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Rob Astorino in the Widening Gyre of GOP Politics

The Reaganite Republican finds himself running for governor (again) in a party frothing about COVID, Cuomo, and critical race theory. Can he keep up?

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Credit: Rob Astorino/Facebook
Former Westchester County Executive and gubernatorial candidate Rob Astorino has long styled himself as a moderate. But to compete in the GOP of 2022, he has shifted his messaging.

After traveling all over the state with an army of volunteers collecting signatures before the April 7 deadline to enter the New York Republican primary, which is on June 28, Rob Astorino barely had time to rest. But it wasn’t the subway shooting in Brooklyn that was keeping him busy, nor the resignation of Hochul’s lieutenant governor, Brian Benjamin, after being charged with bribery. It was a problem affecting every single American, he claims, one driving inflation and taxes up, and posing a threat to “public health, to public safety, and to the public’s right to know”: the “secret” plot to import undocumented immigrants to the interior of the United States under the direction of President Joe Biden. The Department of Health and Human services has said multiple times that no such plot exists,” but that hasn’t stopped Astorino.

“The Biden administration must have such contempt for Americans that they’re importing people from other countries, flying them into the interior, and just dispersing them,” Astorino told Tucker Carlson five days after filing. “And then turning them into voters like in New York City, where they will be allowed to vote with 30-day residency.”

On Twitter, Astorino had recently posted a 10-second video of two white coach buses driving down a street, apparently outside of Westchester County Airport. The video was a sequel of sorts to body camera footage he obtained through a Freedom of Information Act request in August 2021 that shows unaccompanied, undocumented minors coming off planes at night and packing into buses headed to different locations, while one government contractor chaperoning the children can be heard speculating, “If this gets out, the government is betraying the American people.”

Astorino sent a letter to the White House demanding to know the exact number of “illegal aliens” that were flown into Westchester, the percentage of those who were adults, and of the adults, the percentage who were male. “It very much seems that the impacts of the crisis at the southern border are purposely being transferred throughout the interior of the country,” he wrote on February 1.

Astorino never received a response from Biden, which he took to confirm his suspicions, and he claims this new video proves that the flights have “resumed.” But a spokesperson for HHS says the flights were not paused in the first place, and that “the cadence of flights depends on the transportation needs of the children in our care.”

HHS has said repeatedly that these flights are to transfer children either to a new federal facility, or to family members or sponsors who’ve been vetted. Nobody in the custody of HHS is over the age of 17, about half of them come from Guatemala, and the flights go to a number of other states, including Florida, Virginia, and North Carolina. The flights take place at all hours of the day, despite Astorino’s claim that they only happen in the dead of night, and the destinations of these kids is kept confidential to protect their identities, which they’re especially careful about after a New York Post reporter followed one of the buses to a stop in New Jersey. It’s a routine operation—but has served as an especially potent lightning rod for Astorino.

After his Tucker Carlson appearance, Astorino’s schedule blew up, and he set forth on a virtual tour across the conservative mediasphere. Between stops at Newsmax with Greg Kelly and Fox Business with Maria Bartiromo, he barely had time to meet with me, and was still caked in on-air makeup. On each appearance, he more or less asked the same questions—Where were these kids going? What schools were they being sent to? And were they vaccinated? It’s unclear if answers to these questions would sooth his ire. Astorino admits that he doesn’t really care whether anyone is vaccinated—in fact, he bragged on Megyn Kelly’s podcast about how none of his own children are—but he thinks Democrats should, because, “Well, isn’t that their narrative?”

Shifting Rhetoric

If, over the past eight years, you were to ask Astorino about how New York State is faring, you’d get a consistent answer: taxes are at an all-time high, economic output has declined, education spending has skyrocketed but failed to produce results that justify it, the governor is corrupt, urban elites have turned their backs on rural upstate voters, and thousands of residents are fleeing annually. And he’s felt this way before COVID-19 vaccine mandates, before cash bail reform in New York, before critical race theory became a hot button education issue, and before Donald Trump became the Republican presidential nominee.

Astorino entered politics after graduating from Fordham University, serving first on his hometown’s school board for a couple of years and later as a county legislator while working in radio during the day. He was attracted to politics partly, he says, from watching his parents suffer under the high cost of living in Westchester, and partly by his admiration for President Ronald Reagan. When he was 27, his father, Lieutenant Robert Astorino, chief of detectives of the Mount Vernon Police Department, was caught on camera stealing $10,000 cash while executing a search warrant that had secretly been set up by the FBI after they suspected corruption. But that hasn’t stopped Astorino from presenting himself as a staunch advocate of law enforcement, and when he ran against Cuomo in 2014, he said he was proud of his father’s service and wasn’t concerned about the incident being used against him.

