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Ivanka Trump, Tinsley Mortimer, and Lauren Santo Domingo: A Tale of Three NYC Socialites

In 2005, they were co-chairs of the American Museum of Natural History’s Winter Dance. Now one is an embattled first daughter, another a Real Housewife, and the third hates Trump.

Three blonde women walk into a gala, none of them strangers to the embossed invitation, and all of them wearers of society crowns.

The moment in 2005—the night of this party—was just a decade-plus before each would veer onto markedly different paths, their teeny-tiny circle dissolving into a story of schadenfreude, showmanship, and socialite tic-tac-toe.

One was destined (unbelievably at the time) to become a Real Housewife. Another: a powerful and perennially criticized first daughter of the United States. The third: a woman both dubbed the “next Mrs. Astor,” since then, and, commensurately, society’s biggest “resister.”

But this was then.

As Tinsley Mortimer, Ivanka Trump, and Lauren Davis (now Lauren Santo Domingo) made their way, in turns, into the American Museum of Natural History—all three co-chairs of its annual Winter Dance—the night unfolded as so many junior charity-circuit events did in the marrow of the mid-aughts in the center of the world, while at the same time, now, providing a key-hole into the transmogrifications of socialite life since.

“This is like the singles scene from hell! Everyone is just scoping each other out!” Amy Poehler, not a regular on the circuit, was heard exclaiming then, according to Page Six later, as the then-SNL comic took in the rush of Pretty Young Things.

With a dress code calling for “celestial black tie,” and a guest list reflective of the era—OMG, there’s an Olsen Twin! Oh, and that’s Moby!—it was also, like so many of history’s social meridian points, only fully understood with the gift of hindsight.

It was a time post-Hilton, but pre-Kardashian. It was before hashtags, before Instagram, before “influencers”; before the society set—like every set—had fully turned into a public-private House of Mirrors.

Ivanka, then a Jared-less heiress—though already trying to distinguish herself as a media-ready one—was heard speaking in a way that, no doubt, already contrasted to the breathy voice that she uses in TV interviews (her offstage voice is an “octave deeper,” reports The Washington Post).

Being at the gala that night, I also distinctly remember seeing Tinsley and Lauren hitting the dance floor together, and going wild.

For the kissy-kissy crowd, at large, the night would culminate in the Hall of the Universe, where, as it happens, there’s a “Stars Zone” tracing the life and death of stars, in addition to a “Black Hole exhibit,” the latter exploring a phenomenon so vast and so dense that nothing can escape its gravity.

Ahoy, metaphors.

“They were changing into $6,000 frocks in the backs of cabs,” recalls Ben Widdecombe, a gossip columnist for the New York Daily News at the time, summoning up the amped-up, post-Sex-and-the-City, pre-economic crash society tableau, to Town & Country.

Of all of them, Tinsley was arguably the most promising. A Southern Belle-turned-Upper East Sider, she’d managed the hat-trick of turning her marriage to an heir to the Standard Oil fortune and then being endlessly photographed at parties into her own bull-market—a stock so high, she was called, varyingly, both “the next Paris Hilton” and “the next Martha Stewart.”

From the prospective of 2018, in which Tinsley now occupies the same cultural terrain as NeNe Leakes and Erika Jayne—Mortimer begins her sophomore season next week on the New York tent-pole in the Bravo Housewives-sphere—it can be all too easy to forget precisely the sandbox in which she sat.

She’d been honored with her own shade of Dior lipstick back then. She was a mainstay at the Met Gala. She hobnobbed with arbiters like Oscar de la Renta. She was “big” in Japan, reported New York magazine.

Notably, unlike many of today’s “Housewives” who became tabloid fixtures, plus party invitees, only once they begin the process of appearing on TV, Tinsley is the only one of the 100 or so such ladies from all the franchises, past and present, who emphatically earned her way back into the limelight since doing the show. (She’s a pioneer!)

The intertwining years? They have been much chronicled: There was the divorce from Topper Mortimer, which led to a winnowing of her society wattage in the manner of a classic Edith Wharton character, followed, most dramatically, by an acquisition of her own police mug shot, the consequence of being arrested for drunkenly trespassing on the property of her on/off sugar-heir boyfriend, Nico Fanjul, in Palm Beach.

RHONY, as it’s known—oft considered the gold-standard of Housewives franchises—brought her back to life!

The “mug shot” would gets its share of mileage on her first season on the show—Tinsley smartly opting to bring it up herself before any of the other ladies could—as would her bittersweet attempts to re-establish herself in the city in which she ruled as Queen Bee (a narrative expected to continue in the current season).

In some ways, it remains forever 2005, though exemplified by the aging debutante’s refusal to change her hairstyle, despite the urging of many of her cast-mates. The Goldilocks ringlets are nonnegotiable, Tinsley essentially told them.

In some ways, however—because this is the Trump Era, after all—the tableau was very different, Tinsley’s debut on the show coming just months after the father of her old pal, Ivanka, had been made president.

