Revenge of the Nerd?

One of the things Councilman David Yassky, the boyish, 45-year-old Brooklyn policy wonk, learned during his seven years as a legislative staffer for Chuck Schumer is something he refers to as “the Genovesi Box.” It’s named for Mr. Schumer’s late mentor, Assemblyman Anthony Genovesi.

In the course of a recent hour-and-a-half interview at a two-top in Junior’s on Flatbush Avenue, Mr. Yassky—now a candidate for New York City comptroller—had managed to usher much of the cutlery and dishes from one side of the table to another, allowing himself room to rest his rimless glasses within fiddling reach of his right hand. At one point, with a poli-sci student’s delight, he began to diagram his Schumeresque concept with a reporter’s pen on the white-paper tablecloth.

“You need a pen to do the Genovesi Box properly,” Mr. Yassky said, as he drew a square, quartered it with two perpendicular lines and labeled the outside of the four quadrants “important,” “not important,” “urgent” and “not urgent.”

“What Chuck taught me is that … you do the important and not urgent as much as possible,” rather than the urgent and unimportant, which is, he said, how most politicians spend their time.

You see, David Yassky loves public policy. The question is whether that’s enough.

Mr. Yassky’s political instincts have not always been good. They have led him to mount a spectacularly failed bid for Congress and to alienate both sides during last year’s heated debate over term-limits reform.

Now, he faces a bid for citywide office that is something of a do-or-die proposition. If he loses, it would be awkward, if not impossible, for him to turn around and run for reelection to his Brooklyn Heights–based Council seat. And he’s up against three relatively well-known Democrats: David Weprin, Melinda Katz and John Liu, all of Queens. Most spectators say that the race at this point is a toss-up.

DAVID YASSKYgot his first New York Times mention in 1980. He was 16. The Times, which had a bridge columnist then (and, impressively, still does), mentioned him again in 1982, in an article about a match between Dalton, where Mr. Yassky was a student, and Hunter College High School. Mr. Yassky, “with the ebullience of youth,” “chose a jump shift of two hearts, hinting at slam prospects.”

“When I was in high school, I spent pretty much all my free periods with my friends playing bridge,” Mr. Yassky recalled, 27 years later, at Junior’s. “You know, you weren’t really allowed to play poker in school.”

After a career as a corporate lawyer and Brooklyn College Law School professor, Mr. Yassky matriculated in 1991 at one of the great schools of political strategy in the modern United States: the office of then Representative Schumer, where he helped draft and push through the Brady Bill and the Violence Against Women Act.

“There are probably 10 people in the world with the political gut he has, and the instincts,” Mr. Yassky said.

(Representative Anthony Weiner, another Schumer alumnus, calls Mr. Schumer “the Ted Williams of politics.”)

“To me, what makes you a strategist, and none of this is complicated, just not so many people do it—the goal is to pass a [bill]. So what’s standing in its way? And how do you move that piece?” Mr. Yassky rattled on as the waitress removed the detritus of his corned beef sandwich. He stopped his disquisition to thank the waitress.

“Do you want to take it home?” she asked.

“I think that’s all that I’m going to have. I don’t want to take it home.”

“That’s a lot of meat.”

“I know. But I just don’t want to carry it around in the car all day. And what would you really do with it?” Then he answered his own question: “You could put it into an omelet …”

IN 2001, Mr. Yassky, who has a round face and floppy hair and a friendly little nose, put the political skills he’d learned from Mr. Schumer to the test and ran for the City Council seat that belonged to the term-limited Ken Fisher. It was a rough-and-tumble race against an attorney and Democratic operative named Steven Cohn. The New York Times enthusiastically endorsed Mr. Yassky as “Charles Schumer’s firepower when Mr. Schumer, now senator, was in the House of Representatives.” Against the odds, Mr. Yassky won.

During his early years in the Council, Mr. Yassky earned a reputation as a brainy, substantive progressive.

“He’s one of the few people in the council who talks about Medicaid, and he had a very good piece a while back, I think it was in the Post, on the problem of dysfunctional levels of decision making,” said Fred Siegel, a senior fellow at the conservative-leaning Manhattan Institute and a professor of social sciences at the Cooper Union, who is not usually wont to praise council members.

“David has substance, and that’s enormously unusual in local politics,” Mr. Siegel said.

The Rev. Clinton Miller, the pastor of Brown Memorial Baptist Church in Clinton Hill and a longtime history buff, said he was impressed with Mr. Yassky’s “deep appreciation for what has gone on before he’s gotten here, and I think that’s always important.”

It’s difficult, then, to account for what many regard as Mr. Yassky’s two great errors in political judgment: his decision to run in 2006 against four (later three) black opponents in a Congressional seat specifically carved out to increase minority representation in Congress, and his vote last year to overturn term limits. He says that in each case, he acted on principle. But after each episode, he came out looking somewhat clueless and, almost more objectionably to him, cynical.

AT 11 a.m. on a recent Sunday, Mr. Yassky arrived at St. Anthony Baptist Church on Utica Avenue and Empire Boulevard in Crown Heights, just down the block from a recent botched robbery, in which Mohammed Abuzaid, the owner of a deli, and his son Abdul Kareem were shot to death defending themselves. Candles burned before the shuttered metal gate.

