Juicy Scoop with Heather McDonald - The Modeling Pyramid: Predatory Agencies, Cindy Crawford, and St. Bart’s Secrets

Episode Date: June 18, 2026

Welcome back to Juicy Scoop! Today, I am sitting down with the legendary New York Times bestselling investigative author Michael Gross, and we are digging up the most scandalous, glamorous secrets from the worlds of high fashion and extreme wealth. Michael takes us inside the ruthless "modeling pyramid," uncovering how agencies like Elite operated on predatory behavior while stars like Cindy Crawford managed to stay completely untouchable. We dish on his hit books Model and Treasured Island, tracing the secret history of St. Bart's from its days as a pirate haven to a hyper-exclusive billionaire playground where David Geffen and Roman Abramovich dock their superyachts. Michael shares incredible behind-the-scenes stories of fighting off scary legal threats, getting banned from high-fashion runways, and the time Calvin Klein pulled a massive $5 million ad campaign just because Michael dared to write the truth. Plus, we talk about the toxic rise of Instagram selfie culture on luxury beaches and why I am officially trying to ditch the influencer vacation anxiety for good! -Elevate your summer wardrobe. Go to ⁠Quince.com/juicy⁠ for free shipping on your order and 365-day returns. -Right now, when you buy any Nutrafol Men hair growth supplement subscription, you get two free gifts — a full-size 2-in-1 shampoo and conditioner plus a hair serum, a $93 value — plus 20% off a subscription. Take advantage of this great deal at ⁠Nutrafol.com⁠. -Go to RO.CO/JUICYSCOOP to see if you qualify. - Sign up for your $1 per month trial today at ⁠SHOPIFY.COM/juicy Subscribe to my new show Juicy Crimes!: https://bit.ly/juicycrimes Stand Up Tickets and info: https://heathermcdonald.net/ Subscribe to Juicy Scoop with Heather McDonald and get extra juice on Patreon: https://bit.ly/JuicyScoopPod https://www.patreon.com/cw/juicyscoop Watch the Juicy Scoop On YouTube: https://www.youtube.com/@JuicyScoop Shop Juicy Scoop Merch: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://juicyscoopshop.com/?srsltid=AfmBOopTZFUvAeokrJJ6dQ5wuAW1T3nssO6pHk47u7KymJUBtBgKCvfX Follow Me on Social Media: Instagram: ⁠https://www.instagram.com/heathermcdonald/ TikTok: https://www.tiktok.com/@heathermcdonald YouTube: https://www.youtube.com/@HeatherMcDonaldOfficial Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Juicy Scoop is the show to know She talks Hollywood Tales Her real life, Mr. Segment's serial data And cereal sister. Hello and welcome to Juicy Scoop. I'm so excited about today's show. We have a real juicy bestselling author of the kind of books that we absolutely love.

Welcome Michael Gross to Juicy Scoop. Hi, Heather, great to be with you. I'm very excited for your next book, because the book that's out now, because everybody always either wants to go to St. Bart's or has been or wonders it or remembers reading about it in tabloids and all the stars and billioners that have gone there, which is the title of your new book, Treasured Island, the Story of St. Bartz, and it's barbarians, billionaires, and beauties. What a great subtitle. Thank you.

So before we get into that book, though, I have this other bestselling, New York Times bestselling book of yours model, which is all about just the ruthless business of the top modeling agencies in New York and Europe. What years was that book kind of chronicling? Well, the book came out 31 years ago. but it covers the business from its invention in the 1920s, straight through in the copy that you're holding, it goes through 1994. So through the height of the supermodels, then there have been a series of updates.

And so the current version that you can buy on Amazon goes through 2011 and actually has the name Jeffrey Epstein in. So you cover some of that. I know there's been so many legit models that also got sucked into that world unknowingly. So does it cover some of that? You know, Cindy Crawford told me that when she first went to Milan, which was a hotbed of sleazy guys trying to dive into the pants of models, both to get their money and to get other things. she was never harassed. And she said that she always thought that it was because some girls just had that thing

where it said, this one don't touch, she's worth too much money. So, yes, you know, lots of models right now, just the other day, Carrie Otis, who was a pretty top model in the mid-90s, filed a new lawsuit against the guy who used to run elite models in Paris. and it was on behalf of, she's trying to do a class action suit because the statute of limitations has run out on this guy. His name is Gerald Marie, and he's one of the main characters in the book model. Well, the reason I had the book is because I don't know how many years ago it was, maybe like 10 years ago, my agent called me and was like,

this guy wants to meet you to maybe collaborate. I don't know if they had the rights to your book or to try to do like a television series. And so reading it and I just gave, it didn't really go past more than just like a meeting. I don't know what happened with it. But I was like, oh my God, this would make such a great television show. And being that it would be like, you know, that time of 80s, 90s and like what it was like he wanted to do a show kind of about the main. the main modeling people that were a couple that then both ran their agencies. And how many times did that come about being the author that people wanted to try to make your book a series?

Well, model, so there's a process called optioning. And that's where a producer or a star takes an option. They give you a little bit of money to take the book off the market. And then they try to put it together and make it into a movie or a TV show. Model has been optioned five or six times. It went to script twice. Once it was the next thing that ABC was going to do is its movie of the weekend, there was a regime change at ABC,

and it died a sudden horrible death. And then there was another one quite recently that almost made it, but finally just didn't make it. So we're still waiting for model the movie. I mean, I feel like it's going to happen. I feel like this appearance on Juicy, is going to be the tipping point. No, I really do think it could be great. And I think there's such a

yearning for that nostalgia, that period of time, especially with younger viewers that are like, oh, what was life like before cell phones and social media and there were real models and it wasn't just Instagram and influencers? And they want to jump back and escape to that. era. So I think it would make a great series. And the heart of the book is really that moment in the 70s and 80s when models emerged as real celebrities instead of just niche celebrities. And that's precisely the movie that really ought to be made. People have tried and bad ones have been made, but no one's ever done one that got close to the truth. What exactly is the truth? Because I guess someone that, you know, was maybe their age or a little bit younger.

younger, you know, of course, everybody wanted to be a real model when I was in my all-girl Catholic High School. And there was like the cheesy, what was the guy's name? He had like a modeling school. It's like escaping me right now. But you could take this. Johnny Casablancus. Yes. That was one of them. I think there was another one, but that was one. And you could take a course. And the first course is like etiquette. And then the next course is, like, like actually putting outfits together. Then the third course is like having a little fashion show. And then the fourth course is expensive because you're actually going to get real headshots done with a professional photographer and you've got to take the loop and pick out your thing.

