In early episodes of the new FX series Love Story: John F. Kennedy Jr. Carolyn Bessette, JFK Jr. is seen shopping around his new magazine concept, George. During one power lunch at Michael’s in Midtown, he produces a mocked-up cover image of a woman dressed as George Washington.
In reality, that never quite happened. Yes, Kennedy and George cofounder Michael Berman hit the pavement pitching the idea for a political magazine to publishers. But the now-iconic first cover of George—Cindy Crawford in a powdered wig, her midriff bared, shot by Herb Ritts—was so tightly guarded that not even the entire George staff knew what it would be. It was only revealed on launch day, when Kennedy held a press conference at Federal Hall—where George Washington took the oath of office in 1789—and pulled the covering off an oversize mounted version of the cover, declaring: “Meet George.”
The issue itself was no less surprising. It included a sprawling Q&A with George Wallace, conducted by Kennedy himself—a bold editorial decision, given Wallace’s segregationist politics and history as an antagonist of Kennedy’s father. Elsewhere, Chris Matthews penned “Fast Times at Congress High,” illustrated by Sean Kelly, which imagined Capitol Hill as a high school cafeteria. Julia Roberts appeared in a reported piece on her UNICEF work in Haiti. Cindy Crawford resurfaced with Isaac Mizrahi in “To Tell the Truth,” a fashion column that delivered unvarnished, catty observations about political style—including dry banter on the unfortunate conspicuousness of nude hosiery. And under the heading “If I Were President,” Madonna mused about banning handguns, raising teachers’ salaries (“Teachers should be paid more than professional athletes”), and seeing the entire military “come out of the closet.”
“Politics has been, and remains, the most important arena of civic life. But for many Americans it has become remote, dull, and disconnected from everyday concerns,” Kennedy wrote in his first editor’s letter. “We hope to make politics accessible and engaging, without sacrificing substance.” George, he suggested, would be “a place where serious issues are examined in a lively way.”
That spirit—serious but lively—animated every page. Even the advertisements felt in dialogue with the editorial mood: a spare Tiffany Co. diamond ring resting against its blue box; a Movado watch presented like modern sculpture; Giorgio Armani tailoring in moody monochrome. This wasn’t a civics textbook; it was mid-’90s Manhattan distilled.
The editorial experiment would last just five years. After Kennedy’s death in 1999, George struggled to maintain its momentum and ultimately folded in 2001. But for a brief, electric moment, it reimagined what a political magazine could look and feel like.
Nearly 30 years later, as popular culture revisits Kennedy and Bessette through a fictional lens, Vogue decided to return to the source and speak to those who were there in the early days of George. What follows is the story of George—not as myth, but as memory.
RoseMarie Terenzio: Executive assistant to John F. Kennedy Jr. and a founding staff member of George. She is the co-author of JFK Jr.: An Intimate Oral Biography (2024).
Matt Berman: Founding art director of George (no relation to cofounder Michael Berman), responsible for the magazine’s visual identity and inaugural cover concept. He later chronicled the experience in his memoir JFK Jr., George Me (2014).
Sasha Issenberg: Joined George as a teenage intern and became one of the few staffers to remain for the magazine’s full run.
David Janke: First assistant to photographer Herb Ritts (who shot Cindy and George Wallace for the inaugural issue) throughout the 1990s and into the early 2000s.
Jake Chessum: Photographer commissioned for two shoots in the debut issue who would become a magazine favorite.
Kate Harrington: Stylist on George’s first cover and a lifelong friend of Kennedy’s. (Also, the adopted daughter of Truman Capote.)
Chapter 1
RoseMarie Terenzio: I came to George through Michael Berman. I was a PR person working at his firm PR/NY, and unbeknownst to me, he was starting George with John. John started coming into the office, but we didn’t really know why, and then eventually it came to be that he was starting George.
