What’s in David Chiu’s political baggage?

Several months ago, Board of Supervisors President David Chiu was a lawyer and entrepreneur whose highest government office was a seat on the San Francisco Small Business Commission. Today he is the second most powerful politician in the city. Chiu's cool head and shrewd approach to legislating have made him the unquestioned standout in the freshman class of progressive supes, and his no-nonsense efforts to grapple with the city's budget crisis while Mayor Gavin Newsom wanders the state on the gubernatorial campaign trail have reaped particular praise. Chiu's meteoric rise has gone smoothly — with one exception.

Last summer, H. Brown, an ex-sailor and firefighter who has earned a reputation as one of the city's more strident political gadflies, began calling Chiu's liberal bona fides into question. Brown claimed to have unearthed evidence that Grassroots Enterprise, a consulting firm specializing in Internet communications that Chiu founded and was until recently chief operating officer of, had worked for some dubious causes. Among them, Brown said, were the National Rifle Association and the antigay Alliance Defense Fund.

Affiliation with such groups would have been political kryptonite among Chiu's strongest backers. San Francisco's left-wing activists, who propelled the North Beach supervisor and his allies into office, are notoriously fond of constructing litmus tests for ideological purity. Luckily for Chiu, Brown was wrong. Grassroots Enterprise had never worked on behalf of the NRA or Alliance Defense Fund. Chiu nevertheless felt obliged to respond in force. The candidate sent a four-page letter to the board of the Harvey Milk Lesbian, Gay, Bisexual, and Transgender Democratic Club, defending his company's work and stating that Grassroots had never licensed its technology to "antigay, Christian conservative, or pro-gun organizations."

That assertion put the matter to rest. Press organizations, including SF Weekly, accepted Chiu's statements at face value. As it turns out, Brown was onto something — he just didn't know exactly what. Grassroots' caseload may not have included the specific conservative groups he was harping about. But campaign finance reports, interviews, and Grassroots' own promotional materials show that the company has put itself to work for plenty of causes that stand in direct opposition to Chiu's progressive ideals.

Consider a political organization that paid Grassroots Enterprise $300,000 during the 2004 election cycle, according to Federal Election Commission (FEC) records. That group is the Republican National Committee, which, as it happens, makes a particular point of being clear about its stance on guns and gays. During the period Grassroots worked for the RNC, the committee's platform called for a constitutional amendment to ban gay marriage and proclaimed avid support for gun rights. In 2007, FEC records show, Grassroots was paid $33,000 by the Republican Leadership Council. That ostensibly moderate group nevertheless threw its weight behind candidates including Jean Fuller, the Republican assemblywoman from Bakersfield who, in 2007, loudly opposed a bill that would have legalized same-sex marriage.

The list doesn't end there. In 2006, Grassroots won an award from the American Association of Political Consultants for its work on pharmaceutical companies' Internet campaign against California's Proposition 79, a prescription-drug-benefit initiative with the backing of labor and consumer groups. During the 2006 midterm elections, the U.S. Chamber of Commerce hired Grassroots to aid its online campaign against liberal Democrats nationwide. The company developed a Web site, www.37reasons.com, which offered compelling reasons to vote for pro-business candidates. Among them: "Liberal Activist Judges Sailing Through the Judiciary Committee," "Stopping Environmental Zealots," and, simply, "Speaker Pelosi." The campaign is featured on Grassroots' Web site as an advertisement for the company's services.

Chiu, in his letter to the Harvey Milk Club, defended Grassroots as a "bipartisan" company that nevertheless served an "overwhelming majority" of liberal clients, among them the American Federation of Teachers, the Gay and Lesbian Victory Fund, and the Sierra Club. He also stated that he had "emphatically disagreed" with the company's decision to hire a board member and a high-level executive formerly employed by the Christian Coalition and the NRA respectively.

Here again, however, Chiu doth protest too much. Grassroots is not a liberal organization that recently began taking on conservative employees. Chiu founded the company with Matt Fong, a Republican who ran against Barbara Boxer for U.S. Senate in 1998. Among the factors that doomed Fong's candidacy was the revelation that he had donated $50,000 to the Traditional Values Coalition, an antigay and antiabortion group. (When word got out, he signed a pledge supporting gay rights.) Shortly after his failed Senate campaign, Fong and supporter Craig Johnson of the Venture Law Group joined forces with Chiu, his fellow S.F. activist Perla Ni, and others to form Grassroots. Before her role at the Bush White House, Condoleezza Rice was an early member of the board of directors.

"I know David has his philosophical bias, but when it came to being in business he was quite pragmatic," Fong said in an interview. "He would take money from a conservative group just as well as a liberal group." Grassroots president and CEO John Hlinko, a former leader of the progressive nonprofit MoveOn.org, said he wasn't aware of any conservative clients with whom Chiu had worked personally. But Chiu has benefited from the company's brisk consulting trade. In 2006 and 2007, Grassroots paid him an annual salary in excess of $100,000, according to San Francisco Ethics Commission records.

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