And, you know, so so many girls were doing it thinking, oh, maybe I could be a model. And even like so many models were in music videos and stuff. So that was just like, oh, let me put on some black nylons and a tiny black dress and just a red lip and slick back my hair and look real chic. But back then it was so about you had to be tall enough. And if any girl tried to say she wanted to be a model and she was under, you know, five, eight and a half, everyone would be like, good luck loser. Like you're never going to make it. Like it's, it was such a different time than today. When you look at like modeling and fashion and what drives someone being. on the cover of a magazine, what is your point of view or perspective?

Well, you know, what the book is really about is think about modeling as a pyramid. And everything that you're just talking about is the very bottom of the pyramid where there's someone who's a checkout working behind the checkout counter at Walmart in the middle of Iowa and wants to be a model. Then as you ascend up the pyramid to the very top, that's the dirty part of the business because there's a terrible elimination contest that goes on. And I always said that only a very few models can dance on the head of the pin of the industry. And obviously, they're the stars. And by the way, as far as height goes, Kate Moss can say, hey, take that because she changed that. But it's very, very difficult to get to the top of that pyramid. And a lot of

horrible things can happen on the way up and the business is structured in such a way that the predators are living at the bottom. And at the top there are girls like Cindy Crawford who just were untouchables and still are. And that continues to this day. And with someone like a Cindy Crawford, I also feel like her story was one, just like anybody that unfortunately is more susceptible to be a victim oftentimes is someone that doesn't have that family support, maybe didn't have the, you know, the strong kind of confidence in the home coming up. And the predator seeks those more vulnerable souls out. And they have, they have a talent for it. And then there's certain people that were like she said in the same room, also talented, but just, I think she was just very

lucky in that she came from this nice family. She, you know, had gone to some schooling and had pursued it and just, and again, went kind of up the ranks. Yeah, she skyrocketed, but she, it wasn't so plucked out and just, you know, no support, no mom, nothing. She had all that. And so I think that that's really interesting of like, and how difficult it must have been like for a mom to let their like 15-year-old daughter go to Italy or Japan, but then you're looking at all these super successful other models and you're like, well, if I don't let my daughter go, then she could miss out on this time, just like a, you know, just like a professional sports player. Like, you have that small window to make it. And if you don't make it by, you know, 22, good luck.

in the summer of, I think it was 1988 or 1989, two 15, 16-year-old girls arrived in Paris. One was Stephanie Seymour who came without her mother, and the other was Christy Turlington, who came with her mother. Christy Turlington was taken by the Ford Agency, which was run on a kind of maternal basis, and Stephanie Seymour signed with Elite, which was Johnny Casablancus' agency, which was run on a kind of predatory basis. and Christy Turlington ended up happily married with a college degree, kids, runs a charity, is still a working model, and Stephanie Seymour ended up with Apsil Rose, and then Warren Beatty,

and then God knows who else, and married to a guy who'd been in jail, and is rarely heard from anymore. So I think that what you're saying holds true. You know, it's not just heredity. It's not what you're born with, although that's important. It's not just environment, which is whether you come from a good family or not, because lots of top models have come from messed up families, but it's also what you have inside and your strength of character and your desire to succeed, which are two different things that are sometimes in opposition

and sometimes work together. And those are the ones where it all works together, heredity environment and everything that's inside, are the ones who become huge moneymakers and famous models. And they're the ones who end up on St. Bart's shooting the St. Bart's, shooting the St. Bart's shooting the Sports Illustrated swimsuit issue. Yes. So let's talk about that because, you know, Sports Illustrated has been in the news this year with the fashion show. In the last few years, they've really expanded from what

we knew it as as just the top models got it, who was going to get the cover. And then you'd watch the whole filming of the shoot where they'd go to a specific place like St. Bart's and do the whole thing and we got to see how it worked, how they posed them, who the different photographers were. And it was really entertaining to kind of watch as a young girl that just, you know, had just loved seeing beautiful places with beautiful women in it. How cut throat was that to try to make the Sports Illustrated back then between St. Bart's and modeling and all of it? Well, I don't really think it was cutthroat at all. It was a wonderful woman named Julie Campbell who ran the Sports Illustrated issues. And at that time, there was one photographer. His name was Walter Hughes Jr.

And he was a lovely man who I actually knew when I was like five, six years old because he had started out as a sports photographer. And my father was a sports columnist. But, you know, I think with Sports Illustrated, you have the exact same fundamental question as you have with St. Barts, the island. Now, how can an island and a sports magazine be a life? Well, because they're both in a way brands, and they both have to figure out ways to negotiate the path into the future. And St. Bart started out as a rock in the ocean

that nobody loved and became the destination, the place to go, where Sports Illustrated would go to shoot its swimsuit issue because it was, in 1989, the year Sports Illustrated went there, the hottest island in the world.

