The Press Box - New York Magazine's Shawn McCreesh on PR Showdowns, the Media Beat, and Working for Maureen Dowd

Episode Date: February 21, 2023

Bryan is joined by NY Magazine features writer Shawn McCreesh to discuss his profile on crisis communications representative Risa Heller and to touch on his career at the magazine. They dive into how this story came about, which well-known clients Heller has represented, and her relationship with the media (1:36). Then, they talk through McCreesh's career, from working for Maureen Dowd as an editorial assistant at the Times to finding his space at New York Magazine (16:30). Host: Bryan Curtis Guest: Shawn McCreesh Producer: Erika Cervantes Learn more about your ad choices. Visit podcastchoices.com/adchoices

When you're lost in the darkness, look for the pod. Specifically, the Prestige TV podcast on the Ringer Podcast Network, where we're breaking down every new episode of HBO's The Last of Us. On Sunday nights, grab your battery and join Van Lathen and Charles Holmes for an instant reaction to the latest episode. Then head back to the QZ on Tuesdays for a deep dive with Joanna Robinson and Mallory Rubin. From character arcs to video game adaptation choices, story themes to needle drops, we'll parse every inch of this cordyceps-coded universe.

Watch out for mouth tendrils and follow along on Spotify or wherever you get your podcast. Hello, media consumers. Welcome to the vacation week edition of the press box. Ryan Curtis of the ringer here along with producer Erica Servantes. When I was in Phoenix for Super Bowl Week, somebody came up to me and asked, who is the media reporter you like to read? Of course, I like to read all my sports media covering colleagues.

But when I thought of whose profiles and sentences, I look forward to really reading, for enjoyment. The name I came up with was Sean McCreech, a features writer at New York Magazine. And then, as soon as I get back from Phoenix, McCreach publishes this excellent profile of Risa Heller, New York Crisis Communications Bigwig. So McCreach stopped by the pod to talk about that story, about his career, which includes a stint as Maureen Dowd's editorial assistant, and the lure of the media beat. I look forward to more great sentences. Here's Sean McCreach. All right, Sean, let's start by talking about your Risa Heller profile. Heller is someone who practices what's called crisis communications.

For those who are not savvy coastal elites, what does crisis communications entail? Yeah, it's a really strange business. I'm still, even having written the piece, I still don't fully understand it. But she occupies a role that sort of always existed in New York, which is something a little like a fixer. She has this kind of weird six cents for how the media works and kind of how the press sausage gets made. And basically, if you're a powerful person in New York right now and your life blows up tomorrow, you pick up the phone. She's one of the first people who you call. She's got this kind of golden rolodex of journalists and she can sort of walk you through what's going to happen to you as your life goes up in flames and hold your hand and hopefully make it a little bit better.

and she's got all these kind of tactics and these tricks. And as one media executive compares her in the story, is a cross between a Jewish mother and Whitey Bulger. So she's got her own kind of playbook that's made her very in demand in this age of Me Too and cancel culture and, you know, lightning fast news cycles dominated by Twitter. So she's kind of old school meets the new school. Who are some of the people whose lives have blown up that have hired

her? Well, I think most prominently and publicly, after Jeff Zucker was fired from CNN, he got her like in the first hour. And, you know, he wasn't allowed to contractually. He couldn't comment on his ouster. So she basically spoke for him. And that was such a five alarm media fire. I mean, the coverage was just like, it was ridiculous how much that was covered. And her quotes were popping up all over the place. And she was sort of doing battle on his behalf. But she also worked for Jared Kushner, the Kushner companies, and she did some stuff with Ivanka. She didn't work in the White House, but she was working for them that first year after they went to Washington. And then a lot of her clients, her name never gets attached. And I kind of ferreted it out a list of them as I was doing the reporting. But she's worked

with Mario Battali, the famous New York chef, who was Me Too, the frontman for the the rock group arcade fire also metued and uh and then just sort of like this various sort of hilarious litany of people alleged scumbags and uh some of them they didn't get a fair hearing in the media and that's why she takes them on and then other ones people raise their eyebrows at because they are very uh you know interesting characters shall we say yeah the client list you have in the piece ranges from Jeffrey Tumudin to the guy who played Elmo on Sesame Street. Yeah, yes. Well, Tuben wasn't actually a client of hers, but he did call her for advice, which, you know, even people who don't hire Risa, her name among the media elite in New York

