Who’s That Girl?

One day last fall, Ingrid Casares was having lunch at Balthazar with a friend, the model Kara Young, who used to be married to photographer Sante d’Orazio, and nightlife publicist Lizzie Grubman, the daughter of the powerful music-industry lawyer Allen Grubman. Casares, who co-owns Liquid, a spectacularly successful nightclub in Miami, was in the business of trying to open a Liquid in New York and had employed the awesome connections of Lizzie Grubman on the advice of her model friend Veronica Webb, who told Casares, “She’s young and hungry.”

That she happens to be the daughter of Madonna’s lawyer no doubt also recommended her. Casares’s friend Tommy Mottola, who happens to be the head of Sony Music and Mariah Carey’s ex, had told her that she should surround herself with the best lawyers, accountants, and publicists in town if she wanted to open a nightclub in New York, because “you’re going to be under scrutiny for the rest of your life by the nature of what you do.” So Casares hired the law firm of Fischbein, Badillo, Wagner, Harding, who also happen to be Donald Trump’s lawyers. (Trump happens to be a friend of Casares’s and, as it happens, once dated Kara Young.) Ingrid Casares, one can plainly see, has taken the axiom “It’s all about who you know” – or, in her case, who you happen to know – to new levels of hyperconnectedness.

One of the benefits of having lots of superfamous, superconnected friends is that when you have a party or, say, a nightclub, your friends come and the press dutifully reports that your party or your club is superexclusive, thereby creating a powerful, self-perpetuating desire in people to get in. Call it the Studio 54 principle. And if anyone has ever been positioned to be the next Steve Rubell, it is certainly Casares. Take her birthday party at the Kit Kat Klub on May 27. Among the 400 guests: Michael Douglas, Robert De Niro, Joe Pesci, Calvin Klein, Sandy Gallin, Jann Wenner, Tommy Mottola, Madonna, k. d. lang, Amber Valletta, Kevin Aucoin, Russell Simmons, Andre Harrell, Heavy D., Ed Burns, Stephen Dorff, Ian Schrager, Eleanor Mondale … for Christ’s sake, were there any civilians? Liz Smith reported on the party but then wrote, surprisingly, “Actually, I hope Ingrid threw herself a smaller celebration somewhere. It must have been hard to feel cherished by pals or contemplate your life during the frenetic bacchanalia that occurred on Wednesday. On the other hand, bacchanalia is Ingrid’s life as a club owner and friend of the famous. So she probably loved it.”

Casares, whose attempt to take over Les Poulets on 22nd Street had failed the month before, was buoyed by the turnout and said at least once that night, “See? Shouldn’t I have a club in New York?” On the phone a few days later, she patted herself on the back once again: “I was disappointed about Les Poulets, because my heart was set on it. But after having a birthday party like that, I’m feeling better. I had everyone coming up to me saying, ‘If you want us to go before the boards so that we can have more parties like this, we’ll talk for you.’ “

Casares has since been offered the chance to take over several other clubs, including Studio 54, which she turned down. Meanwhile, she’s not exactly slacking. She and her partner, Chris Paciello, have several projects either up and running or in the pipeline, including Joia, a successful South Beach restaurant that opened earlier this year, and Liquid Lounge, which opens in Palm Beach this fall. She’s managing D.J. Victor Calderone, Madonna’s latest remix swami. And she’s got a deal in the works to do a coffee-table party-advice book in the hope that she’ll become, says Grubman, “the Martha Stewart of nightlife.” Even as far as New York is concerned, Casares is sanguine. “I’m definitely still looking,” she says. “It’s now a matter of, out of all the offers, finding the right one, the perfect one, the one that’s going to happen, including the right community board, the right area of town, so it’s a process of elimination.”

The other thing Casares wants to eliminate – and that Lizzie Grubman was also intent on dismissing at lunch – was the notion that she’s nothing more than Ingrid Casares, Madonna’s friend.

“Everyone knows we’re friends,” said Casares. “I mean, M’s a human being. She needs friends, right?”

“It’s not all about Madonna,” said Grubman.

