What Will It Take for New York to Elect a Republican?

On Tuesday night, New York City will be fixated on the results of one race: the Democratic mayoral primary. Meanwhile, in an afterthought for most city residents, a 71-year-old radio host named Curtis Sliwa will capture the Republican nomination and formally become the party’s pick for the general election in November. 

You might think that the Republicans have a golden opportunity to win a race like this. 

There’s a better than even chance that the Democrats will choose 33-year-old socialist state assemblyman Zohran Mamdani to be their nominee, a darling of the party’s far left who otherwise seems designed in a lab to alienate moderates. If Mamdani doesn’t get the nod, voters will almost certainly go with Andrew Cuomo, New York’s tough-to-love former governor. 

The Democratic incumbent, Eric Adams, is so unpopular that he skipped the primary altogether. And Cuomo says he’ll do the same if he loses to Mamdani, perhaps setting the stage for a crowded November contest where the eventual victor could squeak by with just a slim plurality of the vote.  

Will Sliwa be the one squeaking by? No. Allow me to explain.

It’s true that New York City got slightly redder last November, with President Donald Trump winning about 30 percent of the vote, almost double his share in 2016. Democrats—both in New York and across the country—are currently rudderless, with the party’s moderate and leftist wings engaged in a low-grade civil war. The city has stagnated after 11 years of Democratic rule, Mamdani’s platform is truly radical, and Cuomo resigned as governor in disgrace just four years ago amid a flurry of sexual harassment complaints. 

And yet, for all that, the presumptive Republican nominee appears lifeless, short on cash, and destined to lose. 

For decades a familiar face in the city, Sliwa—and his trademark red beret—has become the GOP’s go-to sacrificial lamb in mayoral contests, winning about a quarter of the vote in the 2021 election against Adams. He’s most famous for starting a group called the Guardian Angels, a civilian patrol that looked to help the city crack down on crime during the chaos of the 1970s and ’80s. 

Sliwa’s group was controversial from the start, and he would eventually admit that some of its heroics were staged. But it was also successful enough to earn the ire of the mob—he was nearly shot to death in 1992, allegedly on the orders of the Gambino crime family—as well as praise from local officials. 

But his star has long since faded. While public safety remains a top issue for voters, Sliwa is more likely these days to make headlines for his somewhat unusual personal life (his fondness for stray cats, his romantic relationships with local politicians) than crime fighting. 

Given the state of the Democratic Party and the unlikely rise of Mamdani, there are doubtless Republicans who regret not persuading a more serious candidate to run. And if the GOP had gone with a less eccentric pick, say, an experienced city bureaucrat or self-funding Wall Street moderate, there might be some chance—however remote—of victory. 

Even so, New Yorkers are deeply reluctant to elect Republican mayors. But it still happens, with Democrats locked out of the mayor’s mansion for 20 years during the tenures of Rudy Giuliani and Mike Bloomberg. How those two ran and won, not to mention the environment in which they both succeeded, are instructive here.

For starters, Giuliani and Bloomberg were Republicans in a very loose sense of the word. Both were liberals back when liberal Republicans were still a thing. On the major national social issues of the day, they sided with the left: pro-gay, pro-choice, and anti-gun. Now seen as a hyperpartisan figure, Giuliani was anything but when he ran for mayor for the first time in 1989, when he lost to Democrat David Dinkins, and in 1993, when he beat Dinkins in a rematch. 

Instead, Giuliani—a former top federal prosecutor in the city who had done much to break up what was left of the Mafia—sold himself as an independent voice who would finally crack down on New York’s astronomical crime rate. Some 2,000 New Yorkers were being murdered every year when Giuliani won, a number that would drop precipitously throughout his two terms as mayor. 

Giuliani was able to get crime under control using a mix of innovative tactics and no-holds-barred policing. In keeping with the “broken windows” theory cooked up by conservative intellectuals in the 1970s and ’80s, the NYPD came down hard on petty criminals and even harder on violent ones. Times Square transformed from the pornographic hellhole immortalized in movies like Taxi Driver to the family-friendly tourist trap it is today.  

Although seen by New Yorkers as an oddball with a rocky personal life, Giuliani had quickly delivered on his central campaign promise and was easily reelected in 1997. Crime continued to decline. 

By the summer of 2001, the city was only clocking some 600 murders a year, meaning Giuliani had been able to cut the murder rate by about two-thirds. Still, the city had tired of his antics, and seemed primed to elect a Democrat to replace him. Bloomberg, a billionaire lifelong Democrat, switched parties and essentially bought the GOP nomination from grateful party bosses. 

Democrats that year scheduled their primary for Tuesday, September 11. For obvious reasons, that primary needed to be postponed. And after 9/11, Giuliani went from a relatively unpopular civic official to “America’s Mayor,” the most beloved politician in the country. He rushed to the World Trade Center and led from the front lines on the city’s worst day, a performance so impressive it made him the GOP’s instant front-runner for the 2008 presidential nomination.  

For a moment, Giuliani seemed to transcend politics, with even old enemies—of which he had many—deeply reluctant to say a bad word about him, at least in public. And after a botched attempt at changing city laws so he could remain in office, he threw his full weight behind Bloomberg, who then went on to defeat longtime Democratic official Mark Green. 

The through line you might be seeing here: New Yorkers will elect Republicans if (1) people are dying en masse, whether it be through crime or terrorism, and (2) if that Republican is basically just a moderate Democrat. Neither of these conditions exist today. 

Although it hasn’t fully recovered from the disorder of the pandemic, New York remains the remarkably safe city it has been since at least the Bloomberg era. That’s good news for the city but bad news for Sliwa. Although he’s tried to distance himself from Trump in recent years, he’s never struck people as particularly moderate. And his red beret makes him look more like a Serbian paramilitary leader than a credible choice for mayor. Polling for the general election has been relatively sparse, but surveys show Sliwa nabbing some 13 to 16 percent of the vote, regardless of whether Democrats go with Cuomo or Mamdani. 

So Sliwa isn’t the sort of liberal Republican who used to win mayoral elections. (Even after entering office, Giuliani made a big point of stressing his liberal bona fides, endorsing Democrat Mario Cuomo for governor over moderate Republican George Pataki in 1994. Bloomberg quit the GOP entirely in 2007, two years before his final run for mayor.) And he’s running in an environment that would be hard for any Republican to succeed in, given how much New Yorkers tend to hate Trump; despite the president’s real gains in the city in the last election, preelection polling showed they still preferred Harris by nearly 40 points. 

So where can New York’s conservatives turn? Well, if they’re registered Democrats, they can go with a more moderate option like Cuomo. Or they can back Adams, who dodged federal prosecution via a sweetheart deal with the Trump administration. Or they can go ahead and vote for the guy in the beret who, if nothing else, does have an endearing love of house cats. 

But the fact that we’re even talking about Cuomo—who spent nearly three terms as a progressive governor, enforced hyperstrict Covid lockdowns, and finally resigned amid complaints of serial sexual harassment—as the least awful option for conservatives tells us something about the limits of MAGA’s appeal in New York. The Trumpian right tends to delight when relative moderates like Mitt Romney or Maryland’s Larry Hogan leave politics. But the upside to a Republican Party that still had some sort of vestigial liberal wing was that those liberals could win in places where conservatives couldn’t. 

National Review founder William F. Buckley Jr.’s old advice was that conservatives should support “the most right, viable candidate who could win.” Barring a major disaster, or a miracle, Sliwa fails the last test. Mayor Cuomo, anyone?