Sasha Issenberg: I had just finished ninth grade and started probably right at the end of May 1995. Gary Ginsburg, who was a senior editor, was a friend of my aunt’s, and somehow she wrangled an introduction. I went in and saw Gary one afternoon at his office at 1633 Broadway. I only learned in retrospect that John had seen me walking out of Gary’s office and started ribbing Gary, like, “Gary, who is that? Is that your son?” Gary said, “No, that’s some kid who came in to ask me for a job.” And John said, “Oh my God, he looks just like your son. You have to hire him!”
Matt Berman: I heard JFK Jr. was all over town, selling his magazine. I was happy working and doing great things at Elle, and kind of kept tabs on it. When John finally expressed real interest in Hachette Filipacchi, they set him up in a conference room with Michael [Berman] and Rose [Marie Terenzio]. [Hachette Filipacchi, which also published Elle] put me in the conference room with them, and I was supposed to get them off the ground—design the logo, design the prototype, everything they needed to sell the magazine to advertisers. I didn’t think it was anything more than helping them get started. We were all very young, and we just had a rapport and laughed a lot. I didn’t have a sense of how big this thing might be.
David Janke: I started with Herb [Ritts] in January 1994, and I stayed with him all the way until March of 2001. Herb didn’t share any details about that first cover shoot ahead of time. Nobody said anything to anybody. It was really hush-hush.
Jake Chessum: I lived in London and had been shooting for a lot of trendy magazines—The Face and Arena. And in the early months of ’95, my agent called me and said, “Oh, we’ve had this call from this guy Matt in New York. He’s starting a magazine called George.” I was intrigued, but the level of reverence that John Kennedy Jr. had was not the same in England…because it’s England.
Kate Harrington: I first met John on a boat trip along the Turkish coast with Truman, John’s Aunt Lee [Radziwill], John’s mom, John, his sister, and Lee’s two children, Tony and Tina. On that trip, John was the only one of the four other children on board who showed me any kindness. He went out of his way to include me in the kids’ boat fun and educated me discreetly about the ways of yacht life. This cemented our lifelong friendship. Later, I had moved to LA from New York, after working for five years with Andy Warhol at Interview as their fashion stylist, to work exclusively for Herb Ritts as his stylist for 11 years. I was delighted when John flew out to LA to have dinner with me at The Ivy to conceive the best cover we could dream up!
Chapter 2
RoseMarie Terenzio: It was a little rocky there for a minute. We moved from our little office on 26th and Fifth to Hachette in Times Square and started out, just the three of us, in a conference room with no desks, one phone. It was very much a start-up environment.
Sasha Issenberg: It was a start-up, and so there was no clearly defined hierarchy or responsibilities. Everything was totally in flux. People were still figuring out what they did. The guy who was running the magazine had not only never run a magazine, but also never worked in a newsroom or in journalism. I mean, the only reason that a 15-year-old could end up there and be given some responsibility was that there was a lot of stuff that had to be done.
RoseMarie Terenzio: It was a small masthead—it was one of the things that would always frustrate John. He’d say, “Look at this masthead and look at ours. And they’re putting all this pressure on us to get this magazine out every month and keep sales up!?”
Matt Berman: I remember we counted: It was something like 50 or 60 days of nonstop work leading up to the launch—Saturdays and Sundays. We’d work all day, and then it would be eight o’clock and we’d all eat together. I had a graphic designer in the art department and someone else organizing all the shoots. It was a really shoestring, small group of people, and an amazing workload.
Chapter 3
David Janke: You could tell John was really trying to shake things up—make the magazine and politics a little bit hipper, a little bit more accessible to the younger demographic. I think he wanted to make politics cool.
Sasha Issenberg: The question was about politics and pop culture—I’m not sure everybody at the magazine could entirely agree on what that meant, and certainly the public didn’t have a clear understanding because nothing like that existed before. So, I think there were questions: It’s a political magazine—is there gonna be a politician on the cover? Is there gonna be a political cartoon on the cover? Is John gonna be on the cover? What the hell is a political pop culture magazine going to look like?
