So you worked for the Observer for a couple years, is that right?
Three. Yeah, three years.
When Trump announced he was running, the paper’s policy was not to cover him unless there was a compelling reason, right?
Correct, yes. When he announced in the summer, we didn’t have a national reporter assigned to the race. There were three members of the politics team, and we were all focused on New York, so we would wade into national politics, but there was no real, firm commitment to writing about it every day. So when Trump announced, yes, the policy was we don’t write about him unless we have to. And that was made very public. It wasn’t a policy I thought was ideal. At the time, I was really focusing on covering the mayor and covering New York City, so for me, I shrugged it off and went about my job, and Trump and the Observer didn’t really become an issue until I moved over to national beat at the beginning of 2016, and even then, I naïvely didn’t imagine that Trump and the Observer would become the issue that it did, and I think on my part, certainly being young — I’m 26, and I consider myself worldly — I definitely did not foresee the vast conflict of interest and various ways that my own editor would be involved with the campaign, and then obviously my former publisher, Jared Kushner, how intimately he would be enmeshed with the Trump machine as well.
Was it talked about routinely that the paper had a connection to his campaign?
We always knew Jared Kushner, the publisher, was Trump’s son-in-law. I knew that since the day I started. Jared really was a very hands-off owner. I met Jared once in the time I was there. He came to a little holiday-party gathering in the office, and that was it. I literally had one conversation with Jared Kushner in my life. And Ken Kurson, the editor-in-chief, was certainly a hands-on editor, but he was someone who at least would give lip service to the independence of the newspaper. And I still think my coverage and my work there at the Observer was not at all influenced by Trump, in terms of there were no orders from on top to write about Trump in a certain way necessarily. New York’s Gabe Sherman broke the story that we all suspected, that Ken had assisted with Trump’s AIPAC speech, and for me, that was a huge turning point and a time when I really thought, like, This is deeply unethical, and I should not be here anymore. I mean, look, had it been Bernie Sanders’s speech or Hillary Clinton’s speech, it would have been deeply problematic as well. If he was assisting a campaign — and you know, Ken was a former Republican operative, a former Giuliani speechwriter, so it crossed our minds that Jared Kushner had written Trump’s speech. Well, did Ken help? We had no proof, and then he told Gabe Sherman that it happened, and Ken says he simply didn’t write it, he just looked at it, so I’ll take him at his word. I don’t know truly how much he assisted. I don’t have a lot of inside information on that front. But that AIPAC moment coupled with the endorsement about a week later or so was the final straw for me. And, I mean, the endorsement was so catastrophically bad in a lot of ways. Not in that a paper doesn’t have a right to endorse, or a paper doesn’t have a right to endorse Trump, but it really made no sense for the New York Observer to be endorsing, given how close their ties were to Trump, and it was just something that was immediately noted by anyone with a half a brain. And that was really the moment — and this had been building up for a long time. This was the moment I said, “Look, I have to go.” And it was really more of an instinctual move as an intellectual move. I didn’t plot this out. I don’t have, like, the PR savvy to time my exit to such a moment. It worked out well for me, but when the endorsement came down, I was just sick of everything. I was with my friend that night, actually at a Mets game, and I told him I can’t do this anymore, and I sent an email to Ken and to my colleagues that said I’m putting in my two weeks — I didn’t actually send it from the game. I waited till I got home. I sent it via email sometime probably close to midnight. I don’t remember the exact time I sent it. You know, very polite email, polite response, and that was that. So, I hadn’t been planning that day. I found out about our endorsement that evening as I was driving to the game. I got it in a text from my colleague, and I hadn’t been briefed on it, it wasn’t something I expected at all, and it was that moment when I’d had enough, and I decided it was time to do something else with my life, with journalism, just not at the New York Observer.
Did Ken ever have a conversation with you about it, like editor to reporter? Did he ever say anything about his own involvement or about the paper’s policies and its connection to Trump? Was there ever any editorial discussion about it to navigate that?