And then it only got hotter, just like Sports Illustrated did. For years and years, years and years. But now the magazine business is in decline and Sports Illustrated is in trouble, like all magazines are in trouble. And I was a magazine writer for decades. So I certainly, I live through this. St. Bartz in the same way has become so popular that success has become its enemy. Will success kill Sports Illustrated? Will success kill St. Bart's? And the underlying issue in my new books, Treasured Island, is how does an island like that survive? Not

just survive, but continue to succeed and continue to be the sort of product it is at its peak. How do you maintain that? And it's a very difficult balancing it. So let's talk a little bit about your background as a writer and then also your interest in putting you in this place where you could write so, such, so with such great knowledge of these kind of people, whether they're supermodels or. or billionaires or both, tell us a little bit about that. As I said, my father was a sports writer. He worked for the New York Post back in the old days when newspapers were important too.

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your mission takes you. Inside, an Intel Core 7 processor drives high performance during every session. It delivers the speed and responsiveness you need to keep your game smooth and seamless. We wrapped all this in our signature durable alienware design to handle any journey and look good doing it. This is the Alienware Experience, distilled into one iconic machine. Visit Alienware.com. and so I grew up in Yankee Stadium and Shea Stadium in Madison Square Garden. My father covered the Knicks, Go Nix. And, you know, I have a Nix championship ringing back in my jewelry box from 1970 when the Nix won the championship for the second to last time, although maybe they'll win again this year. And the thing was that when I was growing up, sports was something.

to be obsessed with. But for people my age, rock and roll was something even more to be obsessed with. And so I was obsessed with rock and roll and I started writing for rock magazines and newspapers about rock stars. And for 10 years I did that, I went on the road, I traveled with bands, I wrote about bands. And one of the things that you noticed was that fashion models gravitated to rock stars. And rock stars gravitated to fashion. And so I started getting interested in the world of fashion. And after about 10 years of rock and roll, I'd had enough. I needed a change. And I started writing about fashion photography. And it was partly Cher Shaila Fem. I liked pretty girls. I liked pretty women. Curiously, I almost immediately got married to a fashion designer. But I had then a

10-year run of covering the fashion world, going to Milan, going to Paris, going to London, going to the shows in New York, sitting in the front row at shows. And who did you sit next to if you were in the front rows of shows? The wife of the billionaire, the princess this, the countess that. And so you also become fascinated with the people who are sitting around you and who you have access to. And so I slowly evolved into writing about rich people, celebrated people, not movie stars because I'd already had my 10-year run of writing about stars and it was getting a little tired for me. But the people who were richer than the stars, maybe less famous, but more important in many ways. And I had a good 10-year run at New York, first at the New York Times and then at New York

magazine writing about all of that. During that time, I started writing for travel magazines. And what I wrote about were the places where rich and famous people went. And that was how I first encountered St. Barts. I started going there myself in about 1989 or 1990. And it became my go-to destination for my vacations. And I didn't go Christmas week when all the billionaires were there because I wanted a week off, not a week, another week on. I didn't want to go to the beach and see Calvin Klein coming out of the surf. I wanted to go to the beach and be left alone. So I did that for 10 years. And then as, as, you know, the magazine business started to decline after 1995 or so, I started writing books, I wrote model. And then from there, I segued into writing books that were social histories, that looked at the relationship between rich people and real estate and what their choices in real estate told you about the upper classes and about the world we live in. So I wrote a book about an apartment building in New York called 740 Park that was very old school New York wealth and

how the old school New York wealth evolved. Then I wrote a book about Los Angeles called Unreal Estate that was about how Beverly Hills, Bel Air, Holmbee Hills evolved over 50, 75 years. Then I wrote a book about a condo building in New York and the book was called House of Outrageous Fortune and it was about 15 Central Park West, which was full of all of the international oligarchs and hedge funders and private equity people, the kind of people who have no relationship with the world in which they live, they helicopter in, helicopter out, have private security, live in a bubble, sort of the Jeff Bezos's of the world. And then I was looking for a next book, and I thought, well, where does Jeff Bezos go on vacation to the same place that I've gone for almost 40 years,

same parts. Okay, a couple questions. It's fascinating. When you're writing about these people and you're sitting in the front row of the fashion and, you know, and that's really interesting that they, Of course, the billionaire's wife is going to be invited because she's the top customer and she's going to wear these clothes and she's way more important to the fashion brand than some chick that's going to hope to get the outfit for free and wear or two on the red carpet, you know? When you're meeting these people, did you try to ingratiate yourself? So they're like, oh, Michael, come on our yacht with us. Let's hang out. How did that work because you were like writing about them? Did they want you to write about them?

Did it make them nervous that you were, in fact, you know, a writer? Well, you know, when I was covering rock and roll and I was in my 20s, I kind of had this fantasy that I would be their friend. And you're not their friend. They live in a different world than you. And I pretty quickly came to understand that there was a divide that I could ride in the limousy, but it wasn't my limousy. And I vowed that I was not going to become the,

kind of person who did whatever it took to get invited into somebody else's limousine. So when I started writing about fashion, I didn't do that kind of work. I wrote about the real story. I wrote about how things ticked. What really made a fashion brand? And, you know, there were times when that really annoyed people. Calvin Klein canceled $5 million in advertising in New York magazine because of a story I wrote about him. Christian Laquois banned me from his... Wait, what did you, what did you write that he didn't like? Well, it was a nine-th century. thousand word profile. So there was a lot that he didn't like in there. And you know, the funny thing is I never said he was gay. But there was a picture on the cover of him and his wife, Kelly. And maybe there was a

subtle message underneath all of that. But I wrote about Christian Lacois and I simply said that his second collection wasn't very good and I was banned from his fashion shows. So, you know, you discover that a lot of these people have very thin skin. Um, and I, and, you know, and you, you discover that a lot of these people have very thin skin. And what they count on is that there are so-called journalists out there who think of their job as ingratiation, who are lapdogs. And I kind of decided to position myself opposite that and become a terrier. If you put a bone in my mouth of a story, I wasn't going to let it go.