“If they want to be pigs and get in the mud, that is their choice,” Astorino told the Daily News.

But since that race, there has been considerably more mudslinging in the American political landscape, and Astorino seems to have embraced it. The 2016 election put old guard respectable conservatism in tension with Trump’s vulgar brand of populism. That has resulted in a conservative political sphere that, with the help of people like Chris Rufo, now delights in fighting over critical race theory and transgender issues. The subsequent impact on the GOP—and by extent, Astorino—is especially striking when looking at why Astorino was favored by establishment Republicans in the pre-2016 days.

In 2014, New York State Republican Party Chairman Ed Cox described Astorino to The New York Times as “almost Reaganesque.” Astorino was quick to call Cuomo corrupt, but in order to run in New York, he was forced to put aside his conservative stances on abortion and gay marriage and focus on economic issues that might sway moderate voters. This was a time when MSNBC would not only welcome a Republican gubernatorial candidate, but sympathize with his critique of the state’s high tax policy and fleeing residents: On a 2014 episode of Morning Joe, Astorino had host Joe Scarborough nodding in agreement when he said New York was ranked the “worst place to retire” and another guest lamenting about paying 60 cents on the dollar in taxes.

Astorino even made an effort to court supporters of progressive candidate Zephyr Teachout after she lost the Democratic primary to Cuomo. “When she lost, we reached out and said, ‘She ran a great campaign, now come and support us,’” says J.P. Andrade, Long Island volunteer coordinator for Astorino’s 2014 run for governor. “You guys are tired of Cuomo’s tyranny, all of his negative policies in the state and his attitude toward everything that was going on at that time.”

Credit: Michael Johnson/Wikimedia Commons
An anti-corruption press conference with Zephyr Teachout and Astorino in Manhattan. After Teachout lost Teachout after she lost the 2014 Democratic primary, Astorino’s campaign tried to pick up some of her supporters.

But since Trump, the GOP has pivoted away from the compassionate conservatism of George W. Bush to embrace the culture wars. The war in Iraq and the 2008 recession revealed the failures of two key pillars of Reagan-era conservatism: foreign intervention and free markets. Trump capitalized on this failure by demonizing corporate elites, military contractors, immigrants, and career politicians.

“Trump’s presidency was a critique of establishment Republican positions,” says Matthew Sitman, co-host of Know Your Enemy, a podcast that explores the history and major players of conservative thought. “One distinctive thing about Trump is that he let Republicans do the culture war without some of the religious rhetoric.”

The party had shed Goldwater conservatism and was in the process of warming up to LGBT conservatives, but when Trump arrived in office he revoked Barack Obama’s guidance to public schools allowing students to use the bathroom of the gender with which they identify. Now, members of the GOP spend much of their breath railing against transgender youth issues and queer teachers whom they claim to be indoctrinating students by acknowledging non-heterosexual orientation.

“It’s a party that is, I think, now more populist in a policy sense, but even more so in the kind of pejorative sense of populism, which is to say something crude and pretty freely playing with bigotry and hate,” Sitman says.

Trumpian Influence

Astorino, who told reporters in 2009 that he thinks there should be a separation of church and state, seems pretty comfortable these days on the front lines of the culture war. In many ways, he remains the agitated budget hawk pointing out high costs and inefficiency, and he has resisted some of the conspiracy theories that his GOP peers have embraced—he believes Joe Biden is the rightful victor of the 2020 election, and he’s vaccinated and boosted. But that hasn’t stopped him from following recent developments in the GOP’s messaging.

On an April episode of Bernie and Sid in the Morning on 77 WABC, Astorino said he wasn’t so worried about the polls that had him behind his opponent Lee Zelden, the Republican establishment’s choice. 

“There are important things we have to be talking about,” Astorino said. “Lia Thomas, for instance, is in the news and obviously has been for a while. He’s the swimmer in the University of Pennsylvania swim team.”

“What do you mean, he?” asked one the hosts, pointing out that Lia Thomas, the transgender woman swimmer who’s broken multiple NCAA records this season, identifies as female.