“We got the Madonna thing out of the way,” said Casares. “Okay? What else?” Casares’s and Grubman’s cell phones whistled into activity. While Grubman barked orders into hers, Casares chatted with Tommy Mottola: “Hi, honey. Dinner? Yeah, it’ll be you, me, Gwyneth Paltrow, and Rosie O’Donnell.”

Funny how Ingrid Casares’s life just happens.

Ingrid Casares sprang from the late-eighties South Beach renaissance and onto the gossip pages around 1991 as the original “gal pal,” a snickering, winking term assigned to her and her new friends Madonna, k. d. lang, and Sandra Bernhard, the latter two of whom she had dated. Since then, her photograph has appeared with such frequency in the tabs and party pages of magazines – usually sitting next to Madonna at either a fashion show or a basketball game – that her face and her look (a sort of butch Audrey Hepburn) have become instantly recognizable to nearly everyone who reads, or reads captions, anyway. Still, the question remains: What does Ingrid Casares actually do?

That she had been featured in Madonna’s Sex book tongue-kissing the suddenly more-naked-than-thou pop star naturally fueled the fires of speculation about their relationship. In queer urban circles, Ingrid Casares became an icon almost overnight as the girl with magic lesbian powers who managed to nail all the cool chicks. She was also roundly assumed to have busted up Madonna and Bernhard’s friendship, which only furthered her legend. All of that nastiness eventually lost its teeth, and Casares settled into a less complicated, if no less difficult, public persona as Madonna’s Best Friend. “I could discover a cure for cancer,” she said last year, “and I’d still only be known as Madonna’s girlfriend.”

About a year and a half ago, Casares’s boldfaced name began to turn up all by its lonesome. Casares and Paciello opened Liquid on Washington Avenue in South Beach on Thanksgiving weekend in 1996, and the club helped push South Beach – already lousy with hype and a certain kind of tan, bleary-eyed glamour – into the realm of America’s Official International Playground for the Rich and Famous. Finally, the honky-tonk strip of beach had its own world-class nightclub and four-star hotel, just in time to house and entertain all the VIPs pouring into town.

After having been perceived as a coattail-riding, star-fucking hanger-on, Casares emerged as a strange sort of Regine-Steve Rubell hybrid for the nineties – the potential heir to the nightclub-impresario throne that has remained empty all these years, save for a brief occupation by Nell Campbell of Nell’s and Area/MK ringmaster Eric Goode in the late eighties.

Early in 1997, Casares came to Manhattan to reconnoiter the dismal nightlife landscape, which had been sliding into irrelevance and depravity, culminating in the Peter Gatien trial and the flameout of oddity turned monster Michael Alig, who confessed to murdering his drug dealer, chopping him up, and tossing him into the Hudson. With money from her wealthy Cuban-exile father – and surrounded by lawyers and publicists – she set about the business of looking for space, securing a liquor license, petitioning community boards, transferring leases, and finding vendors. Unlike Miami (where Casares grew up and is a beloved figure – and friends with the mayor), New York presented a challenge. You can’t, for example, simply buy a liquor license for $30,000, as in Miami; you must apply and be deemed worthy.

Casares’s trials were often reported in the gossip columns, usually with a Liquid’s-coming-to-New York! excitement. By March, things got complicated. The landlord of Les Poulets, the Latin-music club on East 22nd Street where Casares wanted to open Liquid, backed away from the negotiations, and the battle ended up in the Post. Jack Newfield – inspired by calls from community-board activists in the Flatiron District – devoted three columns to the story. In one, Deputy Mayor Rudy Washington said, “The city opposes a license for Liquid at this location, or any location in the city,” which seemed a bit severe – bizarre, even – given Casares’s high profile and the importance of nightclubs to the city’s economy (worth $2.9 billion last year), not to mention the fact that Washington’s position, according to Casares’s lawyers, raises restriction-of-trade issues. Most damning, however, was a piece by William Bastone in The Village Voice accusing Paciello, her partner, of being a violent, drug-dealing mobster.