And, you know, it wasn't a great way to make friends. And in fact, I did make friends. I made friends with lots of the people in the worlds that I covered. but the way that I kind of sum them up is there are people who got the junk. They understood that it was all a game and it was a game with journalists and that there was this continuum

between terriers and lapdogs and that you could work with somebody and sometimes you had to bite the hand that feeds you. And as a great, great editor once said, and if you do that, they'll feed you some more. And it really is true. And, you know, I found that if I did, didn't want, care about being invited, I would be invited. And when I wasn't invited,

I could just get the story anyway. So that was how I, that was how I handled it. In writing about them, whether it was in the newspapers, magazines, or in your books, did sometimes did you say who they were and other times kind of, you know, make it that someone could figure it out, but you don't say their actual name? How do you work that as far as not getting, you know, someone coming after you for defamation or whatever. Well, I've been threatened and, you know, lawyers don't scare me. And I've been threatened by some pretty scary people. So, but, you know, I did write a gossip column once for about four months.

I hated it. I hated myself. I hated waking up in the morning and looking in the mirror. I hated what I was doing. And I did write blind items, you know, guess who this is. And I hated doing that. No, what I do is I write real stories about real people and I use real names. And, you know, that might be why some people didn't get the joke.

But, you know, that allowed me to write books that connected with the audience. I don't write for the people I write about. I write for the people who read my books. And what's great is that by the time I started writing these books about, real estate, and I've done four now with the St. Bart's book, people respected what I did, and they understood that I was putting their accomplishments into perspective. And if that meant describing them as the saying goes, warts and all, it still was a way of saying, look at how important this person is, look at how successful this person is. And so by the time I got to the later

books, and especially Treasured Island, there were people who were thanking me for writing it, because they realized that if somebody like me who asked the right questions didn't write that book, then the story of the island was going to vanish and die with the people who created the St. Barts that we have today. And that it was really important that that story be told. And you can only do that if you're willing to tell the truth. So I happened to St. Bart's once took the scary, you know, the little scary jumper plane that everyone talks about. I was very lucky my husband and I were guests on our friends yacht that was docked there. We never took the big yacht out, but we stayed on the big yacht that had a staff,

and then we would take the very nice Tinder out to snorkel and went to dinner and danced on the tables and went out at night and walked around the fancy shops and the more charming shops and took the smoky around and all of that. And we didn't go at the height, tight time, like the Christmas time. We went around Easter. So it was still very nice weather, but some days like rained. And it was interesting then, which was about three or four years ago. It was, yeah, three years ago where we were talking about, you know, they made sure that like there wasn't a place for any kind of big boat to come in so that, you know, or it's very restricted of like how big or what level of hotel and stuff would be there because they didn't want it to be accessible to everybody. They really

wanted to keep it at a level that you had to be pretty darn rich to stay there, get there, go to restaurants there, find a hotel room. Is that correct? Well, yeah, I mean, but you're talking about two different things. The harbor only accommodates a certain length of boat. So when David Geffen comes, he has to park his boat outside the harbor because it just can't get in. And even though there are slips for super yachts in the marina there, there's not room for the really, really, really big boats. So Roman Abramovich, Paul Allen, David Geffen, they have to tender in from outside the harbor. So that's one limitation. But that's a natural limitation. That harbor has been the reason why St. Barts is St. Bairns. Barts is because of that harbor. It was a free port going back to the 17th century.

In the 16th century, pirates operated out of that harbor. The original name was the carinage, and carinage is where boats are repaired. So that's a physical fact of St. Barts, and it was a huge advantage that it had that harbor. As the island began to develop, there was a very conscious decision made that hotels would be limited, that they would originally, they had to be 12 rooms or fewer, nothing larger. And so what they did was very consciously they created an island where there's an intimate scale, there are no concrete box hotels,

there are no beaches full of hotel, hotel, hotel, hotel, with people selling garbage on the beach. And all of those things contributed to the island that you visited three or four years ago, which is very different from the island that I visited 35. years ago. Because it's the same French Island. It's got the same style of life. It's got the same Savoy-Faire. It's got the same croissant, same, you know, de confis. But back then, there were no

palace hotels. There were no glass and marble villas. The villas were made of mahogany antique. The hotels were small, intimate, and charming. They were very luxurious even then. But it was much, it was all on a much smaller scale. Everything was also fly. Everything was also fly. are less expensive then, even though it was probably the most expensive island in the Caribbean. There was a hotel called Taiwan, where the owner would rather keep the rooms empty and have no one staying there than rent to the wrong kind of people. They were consciously trying to, and I hate this word, curate the kind of people who came to the island to ensure that it kept this very lofty luxury image. And over the years, more investment came, and the DNA of the

island didn't change, but the outward expression of it did. And so now there are palace hotels, and they're kind of snooty. And there are stores that really very few people would shop in. And, you know, a lot of those billionaires, they expect to get the clothes for free because they're billionaires. So they don't even shop. I mean, I know one billionaire guy who has a gigantic yacht who I, he told me he was going to St. Bartz and I offered to recommend some restaurants. And he said, why would I want a list of restaurants? And I said, because St. Barts is famous for its food. And he said, I have a shop on my boat. My chef is better than theirs. So there's that kind of billionaire attitude of you bring it with you. And what's interesting is that these people tend to come Christmas week when

they can rub shoulders and butt chests with others of their ilk. And they're all engaged in this gigantic who's as bigger. And I'm talking about their wallets and their boats, not anything else, not their short stubby fingers. And so there's that society in St. Bartz. And then there's the society that you encountered going Easter week. I was there just the week before Easter this year. It's quieter.

