Inside the Life of Westchester’s Seema Boesky

Juggling philanthropy, business, family, and love.

CNBC | NBC Universal

Find out how the Empires of New York icon juggles local philanthropy, business, family, and love decades after New York’s great Ivan Boesky scandal.

On a Friday morning—having driven 20 minutes from Mount Kisco and what seemed like 10 more up a curved drive lined by symmetrical, 104-year-old maples, past orchards and stepped lily ponds and lawns so wide they take a crew of men two-and-a-half days to mow—a general contractor named Pat Morrissey parks his vehicle in the cobblestone courtyard at Northview, the house where Seema Boesky lives.

He carries the plans for a property Boesky is developing a few miles away. He is evidently a prosperous man, oriented, if not at home, in this neighborhood of Snapple magnates and BlackRock barons, and now his professional eye, which has no trouble distinguishing the tastefully vast from the new-money-hypertrophied, takes in the mansion in front of him.It is agonizingly tasteful, built in the style of Monticello and under its fourth generation of moneyed-family stewardship (the Boeskys were preceded by the Revsons of Revlon, the newspaper-publishing Cowles, and the Strausses of Macy’s, who built it).

It is the product of numerous revisions of structure and décor, decorated with antiques (lots and lots of them—this is far from today’s “minimalist” décor) bought at auction, and peonies roused from cold storage to bloom on demand. (Boesky, who has 6,000 peonies on her property, harvests and preserves them in seven refrigerators she has just for that purpose. In season, her peonies grace the entrance and tables of Crabtree’s Kittle House in Chappaqua.)

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Seema Boesky in the cobblestone courtyard of her Bedford estate.

Boesky decides which Impressionist paintings guests will admire in the entrance hall and which will be seen only by family in the upstairs rooms. (She does not care to name the artists, but they are names you might recognize after only a semester or two of art history.) Boesky ordered a dome built atop the master bedroom suite some years ago, because she felt it would complete the Jeffersonian image. “My architect says I’m on the edge. I think of myself as a brand. This house is distinctly me.”

Boesky orders the top sheet of toilet paper in the bathroom off the entrance hall be folded down into a V, the smallest gesture in a house of gestures that communicates to the visitor: everything in this house you see, everything, is deliberate, in accordance with her vision.

She lives here with a pet dog. A housekeeper, Nancy Rojo, who has worked for Boesky for the past 14 years, comes in during the day. Rojo calls her boss “an exception” from all her other bosses. “She thinks it’s amazing that I can wash a dish or do my own laundry,” her boss says. If the place seems vaster than necessary for one woman, consider that at one time it contained one Master of the Universe husband—a man she divorced a quarter-century ago but still speaks of familiarly, as Ivan—and also four children.

Morrissey knocks and Boesky greets. She kept the name after the divorce, not out of nostalgia but practical considerations: the world knew her by the name, and changing it, she reasoned, would change nothing about her life that really mattered.

She is 71 but does not inhabit a septuagenarian body. Parts of her have been surgically refined or replaced (face probably, hips definitely: these are matters of public record, addressed from time to time in the column she writes for the Wag). She has already spent an hour this morning working out with her longtime personal trainer, Rick Schultz. “I detest exercise,” she says.

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She is fitter than women half her age and it pleases her to show it. Today she wears a violet knit dress that cleaves to her chest and hips, along with simple jewelry. In clothes, if not art or real estate, Boesky shops bargain basement: the dress is from TJ Maxx. “I don’t think you have to spend a lot of money to have beautiful clothes,” she says. Indeed, for her son’s recent wedding, she bought two big Indian scarves, $10 each, sewed them together, and cut a hole in the middle “for my head.” The jewelry she buys is costume. “I have expensive jewelry,” she says, “all gifted. Great jewelry is a pain in the ass, a burden.”

She is not, she believes, a natural beauty—not like, say, her ex-husband’s current wife, Ana. (They live in La Jolla, California.) “Women like that wake up, walk out the door that way,” she says. “I do whatever one has to do to emphasize the good things and disguise the bad ones.”

In a small room off the kitchen, the contractor unfurls the plans for a property Boesky bought recently, at what was literally a fire-sale price, after part of the house burned. Plans have been made and revised and revised again. Project costs are growing. “I’m the one writing the checks,” she says. The revising needs to stop and the project needs to get built. “It’s not cost-effective, at some point, to be this meticulous.”

She is not developing property because she needs money: she is a millionaire many times over, and her children are wealthy. One son develops real estate; one teaches; one is a therapist; her daughter is a contemporary art dealer. The money she believes this property might earn could buy a few more paintings but will end up buoying the Westchester charities she gives to anyway. “This,” she says, sweeping her arm to indicate her entire “hundreds-of-acres” estate, “is all going to charity. I have no problem writing checks to charities.” Among her favorites: The Boys & Girls Club of Northern Westchester, the Northern Westchester Hospital Center, and Waterkeepers.For much of the next hour, she will defer to her contractor. But she wants him to know this is not a vanity project. She intends, in a year’s time, to sell a completed house for $4 million or more, at a profit. (“I develop real estate,” she says. “It’s genetic. My family loves land. We love improving it.”) They agree that there is money to be saved on the roof, basement, kitchen, the pergola outside. Should there be a second staircase?

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“The young families looking for a trophy house want multiple staircases,” says the contractor. “They want to see that in a big house.”“But this is not a big house,” she says. “This is a seven-thousand-square-foot house. This is a house for people who are downsizing.” There will be no second staircase.She has a final question for the contractor. The plans, once filed, are viewed by the building inspector, maybe the public: “Will they know it’s me?”