RoseMarie Terenzio: The first creative direction was really important at George because it couldn’t just be different, it had to look different. We didn’t always have cover stories. Sometimes it was intentional. We didn’t need a direct [editorial] correlation to the cover—the goal was to get people to open it and read it. Sometimes it worked, and sometimes it just didn’t. For example, we had several pages on George Wallace in the first issue, but no one wants to pick up a magazine with George Wallace on the cover. That’s where Cindy comes in.
Matt Berman: There weren’t a lot of big-name photographers available to us because the ones everyone knew in town were shooting for Condé Nast. And I was kind of okay with it because we were doing something new, right? I was like, I don’t even want those people; we don’t want it to look like a portrait you’d see in Vanity Fair or Vogue. So I went on this deep dive to meet all these photographers that I didn’t know. I was looking at English magazines and French magazines, and I just sought them out. Some were well-known or getting well-known, like Nick Knight, and some people were like the Jakes, that I just saw little pictures in magazines and thought, “Oh, this guy, at least it makes it look interesting!”
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Chapter 4
David Janke: The whole concept for the cover shoot, I have to say, was really [from] Matt Berman. He was really the driver. Herb was obviously on board, put in his two cents, and got Cindy because they were so close, but Matt Berman was really the one who got John to think about it a little differently and push the boundaries.
Matt Berman: John says, “Hey, no big deal, but I’m going to have dinner with Herb Ritts because I think he might be able to help us on the first cover.” We thought he couldn’t, because he was doing Vanity Fair and Vogue. So it was just John, Carolyn, me, and Herb at this restaurant—a neighborhood restaurant with a lot of vegetarian stuff—and we started to talk about the cover; what the cover could be; who it should be. John was thinking: Should it be like Bill Clinton? Should it be a political person? I’m a big research guy—I grew up with an antique dealer mom—and I brought a little folder full of rough ideas. I was always interested in illustrators. I loved Alberto Vargas, who did the Vargas Girls for Esquire, and those pinups were often very Americana. So I had this printout of a Revolutionary War–style pinup girl in a white wig wearing colonial clothes. I was like, “Something like this would be fun?” And everyone really liked it, but we didn’t know who the person was. Carolyn said, “If you’re gonna do a woman, she should be super-American, like an apple pie—an all-American girl.” And at the time, that was Cindy Crawford. Herb then got up, and he called her—it must have been a payphone—right away, and so it was all agreed upon right there at the dinner.
Matt Berman: How’s it going to look like George Washington, but also Cindy Crawford? I remember we hired Oribe, who was huge at the time. We called the Metropolitan Opera and got some white powdered wigs. And then it was about Oribe styling it to look like George Washington, but still making it look pretty, like it’s Cindy Crawford. How do you get that in the middle?
Kate Harrington: A funny, last-minute, on-set wardrobe-slash-styling decision had me decide to cut the blouse she wore. With fashion styling, sometimes we just have to go for it! Right?
David Janke: I was Herb’s first assistant and in charge of the lighting. I remember the shoot day; it was at Smashbox Studios in Culver City. It was pretty quick, actually. It came together quite fast—I mean, hair and makeup weren’t fast, but the actual shoot itself was pretty fast. We didn’t change outfits, but we did a couple of pose variations. I don’t think Herb submitted very many variations. I think maybe like three or four. That was about it.
Matt Berman: I think everyone was really excited because they thought John was gonna be there. Herb would just point over to me, like, “Well, we don’t have John, but Matt’s here.” It became a joke. He was back in New York, probably doing 10 billion other things with the launch. He really trusted everybody, but it was Herb and Cindy Crawford. I mean, we knew what we were doing.