Paciello, 26, denies all of the Voice’s accusations – except for his troubled and violent youth, which can be verified by a fairly long rap sheet, including felony assault, criminal mischief, disorderly conduct, car theft, and grand larceny; with most of these cases, charges were reduced and he never served a prison sentence.

“I grew up in Brooklyn,” Paciello says. “I have a lot of friends. It doesn’t make me a gangster because I hung out on the corner with people when I was growing up. They’re childhood friends of mine, and they will remain friends.”

Needless to say, the article sealed Casares’s fate. On April 8, anticipating imminent rejection by the State Liquor Authority, she withdrew her application for a license.

Casares, as she and her legion of famous friends will tell you, is not used to hearing the word no. “Ugh! I wake up in the morning and I have this overwhelming feeling of defeat,” she said the day after the SLA hearing. “I just can’t imagine that these fuckers just said no to me! There’s some weird conspiracy going on between the other nightclubs – who don’t want competition – the community boards, and the press. I don’t care how powerful my people are; I can’t compete with people who are demonstrating, and people who are bursting into my landlord’s office, and people talking to the press every five minutes.”

“She is totally bewildered,” says her lawyer, Richard Fischbein. “She’s been hit with a sledgehammer. It’s vicious and sick, but it’s typically New York.”

And Casares, despite her beach-town street smarts, perpetual tan, and world-weariness specific to those who grow up around people constantly on vacation, is at heart a New Yorker: impatient, stylish, sharp-tongued, industrious, clever, and a bit cold. She is used to pulling things off. Ironically, in her big bid for if-you-can-make-it-here legitimacy, she was shot down by New York, and none of her famous and superconnected friends could save her.

I first met Ingrid Casares on Easter Sunday four years ago, at Madonna’s house in Miami. I was there as editor-in-chief of Vibe magazine, nervously orchestrating an interview and an expensive cover shoot with Madonna and Dennis Rodman. After a daylong production in and around downtown Miami, we all returned to Madonna’s house and ordered takeout. While Madonna and Rodman went outside to eat and talk, I hung out in the kitchen drinking beer with Liz Rosenberg, Madonna’s longtime publicist and de facto Jewish mom, and Madonna’s then-personal assistant, now manager, Caresse Norman. Before long, Casares turned up, followed by the actress Debi Mazar, who had only come over to take a bath in Madonna’s tub. At one point, k. d. lang called and the phone got passed around.

There was something delightfully surreal about being with Madonna’s inner circle of best girlfriends, sitting around the kitchen table, gossiping and bickering and talking about Madonna. At one point, someone lit up a joint, and Casares – after admonishing everyone for being a “bunch of potheads” – talked very candidly and hilariously about having been in and out of drug rehab. I instantly liked her.

It is hard to explain her appeal. She is in many ways inscrutable. Still, I enjoyed her company immensely. “When a person is with Ingrid,” says Rosenberg, “you get a different view of the world. She gets you into a certain mind-set and it’s just a great place to be.” Another friend, Tim Rosta, the executive director of LifeBeat, the music industry’s AIDS fund-raising organization, describes Casares as “a Peter Pan.” Rosta jokes, “She suffers from attention-deficit disorder, but it’s sort of endearing.” Says Rosenberg, “She could calm down a little.”

At the time of that first meeting, Casares was working as an image consultant for Emilio Estefan (husband of singer Gloria Estefan), who produces Latin artists like Jon Secada and Albita for his and Gloria’s record label, Crescent Moon. Casares went to high school with Gloria’s younger sister, Becky Fajardo, and has known the family for years. Her first task for Estefan was to make over Secada’s deeply unhip, hairy-chested Miami Vice look – no small feat. That night, in Madonna’s kitchen, she didn’t waste a minute before pitching her pet project to me – a losing battle, I thought, as I hated Secada’s corny music and image. A week later, back in New York, I was walking to work one morning when I noticed a black limousine slowing next to me. The darkened window glided down and Casares, still pitching Secada, popped her head out. “I’ll call you this afternoon,” she said, and zipped away. She did call, and by the end of the day I had assigned a piece about Jon Secada. Like so many other schnooks before and after me, I couldn’t say no.