The scene inside the church was more cheerful. That Sunday was the annual youth service, in which children of the church helped lead prayers, and Mr. Yassky, who sat by himself near the front, seemed at home singing along to a gospel version of “This Little Light of Mine,” and bouncing and clapping to the music coming from the full band up front.

It was here, in the 11th Congressional District, where Mr. Yassky mounted his failed bid to replace the retiring Representative Major Owens.

Neighborhood leaders like Councilwoman Letitia James and Mr. Miller say they pointed out to him beforehand the dangers of the race, and warned him that he would be accused of playing racial politics by banking on a divided black vote to get over the top. And Mr. Yassky claims he was well aware he was treading into potentially divisive territory. 

“I knew for sure that there would be people who would say it’s not the right thing to do to run as a non–African-American in a district where the majority of voters are African-American,” Mr. Yassky said. “I think that people are deeper than that and that the voters in the 11th Congressional District could easily feel I could represent them more effectively than anybody else running and that if they felt that way, I would want to give them the choice to vote for me.”

As expected, the race question flared up during the campaign. (New York Times headline: “Race Question Dominates House Seat Fight”; New York Post headline: “Race Is One Color: Red Hot.”) Someone even hurled a chocolate-covered doughnut at Mr. Yassky during a press conference with Mayor Bloomberg at the Wyckoff House.

Yvette Clarke, a political legacy who garnered endorsements from Mr. Weiner and the city’s heavy-hitting health care and building service unions, ended up winning the seat with 31 percent of the vote, to Mr. Yassky’s 26.

Whatever the merits of his cause, Mr. Yassky miscalculated badly. Afterward, he seemed genuinely surprised not only that he lost, but that his very presence in the campaign aroused such an intense backlash.

“In politics, the appearance of impropriety is as bad as impropriety itself,” said Bruce Berg, chair of Fordham University’s political science department. “And someone who is as astute as he is should have realized what it was going to look like long before he did it.”

Mr. Yassky has worked assiduously since that contest to repair relations in the district, and there’s some evidence that it’s worked: He plans, for example, to announce this week that he has won the endorsement from A. R. Bernard, a prominent black minister who leads the Christian Cultural Center.

Mr. Yassky’s other major political error as an elected official was his handling of the debate over pushing back term limits for the mayor and members of the City Council.

Two Democratic council members, Ms. James and Bill De Blasio, who represent districts similar to and bordering on Mr. Yassky’s in Brooklyn opposed overturning the term-limits law that had been put into place by two voter referendums in the 1990s. Mr. Yassky sided with the mayor in favor of a rules change. Perhaps more damaging, he voted for overturning the law only after co-sponsoring a failed amendment to let the voters decide for themselves in another referendum. Rather than committing publicly to one side or the other, Mr. Yassky appeared to waffle.

Citizens Union executive director Dick Dadey told The Times, cuttingly, that it was “kind of like a John Kerry position.’’

Mr. Yassky acknowledges that it turned out poorly for him. But again, he chalked his loss up to principle. 

“The best thing for me personally would have been for term limits to stay the way they were, because then I knew that the comptroller’s office would open and I could be sure I could go ahead with the race that I think I’m going to win and that I thought at the time I was going to win,” he said. “So I was acting against my self-interest, but that’s not how I judge things.”

Which is all well and good. But from a political standpoint: “That was a real mistake,” said Mr. Siegel. “It made him look like just another run-of-the-mill Council hack. … I happen to agree with him [regarding term limits], but this was not a public-policy vote. This was a Bloomberg-says-I-want vote.”

MR YASSKY brushes off concerns about his three comptroller opponents, all of whom have raised more money than him to date.

“The other people in the race have been stockpiling their campaign accounts for literally now five-plus years, because that’s when they started,” Mr. Yassky said.

He has hired big-deal pollster Joel Benenson and the media firm Blue State Digital, both of whom worked on Barack Obama’s campaign, as well as well-known consultant (and former Schumer chief of staff) Josh Isay. And, he pointed out, he has spent the least amount of campaign money this far, which he says means that he will have more money during the crucial final days of the race.

“[C]ome the last month of the race, when voters are paying attention at the greatest degree of intensity, I expect to be able to outspend at least two of the three opponents materially,” he said.

Mr. Yassky also contends, not incidentally, that he is the best qualified of the candidates to be comptroller. In addition to his work as a corporate lawyer doing mergers and acquisitions, Mr. Yassky worked in the city budget office (where he met his wife-to-be, Diana Fortuna, the former president of the Citizens Budget Commission and the current budget director for the Metropolitan Opera) and has, since 2002, chaired the Council’s Waterfront and then Small Business committees; championed clean-air taxis and tax breaks for freelancers; and helped to create new affordable-housing requirements.

As comptroller, Mr. Yassky says, he will focus on job growth and accountability, in part by drastically increasing the transparency of the city budget: “I’d put the budget online, program by program, with the spending matched up with what it’s producing.”

And if he serves as comptroller, he’ll have a great platform from which to run for mayor. The thing is, first he has to win.