There was absolutely editorial discussion. I don’t want to get too deep into the behind-the-scenes conversation, but it was an ongoing discussion with me, Ken, with Jill Jorgensen, who was my immediate editor there. We were constantly discussing how to deal with Trump. I mean, the consensus from reporters was always we have to treat him like any other candidate. We always put our disclosure in, which I thought was good, that he’s the father-in-law of our publisher. So there were discussions. It was an ongoing struggle. And it wasn’t easy for Ken either. Ken was in a tough spot being the editor-in-chief, being someone who’s very close to Jared as a family friend, someone who is a journalist too and does care about the Observer’s integrity, so it was a balancing act for him and for us. We obviously wanted to cover Donald Trump like anyone else, and for the most part that did happen; it was just the idea of Ken being involved in the Trump campaign in any way was too much for me to stomach.
It sounds like you never felt pressure to change the way you wrote your stories. Do you think this involvement had any effect on how you guys covered the campaign?
To an extent, yes. The odd thing at the Observer is they do give their writers and reporters a lot of independence. I really could decide and craft ways to approach the campaign. At the same time, there were pitches that were rejected, and I don’t want to get into what the pitches were, but there definitely were stories that were turned down in regards to Trump that I suspected might have been related to our ownership ties. I don’t know that for sure, that was never made explicit. At the same time, you’re in an environment where you know who owns the paper, and you know the circumstances, and maybe there’s a self-censoring that goes on unconsciously even. I don’t think I was doing that. I stand by all the reporting I did at the Observer. I’m proud of a lot of the things I’ve actually written about Trump there. I think in some ways I said some prescient things, and there were definitely pieces where I was hard on Trump, but it was not the ideal situation, and there were pitches that didn’t go anywhere. And there was this sense that maybe there were places you couldn’t go. And I never found out exactly what those places were, what I could and could not do. Nothing was ever spelled out. Maybe that was a problem too. But the line of communication with policy was always evolving, always somewhat in flux, and it wasn’t clear there was always direction, and that was an issue too.
Did the experience change your perception of the press, especially political reporting more generally?
The experience of covering the campaign did. I traveled to Iowa, I traveled to New Hampshire, and traveled to South Carolina, I was in Miami and Mar-a-Lago for Trump’s victory in Florida, and my perception of campaign reporting had evolved independent of the problems I had with Ken and with Trump. What I found was you have a thousand reporters writing a thousand version of the same story, and so much of it lacks purpose. And at times I’d be sitting there with all these other people at an Election Night party, or some other event on the trail, and I’m thinking, What’s the point of all this? Why are the dwindling resources of news organizations, of the press that serves a vital role in our democracy so trained on this spectacle 24 hours a day? And I know why: because it means money, it means ad revenue, it means clicks. We know that. We know that certainly with the television networks, and newspapers aren’t immune. In most democratic societies, campaigns are a few months long, a few weeks long in some cases. They do not consume the entire year and years of discourse. So for me, just every single day having to come up with angles to endlessly speculate, prognosticate, about what was going to happen, these little, minor tweaks in the narrative that in the long run would mean nothing, and the whole narrative, the whole idea of the narrative of campaigns is somewhat invented anyway. It was really disillusioning in a lot of ways. I mean, I’m not saying that I was ever someone who had a wide-eyed view of what political reporting is, but I would ask myself, Who are we serving? Who are we informing? Why does writing about someone’s campaign strategy, for example, or the machinations of some campaign operative, why does that matter necessarily? Do we know what voters really need? I mean, how we come up with story ideas are really divorced from the public writ large. That’s an ongoing issue I’ve had. You certainly saw with the Trump phenomenon in general, and I, as an East Coast, middle-class person, grew up in New York City, of course was dismissive of Donald Trump, because I was not living in the middle of the country, I was not living in a depressed town, I was not talking to these people. So there’s this bubble aspect to campaign reporting, and I don’t really think that we’ve learned a lot of lessons as political reporters from this election. I’d like to think that we did, but for the most part, reporters writ large think they’ve done a stellar job. But while there’s a lot of great reporting, there’s a lot of empty calorie reporting as well. Just daily filler. Confronting that, was definitely not a wonderful experience.