RoseMarie Terenzio: Matt had originally photographed Cindy with a bulge in her pants. John was like—he used to call Matt “Maestro” because he always said he was like a temperamental artist— “Maestro, whatcha doing with that bulge? Get rid of that!”
Matt Berman: We tried it, we put a sock in there or something. John and I both hated that, but I remember Herb really wanted it.
David Janke: Cindy and Herb had such a good relationship. I mean, she trusted him implicitly. They were super-close friends, and so she was totally game.
Chapter 5
Sasha Issenberg: John had locked in George Wallace as the interview subject, which was a big deal because there always was this desire to have something [related to JFK]. John had a very ambivalent relationship with trading on his name and family ties. He did not want it to be, you know, JFK Jr.’s politics magazine, but there were these subtle gestures in the magazine in that first issue that kind of acknowledged his family lineage. There was a picture of him in the editor’s letter, and then he sat down for an interview with someone who is a nemesis of his father’s administration. Those were the ways John tried to acknowledge who he was and what he brought to a political magazine without making it about him.
RoseMarie Terenzio: Oh, God, I remember it being really difficult because George Wallace was so advanced in age, and he wasn’t well. I think they had to go back [to interview him in Montgomery, Alabama]. I know John had to be very close to his face, almost in his ear, to hear him, because his voice was kind of weak.
Sasha Issenberg: Gary [Ginsburg] edited all of John’s interviews, so one of the first things I did was all the research for that Wallace interview and prepare the questions. Wallace’s eyesight was effectively gone, and we had just heard, at the last moment, that his hearing was also bad. I just remember the last-minute scramble to make these note cards for John to bring to Montgomery, Alabama. We printed out every question and put them on large index cards so John could show him each question. He was pretty far gone at that point.
David Janke: We went down to shoot George Wallace; he was dying, actually, and he was living in his home. It was kind of quiet and sad, actually. The man seemed deeply regretful of his actions and, in later life, felt terrible about his racist history and completely denounced his actions.
David Janke: [While in Montgomery], we walked into one of those Americana-theme restaurants, with Americana pictures and stuff. John was in front of me and we walked into the restaurant, and there was that famous picture of him as a little boy watching his father’s casket go by. Only the picture was life-size. He walked right in and right into his face. That was a really crazy, crazy memory.
Matt Berman: Herb was using George Hurrell’s, the famous Hollywood photographer who did all the movie stars, retoucher. He did the airbrushing, like real airbrushing, not digital, for George Wallace. It was interesting; the history of it all and the seriousness of it all were so great. I was learning a lot, and I started to feel good because I remember I sent Herb a layout of the cover and the inside story and he had no comments.
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Chapter 6
RoseMarie Terenzio: It was just this spectacular endeavor; it really did blend so many different worlds: celebrity, fashion, politics, literature. We had Caleb Carr write a piece, we had Julia Roberts on her UNICEF work, and Mark Leyner, a satirical writer on politics. We did Cindy on the cover, but also inside the magazine in conversation with Isaac Mizrahi. And then obviously, the first interview with John interviewing George Wallace, which was huge, because he was his father’s arch nemesis.
RoseMarie Terenzio: We actually had Roseanne Barr slated for the first “If I Were President” feature. John had faxed Madonna—they faxed each other back and forth, that was the big thing back then—[to do one for another issue], and she basically said, “If I’m not the first, I’m not doing it.” So iconic. So we bumped Roseanne Barr for Madonna. We were scrambling to close the issue, and we didn’t even have time to shoot her.
Matt Berman: It was all new subject matter for me because I wasn’t a political junkie. I always laugh when I remember looking at the first lineup in the issue because I didn’t know any of the names there—except, like, Madonna. So John would sit on my couch in my office and I had a pad and I had a Sharpie. Just to get my head around it, John would tell me who everybody was and kind of what they were famous for, what the article slant was, and I just drew it out. I think in the first issue, there is a guy on a motorcycle driving across the page, the senator from Colorado. If you saw the sketch, it was that. So I drew the whole thing out and I put the whole issue up on the wall in Magic Marker.