There's still David Gepard. yacht was still there. The richest man in Israel's yacht was still there. But there wasn't this constant game of, I'm more important than you are going on. And you can also, the great thing about St. Bart's is it depends on the St. Bart's you want to see. Because the people who go to the dance on table restaurants, they're getting drunk at three o'clock in the morning. They're not getting up at 7 a.m. and they're not on the beach at 9 a.m. And they don't know which beaches are great for swimming. they probably don't swim. They'd probably sink from the weight of their wallets. Yeah. So, so, and they, they go to their restaurants, but there are other restaurants that the people

who love the old style St. Barts go to. So there's, there's this, it's like a multi-layer cake. And you can choose your layer. And then you can, if you want, go visit the top layer and have some caviar and have some foie gras, dance on a table, and then go back to the real St. Barts the next day. And so now, how do you see it today? Like, is it too many influencers, so many places, whether it's a restaurant that has a great frozen yogurt in New York City to a bagel place to an actual vacation spot where influencers would go and film it and make people aware. And now it's like, I got to go there. I don't care how much it costs. I just got to go there once. Get these photos. and it really isn't the vibe that it was of yesteryear. Do you find that? Yes. You know, I have an Instagram account.

And when I started promoting my book, one of the things that I put up on there was a picture of eight influencers on the beach at a beach called Enstagallette in St. Bartz at a day club called Shalona. And they were all primping and posing in their little metallic bikines. and with their selfie sticks. And I did put up a post making fun of the influencers. And the great thing is that while they're looking at themselves and at each other, all you have to do is turn your head and you can look out at sea and see what St. Bartz is really about as opposed to, they look, I'm here. You know, I have never cared about the frozen yogurt place that people line up for.

That whole culture, you know, I spent 10 years covering that culture. for the New York Times. And it was a job and I got paid for it. And the notion that this is what our society has become is a fascinating one. And the one thing that I am willing to guarantee is that the culture will move on. This too is reaching the saturation point. And at some point, people are going to start looking out to see instead of it themselves in their cell phones. I mean, even my own life with social media, you know, it is such a great tool for someone like me who's a comedian who is responsible for getting her own opportunities, own ads, own jobs, all that stuff. It's extremely valuable. But I have looked back on vacations in the recent years and then

like I was too, there's like an anxiety where you're like, I got to take these photos. I've got to take this content because it's so beautiful. I got to get it. Then I was like, okay, I got to get it, but then I won't post it until I'm home or, you know, in my room or whatever so that I can enjoy the experience. Now I'm going on a trip next week to these Bahama Islands. And I'm so excited because I love, I do love swimming in the ocean. I, you know, but now I'm in a place where I'm like, I'm going to bring. one carry on, that's it. I want to just enjoy it. I'm fine taking it. I'm not bringing bags and shoes

that match because that takes up a lot of room. I'm ready to just really experience the beauty and have the fun and I don't care to have to show it off. Now, you know, someone would be like, really, Heather, you just came to that now, like at your age. But I do think that eventually people do get to that place where it's like it feels like work. You know, I went on this one vacation and I didn't want people to know I was there because we had planned it and it was, there was bad things happening in the world. So I didn't want to look clueless posting this great time, you know? So we took photos and I, and I never posted it.

But it was like, it wasn't a great vacation because I was stressed about the things going on in the world. But it made it so nice just to be like, oh, my God, you know, take maybe one, one morning photo and one when you're cute to go out to dinner and like that's it. Like to be filming it all around and stuff, it's, you do get to a place where you're like, I'm not living in this moment and I don't now even remember it. You know, one of the, one of my great St. Bards memories is the second or third year I went. And as I was in St. Barts, the Gulf War, George Bush and Saddam Hussein broke out. And you couldn't get a newspaper at St. Bart's.

then you had to you could get a day and a half old new york times at four o'clock in the afternoon the next day if they happened to pick up the papers in porto rico and fly the man there was no television there were no telephones and i'm i am so serious about this there was a boutique that was called sorry no telephone and i still have some sorry no telephone t-shirts and at the time you know you didn't realize what an amazing thing it was to be in a place that was cut off from the world. So now the Gulf War breaks out, and the only television reception we had in the house that we were renting was reverse image snow. So it was all static, and you could just about hear that very horrible things were going on in Iran, in Iraq, and I thought, how lucky are we turn it off?

And, you know, it sounds like you've got the right idea, but I'm going to pose a challenge to you. leave your phone at home. Well, that I don't think I can do. Because unfortunately... Get an old-fashioned flip phone. Yeah, I'm going to try to... I've been getting better. But, you know, again, with my business,

I have to post, you know, this is going to be dropping while I'm on vacation. So it's like I have to post about it, you know, and I can have Drake work with me so that I'm getting to a place where I'm like, I don't want to, I definitely don't want to, be doing too much. But yes, you do kind of have to do that. But yeah, it's great. When somebody,

I've interviewed people that have done young kids that have done reality shows where they take their phones. And they said, you know, the first day it was weird, but after that, we loved it. We loved every second of it. Nobody else had their phone. We, that's why we were able to make friends or even maybe, you know, get romantic or whatever, because we weren't looking at the phones. It's just such a, a thing. And I do feel like there's going to be a pendulum swing and it's already starting where people are really making events and things like that where you drop the phone or you hire a photographer and that's the photos and you don't need to worry about getting them. And it really makes such a difference, you know? You know, and I realize that it's both ironic and perhaps a little hypocritical

that I'm here, now here comes the advertisement, talking about my book. Treasured Island, the story of St. Bards out on June 16th in bookstores everywhere, while talking about an island where there was once no telephones and no television and no newspapers and how much I loved it. But the fact is the world can accommodate both of those things. You can be both the person who does your job and takes pictures and posts on social media and also someone who can just throw the switch and turn it off for a few days. And it's a place like St. Bartz, where the world is in your face. You go down to Gustavia Harbor and what you are looking at is wealth inequality,

without question. That's what you're seeing. You are seeing the epitome of inequality. You're seeing, if you look hard enough, how this all happened, how luxury became this thing, how social media, the fuel of ambition and avarice and jealousy and envy that drives social media. And yet, you're also in this stunningly beautiful place where you can just turn it off and relax. And, you know, there it's just being able to keep two thoughts in your head at the same time. So it's not hypocrisy and it's not irony. It's just the way the world works now.

