Rockin’ the Suburbs: Rob Astorino Hopes Westchester Wins Translate Statewide

Astorino vs Cuomo

One October day on the campaign trail last year, Rob Astorino was heading to a street festival in Mount Vernon, a heavily African-American city just across the border from the Bronx. Not a place where a Republican politician is a natural sell.

After hearing word that several local residents had jokingly threatened to fight him in a nearby boxing ring, the Westchester County executive just went with it.

“Who wants to fight me? Who wants to fight me?” he asked the crowd when he arrived, according to his re-election campaign manager, Phil Oliva.

It turned out to be the perfect ice breaker, his handlers say. “These guys just burst out laughing. They talked for about 10 minutes,” Mr. Oliva said, adding that the would-be boxers then asked for an Astorino campaign poster and hung it up. Mr. Oliva took a picture to remember the moment.

Rob Astorino campaigning in Mount Vernon. (Photo: Phil Oliva)

Rob Astorino campaigning in Mount Vernon. (Photo: Phil Oliva)

Mr. Astorino, who easily won his 2013 re-election bid as Westchester County executive in the two-to-one Democratic county, is once again in the ring. This time, he is swinging at Gov. Andrew Cuomo, a seemingly unsinkable Democrat seeking re-election in the decisively blue-hued Empire State.

By all accounts, Mr. Astorino, who is expected to formally kick off his campaign tomorrow, is a distant long shot: anti-gay marriage, pro-life and on down the list of conservative positions. But many of those who know him, including those across the proverbial aisle, are not so quick to dismiss him.

“I don’t agree with basically anything he’s done governmentally,” said a Westchester Democrat. “But I respect Rob. … Rob’s good. Rob’s real good. He’s charismatic. He’s charming. He’s down to earth. He’s a terrific retail politician. He’s going to be tough. He’s definitely going to be giving the governor a headache.”

In many ways, Mr. Astorino, who was born and raised in Westchester, embodies the suburban stereotype his county carries. Clean-cut and often smiling, Mr. Astorino lives in Hawthorne, population roughly 5,000, with his wife, Sheila, and three young children: Sean, 10; Kiley Rose, 8; and Ashlin Grace, 4. He is Catholic but said, “It doesn’t involve doing the rosary every day.”

“He’s just a regular guy. You go around his neighborhood, and he’s a regular guy. It’s his magic,” said Bill O’Reilly, a Republican consultant who works for Mr. Astorino.

In any case, plain folk do seem to be having a moment. Tweaking Mayor Bill de Blasio, another aggressively regular guy and on-camera sidewalk shoveler, Mr. Astorino recently tweeted a photo of himself, shovel in hand: “Okay, BdB. How about a shovel off? 6 am tomorrow? (Sharp.)”


Mr. Astorino is in his soon-to-be campaign headquarters in White Plains, running through his campaign’s raison d’être. “It’s my love and passion for the state that I was born and raised in,” he tells the Observer. “It’s now time to put the state back in the winning column.”

“By any standard of measurement, New York is losing, and we have to change that,” he argued. “The biggest outflow of residents than any other state in the country, a lagging unemployment rate with some areas exceedingly high with no growth whatsoever, the upstate economy is dead, the taxes are the highest in the nation. And we’ve got the worst business climate for people to expand or to come here.”

“So when you look at all that,” he concludes, “and then you look 10 or 15 years down the road, where we’re going to be, and it’s not a pleasant place. So this is the time to step and say, ‘I’m gonna change things like we did in Westchester.’”

Rob Astorino.

Rob Astorino.

If Mr. Astorino, 46, comes off like a political pro, it’s because he has been at it quite a while. He got his start in public life while a still a senior at Fordham University, joining a coalition of activists to win a seat on the Mount Pleasant School Board.

“He was always a great leader,” said Laura Schwartz, an accountant and Astorino campaign treasurer, who met the future pol as a teen. “Even when we were in high school, he was a lot like the way he is now. He became friends with a lot of the teachers in our high school, which is a little unusual for a teenager.”

At 23, Mr. Astorino went on to serve on the town board and stayed at that part-time post for a dozen years. Later, he would hold a full array of county positions, including county legislator and vice chairman for the county board of ethics.