“I was waiting for one of you to pick that up,” Astorino said with glee. “When somebody gets out of the pool and there’s a bulge in his speedos, I don’t have to call him he.” He corrected his joke, “I mean she.”

Like other conservatives who’ve criticized Thomas, Astorino claims he is concerned for the integrity of women’s sports, and he spoke about the issue not just as a politician, but as a coach of his 12-year-old daughter’s Catholic Youth Organization basketball team.

“The fact that she may lose a roster spot, or a championship, or a scholarship to a guy who is playing on her team makes me crazy,” Astorino said. The Catholic Youth Organization did not respond to a question about whether there were any transgender females in its leagues.

Astorino’s stance on the issue is similar to most of his primary competitors, though his rhetoric is a bit more moderate, especially compared with Andrew Giuliani, son of Trump lawyer and former New York Mayor Rudy Giuliani, who said about his daughter at a rally on Long Island, “I have looked under the hood. She’s a woman. I’m gonna be the last guy in a long time that looks under the hood right there. But guess what? She was born a woman and she’s gonna stay a woman, it’s that simple.”

It makes sense that Giuliani, in his first bid for public office, has embraced these developments in Republican messaging. He began his political career as an assistant in the Trump White House and his father was instrumental in pushing what is perhaps the most Trumpian of claims—that Trump only lost the election because of voter fraud.

Credit: @RobAstorino on Twitter
Astorino visited the West Wing in December of 2017, sharing this photo on Twitter.

But Astorino has a more complicated relationship with the 45th president. He’s vying for Trump’s endorsement this year, but there was a time when the two were at odds. In the fall of 2013, Trump was considering running for governor as a Republican. He and his advisers saw it as a “springboard” to a presidential run in 2016, but Trump would only enter the race if he didn’t have to face a primary challenge.

Astorino had just won re-election as Westchester County Executive, having previously ousted the Democratic incumbent, and had developed a track record that managed to please both card-carrying Republicans and moderates who were frustrated with high taxes. By pre-Trump GOP metrics, Astorino was poised to be the kind of fiscal Republican that could resonate with independents and disaffected Democrats.

Astorino had considered Trump a friend and a reliable donor in local races. The two attended a fundraiser at Trump National in Briarcliff Manor, hosted by the Eric Trump Foundation for St. Jude’s in September 2013. But a few months later, Astorino’s continued campaign developments made a target of Trump’s Twitter rage.

“I like Rob Astorino. He’s a friend and really good guy. Sadly, he has ZERO chance of beating Cuomo and the 2 to 1 Dems for governor!” Trump tweeted on December 19, 2013.

After party leaders declined to clear out the primary race and make way for the man who now sets many of their talking points, Trump summoned Michael Long, then chair of the Conservative Party of New York State, to Trump Tower in Manhattan. But when Long showed up, Trump wasn’t there. Instead, there was a telephone in a room, and Trump was on the line.

“He said, ‘Give me 30 days to see if I can put together a campaign,’” Long says. But after 30 days, Trump said he needed more time. Long got the impression that he wasn’t all that serious about a run and told the former Apprentice host that the party would be moving forward with nominating Astorino.

Astorino is careful with his words when he talks about his conversations with Trump about the race. He denies that there was ever any bad blood between the two and says, “I told him I wasn’t leaving, so if we want to have a primary, that’s fine.”

Despite a barrage of negative TV ads and a significant name-recognition gap, Astorino ran a campaign railing against Cuomo’s corruption, with the help of $1.55 million from right-wing megadonor Robert Mercer. He lost by 13 points to Cuomo, who got just 54 percent of the vote. It was far lower than the 62 percent of the vote Cuomo enjoyed against Carl Paladino in 2010, and significantly lower than his father Mario’s 33-point landslide in his first re-election campaign. It was far more promising than anyone, save maybe Astorino, could have imagined.

Harnessing Outrage

Astorino’s crusade against Cuomo was, in many ways, ahead of its time. Cuomo’s 2014 stifling of the Moreland Commission, which he created to unearth corruption in state politics before ordering it to withdraw a subpoena that it had issued to a media-buying firm that his campaign used in 2010, revealed how willing he was to put a thumb on the scales to maintain control of his administration’s image. And even though Astorino made the commission a major talking point on the campaign trail, he struggled to evoke from voters the kind of outrage that now animates much of the popular opinion of the former governor.