Casares occupies an odd and singular place in America’s celebrity culture: Best Friend to Very Famous Sexually Ambiguous Women. Strangely enough, there is a precedent – a Cuban woman named Mercedes de Acosta who was the nonfamous best friend to both Greta Garbo and Marlene Dietrich, for all intents and purposes the cool bisexual chicks of their day. In Antoni Gronowicz’s book Garbo: Her Story, the actress reminisced: “My most original friendship was the one with Mercedes de Acosta, a woman with a small figure, a sharp nose, and a great appetite for arts and for life.” Physical parallels aside, the two women share an old-fashioned social role usually reserved for gay men by Upper East Side ladies: the perfect accessory, or “extra man.” Ingrid Casares is a lesbian walker, a female Truman Capote minus the writing chops.

“She became the ideal escort, the total confidante, pal, and glamorous companion for Madonna, or Sandra, or Ingrid Sischy editor of Interview,” says Sarah Pettit, the former editor of Out magazine, who has traveled a bit herself in the ever-more-crowded fabulous-lesbian orbit. “In a funny way, she has played this dashing Holly Golightly girl that a lot of lesbians would hate to admit that they want to be but actually do.”

When I asked Casares to define her sexuality, she said, “I don’t define myself in any way. I fall in love with someone’s soul – I’m not gender-specific. I’ve fallen in love with men and women.”

“But you’ve become a famous lesbian,” I said. “Yeah, I guess so,” she said with a shrug, “but that’s because I’ve had high-profile female affairs.”

While Casares is not a household lesbian name in America like Ellen DeGeneres or k. d. lang, in queer circles she definitely stands for something, whether she likes it or not. There’s the simple fact that she’s attractive to women. “There was a period where it was all about Ingrid, the girl-toy,” says Pettit. ” ‘Who is she sleeping with?’ I was actually very embarrassed to find myself the other day discussing her with another lesbian, and I said, ‘You think Ingrid’s cute? I would never have expected that of you.’ Ingrid has that versatile mixture of being very impish and pixie but also being sufficiently butch. You sort of feel like she’s wearing the pants when she’s with Madonna.”

Additionally, she has confounded people by being so publicly associated with fashion and beauty, things not considered serious enough for a lesbian. “What she really is,” says Pettit, “is the worst vice that you could be as a lesbian, which is somebody who is extremely social-climby, fairly concerned with artifice, and totally unashamed about it. In earlier times, that was considered a total lesbian no-no. But obviously, she’s nobody’s fool, and she sort of said, ‘Screw it. I am this person.’ She became her own inventor in a way, and if she had to go before a panel of lesbian experts, they would have turned her down. You have to be doing something for the cause.”

Other lesbians have a much less generous take on Casares. “She’s a loathsome, pretentious, shallow social butterfly who’s been skating along on her family’s money,” says Camille Paglia. “She’s turned herself into Madonna’s flunky and yes-girl, and I think Madonna’s dependence on Ingrid Casares is a self-stunting sickness. Madonna should go to the Betty Ford clinic to break her addiction and detox from Ingrid Casares.”

Ingrid Casares was born in 1964 in Miami in Little Havana, just a couple of years after her parents, Nancy and Raul, left Cuba during the revolution. She was raised in tony Coral Gables, a wealthy Miami suburb where Wasps and rich Cubans play golf together. Theirs is the classic Cuban-exile story: lost everything, worked hard, became wealthy Republicans, sent kids to private Catholic school. Casares has a younger sister, Lourdes (!), who is now a psychologist, and an older one, Nancy, who has two kids and works in her father’s business, which Casares describes as “aluminum, windows, and sliding glass doors for high-rise construction.” Their mother is a housewife, “very beautiful, very young-looking,” says Casares.