And, you know, we have to take pleasure where we can find it, even in troubled times. In being in St. Bart's and things, I'm imagining you encountered like a lot of maybe you know infidelity or social climbers or gold diggers or jigilos or wife swapping

scandal can you share any of that? Well you know a lot of what goes on in St. Bartz stays in St. Bartz because there is an entire ecosystem of people

who are paid very well to protect the privacy of the people who go there. So the concierges, which are both hotel concierges, but also concierges for the people who rent villas. You know, they might tell me the story about the maid who walked in one day and one of the guys in the house was snorting cocaine off the bare bottom of one of the women in the house or the clothes were all over the place and who knows who was in what bedroom, but they're going to protect their clients. So, and, you know, really there's something kind of banal about all of that. But at the same time, this is an island where hedonism has reigned for decades. And there was a point when all of that

was very, very public. So there's a whole section in the middle of the book about the era from the 70s to the 80s when St. Barts was overrun with drug smugglers, models, fashion photographers, and rock stars. And that was one of the things that, you know, there were a whole series of waves of people going there that put St. Bart's on the map. First, there were multi, multi-millionaires like David Rockefeller and Edmund de Rothschild.

So, you know, you had the American and the French Uber-rich guns. Then you had the kind of Connecticut pioneers, Republicans who like to sail, who built houses. One of those houses that was built by a fellow who was later the mayor of Wilmington, Delaware, became the den of Iniquity, the most raucous lush hotel club on the island. It was called O'Teuxet.

It was ostensibly owned by Jimmy Buffett, although Buffett was really just a front man. He owned about 2%, 3%. But Buffett described it as the scene of some of the worst behavior I have ever seen. And he was a rock star, so you know that he's seen a lot of bad bad. behavior in his life. And so there's a very long section of Treasured Island in which things that

went on there are described. And a lot of it is not fit for a family podcast. No, this is not a family podcast. Oh, good. So there's the guy, there's the guy, there's the bartender who had sex with so many girls in the bathroom that they ripped the sink off the wall three times. He had a, he had a reputation for going down on women for an hour and a half at a time. So they would hand him from one to the next. Girls left their boyfriends to be with this guy. Drug dealers traded girls. You know, they would be having sex on the pool table while snorting cocaine from somebody handing it in through the window into the nightclub. It was what? And when I asked one of these drug smugglers whether a night like that was the worst thing he ever saw, he kind of paused. He kind of paused.

was for a second and he went. No. Now, in all this research, was it never darker than that? Like, this wasn't never Ebstein Island type stuff? Or was there some of that where girls would come that maybe were not 18 years old, but were in the modeling world and looked older. They themselves were trying to get on the yacht. We always hear everybody's like, oh, I want to go on a yacht.

I want to be a yacht girl. I want to find friends who have, you know, girls. that could bring me on a yacht. And then people are like, be careful when you get on that yacht. You know, they're not just, they're not looking to find out about what your, you know, high school career was like

before you got on this yacht. They don't give a shit about that. Between the late 1990s and the 2010s, there was a period when almost every Me Too perpetrator on earth was going to St. Bartz. Usually, again, during Christmas week, easy to avoid. You just don't go during Christmas week. But Harvey Weinstein was there. Puff Daddy was there. Russell Simmons was there. There's a PR woman in New York who's kind of been disgraced by her association with Jeffrey Epstein. And just out of curiosity, this was long after I'd written the book. But the Epstein files came out and I plugged St. Barts into the Epstein files. And she was constantly trying to get him to go from the Virgin Islands to St. Barts. And interestingly, he was like,

Well, you know, what do I need that for? I've got my own island and I have my own girls. So I guess Jeffrey Epstein probably, you know, only went there a few times. But all of the rest of them were there. So there's an entire roster of the council who are on the scene on St. Bart's list. So did bad things go on there? I'm sure they did. I'm frankly more interested in financial skullduggery, in real estate skullduggery,

in the machinations of uber-rich people trying to impose their vision on an island that will tolerate them and take their money but really doesn't want them running things. And so those kind of larger societal forces are what I paid more attention to. You know what I wonder about is like sometimes when I think about like a saint bar, it's like let's just say I wanted to go and plan with my friends. I mean, I'm a little bit famous, but not much. I always panic, like, how on a busy time, how am I ever going to get a reservation anywhere? Like, how does it work out that all these people, because each person is more powerful than the next, that can say, no, I want an eight o'clock table, whatever. I want a two o'clock table on the beach at this place, the big round table near the guy playing the trumpet. Like, how does it always work out that that everybody seems to get their spot. Well, first of all, you don't have to compete with me because I would never go to those places. Okay. But, you know, first of all, where do you live?

Where do you work at? I live. I'm in just outside of L.A. Okay. It's just like it used to be to get a table at Mortons or at Craigs or whatever the place right now is. If you're somebody, you'll get a table. If you know somebody, you'll get a table.

If all else fails, money talks, the better thing to do is plan ahead. You know, I hate this, but I know now that there are certain places on St. Bartz where I have to call a week or two in advance and email and make reservations and plan ahead. I remember years and years ago, I wrote a cover story for a travel magazine

about the island of Capri off of the Italian coast. And when I went to Capri, it was in a slow moment. It had been a very famous place in the 50s and 60s, and it had kind of fallen off the map of rich people. And I wrote a cover story about it, and I'm not giving myself full of credit for this, but it started to come back until it became the place again, full of yachts and rich people and Jeff Bezos and blah, blah, blah. But, you know, we would wake up in the morning on Capri, walk down to the concierge desk, and say, which way is the wind blowing today?

