Jessica Pressler Investigates Brooklyn’s Fanciest Preschool

A Q&A with New York Magazine's Jessica Pressler on her feature about a preschool scandal.

Jessica Pressler, a staff writer at New York Magazine, has a knack for tackling stories that spark discussion. (Remember that The Cut story on glamorous scam artist Anna Delvey or the Robin Hood strippers?) Most recently, she penned a deep-dive on the infighting within an exclusive Brooklyn preschool and managed to make the internal drama fascinating to outsiders. We talked to her about finding that story, deciding it was worth telling, and what her reporting process was like.

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Study Hall: First of all, I’m curious how you came across this story, which is about pretty insular drama within an exclusive group. How did you find it?

Jessica Pressler: I for sure wouldn’t have come across this story if I didn’t have preschool-age kids of my own. When you have kids in New York you notice new things, like playgrounds, and that the grass at the park is actually incredibly gross, and you actually hear those kinds of stories where, if someone started telling them before you had kids, you’d be like, “I’m getting a drink.” This was one of those stories.

I heard, thirdhand, that the director of this private preschool in Brooklyn had been suddenly fired, escorted out of her office in the middle of the year, and there were all of these wild rumors because no one really knew what happened, but it had something to do with favoritism. This was before the Varsity Blues story broke, but the inference was that it was that kind of scenario, like a Varsity Blues Preschool Edition. As I sort of looked into it and heard about what happened from people closer to the situation it very quickly became clear that was not the case.

SH: At what point did you realize it was a story worth telling and not just insular gossip?

JP: I think probably some reporters would have written the thing off as a non-story at that point, but I perhaps weirdly thought that made it more interesting, because to me it kinda said something about how anxious parents are today and how cynical people have gotten that people leapt to the conclusion that there must have been quid pro quo.

The reality was, there was this whole slew of other stuff going on — social climbing and side-eye and backstabbing and woke white people trying to do the right thing but ham-handedly — that contributed to this kind of hysteria that took hold in this closed environment. Meaning, the school, but also Brooklyn Heights, which has always been its own little universe, but has lately been opened up to the outside world because of all of the development and other sort of changes that have been taking place all over the city. And it all came together and resulted in what felt like, to me, this kind of hysterical act, which was the firing of this director in a really melodramatic way. (I will probably get in trouble for saying that with the people who had issues with Amy Morgano, but I am from near Salem, Massachusetts, and I know a Crucible situation when I see one.)

Anyway, the whole thing, plus the fact that pretty much all of the parents were Somebodies, added up to a classic New York magazine story, almost a parody of a classic New York magazine story. Which made it kind of funny, although it was obviously quite serious for the people involved.

SH: What was the reporting process like and how long did it take? Did you find people were reticent to speak (I could also see the opposite being true!) How did you find dealing with the parents? The school itself? 

JP: It wasn’t the most fun I have ever had, honestly. Calling people about a scandal at their toddler’s school kind of automatically makes you a huge creep. People were very reticent to speak about it at first, and understandably so. First of all there were the various NDAs people signed and the things going on with the school and the director that I will describe as “legal stuff” because I do not know the proper verbiage. And Brooklyn Heights is a very small community, it was described to me more than once as “Mayberry.”  No one wants to get caught talking out of school, so to speak. Fortunately, a few people saw the bigger picture and thought it was interesting and worthy subject and helped me out, and those people led to more people, and so on.

SH: The story is really dense with information and details but has relatively few on-the-record quotes. Can you talk a little about crafting a story around these constraints (or if you even view them as constraints)? 

JP: Because people were so nervous, at some point, I was like, “Ok, I’m going to Bob Woodward this shit,” and just have everything backed up by multiple sources so I can write it just like, “This happened.” Which is a RIDICULOUS thing to do for a story about a dustup at a preschool. But it was also kind of a fun challenge and it allowed people to speak freely, which is nice.

There’s nothing worse than talking to someone who is weighing every word because they are worried about how they will come off. I mean, there are worse things,  but that is annoying. There’s a lot of blind quotes [ed. statements from anonymous sources] in this story which Serious Journalism people scorn as a rule. I happen to love blind quotes. Mainly because I just love people’s voices and I feel like in this case the references, like “Notes on a Scandal” or “Sweet Valley Twins,” give you a sense of who the people in the community are without revealing, you know, who they are.

SH: You tweeted recently about the likability of the piece’s subjects. Can you talk a little about the challenge of portraying these subjects, especially since they’re subjects that readers are almost sure to find unlikable (whether they are or not)? The tone of the piece maintains a sense of humor and awareness of the stakes while also treating the subjects fairly and not making them outright caricatures, which I imagine might be a difficult balance to strike.

JP: I’m going to blame this one on Bob Woodward because as it turns out, his style does not lend itself to emotionally layered storytelling. It’s difficult to describe the motivation and outlook and feelings of people with just “this happened”-style information, especially when the information in question makes them seem like, as you say, caricatures. It was a bummer. Thanks a lot, Bob.

SH: What’s your writing process like? Is it agonizing or fun for you? What time of day do you find is best for writing? 

JP: Mostly agonizing and intermittently fun! My best hours are in the early evening, when people are leaving work and going home and everything stops being distracting for a little while.

SH: Any reporting or writing tips for writers tackling a longform piece like this for the first time?

JP: A former coworker used to say, “You have to give yourself permission to write,” and I always kind of rolled my eyes at the grandiose artiste-ness of it, but now it pops into my head whenever I am stuck, and I am sorry to say, it’s true. You just have to let yourself write a bunch of garbage, and then go back and fix it later.

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