Letter From Sag Harbor: Can John Avlon Ride His Centrism From CNN to Congress?

John Avlon had just returned from a campaign event at the other end of Long Island when he greeted me at the door of his Sag Harbor home on a recent Friday afternoon. It’s in a semi-secluded enclave that’s like a combination of a woodsy suburb and a New England fishing village, with a smattering of modern fancy homes because, well, obviously. Avlon’s place is not one of these, but a modest domicile that looks like it could belong to a nice elderly couple. (In fact it did previously belong to a nice elderly couple, God rest their souls.)

Sag Harbor is part of New York’s First Congressional District, which stretches all the way from Huntington to Montauk, with a wide array of constituents who range from the ultra-wealthy to the working class. On February 21, Avlon announced he had entered the race to flip the district’s Republican-held swing seat, which explained his resignation a couple weeks earlier from CNN, where he’d been an anchor and political analyst for years.

Avlon invited me in and asked if there were any particular topics I wanted to focus on. Yup, just a few: Chris Licht, Don Lemon, maybe a little about Jeff Zucker and Allison Gollust. Kidding! After the color returned to Avlon’s face, we went out to the backyard overlooking his own little Hamptons cove, where Avlon delicately answered the one question I did have about CNN: Was the turmoil there these past couple years as bad on the inside as it seemed from the outside? “It’s not exactly news to say it’s been a chaotic time,” Avlon replied.

Avlon, a 51-year-old Democrat, says he would still be working at CNN were it not for Donald Trump, a frequent subject of Avlon’s “Reality Check” segments on the former-maybe-future president’s least favorite cable news network. He told me it was around spring 2023 when locals first started approaching him about running. Avlon and his wife, Margaret Hoover—a veteran Republican political strategist, PBS host, and the great-granddaughter of Herbert Hoover—were hesitant at first, considering the gravity of running for a major political office when you’ve got two young kids. “But once we both realized that Donald Trump was actually going to be the Republican nominee, that just changed our thinking dramatically,” Avlon told me. “The moral urgency started to kick in.”

Here’s a CliffsNotes version of the New York 1 race. The seat is currently held by Nick LaLota, a Trump-endorsing first-term Republican who has sought to portray Avlon as a carpetbagging “Manhattan elitist,” though Avlon likes to point out that LaLota himself resides outside the district, as public residency records would appear to confirm. (Avlon and Hoover bought the Sag Harbor pad in 2017 as a second home, after renting it during their vacations; Avlon moved there full time in February, and the rest of the family plans to join him after the school year.) Avlon’s main opponent in the June 25 Democratic primary is Nancy Goroff, a wealthy, progressive-leaning retired chemistry professor who lost when she ran against the MAGA-ish Lee Zeldin in 2020. “Nancy Goroff is a champion for Long Islanders who has spent her life serving and bettering her community,” reads the endorsement she received from Emily’s List on March 14. “She’ll fight for our reproductive freedom and stand up to the Republican plan to ban abortion not just for New Yorkers but for all Americans.”

Avlon, who also supports a woman’s right to choose and is running on issues like affordability, cost of living, and middle-class tax relief, positions himself as a center-left alternative with a better chance of defeating LaLota. The calculation is that Avlon’s communication skills and stature in the media/political world will give him an edge over Goroff in flipping the seat. His endorsements include the New York State assemblyman Fred Thiele, and on Monday, Avlon’s campaign announced that they’d raised north of $1 million in just over five weeks.

“This is a swing district, but when you look at the battleground maps in New York, it wasn’t being treated as one,” Avlon said. “We just got the new district registration numbers, and in New York 1, we have the highest number of independent voters in the state. That’s prime for swing. And this also goes back to, as a columnist and an author, there’s basically been one major theme I’ve tackled from a bunch of different angles, which is the dangers of hyper-partisanship and polarization. … So in some ways, I see this as continuity. I didn’t want to just talk anymore. I didn’t think observing was enough.”

The grandson of Greek immigrants—one of whom lost his entire family in the 1918 flu—Avlon had a privileged Manhattan upbringing and an education at the Milton Academy in Massachusetts. He sang in bands (the keyboardist for one of them was a future national security official named Matt Pottinger, a close friend since childhood) and gravitated toward music like U2, the Pogues, and R.E.M. After Yale, Avlon volunteered on the ‘96 Clinton campaign and then got a job as a speechwriter for Rudy Giuliani—he considers the 9/11 eulogies “the most formative thing in my life other than having kids”—followed by a columnist gig at The New York Sun and a fellowship at the Manhattan Institute (where he ran afoul of the powers that be for writing about rising Republican extremism). I told Avlon I always assumed he’d been a Republican given those latter three credentials. “I guess it’s understandable,” he said. “But because I worked in New York City Hall and not Washington, I never thought about politics as a tribal conflict.” (Avlon, who also served as editor in chief of The Daily Beast, became an independent in the early 2000s as his journalism career was taking off. He re-registered as a Democrat in 2020.)

