32 Minutes With  Joe DioGuardi

Photo: Jessie Adler

’Is that a classic look or what?” Joe DioGuardi says, standing back in admiration of the gleaming grille of his emerald-green 1965 Cadillac DeVille. It’s as large as a swimming pool and parked outside 8 East 69th Street, headquarters for the Columbus Day Parade, in which DioGuardi, 70, had been marching as part of his underdog campaign for a U.S. Senate seat against Kirsten Gillibrand, who was born the year after the Caddy was. Not many New Yorkers know who he is—he’s polling eleven to fifteen points behind her—but DioGuardi was never supposed to win the Republican primary either. So he’s trying to get into gear.

In an election season defined by unpredictability and abnormality, a conservative like DioGuardi, who’s lost five elections in a row since serving in Congress in the eighties, is convinced he has a puncher’s chance in the special election against Gillibrand. After all, she was the pick of the unpopular Governor David Paterson to fill Hillary Clinton’s seat, and even many of her fans think she’s been too willing to do whatever Chuck Schumer wants. (Schumer is running this fall too, against GOP consultant Jay Townsend, who trails him by 31 points.)

Right now, DioGuardi needs money if he’s going to have any chance at all. Lingering around the Cadillac, he pops the hood for a new donor who wrote him a $2,400 check.

“Look at all that room,” the donor says, checking out the engine. “That’s original,” DioGuardi says, sounding a bit like a used-car salesman. “Nothing rehabilitated, and it works really fine. And that’s the kind of senator I’ll be.”

The Caddy does not come out very often. He drives it only twice a year, mostly for parades. DioGuardi, who’s a CPA (he worked at Arthur Andersen), prides himself on his stinginess. (His shoes? “Florsheims, $79.”) He’s also the father of Kara DioGuardi, a songwriter and singer who was a judge on American Idol.

“Everybody thinks Kara is my secret weapon,” he says. “What about me? Am I chopped liver?” He can sing: He breaks into Sinatra (“It happened in Monterey / A long time ago / I left her in Monterey”).He can dance the tango (“It has a beat, right?”). “We’re both phenomenal dancers,” confirms his wife, Shirley Cloyes DioGuardi. “Only I’m better.” “You should have seen us at the Waldorf on Saturday,” he says.

As of the August campaign filings, DioGuardi had raised only about $300,000 in donations, which could land him on City Council, but it’s nothing like what you need to win senator. By contrast, Gillibrand has already spent almost $7 million. She has $4.5 million left. “She got a lot of money from Wall Street and voted against Wall Street,” he says, referring to a financial-regulation-reform bill. “Now I’m going to Wall Street and she’s not. You can’t shoot an industry that is trying to balance the books in New York in the foot.”

The strategy for Team Gillibrand has been to buy airtime upstate and brand DioGuardi “not a 21st-century candidate,” as one source close to her campaign puts it. (“He’s got the bad hair, he’s short, he’s got a goofy lilt to his voice …”)

Gillibrand’s advisers would have preferred to ignore him. But one early poll showed DioGuardi within six points of her. So in early October, Gillibrand went negative, putting out an attack ad that was a bit misleading in that she tried to tar him as a “congressman turned lobbyist.” Except the group DioGuardi was a registered lobbyist for was his own nonprofit that he started to advocate for peace in the Balkans (he’s part Albanian). Even now that Gillibrand’s lead is in the double digits, she hasn’t let up (see her website ponzijoe.com) But “she has no message,” he says. “I have a message. You want to hear it?”

I nod and he grabs my arm, holding me in place while he goes on about Slobodan Milosevic, bad laws, lack of oversight in Washington. And now he has his hand on my shoulder, telling me about taking orders at his father’s grocery store, working as “Joey the waiter” at a country club for wealthy Jewish garment manufacturers in Westchester. He grabs my lapels, as if pulling me in for a kiss, and goes on about how he worked the backroom gin-rummy game at the club and earned enough to buy a Corvette.

So what’s his strategy? “You remember Bunker Hill?” he says. “ ‘Don’t fire until you see the whites of their eyes.’ ” In other words, he’s saving all his money until the last two weeks of the campaign, which is now. “Don’t you think we are running ads right now upstate? But we need money, real money, so we come down here.” To the Columbus Day Parade. “And we are raising it. This guy right here just gave me 2,400 bucks.”

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32 Minutes With  Joe DioGuardi