is now so prolific that, again, if some shit's going down, you pick up the phone and you want to call her, even if you don't end up retaining her. And she pretty much will take it people's phone calls. So, yeah. So let's say Heller takes on one of the of these people. What does she ask from them? She claims that, and they, some of them told me this, too, that basically she walks in the room and she wants you to tell her everything that you've done, you know, the worst aspects of it, just be completely honest. She needs to know the full story right up front. And then she can kind of develop a media strategy. And I think even among the rich and powerful, very few people understand how the media actually works. And she, you know, she says that

she spends a lot of time explaining what this means, who's going to write about it, what the stories are going to be like, here's how we can shape them, here's what you should say. I think she is, you know, 50% of what a crisis comp person does really is handholding. I interviewed this expert in crisis communications. This didn't make it into the story, but this guy studies the physiological effects of crisis. And there's a phenomenon in the body that occurs called the amygdala hijack when you're you're under fire. Your critical thinking shuts down and your body pumps full of all these chemicals.

And it dates back, you know, to the primal fight or flight instinct. And basically, you need somebody in the room to tell you like, no, no, no, no, no. You're not thinking clearly. Here's what we're going to do. Here's how this is going to go for you. You need to either apologize. You need to fight back. She sort of knows she's such an understanding of reporters on a person to person level that

she has a feel for which reporter she should give the client to either on the record or off the record to try to get the redemption piece or she just kind of knows exactly what to dangle and how to dangle them. And I think that's why people hire her. How does she work over reporters? She's very charming in this funny way. I mean, she's very aggressive and she's about as subtle as a sledgehammer, but it sort of works. She's got a real moxie. And I think that you know, as a journalist, we have to deal with with PR people and, um, spokespeople and comms people all the time. And I get the sense that a lot of them actually really don't like journalists. They either, um, hate us or fear us or think that we're sort of lowly,

annoying creatures, which, you know, they might be half right about some of that. But she, unlike most of her counterparts, I think she actually really likes reporters. I, I, there was this whole sense as I was going through it that almost her shadow constricted. is the press, because the press is always around and the reporters stick around. The clients come and go. And she, you know, her formative years was as working for the comms director for Senator Schumer. And I think he really taught her that. And so she's got a real kind of actual genuine love for the press. It's interesting because her whole job is about manipulating the press or being in an adversarial role to us. But she actually really digs it. And I think she kind of plays it like a sport. So she understands journalist brain. She's socializes with them. She gives them advice. She kind of co-ops them. She's very charming. And, you know, several points in the peace show reporters in New York, I mean, almost literally

eating out of the palm of her hands, you know, coming to these cookie baking contest she has, and she throws the book parties, and she's eating lunch at the Odeon three days a week with a different journalist. I mean, she's very, very good. And reporters, I don't know, we're not that hard to manipulate. It turns out. I mean, I love this detail in the piece that you have people in New York, reporters who

are friends with Heller, but will not say on the record that they are friends with Heller, because that will look really bad. Yeah. At the same time, she's throwing a book party for Maggie Haberman. Yes, it's true.

I think, I mean, I think the reality is the optics are not great, but the way the world works and certainly the way the establishment works is that a lot of these characters have been around for a long time. You have relationships with people. There's such a thing as source management. I think, you know, the charitable view of her relationships with the media,

and this is what she would say, and this is what they would say, is that you can do battle and you can do hard-hitting stories, and you can behave like adults and put it behind you at the end of the day and understand that everyone here is just doing their job and that you're going to meet on the battlefield again, because there's going to be some scoundrel who screws up that she's going to represent. And you're going to have to get a story and your editors are going to want you to get it. And, you know, boom, you're going to cross past with this person again.