When COVID-19 first arrived in the Empire State, New Yorkers embraced Cuomo as the voice of reason whose press conferences provided a sense of security compared to Trump’s White House briefings. Some people idolized not just Cuomo’s basic competency but his domineering demeanor and bossy tone, which sometimes edged into condescension when reporters asked questions he didn’t like. Some even took to calling themselves “Cuomosexuals.”

While this fandom blossomed, Republicans, including Astorino, took aim at Cuomo’s March 25, 2020 executive order requiring nursing homes to accept COVID-positive patients, arguing that the death toll stemmed from his political incompetency instead of the virus’s capacity to kill. Cuomo called these claims politically motivated, but he rescinded the measure that May, a tacit acknowledgement that maybe burdening elderly care facilities with infectious residents wasn’t such a great idea.

But the damage had already been done—and then it was covered up. Not only did New York State refuse to report the nursing home case count in addition to the death toll, which many other states did on a weekly basis, but according to reporting done by The New York Times, the Cuomo administration refused to count deaths of nursing home residents who were transferred to hospitals before dying, claiming the mortality number was around 8,500, when it was really closer to 15,000.

The revelation attracted plenty of media coverage, but it wasn’t until revelations about Cuomo’s sexual harassment that the governor was shamed into resigning. Republicans delighted in his downfall, though it’s easy to imagine the party defending Cuomo as a victim of post-#MeToo era workplace policies had he been one of their own.

Cuomo’s disgrace allowed Astorino, who had long billed himself as the common man’s protector against Cuomo’s tyranny, to go on the offensive. Almost as soon as Hochul entered office, Astorino turned his attention from the former governor to the woman now tasked with cleaning up the mess, whom he labeled “Governor Spiteful.” Throughout this past winter, Astorino promoted rallies on his Facebook page to protest mask mandates in schools and vaccine mandates in workplaces, embracing and being embraced by a new conservative faction of voters displeased with the government’s handling of the pandemic.

At one rally in November, Astorino was photographed with a crowd in which one woman held a sign with a swastika on it. He says he did not notice the sign until seeing photographs of the event later, but one feature of the new brand of brash rhetoric Astorino has embraced is a kinship to a variety of far-right positions. His was not the first anti-mandate rally to attract Americans who’ve compared lockdowns to Nazi Germany, and it wasn’t the last. While Astorino has publicly tried to separate himself from that fringe, he’s happy to receive support from people who share their frustrations but express them differently.

Credit: @JeffreyDinowitz on Twitter
As the Republican Party moves further right, Astorino’s rallies have attracted some of the extremist fringe.

On February 10, Hochul rescinded the New York State mask mandate except in schools; almost in lockstep, Astorino turned his sights to school mask mandates. On February 25, on his Facebook page, Astorino promoted what he called “Operation Smile,” inviting parents to join him in sending their children to school unmasked. But one day before the operation, Hochul announced masks would no longer be mandated in schools.

Now Astorino is tasked with preserving that parental outrage for six months until November. But he’s not worried. He’s confident voters will think about “when we have the next pandemic down the pike, or when the virus comes back and they’re threatening to shut things down. Or, the day after the election, the question is who is going to shut everything back down,” he says. “People are not going to forget the experience they’ve been put through over the last two years.”

Turning and Turning

It’s clear what Astorino believes; it’s less clear why he believes it. The only substantive vision he’s offered is one where New York didn’t have the highest taxes, skyrocketing crime, or undocumented immigrants. He believes all those things are bad, but when pressed on why, he defaults to checkbook explanations—more immigrants means more money in the state budget for social services for them, which means more spending and thus, more inflation which drives up the cost of living in New York.

Perhaps he really is only concerned with cutting costs, but that argument is not only stale by recent Republican party standards—it’s diametrically opposed to the vision of other Trumpian conservatives, who’ve pivoted away from worrying about finances to what they claim to be the material concerns of their constituents.

The difference is especially noticeable when comparing Astorino to nouveau Republican candidates like J.D. Vance, who is running for governor in Ohio on a platform of eliminating funding for state colleges that teach critical race theory, returning manufacturing to middle America, and punitively raising taxes on companies that ship jobs overseas. He just received Trump’s endorsement. People like Vance feel that with the middle class gutted and schools teaching unpatriotic curricula, there’s not much left for conservatives to conserve and a new vision must be offered. The version of this new vision varies on the time and tenure of the politician presenting it, but most describe it as a local, family-oriented, socially traditional politics with robust social programs and child tax credits, and offer it in direct contrast to a secular corporate media industry whose content endorses progressive understandings of race and gender. 