In an unorthodox move, RHONY actually veered into a plot-line encompassing the national election just held—one focused mainly on cast regular and Hillary-die-hard Carole Radziwill—but one from which Mortimer recused herself.

In fact, when pressed about her own political views in a follow-up with Jezebel, she dodged the question with all the footwork of a triple axel jump, putting it this way in an email: “Politics are fueled by a lot of passion, and for good reason. If someone is passionate about something, that is their choice.”

During the reunion that capped the season—that rite of “closure” that sees out every franchise—the conversation came up, once again, when the always-incorrigible Andy Cohen specially grilled the ladies on their votes, and at least half of them wound up pleading the fifth.

When it came to Mortimer, specifically, she played two different cards, saying she wasn’t “able to vote” because she is still a Florida resident, and also adding that voting is “not my thing.”

The interesting thing, though? Tinsley’s M.O.—a classical one in the long history of socialites who have traditionally been loath to wear their politics on their couture sleeves—couldn’t be more different from that of her old dance partner, Lauren Santo Domingo.

She’s the one who, more than anyone, has bloomed into the number one anti-Trumpist in the creamy circles that once included Ivanka as a ranking member.

An agitator in Proenza Schouler, the Twitter feed of LSD (as she is frequently known) takes her war on Trump’s Washington to her 100K followers.

Exhibit A: “In the end, it will be @realDonaldTrump and @IvankaTrump alone in the bunker.”

And then: “Like his trophy wives he has trophy hires, @Omarosa, @KellyannePolls, @IvankaTrump,” she also boomed, back in November. “Smart honourable women need not apply.” (Note the actual Twitter handles spelled out in the tweets! She wants her old friend to see them!)

On another occasion, when a story broke about the first daughter sitting in Putin’s chair during a visit to the Kremlin, LSD quipped (about her erstwhile gala co-chair, ironically!): “She LOOOOOOVES to sit in important chairs. It’s kinda her thing.”

In her own intertwining years, the “Poland Springs heiress,” as she was once primarily known, had fully rocketed, it’s safe to say, owing first to her much-ado wedding held in Cartagena, Colombia, to the extraordinarily-wealthy-in-his-own-right Andrés Santo Domingo, dubbed “the first real society wedding of the century” (and during which Tinsley served as one of nine bridesmaids!).

There was also the span of her social reach (“Pick a high-profile charity event, and Santo Domingo has likely hosted, chaired, or sponsored it,” New Yorkmagazine once exclaimed).

A contributing editor at Vogue; the co-founder of the quite successful online-retailer Moda Operandi; the favorite of the “Truman Capote of Instagram,” as her BFF, Derek Blasberg has been crowned; inducted into Vanity Fair’s International Best Dressed List… the dynamo has been everywhere, including on Gossip Girl, where she played herself.

In fact, that’s something all three women—Tinsley, Ivanka, and Lauren—share, all of them having appeared, at one point or another, on the ultimate, one-time rich-kid serial.

That might be the only thing they have in common these days.

Lauren also goes after Ivanka’s husband for his adventures in nepotism, for example: “Hey Jared, how’s that peace in the Middle East thing going?”

At times, Lauren’s tone has shifted into one that is pitiful, if not plainly melancholic. When Ivanka, during one interview, mused that her father’s idea of arming teachers, in the wake of the Parkland massacre, might not be a bad idea, Santo Domingo struck this way: “Arming teacher is a terrible, no good, very bad idea. @Ivankatrump, what they done to you?”

It was a question that managed to strike deep at the heart of the deep fissures in New York society since the election of an emphatically New York character to the presidency—one that most New Yorkers did not vote for.

What, indeed… Ivanka? It’s hard to say where it goes from here for her. Raised as the girl who literally had a window-spanning view of Central Park from a 68th-floor bedroom—the princess in the black and gold tower!—and one who famously had Michael Jackson come to watch her perform in The Nutcracker one year, as revealed in the book Raising Trump, her personality, as I’ve long seen it, was once a palatable composite of her dad’s warrior ferocity, but also the savoir faire and Euro-ease of her mother, Ivana.

But while, before, the Wharton School graduate was able to lean mainly into her corporate-warrior, power-mommy, shoe-peddling-scion image—when I interviewed her, in 2014, she ably talked about real estate, but also about how much, as a fledging cook, Jared likes her “stews and steaks”—after the presidency run and win it’s been a whole other trampoline act.

While more world-famous than ever, she and her husband finds themselves on an “island”, as various articles have described, a former pal in New York going as far as to tell Vanity Fair recently,“Now their names are kind of their downfall.”

Can she come back? Who knows? But even just optically, it’s hard to see.

While Tinsley makes the most of it on TV these days, and Lauren continues to rule the roost, Ivanka’s own “brand” continues to be a question mark, at least within the genteel tribe with which she mixed.

Oh, the socialites: They zig, and they zag—in our present media-saturated culture, more than ever, perhaps. But who would have predicted exactly how much since one particular dance, held under the stars, a mere 13 years ago?

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