She attended Our Lady of Lourdes (!!) Academy, a strict private girls’ school, where she was, all at once, bad girl, class clown, and star athlete. (Casares was an all-county basketball player with the highest scoring average in Dade County.) “Boys, parties, and sports,” says Casares, listing, in order of importance, her main activities in high school. “At some point, sports weren’t important to me anymore. I should probably have kept going on that road. I was very good. I was the leader in a lot of ways, and I hung out with all the popular kids and the athlete boys and the cheerleader girls. It was the whole Cuban, decadent, A-crowd thing. But I always felt a bit different. I was a lot more liberal than most. There’s a certain way that Catholic Cuban girls are raised – very conservative – that I didn’t necessarily adhere to. It was very confining, and it wasn’t me.”

“She was always in trouble,” says Becky Fajardo, Gloria Estefan’s sister, who has known Casares since she was 14. “In her senior year, in order for her to graduate, her mother had to sit in every class with her.” Casares is allergic to cats, says Fajardo, “and she used to rub cats on her face in the morning so that she wouldn’t have to go to school. She was a bit of a freak.” When I ask Fajardo if any of her old friends are surprised by her fame, she says, “Not at all. You just knew that Ingrid was going to be infamous, because I think she’s infamous more than famous. I can’t get over every time I see her with the biggest celebrities in the world in the oddest places in the world. And this is a person who’s never really done anything.” Fajardo, who says they’re still good friends, can’t hide her hostility: “She kind of whirlwinds into your life and whirlwinds out. And whenever she needs a little sanity, she calls, and that’s it.”

After high school, Casares went to the University of Miami for a year, where she fell in love with a fellow student, took off with him on his motorcycle and moved to North Carolina. “It was a very dysfunctional relationship, to say the least,” says Casares. She laughs at her stupid, youthful self. “I really wanted to be a free spirit. But I don’t think that anybody interpreted it then as free spirit. There was a lot of experimenting with drugs, drinking, sex. I don’t think my parents slept.”

Casares, who, like Madonna, was once a fanatical runner and now does yoga, is in great shape, though over four lunches I never saw her actually consume anything but coffee. “I never eat,” she says. One afternoon in February, over lunch – well, my lunch – at Jerry’s in SoHo, I mentioned the time we talked about rehab at Madonna’s house the day we met. “Well, they were all getting stoned,” she said, laughing. “By nature, I’m very addictive, compulsive, obsessive. In the long run, it paid off, because I’m that way with my work now. I’m that way with everything: drugs, alcohol, food, sex, working out, whatever makes you feel good. And you know it doesn’t feel good anymore. I led that overindulgent lifestyle in the eighties that everyone did. I’m an excitement junkie. The adrenaline, I need it 24-7. I don’t need it as much anymore, but back then that’s all I lived for. We should have had extreme sports back then because I would definitely have participated – it would have been healthier.”

For seven years after high school, Casares drifted around, attending “a lot of colleges” and working at menial jobs (tanning-salon receptionist, valet parker) before finally getting a degree in English and public relations from the University of Maryland. In 1991, she moved to Los Angeles and started working as a model booker for Wilhelmina Men – a job she hated and “wasn’t very good at.” She started dating Sandra Bernhard (whom she’d met backstage at Bernhard’s one-woman show in Miami the year before). Bernhard took Casares to Madonna’s birthday party, where Madonna was “very nice to me. She was polite and interested in what I had to say.”

Their relationship developed in Miami, “when I shot the Sex book with her,” says Casares. “We realized we had a lot in common and liked to go running, and that’s where we kind of bonded.” Queer-gossip legend has it that Madonna stole Casares from Bernhard, and that Bernhard felt betrayed. Whatever happened, Casares and Madonna remain estranged from Bernhard. (When I contacted Bernhard’s publicist to ask for an interview, she snapped, “Why would Sandra want to talk about her? What good could possibly come from it?”)

“We’re cordial,” says Casares. “There’s no animosity.” But then she can’t resist: “Obviously, I’m not the one with the animosity. Did you see her show? It was brilliant. I laughed my ass off, but it was based on putting a lot of people down and joking about their misery. It provoked a lot of anxiety for me.” Then, schizo-like, back to the nicer version: “She’s one of the funniest, most brilliant people I’ve ever met. I have nothing bad to say about her.” Finally, she arrives at this: “I’ve always had a theory that you meet people to meet other people. I met Sandra because I was supposed to meet M. It’s very obvious.”