Astorino got the memo on critical race theory—“It [teaches]: America is a hating country. It was born out of making sure people were enslaved. It is teaching people to hate each other based on the color of their skin,” he recites—but when asked how he would eradicate it from schools, he shies away from the measures others have supported, saying he would never enforce speech codes, for example.

There is a similar disconnect when he speaks about the decimated industries of upstate New York. Astorino channels the Trumpian concern for the working class when he says that the region has been stripped of its manufacturing and abandoned by urban-centric politicians. But after telling me he was pro-union, Astorino backtracked when I asked what he thought about the first Amazon warehouse voting to unionize in Staten Island.

“There are some unions that I think are just going to not be good,” he says. “That might be one of them, but that’s up to them…It’s just going to raise the cost of doing business in some of these places and the prices. They voted for that. That’s their legal right. I could care less.”

He added: “There are unions that I think are completely bad. I’m not going to name them, but I believe they have been disruptive to the economy. Politically, [they’re] driving us so far to the left. There are some unions who want complete open borders.”

Again, Astorino is almost there in his realignment with this new conservatism, especially with the invocation of “open borders,” but he missed the opportunity to dunk on a large corporation which uses progressive messaging to attract college-educated customers—what some Republicans call “woke capital.”

Compare Astorino’s response to that of Tucker Carlson when he interviewed Amazon Labor Union organizer Christian Smalls: “I’ve never been particularly pro-union, but it does seem like Amazon needs some counterbalance. It’s this huge company, the workers have no power, and maybe we could…share a little power with the people who work there.”

Astorino is better versed in the updated GOP talking points on gun control, perhaps because it’s an issue he’s run on before. In his 2014 run, he took aim at the SAFE Act, which Cuomo passed after the Sandy Hook shooting to increase regulations on certain assault rifles and magazine capacities.

“The SAFE Act made no one safer in New York. All it did was make criminals out of law-abiding citizens,” Astorino said at an event in March 2014. At the time, he was not a gun owner, though his spokesperson, Bill F. Buckley O’Reilly, nephew of National Review founder William F. Buckley, says he shortly became one after the event. 

Recently, Astorino has embraced a more extreme 2nd Amendment position, along with most of the GOP. In 2015, a poll by the University of Texas at Austin found that only 10 percent of state residents supported the permitless carrying of guns, or what supporters call constitutional carry. But as was the case with other fringe positions, between 2016 and 2020, permitless carry became a statewide conservative talking point throughout the South, and now 21 states allow it.

Astorino is skeptical that such a law could ever pass in New York, but he says he would support permitless carry if elected. He hedged that support by saying he would also require background checks, but his willingness to embrace a position so recently and ferociously opposed by a plurality of Texans, let alone a plurality of New Yorkers, demonstrates Astorino’s political malleability. He’s willing to support most of these updated positions, even if the Reaganite in him might not be as privy to the economic developments.

A Wide-Open Race

In the end, it might not matter whether Astorino has fully mastered the latest GOP positions. To hear him tell it, his past success has depended not on what he’s said but the race in which he’s said it.

He lost in 2005 running for county executive, he believes, because of a backlash against Republicans for the post-9/11 expansion of the security state and the failed war in Iraq. Four years later, Astorino says his victory against the incumbent Spano was part of a larger backlash against President Barack Obama, whose party lost control of the House of Representatives the following year.

“The things we said in ’05, people realized to be true,” Astorino says. “Maybe we were ahead of our time in ’05 just like we were ahead of our time in ’14, but everything we said was correct. People were listening, but it was the wrong political climate.”

Now, he’s hoping to surf the red wave many pollsters predict this fall. While Zelden, the establishment choice, outperformed Astorino in a poll taken just one day after accepting the New York Republican Party endorsement, Astorino was the only Republican candidate polled who held Hochul to under 50 percent of the vote.

More recent polls from late March, after Hochul announced controversial plans to build a new stadium for the Buffalo Bills with up to $1 billion in taxpayer money, have the governor with just a four point lead against Zelden. Cuomo had a six point deficit against Zelden in the same poll. They show an election in which none of the establishment candidates has a certain path to victory. With Zelden embracing support from reliably red Long Island voters, Astorino is focused on the same moderates who allowed him to exceed expectations in 2014, hoping they’re finally as outraged as he is.

“Part of leadership is going against the grain,” he says, “and telling people the truth.”