So you might as well just kind of be respectful about it and, you know, socializing. I don't know. This is how things get done in New York. But then there's the other view, which is that it's all just this sort of giant, muckety, cozy, backscratching cabal, which I don't know. Maybe that's true, too. both can be true at the same time. I mean, you nodded this in the piece that these confrontations become almost like a game

between the PR person and the reporter. And whenever I hear the word game, I certainly understand that, but it also feels like as soon as it turns into a game, the PR person has the advantage because they are setting the rules of the game most of the time. It's true. There are all different kinds of tactics and you have to be careful. And this is why, I mean, this is why certainly Washington journalists, they don't like to go into off the record because once people can trap you with off the record, they tell you things that, you know, you're not, then you hear it and you're not allowed to use it. And so it can get tricky. And you have to sort of keep your wits about you, especially when you're dealing with somebody as sophisticated as Risa. When I did this interview with her, I was trying to, you know, put her on the couch a little bit and have her be introspective about her. the strange nature of her relationship with journalists.

And I described it as a little bit like, you know, the cobra and the mongoose. And you don't see the snake throwing the book party for the mongoose. It's just a little unnatural. And that's because she can be a little dangerous, I think. And she can play hardball. On the other hand, I talked to other reporters who, you know, went to battle with her. They didn't fall for any of her tricks, didn't do any of the background dance, didn't take any of the off-the-record meetings.

They just really went at her client very hard. and the piece comes out and it's pretty brutal. I don't think that Risa got scored any points there. And still, at the end, she sends the reporter a blank email with the subject line that just says good headline or fun headline or something like that. So again, I think they know that she. Yeah, I mean, I think she kind of, you know, she respects a good story at the end of the day. And she just sort of tries the best she can to sort of lessen the blind. force hit for the client, but I don't know.

It's tricky. You mentioned the Zucker story, and what's so interesting to me about that is it's such a common scenario in media reporting where something very, very big happens. And there is a eight-hour window, a 24-hour window, a 48-hour window where a reporter is staring at their editor and the editor saying, you've got to get me something on this. and you're not going to know the whole story, but if you can bring me back those two or three details that will make your stand out,

then you get your merit badge for the day. And she is the person in that encounter who has one or two or three of those details? Yes, and again, because she has such this strange understanding of the way the reporter brain works, I think she will do something like, you know, on a phone call with a journalist,

she'll give a couple color details that makes the journalists feel like they're in the room where the thing happens. And that's the sort of thing that makes the story shine. And, you know, our eyes sort of widen when somebody dangles these shiny objects in front of us, like an anecdotal lead or, you know, she can sort of do that and make the reporter feel as though she's giving them something. And I think at the same time, she's probably slipping in a helpful narrative to her client or bringing the reporter around to the idea that the story is more complicated and it's not black

and white. And so it's this sort of dance. And again, she's just good because she knows how to give the reporter what she wants. And in the case of the Zucker story, I was talking to another journalist last night at a party. And they were like, yeah, 45 minutes after that news broke. And I'm desperately trying to contact Jeff Zucker and Alison Gulles for comment. Within 45 minutes, like, it's Risa who I hear from. And she was just in control of the story. And from hour one, all the messaging went through her. You know, her competitors and other people will say, well, that wasn't some big huge success. That was a giant mess the way that story unfurled. But again, there's only so much that a crisis person can do.

But she was sort of on top of it from the beginning. So every reporter had to go through her. How'd you get the idea for this story? Well, I was, I'd started at New York Magazine shortly before the Zucker story happened. And my editors wanted me to jump right on top of it like every other reporter in town. So I tried. And I really wasn't getting very far. eventually in the first week or two, I had to meet with her because I had ferreted out some things about the story that I needed answers on.

And I was begging to sit down with him, even if it were just off the record. And she wasn't going to give him to me, but she agreed to meet with just me off the record. And she was very intriguing. And I walked out of there much more interested in her than him. I was sort of like, who is this person? So I started calling around to other longtime reporters I knew in town. And they were like, oh, this is your first time tango. with her. Like, she's a pit bull, but if my life blew up, I would call her. And so I just became

really interested in her. And she was not, it took her a very long time to agree to be profiled. But I just thought that she was an interesting prism through which to show how the media works. And also, she's just a great New York character. Here's a person who works over the media for a living. So what did she think of your piece? We haven't really talked about it. I mean, this is what's so strange you go through these things with the profile subject and you don't want them to like it necessarily. But, you know, there's something about her that's very kind of keep it moving. And I think she respects that it was fair. And ultimately, I think it was a nice piece. So I think, you know, she didn't, I don't think she hates it. But we haven't really talked.