And that was how we knew whether we wanted to go to Luigi, which was on one side of a mountain, or Scalineatella, which was on the other side of the mountain, which way was the wind blowing, where was the water going to be nicer? You know, unfortunately, unless you go places that are not yet discovered, you can't do that anymore. You have to either plan ahead, be immensely wealthy, be somebody or know somebody. And that's just, again, the way the world works. Or be very lucky. and walk in just when somebody really rich who had that big table on the beach cancels.

Yeah, that's why I wonder, like, are there ever groups of very attractive girls that go there in the hopes of having a great time, going to villas, going to parties, getting on yachts? But it seems to me like most people that go, it's men that bring a girlfriend with them or bring a wife or a miss. or whatever. It's not like going to Vegas and meeting a group of guys playing poker at the steakhouse or whatever. Have you found that? One will

see groups of incredibly beautiful women in incredibly skimpy clothing, sitting in highly visible places on St. Bards, and some of them are even amateurs. But yes, that happens. It's

going to happen anywhere where a lot of money congregants. It's part of the scene. But I think that you are right. Most people who are going to St. Bartz will bring a date. Yeah. And then what do you feel about people bringing kids? Has that always been a factor where they bring the kids and the nannies?

Or was there a time when it was like you saw very little children on vacation there? Well, remember I told you about that hotel where the hotel owner would leave it empty in order to appear exclusive? he once sent Madonna away when she showed up with a baby and a nanny because he didn't want the baby and the nanny there. But most places on St. Bards, you see children all the time. It's also, it's a family island.

It's an island where there is an entire society that lives there. There's that beach I mentioned with the Instagrammers called Shelby, John Stigallet. There's an elementary school right next door to that beach. There are children all over the island. There are children-friendly hotels.

There are children-friendly beaches. It's a very sophisticated place. And so well-behaved children do not stand out. And especially on the weekends, when the islanders have the day off and they're going to the beach, you see kids all over the place. It's really kind of sweet. Yes. It also says, you know, right now locals are dealing with. with insane overdevelopment, ecological threats,

hospitality groups are taking over. So where does that leave it now? Well, it's an ongoing battle right at this moment. A few years ago, there was an election where development-friendly candidates were running against development-unfriendly candidates, and the slate that was elected was kind of right up the middle.

So there's an acute consciousness of the fact that St. Bartz could become the victim of its own success. And there's a very careful process going on, which includes a lot of political battles between, you know, the St. Bart's equivalent of the left and the right, although they're not left or right on St. Bartz. They're pro-development or they're pro-preservation. And I think that what's going to happen is they're going to find a balance. but at the moment, it's a political argument. It's a tug of war. And so when you go there, there are lots of construction trucks. There's lots of construction. But the process of issuing permits to allow new construction has slowed way down. So what's happening now is all the permits that are

outstanding, those places are being built. But for instance, you're no longer allowed to build a villa just to rent it. If you're a family and you're you're building a villa for your family to live in, no problem. 60% of the island has been declared green. It will never be built on. And boy, does that frustrate some people who own land. Let me tell you. So it's a process and it's ongoing.

And again, that's the underlying narrative of my book is the story of progress, profit, preservation, all of these things, you know, greed. it all is in this stew of St. Bartz, and it just makes it the most fascinating eight square miles in the world to me. Question about building a house. You're building a villa for your family, for yourself.

Is it one of those things where you can only rent it out to one person a year, or you cannot rent it out to anybody? You have to be there with your guests. Well, now there's an effort being made to stop the construction of purely rental housing. There's also a huge shortage of housing for staff. So you have these five-star hotels where their staff can't find any place to sleep, which is a huge issue on the island. And again, this is all stuff that is in the process of being worked out.

Most of the – most people on the island, they thought that beachfront property was kind of yucky. because beachfront property made you subject to hurricanes and bad weather. Beachfront had mosquitoes. Beachfront wasn't considered good property. They lived back from the beach and up from the beach. And then they saw these people coming to go to the beach. And so they built houses on their properties on the beach that they rented. And the joke was that they would move out and sleep in the backyard in a hammock back in the 80s.

But, you know, nowadays, I mean, I rent a little tiny house from a family that has a compound where mom lives in one house, daughter and husband live in a second house, and my wife and I rent the third house. That's very frequent. There are people who have houses that they use once a week, and they once a year, excuse me, and they rented out the rest of the time. There are a million rental agents. There used to be one. It used to be a, there used to be two. It was a duopoly. And it was a much more civilized society when that duopoly was in charge. Nowadays, it's a real estate free-for-all. And so you have, you know, there's a house around the corner from the one I rent that is, I think, $80,000 a week during

high season. But if you want it for Christmas, you have to take it for two weeks at $250,000 a week. Wow. Now, has anybody or, you know, been such a drunk asshole something that you get, like, banned from the restaurant or banned from the island or anything like that, even though you're super wealthy. Funny you should mention that. That same restaurant, hotel, where Madonna was turned away, which, by the way, was famous in the 1980s for having the world's most expensive lentil salad. He once threw Puff Daddy out for being too rambunctious.

And that exact same weekend, Puff Daddy's yacht rental company took the yacht he had rented away from him. because he was trashing the yacht. So the answer to your question is, yes, it at least happened to Puff Daddy. Yeah. Yeah, I think he had a good sense of judgment, this guy, as far as that goes, and seeing that this is not going to get better

or this wasn't a one-time incident. But to show you how tolerant St. Farts is, that guy, the guy who threw Madonna out and threw Puffy out, that guy has been in jail, has sold his hotel to two different, people, has been engaged in all kinds of contractual skullduggery, and is still a very beloved person on the island. So St. Bartz is tolerant of bad behavior, but only up to a point. So you live most of the time in the city, in New York City? I live right near the U.N. in Manhattan, yes.

And so how often then do you go to St. Bards? I used to be once a year, lately twice a year. My wife and I travel all the time. We're back and forth to Europe all the time. We go to, we go all over. But St. Bart's is an every year thing. I've rented, I've reserved the house that I rent on St. Barts through 2028, so I'm a true believer.