Sasha Issenberg: Julia Roberts was in the office one day. Manny Howard did a profile on her for the first issue, because she had just gone to Haiti as a UN ambassador and he did the interview in our office. With 30 years of hindsight, I suspect there were people and celebrities who could have been interviewed in their hotel suites who may have wanted to come into the office to meet John. But John evacuated his office for an hour or so so they could do the interview in privacy; he didn’t want to go in because I think he knew if he went in, it would become all about him, and he would blow up this interview and be this massive distraction.
Jake Chessum: There’s never been another thing that I’ve done that had that level of looseness. Matt and I became friends, and then he said, you know, there are these two shoots for the first issue: one of which was Ben Nighthorse Campbell, who sadly just died a few weeks ago, and Heather Higgins, who was this super-wealthy socialite…so Ben and I spent the day together just trolling around and met up with his friends, who were big bikers. They were all on their Harleys and geared up with the bandanas and the leathers and I followed them and shot pictures of them out the car window while we were driving along.
Chapter 7
RoseMarie Terenzio: I would get a box full of mail twice a day that was just mail for him. So I would sort through the mail, making sure sketchy mail didn’t get through. And the phone lit up like a switchboard. It was insane. It rang nonstop. John told me that when he was at the DA’s office, he shared an office with a bunch of other people, and no one was calling. But at George, you’d have Tom Green on the phone from MTV, a celebrity publicist calling about being on the cover, Mr. Armani’s office to see if he could come to Milan for x, y, z…Cindy came up to the office. Julia Roberts came up to the office. Every issue was like a new adventure. You never took a day off, and you never called in sick because you didn’t want to miss anything.
Matt Berman: We didn’t have an official office party to celebrate the launch. We had so many dinners and fun things anyway. John liked this Irish bar on Times Square, and we had lots of parties along the way. It was a really fun time.
Sasha Issenberg: John would tear reviews out of the New York Times on Sunday and be like, “Hey, I want this book.” We had a charge account at Coliseum Books at 57th and Broadway, so it felt like every week or two, I would go and get a bunch of books that John wanted. Some of them were by writers he was interested in having write for the magazine. Some of them were topical, newsy things. Some of them were just things that he was interested in for his own amusement.
RoseMarie Terenzio: I remember one of the things I had to do was find a cherry tree. John and Michael wanted to send Cindy Crawford a cherry tree—because George Washington chopped down the cherry tree—as a thank-you gift. You couldn’t because they weren’t in season—you’d have to get it from Michigan or something and bring it—and I was like, this is crazy. By the time it gets there, it’s gonna be dead!
Jake Chessum: Herb Ritts had a show in London, and I door-stepped it and engineered a situation to meet him. Three or four years later, to be in a contributors page alongside him—it was like, my God, this is nuts. Like, I’m actually a photographer!
Chapter 8
David Janke: You know, when we were shooting, it didn’t really feel like that big of a deal. Herb shot Cindy for Playboy and we’d done so many boundary-pushing-type things with her prior to George—remember those Vanity Fair photos of Cindy with K.D. Lang? Cindy is in a swimsuit, shaving K.D. But I guess in the world of politics, it was pretty explosive, and in the context of the audience, it probably was pretty, pretty shocking.
RoseMarie Terenzio: The first issue culminated in this amazing extravaganza of a press conference at Federal Hall. We had all gotten to know John in an office setting, and I don’t think we really understood until that moment the breadth of his fame and how interested everyone was. I remember Matt and I were outside, surrounded by live TV trucks, tons of media, tons of people, and tons of paparazzi. And Matt says to me, “What’s going on here? Is there another thing happening while our press conference is happening?”