You're still waiting on that nice headline. Yeah. She survived. I think she's really happy it was over. One of the fun things about doing this piece is that she is so used to being in control. And to be the subject of the piece was, I mean, she was freaking out the whole time. It was really, really fun for me. I mean, she would call me and email me and say things like, how many words is this going to be? Macriest, and I would just keep adding on another couple hundred every time just to watch her freak out. It was, and she was, you know, she was trying to play it cool and not control it, but that's just not in her nature. So at a certain point, she called me and she was like, was this a huge mistake?

Why did I agree to do this? I'm having buyer's remorse. I was like, you haven't even seen it yet. So I think she's just relieved. It's over. Is it role reversal? You're counseling her. Yeah, yeah, it was pretty fun.

Let me ask a little bit about your career. Early on, you were Maureen Dow's editorial assistant at the New York Times. How did you get that job? Yes. Well, I was an intern at Rolling Stone magazine. and then an editorial assistant at men's journal, which was also owned by Yon Wenner. And I did that by day, and I was bartending by night,

and I just would check the Times website constantly. It had always been a dream of mind of work there like anybody else. And I saw that that job was open. So I just wrote this sort of voicy cover letter and guessed what her email might be. And she opened it and said, sounds great. Where do you live?

The letter you. And she was in Washington and I was in New York. And I just said New York. and thus began a long interview process. It took like six months and many interviews, but then eventually she picked me, and I moved to D.C., and it was, you know, the adventure of a lifetime, basically.

Many interviews with her about what you would be like as her assistant. First, I had to go through a couple other layers. She has a, the Maureen assistant job is sort of this very funny, like fraternity. I mean, I interviewed with her former assistants, people like Ashley Parker, and her best friend in the Washington Bureau of many years, Carl Holst, and I had to talk to another editor at the Times. And then finally, I met with her in person. Our interview was on St. Patrick's Day, actually,

which was fortuitous. And it went well, yeah. For people that don't know, this job leads to good things. Alex Thompson and Axios, Julie Bosman at the Times, among many, many others have come through the editorial assistant track there. What does the job entail on a day-to-day basis? It's, yeah, I mean, it's really the last of its kind. Something like this doesn't really exist anymore.

But basically, you're like a producer for like what I always thought of as like Dowd Industries. You know, we would do our weekly column about politics. And then they also had her doing these huge style section profiles on everybody from Tom Ford to Bob Eager to Jane Fonda. And so there were certain months where we were moving. I mean, I don't know, probably like 12,000 words of copy. through that newspaper. I mean, two, four thousand word pieces a month on top of four weekly columns at 900 words. So it was a lot. So as the editorial assistant, you're setting up the interviews, you're dealing with the publicist, you're sort of dealing with their editors in New York,

you're making sure there's a photo shoot set up, you're fact-checking the pieces, you're providing her with the research. And then what's so amazing and generous about her is that she would go out of pocket and pay to bring me to these interviews. And I would come in the room and I would have a chance to ask the subject questions. And so, you know, we flew around the world and interviewed prime ministers and presidents and movie stars. And it was, it was incredible. There's a picture of you online. And it's you, her, Times reporter Jeremy Peters and Charlie Steron, which is exactly what I pictured the job being like. Yes, it would be like, you know, lunch with Warren Bady at the polo lounge and, you know, drinks with Sean Penn. And then the next second, we're asking Tony Blair, if