And what's the time of year that you say you like to go? any time from October to early December. So around Thanksgiving is really nice. Then we used to go from Chinese New Year, which is the end of January, anytime right up to Easter, which is very nice. I try to go during slack times of year when the island is a little less crowded and a little less high pressure. And so when is kind of not the ideal time to go weather-wise? Well, you know, you don't want to go, you probably don't want to go in September and October

because there are these little things called hurricanes. And, you know, there's a treasured island tells the story of a number of these hurricanes that basically devastated the island. And then the island is very quickly rebuilt. And in certain instances, those hurricanes have been moments of reset for the island when the culture changes a little bit. Like Hurricane Irma in 2019 was a moment when people began to take. take stock of overdevelopment for the first time. So probably September, October, not ideal times to go.

The European crowd tends to go in August, which is European vacation season, and they don't want to go to San Troupe because it's overcrowded, so they come to St. Bartz because it's underutilized at that time of the year. And, you know, you would say about the weather, well, in August, I went once in August, and at 3 o'clock every single afternoon, like clockwork, there would be a torrential rainstorm. And it would last for 15 minutes. And then the sun would come out again. That's not too bad. No.

What about like the real housewives of New York and places like those reality shows that come to the island and film? Are they restrictive of that kind of thing now? Or did they do it once and regret it? Well, you know, keeping up, was it keeping up with the Kardashians? That's their television show. Yes. Keeping up with the Kardashians did an episode once. And they spent a week there filming. And they rented a villa that had once been a hotel restaurant that was famous for its transvestite cabaret shows. So it was kind of appropriate that, you know, trashy people in high hills would film their show there.

and people on the island laugh at it. You know, nobody cares. They'll, if you're decently behaved, no one minds. I don't know if there are rules about bringing a camera crew to the island. You don't see that very often. You see a fashion shoot far more often than that. But, you know, do reality TV people go there?

Yeah, sure. But so do people who actually accomplish things in their lives. And writers and artists and musicians and politicians and billionaires. Speaking of real housewives is something I cover. I know that's not like your forte or anything. But they always want to get someone that is the billionaire's wife, the rich wife that's led this very, very fabulous life.

But she's not an actress and she's not famous in her own right. But sometimes those women want very badly to be famous because it's the one thing they really can't buy. And then other times they're very hard to get because the husband or whatever is like, hell to the no, we're not going to have our lives exposed and be a target for someone trying to fish into our financials. But in you dealing with these wealthy wives of, have you ever found that they do desire to have a higher profile than what is allowed of them as being the wife of? I, in my experience and to my knowledge, which is limited because it's not a world I cover, the kind of people that you're describing are second tier in whatever world they're in. If they're rich guys' wives, then they're second tier rich guys, and they might even be second tier wives.

They're people who haven't actually gotten to the top. And they are looking for something. they're still looking for something better, and there's a level of desperation there that lots of people are willing to take advantage of. And, you know, it's, I'm far more interested in accomplishment. I'm far more interested, whether it's business accomplishment or creative accomplishment. Those are the people who do things are the people who interest me. So on St. Barts, I'm actually far more interested in the people who built hotels, who created restaurants, who built important houses and attracted other influential, important,

accomplished people to the island than I am to the people who come in the third wave where they're like looking around going, I don't see any Rockefellers. So it's not, I don't think it's an island. I don't think St. Bart's is an island that would reject someone like that, but neither would they be an important person on the island or to the island. Right. And one thing I've kind of, I was surprised that I discovered this because I didn't grow up in the world of this kind of wealth or even close is that billionaires kind of are attracted to other billionaires. whether they're divorced or whatever, that these women, you know, you sometimes think, yes, some rich guys go for the youngest, hottest thing, for their third or fourth wife, but oftentimes they go for the woman that knows how to live this life already. And if it's sort of a competitive

thing that they would get some guy that was sort of in their league or maybe even a little above their league, their ex-wife. Have you seen that at all, that dynamic? Yeah, but again, it's only interesting in terms of sort of the life of the French aristocracy in the 19th century. It's not in any way about good energy, creativity, accomplishment. All they are, you know, the wife who knows how to do things is really no different from the fashion model with the bodacious body. It's just another. possession for the kind of person who would do that. The kind of man who would do that is simply looking for a better car, you know, a Lambo with a bigger engine, a house with a second swimming pool. It's banal. It's not a higher expression of human existence.

Yeah, it's so interesting that there's those kind of wealthy people, like you said, looking for the next thing, they want to have the best thing, they want to have the flashest item or car. And then there's people that are just rich and relaxed because of it. And it's a peaceful life, it's a generous life, it's a fun life, it's a creative life. And, you know, I've experienced both. Like, it's so interesting, you know, and because it seems like, you know, it's such an astratosphere of money that you cannot relate to. It's really interesting to see how certain people navigate that life, protect themselves, but are also still open to new friendships and things.

Well, and, you know, on St. Bart's, that expression is more often through the bigger boat, the bigger party, the bigger house, the bigger piece of land. It's not so much, you know, the girl, the arm candy, you're walking around with. I'm sure, those guys have great-looking women on their arms. But it's, again, it might be important Christmas week. But the rest of the year, St. Bart's is really, the heart of St. Bart's is not about the money.

It's, the money is simply a means to a higher end in that context. Yeah. Well, this was so interesting. I know everyone's going to love the book. It is called Treasured Island. Comes out June 16th. Thank you, Michael Gross. Check out as other books.

You listed them and they all sound so juicy and interesting, which is why I'm glad you're on juicy scoop. And a world that, you know, it's fun to crawl inside and really get to learn about and know about and just kind of escape. And I'm really grateful. for you being so open and what a life you've led. Thank you for coming on. Thank you. And people can find out all about those books at my website, which is simply mgross.com. And Treasured Island comes out on June 16th, and I hope people enjoy it. Thank you so much. This is great.