At the same time, Mr. Astorino had a budding radio career, doing ESPN sports radio and traffic reports from helicopters and planes. “My whole thing was media, and I wanted to do TV and radio. And you know, [with] some people, the career advice was, ‘Go start in Iowa, and go get some experience,’” said Mr. Astorino. “I’m like, ‘Why would I leave the capital of the world, where everyone is, to try and fight my way back? Start here. Start here and try to catch a break and to work hard.’ So I never left New York.”

Eventually, Mr. Astorino’s broadcast work translated to a career as a host for the Catholic Channel on Sirius Satellite Radio, where he hosted a Thursday night program with Cardinal Edward Egan, the archbishop of the Archdiocese of New York. Radio experience helped him transition into politics; the airwaves require staying on message and summing up complex ideas in easy-to-grasp rhetoric.

“I love to do radio,” reflected Mr. Astorino. “It’s so intimate, it is. You can get someone captive and captivated in their car. I think the greatest testament to an interviewer or someone being interviewed is what I call driveway radio: When you get home, you listen to an interview; you sit in your car in the driveway, because you don’t want to miss it.

“And I just think it’s a great vehicle to, unfiltered, get out a message in politics or government,” he continued. “They’re hearing your tone, they’re hearing your passion.”

He also gained a deep well of sports knowledge, which can be handy for bridging divides in politics. “I’m a bit of a sports nut, and even if you don’t agree on ideology, you talk Yankees, Knicks,” remarked State Senator George Latimer, a Westchester Democrat who said he has “known Rob for probably the better part of 20 years.” Mr. Latimer jokingly said he was trying to keep Mr. Astorino’s Miami Dolphins fandom “under wraps.” (“I’ve always been a Giants fan too,” insisted Mr. Astorino. “I’m not crazy about the Jets.”)

Even Mr. Astorino’s critics, many of whom work in politics and requested anonymity to speak candidly, readily acknowledge Mr. Astorino is adroit at getting his point across.

“He’s shredded county government,” kvetched one Democrat, cautioning: “He’s a really, really, really good communicator.” Lamented another operative who once faced off against Mr. Astorino, “We could not get the guy to go off-message.”


Assuming Mr. Astorino sails through his Republican primary, Mr. Cuomo will be waiting. One year after Mr. de Blasio beat Republican Joe Lhota by a jaw-dropping 50-point margin, Mr. Cuomo will be looking to similarly dominate in his own contest.

Mr. Cuomo, who was a top political adviser for his father, ex-Gov. Mario Cuomo, has built a reputation as a moderate on fiscal issues—“I’m progressive, but I’m broke,” he has quipped—and a liberal on social issues. He effectively moved much of his agenda through the notoriously constipated state legislature, including on-time budgets, pension reform, same-sex marriage, gun control, a property tax cap and an extension of the millionaire’s tax.

These accomplishments, plus the attention automatically accompanying any governor of the Empire State, have put Mr. Cuomo on the national map, even as he rarely leaves the state. Though Hillary Clinton is currently the New York establishment’s top presidential candidate, Mr. Cuomo is considered a potential contender in the future. If Mr. Cuomo can win re-election by an even wider margin than his nearly two-to-one dusting of Carl Paladino in 2010, national pundits will take notice.

Mr. Astorino is likely to minimize the governor’s accomplishments. “On-time budget?” he asked the Observer. “You’re supposed to do that. If that’s his crusade, that you’ve ‘brought an on-time budget,’ congratulations, you’re doing your job.”

He also characterizes Mr. Cuomo as an opportunist who doesn’t stand for anything in particular. “Everything is political with this governor. His finger is constantly in the wind. I don’t know what he would die on the hill for. I really don’t,” he said, castigating Mr. Cuomo’s “gimmick” plan to have special tax-free zones upstate to stimulate economic activity.

Mr. Cuomo’s potential attacks aren’t hard to script. His surrogates are likely to highlight the county executive’s down-the-line conservative positions: how he opened the county up to new gun shows; how he’s quick to cut what opponents describe as vital services in the name of fiscal pragmatism; how he’s battling the federal government’s demands that Westchester provide more affordable housing. And where Mr. Lhota was able to stress his ideological deviations from Tea Party accusations by pointing out his own pro-choice and pro-same-sex-marriage beliefs, Mr. Astorino may struggle even more to define himself as close to the political center.

