Succession (Part III)

Why NY-12 is Not Friendly to Insurgent Outsiders

Cameron Kasky, Jack Schlossberg, and George Conway, much like Jared in this episode of Silicon Valley, are all on the outside looking in.

This is part III of an ongoing series on the June 2026 Democratic primary for New York’s 12th Congressional District. You can check out part I here and part II here.

There are three serious candidates running for New York’s 12th congressional district who have never held political office in Manhattan (or anywhere else): Cameron Kasky, Jack Schlossberg, and George Conway. They are all quite famous, in three completely different ways. All three have high-profile personal stories that inform their political journeys. Kasky survived the 2018 Stoneman Douglas school shooting in Parkland, Florida, and organized the March for Our Lives in response to advocate for a nationwide assault rifle ban. Conway dramatically split up with his wife, Kellyanne, Trump’s 2016 campaign manager, over their political differences, and became a leader of the anti-Trump Republican organization The Lincoln Project. Schlossberg is the grandson of JFK, and is trying to rebrand himself as the nation’s First Family’s palatable, electable heir after many years of… not being that. All three will generate plenty of national media coverage, and the Times, not immune to the attraction of shiny objects, may join them against the urging of their more seasoned metro desk reporters.

I too am not immune, so I plan to write about each one next week. But before I do, I feel that I should warn you not to get too attached to any of them. None have much of a shot. To illustrate why, let’s take a detour downtown to another hotly contested congressional primary.

This week, Brad Lander posted his campaign’s first video ad in his bid to unseat two-term congressman Dan Goldman in New York’s 10th congressional district. “I knew Brad before he came into political office,” Michael Schweinsburg tells the camera, “because I heard about this guy way out in Brooklyn, building supportive housing before it was cool. This was decades ago.”

Though he is introduced in the video’s caption only as “Michael, a great neighbor,” Schweinsburg is the president of the 504 Democratic Club, the city’s leading disability rights advocacy organization. Based on the Lower East Side, 504 is a formidable influencer in local Democratic politics. They send out surveys to candidates running for all elected offices on their stances on key disability issues, surveys that all candidates know to respond to carefully if they are interested in the club’s coveted endorsement. And once in office, Schweinsburg and his club-mates hold their endorsed candidates to account. They are prolific lobbyists, organizing events, testifying in committee hearings, and speaking at press conferences in support of their legislative agenda. In an interview he gave to the City and State in 2022, Schweinsburg reported that 20 different pieces of legislation that 504 had advocated for had passed through the State Legislature in their Spring 2022 session. Since then, they fought to delay the closure of the East Village hospital Beth Israel (which finally did close last spring), and have been vocal supporters of the MTA’s court-mandated efforts to install working elevators at enough stations to come into ADA compliance.

In July of 2024, Dan Goldman honored Schweinsburg’s 25th anniversary of advocacy with an official congressional proclamation from the House floor: “For two decades, Mike has been an integral part of the 504 Democratic Club, the Nation’s first and largest club advocating for the civil rights of people with disabilities. I am truly honored and blessed to work alongside him to ensure that everyone in New York City and our country gets the proper representation they deserve.”

As we learn in this video, all has not been well in the Goldman-Schweinsburg relationship behind the scenes. “Brad’s opponent asked me to put together a roundtable for him… I brought a bunch of community leaders, and they poured their hearts out.” Schweinsburg tells us. “We never heard anything from that guy. But at Brad’s roundtables, he puts the staff to work on what he hears the community talk about.” Schweinsburg then describes his experience marching down 5th Avenue at a No Kings event last year with Lander, and about how he spent the entire time guiding one of their fellow advocates, a blind woman.

Brad Lander is a heavy favorite to defeat Goldman in the NY-10 primary, and this is why in a nutshell. Though he is not the incumbent, he has better relationships with local political clubs and advocacy groups. These groups usually wield their power through sheer physical might. They have email lists, and on the other end of those lists there are bodies who will knock on doors, pass out leaflets, call up every registered voter on your target list, collect signatures, and otherwise “pound the pavement” and help with “ground game.” They do not traditionally wield power through social media. Schweinsburg has fewer than 200 followers on Twitter, and double digits on Instagram. But that’s not the point. Politicians seek out endorsements from high-profile celebrities like Bad Bunny and Jason Aldean in part to gain access to their massive audiences, but those celebrities usually don’t have much sway over the door-knockers. Politicians seek out endorsements from high profile government officials (Kathy Hochul, AOC, Zohran) because they can deliver both access to a massive audience, and specific connections to door-knockers. The 504 Democrats Club is the opposite of Bad Bunny (at least in this one respect).

Kasky, Schlossberg, and Conway are all pretty famous, though not nearly as famous as Bad Bunny. That fame will help them get media attention and social media traffic, which they hope will translate to campaign donations (Two of the three will have no trouble raising millions of dollars even without this; the third is allegedly struggling.) They also hope their fame will generally help them get their message out to persuadable voters. What it definitely will not do is impress Michael Schweinsburg and his door-knocking ilk.

Political activists and organizers are, almost by definition, dissatisfied with the status quo political system, and as a result, deeply skeptical of anyone in it. They do not trust easily. If they have been doing this for a while, they likely have many experiences with elected officials who solicit their input, listen to their concerns, and then never follow up. They have very few experiences with officials who take their concerns seriously, amplify them, and then deliver solutions. When they develop a relationship with someone who can do this, they become fiercely protective of this relationship, and loyal to this official. There’s absolutely no reason to window-shop. Chances are, the new guy will not be anywhere near as responsive. They’ll have to start from scratch.