Matt Berman: We had so much attention from the first cover, I remember John and I saying, “We’ll just keep doing George Washington!” I remember a lot of people arguing, that’s stupid. But it was just kind of reinforcing the name and the idea of George. Later, we started to branch off into other icons and other American historical characters. But for the first few issues, we did George Washington.
Chapter 9
Sasha Issenberg: I think the magazine became this kind of safe space for him, where he didn’t have to perform the way he did out in public. I was pretty chill around John at the office, but older family members and friends would ask me for every tiny detail. I just didn’t think what he ate for lunch was that interesting?
RoseMarie Terenzio: As far as his lunch went, there were a few staples: a Brazilian restaurant, Rice and Beans, on Eighth Avenue—it was like this lady in the back cooking and her son running it. It was tiny. Sita Thai, which was on 51st or 50th Street near Ninth Avenue, that was his favorite Thai place.
Matt Berman: Once you spent more than five to 10 minutes with him, it kind of all went away—all the intimidating parts, because he was such a warm person. He was excited by the whole thing—film would come in, you’d show him, and he’d get excited. And that was kind of a great feeling because you didn’t have any fear. It was a really creative atmosphere.
RoseMarie Terenzio: He mostly wore a suit to the office because you never knew who was coming in. Or he’d have to go to a board meeting after work, or he was meeting a writer. But on other days, it was khakis and a shirt. The only time he ever came in dressed down was if it was a weekend and he was playing football in the park in the morning or going to rollerblade or bike or kayak. He also always had a bunch of clothes in the office: shoes, sneakers, helmets, bike chains, rollerblades.
Jake Chessum: He definitely had charisma and real presence—good-looking, debonair—but he had that level of self-confidence. He would always come and say, “Hey, Jake, great to see you. How are you?” and you’re putty in his hands at that point. It imbued you with a sense that you wanted to do something good for him, you know what I mean? There was no ulterior motive other than to motivate people to do something good.
Matt Berman: He’d see me on TV doing like an Access Hollywood segment—and I was terrible on TV—and he would say, “Okay, when you don’t know stuff or if you can’t answer something right away, just, you know, watch me….” And he just kind of looked up. “It looks like you’re thinking of something, and then it gives you a minute to think of what to say. You were looking all over the place!”
Chapter 10
Matt Berman: I had just designed all the logos, and John couldn’t make up his mind. I was trying to impress him, so I did just a bunch. John had just started dating Carolyn, and he said, “My girlfriend—she works at Calvin Klein and she’s really good at this stuff—do you mind if she comes in and looks at your logos?” I remember being nervous about it. I’d never heard of her, and all of a sudden, there’s this kind of knock at my door, and this really pretty girl leans her whole body into my office. And she’s like, “Are you Matt?”
RoseMarie Terenzio: Carolyn would stop in the office just to say hi. She’d be funny, laughing, and telling stories about her cab driver or something at Calvin Klein. I wouldn’t say she was involved with George, but she had her fashion background, she had access to stylists, and knew some of the models and some of the photographers. So that was helpful, especially to Matt, because he could kind of pick her brain.
Jake Chessum: I was shooting Billy Graham. It was 1996, and he was an icon of American popular culture, religious history, and political history. John was gonna do the interview, and he and Carolyn [were there] and they said to me, “Would you mind taking a photograph of the three of us? Because we just got married.” Years later, having seen the paparazzi pictures of her coming out of their flat that same day—in that same outfit, my wife tells me it’s Prada—it amazes me. Nobody was really interested in this picture. I think [Vogue] is like the second person I’ve sent it to.
David Janke: Herb went to Hyannis Port one summer and took the most beautiful pictures of the two of them, kind of rolling around in the grass—the most beautiful pictures he’s ever taken of anybody. They’re super-personal. They’re all black-and-white, and they’re really casual. When I saw them, I just about passed out. They were just so gorgeous. They’d never seen the light of day, and they never will, because John didn’t want that. But I wish people could see them because they’re just so beautiful.
Interviews have been edited and condensed.