regretted going into a rock. You know, it was just this sort of crazy, crazy, crazy ride. And, yeah, and we're, and, you know, and then, and then all the other fun assistance stuff, like expenses and calendar and correspondence and, you know, that sort of housekeeping thing. But it was a really, really immersive job. And, and you kind of just, yeah, it was great. You write a bunch of stories for the New York Times and then you leave for New York Magazine in 2021. Why New York Magazine? Oh, God, I've always wanted to work at New York. I mean, I, so many of the pieces that appeared in that magazine over the years are what made me want to be a writer and I always had the anthologies and I, you know, this is exactly this sort of

magazine that I love. And yeah, I started freelancing for them a little bit while I was at the times and then something opened up and it just worked out. There's a great tradition of media reporting there, semi recently from Joe Hagan and obviously going way back before that. What kind of media stories do you like to write? Yeah. Yeah, he's great. The stuff that sort of inspires me, I inhaled a lot of the journalism of the old Vanity Fair and the old New York Observer and Spy Magazine and that sort of thing.

And, you know, I've always been inspired by people like Ken Aletta and Alessandra Stanley, Vanessa Grigoriathis. I think about Lynn Hirshberg's stories and obviously Maureen, too. And I think that those people all have this sort of very voicing, knowing, Rye sensibility about this sort of power crowd in New York and who was up and who was down. And I think about my job in terms of that. And I guess I am a media reporter, but I don't really think about it like that. I think about this kind of tribe of people in New York and a little bit in Hollywood and a little bit in Washington. And those are the players.

And I feel like I'm just trying to chronicle that a little bit and less, you know, straightforward media reporting. I got you. So it's the whole, the whole scene, the whole power structure and media is one part of that. It's yeah, I think it's all interconnected. I mean, I think that's why Risa was a story that interested me because I felt she was a behind the scenes player that's plugged into that whole world. And, you know, I just did before her, I wrote about the fall of the Penguin Random House CEO. And before that, I did like a 6,000 word profile of the German executive, Matthias Dapfner, who's trying to become a real player in the American media and buying up Politico. And so, you know, these characters emerge. And it's like,

where in the narrative are they? And, you know, does a piece make sense? And, you know, how to how to sort of advance the narrative around them. I think of a piece in terms of that. When you're interviewing reporters, do you find them performing a meta analysis of your questions in real time? Like, what's his angle here? Is this your lead? Is this your nut growth? Totally. Yes. Absolutely. For sure. I mean, what's so strange about writing about this world that's so different from? I've done a few other pieces in reporting about, you know, I did a lot of like political coverage and, you know, covered riots and protest.

And it's just so different when you're interviewing regular people versus people in this world because everybody's so media trained and they know how it works and they're really careful about how they speak. And they know that there's something sort of parasitic. about the way reporters, you know, we're all kind of playing a little game and you never really know how your quote's going to get used. And I take it really seriously and I try, I go to extreme lengths to make sure that I'm being fair and providing context. But it's a dangerous game to talk to a reporter. People like to do it because it's fun. But certainly the people I'm talking to are very aware of the, you know, the dangers involved. And so it takes a lot to get an on-the-record quote or to get somebody to say something or say how they really feel. And, you know, a lot of these pieces also require

tons and tons of background calls with people. And you've got to be careful and you've got to be discreet because people are risking a lot talking to a reporter. You wrote a story about the new executive editor of the New York Times, Joe Kahn. How did the Times regard you coming back to report on your old employer? Yeah, again, that was a, that was a really lucky thing. I had just started at New York Mag not long before. And I, they didn't tell me this, but I always assumed the reason why they went with me is just because they knew that, you know, they were about to name him.

They should probably participate in one magazine profile. And they had their pick. Everybody wanted that interview. And I think they just thought, this guy used to work at the times. He worked for Maureen. He appreciates the paper and, you know, we might as well go with him. So they did, and it was, his announcement was made on a Monday. The interview was on a Friday.

And they, you know, he was generous with his time. He gave me an hour or two in a conference room. And then I just ran home and just like chained myself to my desk and wrote 6,000 words that weekend. And the peace dropped Tuesday morning. I guess actually that was when his announcement was made. But I was very grateful that he gave me his time. Khan became executive editor last June. Where have you seen his fingerprints on the paper so far?