Traditionally, successful elected officials cultivate this kind of relationship with as many organizations as they can. The ones that stick around for decades, like Nadler, do so because they have relationships with every single organization, and carefully manage and nurture each one. If, at any point in the last thirty years, a well-organized Upper West Side disability advocacy organization came to Nadler’s office with a request or complaint, he knew to respond as quickly as possible.

There are benefits to this system. We want elected officials to be responsive to the needs of their well-organized constituents. On the other hand, not all groups are as sympathetic as the 504 Democrats Club. Swap out “disability rights advocates groups” with “the business community” or “real estate developers” and this kind of hyper-responsive constituent service starts to look like corruption. And even the 504 Democrats Club might occasionally want something objectionable; in 2022, for example, they successfully advocated against year-round outdoor dining because of concerns about street accessibility during snowstorms. Your mileage may vary on that one; COVID-era outdoor dining was a huge social and economic benefit to the city, the City Council’s seasonal policy essentially killed it, and, I don’t know, snowstorms have become pretty rare around here.

Either way, this positive feedback loop–where the incumbent is responsive to specific groups, who then endorse him for re-election, which encourages other groups to develop relationships with the incumbent, who then must take care to be responsive to them as well– this is why incumbents have a huge advantage in local elections, even if a challenger may be more aligned with the views of a district’s voters on a pure left-right spectrum.

Or do they? In his 2015 paper “It’s Nothing Personal,” UCSD political science professor Gary Jacobson assembles survey data and election results from all levels of federal, state, and local government that show the incumbency advantage consistently declining year-over-year from the 1970s to the 2010s. This trend has likely accelerated since then, punctuated by the rise of three New York City political outsiders who built grassroots movements that defeated lifelong machine standard-bearers against all odds: Trump, AOC, and now Mamdani. “Everything is national now,” longtime political operatives like to complain. As union membership declines, local newspapers collapse, and local political and civic groups of all kinds become less central to the daily lives of most Americans, voters are increasingly focused on the same high-profile national issues, which they learn about from the same national media (MSNBC, CNN, and the Times for Democrats), no matter where they live. Lander’s decision to turn Schweinsburg’s endorsement into a social media ad is a sign of this trend. In the old days, a local activist endorsement is an end in and of itself, because of the connections and influence he has on door-knockers and other officials. Today, Lander needs it to create a viral moment on Twitter, and maybe even generate some news coverage if he’s lucky. Maybe in this new neoliberal order, where individuals matter more and groups matter less, social media dominance is paramount, and a connection to a local political club, or an endorsement from a city councilor, isn’t worth as much.

The outsiders running in NY-12 will hope this is the case. But don’t bet on it. Though Goldman is the more familiar face in national media, mostly because of all the MSNBC airtime he got during Trump’s first impeachment as lead counsel, Lander is universally viewed as the favorite in NY-10. In New York, Mamdani and AOC are relative outliers; the “Squad” has only five members, and the vast majority of state legislators in New York get reelected easily. And while both are regularly described as superficial, social media phenomena (“Twitter isn’t real life”), they are both absolutely obsessed with local retail politics. These days, AOC wins re-election by double digits every cycle not because she is perfectly aligned with her district’s median voter on a left-right spectrum (plenty of her 2024 supporters voted for Trump on the same ballot), but because her local organizing arm Team AOC is deeply enmeshed in the community, running mutual aid programs, attending every county board meeting, and even offering free one-on-one tutoring at the height of COVID. Mamdani may not have had support from the classic Democratic clubs of Manhattan and Brownstone Brooklyn, but by 2025, there was already a different, well-oiled political machine ready for him in the Astoria-based DSA. In January of 2025, when he was still polling below 5%, Mamdani was by far the most prominent candidate on my feed and in my neighborhood, not because his videos were especially entrancing (that came later), but because so many different people in my life knew him personally; they’d gone to protests with him, or knocked on doors for Tiffany Caban on a canvassing shift that he led.

AOC and Mamdani (and Trump) had one further advantage: the machines they ran against were incredibly unpopular. Cuomo’s favorability ratings were extremely negative, even when he led the race by double digits,. Joe Crowley and the Queens Democratic party had, in 2018, become hopelessly out of touch with the western neighborhoods that had undergone a rapid demographic shift, and were now teeming with young, college-educated socialists. Republicans in 2016 were fed up with their Bush-era leaders. This can be easier to spot in retrospect, plenty of commentators confidently predicted that Cuomo, Crowley, and Jeb Bush (!) would prevail.

But NY-12 outsiders face a tougher climb than the successful insurgents in any of those races, because the Manhattan Democratic Party machine is widely beloved. Gale Brewer, Mark Levine, and most of all, Jerry Nadler, are not seen as out-of-touch self-serving bureaucrats. They’re familiar neighborhood mascots who have impressive records of accomplishments. There’s no polling on this, so perhaps there’s a subterranean vein of populist rage that an outsider can tap into. Or perhaps the national party, which Democratic voters do hate with increasing fervor, is so toxic that the local party will become tainted by association, and a challenger can score some points out of Nadler’s close friendship with the now-despised Chuck Schumer.

This week, I’ll cover each of the three serious outsiders who will try to pull this off. They’ve all got a long way to go.