New York has two Democratic senators, both of them up for election this year. In the first race, Chuck Schumer has a commanding lead. In the other, Kirsten Gillibrand may be in trouble.

The seat Gillibrand occupies was vacated in 2008 by Hillary Clinton. It was dangled in front of Caroline Kennedy before being handed, by Governor David Paterson, to Gillibrand, an attractive, centrist Democrat just beginning her second term in the House of Representatives. Yet five polls recently had her less than 11 points ahead of her underfunded Republican challenger, Joe DioGuardi. Two polls show her lead in single digits. At the national level it had been assumed that the Gillibrand seat was entirely safe. This is no longer the case.

People have been slow to understand Gillibrand’s situation because the polling on her race has been wildly divergent. The Real Clear Politics average has her at +14. But that number probably overstates reality. Seven polling groups are in the field, and five of them have had the race very close—anywhere from Gillibrand +11 to Gillibrand +1. One poll, from Siena College, is an outlier pulling the average up: It has Gillibrand at +26.

Superficially, Gillibrand should be in great shape. She’s young and vigorous and is from a state where Democrats outnumber Republicans nearly 2-to-1. She’s the incumbent. And she’s sitting on a pile of money, having raised $11.3 million so far, with $4.5 million in cash on hand (as of late August). But her political foundation is less solid than it seems.

Gillibrand still carries the stigma of being appointed by a deeply unpopular governor. (Paterson’s approval ratings have recently crept upward to the mid-30s.) She has been a senator for only two years and has never won a statewide race, meaning that she has all the problems of incumbency, but few of the benefits. Her name ID numbers, for instance, are quite weak. Even in the poll most favorable to her, 30 percent of respondents answer “don’t know/no opinion” when asked if they favor her. Compared with the personages who held the seat before her—Robert F. Kennedy, Daniel Patrick Moynihan, Hillary Clinton—Gillibrand is an unknown.

All of which has provided an opening for Joe DioGuardi, the 70-year-old who won the Republican primary in September, defeating the state party’s preferred candidate. He lacks many of the traditional advantages: He too is little known, and he can’t self-fund. But he is an experienced campaigner: DioGuardi won two terms in the House in the 1980s before being defeated by Nita Lowey, and later ran two unsuccessful insurgent campaigns against GOP incumbents in 1994 and 1996.

DioGuardi is a social conservative and as such not an obvious fit for New York. But the thrust of his campaign—and all of his previous campaigns—is fiscal responsibility. His pitch to voters has always been that he wants to fight against “spending money we don’t have.” He constantly reminds people that he’s a practicing CPA with the professional instinct to pinch pennies and watch the bottom line. And this time around, his message is on point.

“She voted for the $787 billion economic stimulus package that was supposed to create jobs, but New York has lost 110,000 jobs since then,” DioGuardi wrote recently. “She voted for the trillion dollar health care reform legislation, which disproportionately raised taxes on New Yorkers.” If DioGuardi had the money to air these attacks more broadly, Gillibrand would be in even greater peril.

Oddly enough, Gillibrand doesn’t seem worried about DioGuardi. Instead, she spent the early part of this year focused on possible primary challenges. Last year a string of New York Democrats circled Gillibrand’s seat, contemplating runs against her. The White House convinced them all to take a pass.

But Gillibrand’s obsessive concern about avoiding a primary challenge may actually have hurt her. First, it led her to abandon her moderate background in an attempt to court the party’s far left. As a result, she’s now a conspicuously liberal senator. Gillibrand has tacked so far to the left that she was one of only seven senators to vote against cutting off ACORN’s funding last year. And avoiding a primary deprived Gillibrand of the chance to earn a statewide vote and establish a persona on her own terms.

DioGuardi, meanwhile, actually has an inside draw to beating Gillibrand. New York is divided into three regions: upstate, New York City, and the New York suburbs. Upstate is a place of relative parity between the parties where the outcome often tracks with national results. New York City is heavily Democratic. As Real Clear Politics’s Sean Trende notes, since 1994 Republicans have averaged only 27 percent of the vote in the city in contested statewide elections. DioGuardi is poised to do at least that well. He’s already over 27 percent in most polls; one has him at 35 percent in the city.

That’s not unheard of: Republican George Pataki won 38 percent of the city vote in 2002. Trende argues, somewhat convincingly, that DioGuardi’s Italian-American heritage will serve him well in the ethnic enclaves of Brooklyn, Queens, and Staten Island, where white voters have been willing to vote Republican in the past. If New York City’s black voters don’t turn out as they did in 2006 and 2008, DioGuardi has a chance to perform respectably in the city, where his winning even 30 percent will make Gillibrand uncomfortable on Election Night.

And then there are the suburbs. The off-year elections in Virginia, New Jersey, and Massachusetts all featured suburban voters revolting against Democratic candidates. That movement is taking place in New York, too, albeit on a slightly lesser scale. Obama won the three major suburban counties, Westchester, Nassau, and Suffolk, by margins of +28, +8, and +6, respectively. This year polls show Gillibrand trailing in the suburban counties by anywhere from -4 to -12. If the Republican wave lifts DioGuardi further ahead in the New York suburbs—or the National Republican Senatorial Committee decides to push some money into the race—Gillibrand could well be in trouble.

Joe DioGuardi is still a long-shot candidate. But in this extraordinary year, all kinds of once-safe seats have swung into play. Kirsten Gillibrand’s is one of them.

Jonathan V. Last is a senior writer at The Weekly Standard.

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