“He is a nice guy,” offered Barry Caro, a Democrat who worked on the unsuccessful campaign to defeat Mr. Astorino’s 2013 re-election. “But he is really, really conservative. I know Democrats always say that, but the guy is legitimately conservative. … He holds Republican positions on literally every issue.”

“I’ve served with Rob. Rob is an affable guy who is very focused on what he sees is his mandate to make government smaller,” said State Senator Andrea Stewart-Cousins, who leads her chamber’s Democratic conference and used to serve with Mr. Astorino in the Westchester legislature. “But in terms of his ideological views, he is, I think, just a hard sell for New York.”

But Mr. Astorino has been bombarded by many of those same attacks before and easily won his last two elections by larger-than-expected margins despite them. The right-wing extremist argument simply couldn’t stick to a candidate who projected political pragmatism in every campaign ad and stump speech. “That was their whole game plan in 2009, their whole game plan in 2013,” said Mr. Astorino. “And people rejected it.”

"Trabajando para Westchester." (Working for Westchester.)

“Trabajando para Westchester.” (Working for Westchester.)

Mr. Astorino is vowing to campaign in the hard-core Democratic turf in the five boroughs as well. “I’m going to go where Republicans don’t go,” he said. “That’s what I did in Westchester.”

“When he walks around, he’s got an urban strategy, which a lot of Republican candidates don’t have. He walks into the Boy’s Club in Mount Vernon, and they love him. He walks into a Latino church, and he speaks Spanish,” said Jim McLaughlin, a G.O.P. pollster who has worked with Mr. Astorino since 2005.

“I have worked hundreds of campaigns and never am surprised when a candidate memorizes two or three sentences in a foreign language and goes to a festival or a church where a certain group is gathered and blurts out, in a kind of battered tongue, some phrase in their ethnic language that makes them endeared to the group,” said Tony Sayegh, a Republican strategist. “Particularly a Hispanic event or a Hispanic area of the county, I see Rob deliver not just a few words in Spanish but deliver entire speeches in Spanish, do jokes in Spanish.”


For his part, Mr. Cuomo is reportedly taking Mr. Astorino seriously.

Last week, The New York Times ran a front-page story detailing Mr. Cuomo’s outreach to Republicans, allegedly trying to bat off support for Mr. Astorino even as he publicly denies paying any attention to his own re-election campaign. “Some think he is simply trying to muddle the Republican race in hopes of gaining a stronger margin of victory when he seeks re-election in November. Others suspect that Mr. Cuomo may view the ambitious Mr. Astorino, who won re-election last year in the heavily Democratic suburbs north of New York City, as a more capable rival than he is letting on,” the Times speculated.

And Mr. Cuomo was already said to be hitting Mr. Astorino on social issues. “He’s told me that if Astorino runs, he is going to pound the hell out of him and talk about guns and gays, and it won’t be pretty and will hurt all of us,” an anonymous Republican state senator told the paper.

Mr. Astorino, reacting to the story, mocked the idea of Mr. Cuomo trying to quietly push him out of the race.

“I find that pretty funny. I think it’s the arrogance of power,” Mr. Astorino told Time Warner Cable News Friday. “I think it’s complete bullying in what he’s trying to do. This is not the Kingdom of Cuomoland. This is the state of New York. In this country, we have a democracy; I and others might have the temerity to challenge him.”

Mr. Cuomo and his spokesperson dismissed the story, labeling it distracting “political gossip” as the governor focuses on the work of the people.

“I want to get the budget done. I work very well with my Republican colleagues. I work well with my Democratic colleagues. One of the reasons is we stay away from the politics when we’re in the middle of the budget. We have a month to go to get the budget done. Let’s get the budget done,” Mr. Cuomo said when asked about the story, also speaking during a Friday media interview.

“The politics will start in June,” Mr. Cuomo offered. “And then we’ll officially start the silly season.”

Every neutral political observer predicts that “silly season,” which will involve the governor unloading perhaps $40 million in campaign ads and deploying a battle-tested political armada, will end favorably for Mr. Cuomo.

Some Astorino supporters have privately said their man will walk away a winner if he can simply post a respectable margin, perhaps losing by just 10 points, against the formidable Mr. Cuomo. But the Westchester pol, deploying a sports metaphor, insists he will surprise people.

“Nobody,” he said, “goes to the Olympics and wants the silver medal.”