Yeah, that's a good question. I have to say, I think there are plenty of people who are Times haters and there's always something in the paper to roll your eyes about. But what makes them far and away the best newspaper that we've got is, I mean, that A section is just unparalleled. When you pick it up on a Sunday, you can go around the world in an hour over coffee. It's incredible. I think their Ukraine war coverage was incredible.

I think a lot of the stuff comes out of the London Bureau, which he grew a lot. And my favorite thing about getting to talk to Joe was not just about the big questions of journalism right now and the controversies at the paper and whatever, but his career was incredible. I mean, this guy was in China for like years and years and years doing like kick-ass reporting about the Communist Party and all this sort of stuff. So I think he has this really strong appetite for international news and sort of driving the story. And I just feel like the A section of that paper is so good. Last night while you and I were DMing, you had been at the New York Times building for a party for the opinion section. Yes. And the guest list included everybody from Mayor Eric Adams to gossip columnist Cindy Adams.

Yes, yes. Speaking of covering the waterfront, can you give us a flavor? of the New York Times opinion section party. Yeah, it was super bizarre. So it's this tradition that Gail Collins started a while back that they throw around Valentine's Day. And each one of the columnists is supposed to invite people from outside the paper. And they try to get sort of a starry, fun mix. And, you know, it was fun because it was really weird.

Like, the mix was really strange. You know, you're standing next to, like, Lucy Lou and Nick Christoff and Zach Posen. And then you see the governor talking to, like, I don't know, Cindy Adams is, like, prowling around. and it was just super bizarre, only in New York mix, and it's not chic at all. I mean, it was this horrible bright lighting and room temperature chardonnay, and the furniture wasn't even moved out of the way, and it was by all, you know, all metrics a bad party,

and yet it was really fun, actually, because it was just such a crazy mix that you would never see anywhere else. And it's sort of funny who they're able to get to come to that. And I think it's just because no matter what people crave the approval of the New York Times and certainly insecure celebrities do, they already feel like such intellectual lightweight. So when they get an invitation from a collection of columnists who are writing about like, you know, international war and child slavery and Capitol Hill, they come running. And it's just, it was a funny, it was a funny spectacle. Room temperature chardonnay sounds exactly right to me. Yep.

And I drank a lot of it. It's like the oldest go-to or the media beat, right? I'm going to show up at a media party. I'm going to bring my notebook. I'm going to schmooze. How much of that do you find yourself doing? I do it. I've been doing it a lot.

In my job, the things that are most rewarding are these big, long profiles, and they take a lot of energy. But every now and then something pops up on my calendar and my inbox, and I think I should just go hit that with a notepad and just throw 700 words up onto the web the next morning. And I've done that with, you know, there have been a few book parties and other things that I think spoke to a certain moment in the media or, you know, if there's an angle there that's worth doing. And then you can sort of be a terrorist at the party and go up to powerful people and ask rude brady questions that they would never otherwise submit themselves to.

And it's sort of fun. And, you know, and again, it's sort of like seeing the power crowd come together in real time and writing about that. And I did that recently. There was like a status funeral for Joan Diddy in Uptown. And it was a really amazing array of like the sort of literati and, you know, what power players exist in the book publishing world still. And there they all were in the VIP section in the church. And it was very interesting.

The status funeral. This is such a great moment for a journalist, right? I think of Mark Leibovic writing about Tim Russert's funeral in Washington. Yeah. Yep. Yep. And that opened the book. Yeah.

and New York, New York. I did that also. There was a status funeral for Andre Leontali, which was this incredible vivisection of the fashion world and a lot of unsaid anger, you know, Anna Wintour in there, and they had a big falling out before he died, and it was just a really, really interesting way

to observe a lot of the, you know, just kind of cross-section of the fashion world in there. Sean McRish, look forward to the next vivisely. section and thanks for coming on the press box. Thanks for having me. That's the press box. I'm Brian Curtis.

Production Magic by Erica Servantus. We are going to take the rest of this week to recover, rejuvenate, to read. The press box will return next week with an interview with a big person from the world of TV news. At least I think it will. And then David and I are back Monday, February 27th with more lukewarm takes about the media. I'll see you then.