This interview would hardly be complete without asking Avlon about Giuliani’s descent into the MAGA fever swamp. “It’s obviously a tragedy in the Greek sense,” he said. “I had been on speaking terms with him in the run up to the 2016 election…but when Trump won, I started to see signs that Rudy was not the same person I knew and worked for. There’s a quote of his I always loved, which is, ‘To be locked into partisan politics doesn’t permit you to think clearly.’ I think he stopped thinking clearly when he got locked into partisan politics. He destroyed his reputation and his finances for Donald Trump.”

Avlon’s past Giuliani ties are something Goroff can use against him in the primary. The New York Times reported last month that “her allies were already sharpening attacks on Mr. Avlon’s residency and his political history with Republicans.” On the other hand, in the general, that same political history could prove advantageous in seducing moderate Republicans, no?

“Having a candidate who can speak strongly as a matter of experience from the vital center, the math indicates that will help win a swing district,” Avlon said. “There’s a deep desire to break out of this sort of fever dream we’re in, and to do it, Democrats need to win. Here’s the math of how you win a swing district, especially one like New York 1 here in Suffolk County. You need to fire up the Democratic base, but you also need to win over a majority of independent voters. That requires a candidate who can reach out, who can energize but also seem centrist and say, look, we need to find a way to bring people together again, and that’s actually how you solve problems for Suffolk County families. It’s not by playing to the base. One of the biggest differences between myself and Nick LaLota or any of these Trump flunkies is they’ll abandon their conscience and common sense when Donald Trump tells ’em to on a dime, but moreover, they see bipartisanship as a problem. We know it’s a solution, and I think the vast majority of Americans think that way.”

If Avlon wins, his jump from cable news to Congress would be somewhat curious. The pipeline of politicians and operatives who end up with lucrative TV gigs has arguably never been hotter, as NBC’s potentially $600,000 Ronna McDaniel misadventure lays bare. But TV news personalities who take pay cuts to work in government are a rarer species—or a “lost tradition,” as Avlon likes to think of it.

“Long Island’s own Teddy Roosevelt is the obvious example, but it’s not just him,” he said. “In the Progressive Era, I think there were two dozen newspaper editors who were serving in Congress, because it kind of made sense, right? It makes sense to me. It’s not that I don’t fully appreciate the tension that needs to exist between journalism and politics, but it also always seemed to me, commonsensically, two sides of the same coin, right? I mean, we should be in it for the same reasons. You care about civics, you care about civic debates, you care about finding solutions to problems, you want accountability. They should be the same drivers.”

As an anti-Trump centrist Democrat, what are some areas where Avlon thinks the progressive left has lost its mind?

“I think Democrats often get spun around the axle when they start obsessing about culture-war issues.”

Such as?

“Defund the police, one of the worst, most self-defeating political slogans imaginable. But in reality, in the last Congress—I counted this up—there were seven members of the Democratic House who supported the policy known as Defund the Police. There were 139 members of the Republican House who voted to overturn the election after the attack on the Capitol. That’s asymmetric, that’s not the same moral universe.”

In other words, sounds like Avlon is saying the far right is more dangerous than the far left.

“Absolutely. As I wrote in my book Wing Nuts over a decade ago, the far right and the far left can be equally insane, but there’s no question who’s far more powerful and more dangerous in our time. I mean, the Democratic Party nominates and elevates centrists, right? The party is evenly divided between liberals and moderates. The Republican Party is nominating Donald Trump for a third time after he tried to destroy our democracy on the back of a lie, with totally fact-free rants that are contrary to everything that party allegedly once believed. So there’s just no equivalence at all. The problem is, it distracts from a lot of the issues that we really need to deal with that are right in the Democrats’ sweet spot.”

I asked for his centrist view on Israel and Gaza.

“As someone who was formed by 9/11, fundamentally, in the wake of the absolute horror of the October 7 attacks, our impulse should be to stand with the victims of terrorism and not blame the victims of terrorism. … It’s absolutely legitimate to not only defend yourself, but to ensure that Hamas leadership is taken out. You’re dealing with terrorism, but you’ve got to maximize humanitarian aid and minimize civilian casualties, because that ends up playing into the terrorist narrative. I think the Biden administration is walking a difficult line well.”

Before we wrapped up, so that Avlon could take me on a walk to the famous Steinbeck House—which he and a group of other Sag Harbor locals successfully fought to preserve—I asked him the big question that’s on every sanity-loving person’s mind these days: Is the 2024 election an existential moment for American democracy?

“Yes, absolutely,” he said. “I think minimizing it actually is how we sleepwalk into a disaster. That’s a real danger right now, because people feel exhausted. But now is exactly the wrong time to tune out from politics and civics and the news. That’s exactly why we need to have a Democratic Congress. If, God forbid, Donald Trump is reelected by some fluke, while losing the popular vote by a massive amount, that’s why we need to strengthen guardrails around democracy. … There are moments in history where citizens need to step up and defend our democracy and defend freedom, and those are absolutely the stakes in this election.”