"A lot of the traditional interests in the city, a lot of the day-to-day players in city government-my guess is the bulk of those vested interests will be supporting one or another of the other candidates," said City Council Member David Yassky (D-Brooklyn), mulling his run for comptroller recently over ice coffees at Starbucks. "That's okay by me."

This is familiar territory. In 2001, he ran for Council against the establishment candidate and won by 10 points. Five years later, he ran as the only white candidate in a four-way primary for a Congressional seat traditionally held by African Americans. He came in second, by just three points.

Next year, his opponents once again have high name recognition and large campaign war chests, a fact he eagerly points to when discussing the race.

But though he is grasping for the underdog mantle, Yassky has already secured support from some of the city's vested interests himself, raking in hundreds of thousands of dollars from top law firms, real estate developers, investment firms and hedge funds. For example, he received over $11,000 from several lawyers at Sullivan & Cromwell LLP, the 15th largest law firm in the world. There are donations from several other top firms as well, either from the firm or from several partners. Two of the city's powerful real estate developers, Thor Equities and the Durst Organization, have also donated to Yassky's campaign.

A Yale law school graduate, Yassky said he appreciates the support he receives from friends and former colleagues.
"Law guys and gals stick together," he said.

Yassky is one of five announced candidates for comptroller, trying to find a spot at least into a run-off among Council Members Melinda Katz (D-Queens) and David Weprin (D-Queens), Assembly Member James Brennan (D-Brooklyn) and Bronx Borough President Adolfo Carrión (D). Queens Council Member John Liu (D) may also make the race.

With the end of his term fast approaching, Yassky said he began to seriously consider his next move last summer. After consulting several past comptrollers and former aides in the comptroller's office, Yassky was convinced.

"The more I thought about it, the more I talked about it, the more enthusiastic I got about just how much you could accomplish in that job," he said.

He quickly put together a new campaign operation, positioning himself as the activist, environmentalist candidate who will use the powers of the comptroller's post to improve the efficiency of city government. He said he is modeling his platform on the current and former attorney generals, Andrew Cuomo (D) and Eliot Spitzer (D).

Yassky said he admired the way Spitzer and Cuomo were aggressive in their use of the office, adding that he hopes to be a similarly aggressive comptroller.

"A lot of issues go through that office," he said. "I'm not going to let them go by just because I don't want to make waves or because I don't want to ruffle the feathers of the powers that be."

As he reaches out to new donors, Yassky has also begun to eye areas of the city where he hopes to gain an edge over his rivals. In a race with no Manhattan-based candidates, Yassky is trying to position himself as a surrogate Manhattan candidate, increasing his visibility in Manhattan-especially in the Upper West Side, with its cache of big-money donors and high-turnout neighborhoods. In recent weeks, he held a fundraiser on West 87th Street and was spotted at a political club meeting across from Lincoln Center.

"It's shaping up for Manhattan to be the battleground," Yassky said.

But he sees other unclaimed votes as well.

"Don't forget Staten Island," he said, insisting that his prospects are good in both boroughs.

If he wins, Yassky said he plans to capitalize on the comptroller's sway over policy. He said he plans to make all audits require city agencies to report on energy efficiency and conservation. He will make economically targeted investments with the city's pension fund to stimulate the economy and provide for more affordable housing. And, with the City Council slush fund scandal in mind, Yassky said he would be more aggressive in vetting the city's budget.

"I'll pick each year a handful of earmark recipients to audit to make sure they are delivering results," he said.

Yassky said he supported Speaker Christine Quinn's (D-Manhattan) proposal to make the distribution of discretionary funds more competitive, even though a majority of Council members eventually convinced her to pull back the plan.
He added that he was infuriated by the revelation that earmarks were being parked in fictitious groups in the city's budget. As comptroller, Yassky said he would strive to hold the Council and any community group that receives earmarks accountable.  

A proud policy wonk, Yassky said he plans on making his case as much on the issues as possible, even as others focus on demographics and other bits of politicking in what may well prove the most crowded, competitive and expensive race of 2009.

"I think voters aren't going to read your 100-page white paper on health care or budget reform," he said, taking his glasses off and furrowing his brow. "But they will look at a candidate enough to decide if this person is real."