, he was fired from a Philadelphia mayoral campaign for being linked to a dirty trick: A friend of Sirota’s created a phony website for a rival campaign that featured some racially inflammatory language. (Sirota denies any direct involvement.) He then went to Washington, working for aipac and Vermont Representative Bernie Sanders before joining the Democratic staff of the House Appropriations Committee. There, he won acclaim for crafting well-researched, soundbite-filled attacks on the Bush administration that he e-mailed to fellow Democrats and journalists. In one, he mocked the now infamous “Mission Accomplished” speech, asking, “President Bush has time to take a water safety class and spend taxpayer money flying out to an aircraft carrier for a stunt photo-op?”

In 2004, Sirota joined Brian Schweitzer’s campaign for Montana governor, where he honed the research and rapid-response skills that he will now put to use for Lamont. After a Republican group ran a TV ad featuring complaints from people who claimed they’d had bad business dealings with Schweitzer, Sirota, according to Schweitzer’s then-campaign manager, Eric Stern, “found out that one had a criminal record, one was heavily involved in Republican politics, and another had been investigated by the IRS.” Stern adds, “He really goes for the jugular.”

Sirota is equally skilled at self-promotion. “He’s a dial-a-quote—a left- wing populist version of Norm Ornstein,” says Ed Kilgore, a political operative with the Democratic Leadership Council, which has been a frequent target of Sirota’s blog broadsides. (Full disclosure: Sirota has also launched his fair share of attacks against The New Republic and its writers, although he has not attacked me—yet.) Two years ago, after Schweitzer’s victory, Sirota took up residence in Montana and began accessorizing his suits and sports jackets with oversized belt buckles and string ties. He refashioned his rhetoric as well, railing against the “Beltway Establishment” and the “Washington cocktail party circuit”- -leaving at least one old D.C. acquaintance to ponder why he’d failed to notice Sirota’s proletarian misery as he sipped drinks alongside Alan Greenspan and Chris Matthews during a party at Maureen Dowd’s Georgetown house a few years earlier. Sirota, for his part, claims the Dowd party was a one-time, Heart of Darkness-like expedition.

Gerstein is safe from charges of having ever sipped or supped at MoDo’s. Over the last decade, the Connecticut native has been too busy doing Lieberman’s bidding. Gerstein began working for Connecticut’s junior senator in 1994 and stuck with him for the next ten years—playing a Zelig-like role in all of Lieberman’s major moments. Lieberman’s 1998 speech rebuking President Clinton for his dalliance with Monica Lewinsky? Gerstein helped write it. Lieberman’s turn as Al Gore’s running mate in 2000? Gerstein was his spokesman. And Lieberman’s ill-fated 2004 presidential campaign? Gerstein served as deputy communications director and was tasked with telling reporters, despite all evidence to the contrary, that the campaign was gaining “Joe-mentum.” Before reenlisting with Lieberman this summer, he ran a consulting firm in New York, a perch from which he penned a Wall Street Journal op-ed mulling the ability of Nancy Pelosi and Harry Reid to “successfully fight a parking ticket, let alone the war against terrorism.”

Gerstein’s impact on the Lieberman campaign has been dramatic. He has sharpened Lieberman’s speeches so that they no longer meander or seek to avoid crucial and contentious issues, such as Lieberman’s support for the war in Iraq. And he’s pressured reporters to toughen their coverage of Lamont, personally peddling stories about Lamont’s past membership in an exclusive Greenwich country club and anti-Semitic comments from Lamont supporters on a message board. “Dan is a tough streetfighter,” says Bill Andresen, Lieberman’s former chief of staff. “He can get in people’s faces and make sure they do what he thinks they ought to do.”

This, of course, doesn’t always endear him to those who cover Lieberman. “He’s a master of sustained fake outrage,” complains one reporter. “He won’t break character, which makes him very unpleasant to deal with.” And Gerstein’s pugilistic nature can sometimes land him in hot water. In response to a commenter’s question on the Lieberman campaign’s blog about a news report that the GOP has steered money to Lieberman, Gerstein blustered, “What’s next, you want us to provide evidence that Joe Lieberman doesn’t beat his wife?” Which subsequently forced Gerstein to issue the sort of statement no campaign spokesman ever wants to make: “Joe Lieberman does NOT beat his wife.”

NOW THAT GERSTEIN has an official position with the Lieberman campaign, he’s pledging to take the high road in his feud with Sirota. “I’m not going to make this personal about David,” he told me—before plunging right back into the mud pit with a comment about how “it’s sort of interesting that the Lamont campaign said they weren’t going to hire any outside operatives and now they bring in David Sirota. ... It’s just another hypocrisy for them.”

Sirota doesn’t even feint in the direction of the high road. He’s practically giddy about the fact that any shots he takes against Gerstein will now have the added bonus of hitting Lieberman as well. “The Lieberman campaign has been more bombastic and caustic and nasty [since Gerstein joined it],” he told me over the phone from Montana, as he prepared for his move to Connecticut. “I really do believe that he’s hurt the campaign’s credibility with the media and the public.”

And the issue of exactly how deep Sirota’s connections to Dark Lord Lieberman were three years ago has remained a serious bone of contention. Early this month, Sirota dug up a chain of e-mail correspondence between him and Lieberman’s office documenting that he did indeed cut off discussions with the Lieberman camp after one interview—and that he was not rejected by Lieberman, as Gerstein has claimed. On his blog, under the headline “HERE IT IS: THE INDISPUTABLE PROOF LIEBERMAN’S CAMPAIGN LIES,” Sirota posted the e-mail exchange, accused Gerstein of libel, and, lest anyone think he was merely grinding a personal ax, mused on “the bigger political sense” of the whole affair. “Why,” Sirota wrote, “does Joe Lieberman, a man of supposed `principle’ who is supposedly pursuing a `new politics of unity and purpose’ allow someone with such disdain for the truth like Gerstein to publicly represent him?”

Gerstein wouldn’t directly answer Sirota’s question. “I have never told one lie about David Sirota,” he replied, quickly pivoting to try to reframe the dispute. “This is one of the problems with the Lamont people. They make wild accusations about lies when they don’t even know what a lie is.” In an e-mail, Gerstein was even more blunt. “THIS PROVES NOTHING,” he wrote, “OTHER THAN SIROTA HAS GONE OFF THE DEEP END.”

This article originally ran in the October 2, 2006 issue of the magazine.