Liz Rosenberg, who has worked with Madonna since the beginning of her career in the early eighties, adores Casares. “She’s been a wonderful friend to Madonna,” she says, “in ways that people will never know. She takes a lot of shit for being Madonna’s friend. And I find her very brave for that. People think, ‘Oh, she’s just using Madonna. She’s the PPF – Paid Professional Friend.’ But she’s as great for Madonna as Madonna is for her. In a very cute way, Ingrid just refuses to take Madonna seriously. Like, they’re in the car and Madonna will be screaming, ‘Ingrid! Why did you turn there?!’ And Ingrid will just say, ‘Shut up, Madonna.’ And laugh. People need to tell Madonna to shut up. Madonna hates getting her ass kissed, and Ingrid is the last person who would do that.”

Becky Fajardo says the reverse seems to be true, too. “Madonna seems to be the only one who can control Ingrid. She is the only person who I have ever seen singlehandedly put Ingrid in her place, because it’s not easy. Don’t get me wrong: Ingrid is the sweetest, most harmless person in the world. It’s just that she kind of imposes almost a fear in people, which makes her seem untouchable when she’s really not. She’s really just this little girl.”

When Casares showed up at Jerry’s that day in February, one of the first things out of her mouth was “Madonna would be happy to talk to you for this piece.” A couple of months later, when I decided to cash in my chip, she’d changed her tune. “She doesn’t want to do it,” Casares said. “You know how Madonna is.” (Well, no, actually I don’t.) Eventually, I got a canned, boring quote through Rosenberg’s office. I pushed Rosenberg again to get Madonna on the phone, and got another, slightly longer quote dictated through Rosenberg’s assistant: “I don’t really like talking about friendships because it trivializes it. Ingrid looks at life with innocent eyes. She is like Puck in A Midsummer Night’s Dream. She is always up, smiling, and happy. She’s a joy to be with and she’s up for anything. She has a great sense of adventure.” One can either look at this cynically – that when push comes to shove, Madonna doesn’t want to talk about anyone but herself – or kindly: that her friendship with Casares might actually be one of the most important of her life, and she doesn’t want to turn it into magazine fodder. Either way, what she finally did have to say is echoed by Casares’s other friends.

“There’s something very calming about Ingrid’s childlike approach,” says k. d. lang. “She’s trustworthy on a very deep level to people who have lost trust, people in the public eye. And there’s consistency in Ingrid that a lot of people don’t get. She’s always, always behind Madonna, no matter what’s going on. She’s always there for me. She’s really solid on a very personal level, which is different than what one would perceive of her in the press.”

“That she’s a star fucker?” I say.

“She is a star fucker!” lang shoots back. “And one of the things I love most about Ingrid is that she has definitely said to me, ‘I’m a star fucker.’ To me, that’s more respectful than someone who is and denies it. She knows she’s a socialite.”

On a drenching April afternoon – the day Casares is turned down by the State Liquor Authority – she leaves her lawyer’s office on East 54th Street and ducks into a Town Car, clutching a sleek, black leather briefcase to her chest.

“In Miami we welcome everyone from New York with open arms. I come up here,” she says with disgust, “and I feel like I was treated like shit. In Miami, I can make anything happen. It’s easy. Two seconds, it’s done. I’ve always considered myself kind of a New York girl. My friends, connections, business associates are all here, so I always found myself very accepted in that way, but when it came time to own a business here, I was vetoed so bad. I wanted to be able to pick up the phone and call the mayor like I do in Miami, and I can’t do that here.”

As the car inches through the rain, Casares grows quiet, sinks further down into the black leather seat and stares out the darkened window. After a minute or two, she laughs her funny, nervous, staccato giggle. “You have to keep up with the Joneses, and you have to have the right people and the right elements and all that right shit, and it’s exhausting. Next time,” she says with a smirk, “I’m going to open a nightclub in Cincinnati, by the airport. Someplace where I don’t have to be fabulous.”

Who’s That Girl?