An odd question, but not an unreasonable one. Not when you’ve been in the public eye and super-rich for so long. Boesky was 13 when she inherited a 48-percent interest in the Beverly Hills Hotel Corporation, a real estate and hotel empire built by her father, Detroit-based developer Ben Silberstein. Her sister, Muriel, inherited another 48 percent; a cousin, 4 percent. The arrangement left no one happy. In Boesky’s telling, the sisters had warred almost from birth, because their father favored her. Years later their rivalry was played out in public as they fought for control of the company. Boesky won that battle, buying her cousin’s shares and majority ownership of the company in 1981. It sold, in 1986, for $136 million. With the sale finalized, her relationship with her sister effectively ended. “It’s sad,” she says.

The corporation owned the Vagabond chain of hotels, among other assets, but its jewel was the Beverly Hills Hotel, a gathering spot for Hollywood stars and world royalty. Boesky instantly became a multimillionaire and an object of fascination. She ran into Elizabeth Taylor at the hotel’s hair salon; she ran into trouble with the law when she left the hotel in a Mercedes roadster that was similar to the one she owned but belonged, in fact, to the Shah of Iran.

“Everybody wanted to know what I did,” she says. “It made me interesting to other people. I learned to capitalize on that.” At Mumford High, the public high school attended by the children of most of Detroit’s well-to-do, she was part of a clique known as the Emerald Club. “My group of friends were the prettiest girls in school. Within that group, I couldn’t hold a solid position, so I was a raconteur, a storyteller. I always had something to say. I honed those skills.”She matriculated at Michigan State, took a degree in psychology, got serious with Ivan. He came from a middle-class family that ran delicatessens and bars in Detroit. In the years to come, he would show himself to be enormously ambitious, disdainful of convention but desperate to prove himself. The story of how he visited one of the most expensive restaurants in New York, ordered every entrée on the menu, and ate just a bite from each dish would pass into Wall Street legend.

But he made little impression on Seema’s high school friends. Bluma Schechter, a friend of Seema’s since grade school, remembers a “hippie,” who usually appeared with “a backpack and a toothbrush in his pocket.”

Seema was 23 when she married Ivan, in 1962. Soon he was studying for the bar and serving a prestigious clerkship under one of her relatives who was a judge. He moved from law into arbitrage; she was raising their children. Ivan worked 18-hour days but called home from the office hourly. It thrilled her. “I thought I had the love of someone who was unattainable,” she says.

The two of them launched a successful arbitrage business with $700,000 in capital, much of it from Seema’s family. The first year their names appeared on the Forbes 400 list of richest Americans, she expected him to be happy. Instead, he was angry and humiliated, and promised her that never again would they rank so low.

Her reaction was “disbelief,” she says. “There was a total disconnect between us.” They moved from New York City to a house in Greenwich; then, one Sunday morning, rushing to avoid a massive tax bill from the state of Connecticut, to this house. She loves to tell this story, loves the memory of it, the two of them in the real estate agent’s office that day. “He looked his usual disheveled self on a Sunday morning. He had an outfit he always wore—old khakis and an oxford cloth shirt he wouldn’t let anyone wash—and he sees the picture of this place on the wall. ‘I want to see this!’ he yells.”

The real estate agent drives them over, pretty sure she’s dealing with a crazy man, and everybody steps into the entrance hall, looks north out a wall of windows over the sloping lawn. “Do you like it?” he asks her. “I love it,” she says. “Then stand over here while I make a deal,” he says.

“I’ll take it,” he says to the agent. “If it’s too big, I’ll take something off it. If it’s too small, I’ll add to it. Just take it off the market.” They paid $850,000, making it, at that time, one of the most expensive pieces of real estate in Westchester.

The business became hugely profitable. “Ivan,” she says, “is a genius.” By the mid-’80s, he controlled a $1.2 billion portfolio. Seema turned herself into a serious collector of paintings and sculpture. She focused on French Impressionists, some of the same artists her father had loved. She made big commitments of time and money to local charities. It was, by outward appearances, a model life.

Then came the Crisis, as Seema still calls it. Ivan was convicted of insider trading in 1986. He was sentenced to 18 months in prison and fined a record-breaking $100 million.

Seema had not been convicted or accused of anything, but national charities whited out their names from donor lists. Their names were removed from the library of the Jewish Theological Seminary. Newspapers reported the story of Northview’s dome and neighbors’ objections (“superfluous and useless!”), as if it were somehow the crowning indecency, proof positive of their guilt.

She began to do her shopping under an assumed name, identifying herself as Mrs. Gross. After one particularly savage story in the New York Post, she says, “I wanted to die. I sent my employees out to buy all the newspapers in town.” In an interview after news of the scandal broke, she told Barbara Walters that “overnight, I went from being someone who was socially acceptable to a social outcast.” She began divorce proceedings against Ivan in 1991, eventually agreeing to pay him $23 million and $180,000 a year for life.

Seema “wanted someone who was like her father—successful but at the same time possibly a little eccentric,” says Maureen Schwartzberg, another childhood friend. “If she felt he had cheated to get to where he wanted to be, she couldn’t respect him. The wealth wasn’t important.”

But the Crisis didn’t kill their marriage. At most, it hastened its demise. Seema learned that Ivan had been cheating on her and called him a “rat,” according to The New York Times, though she denies having ever used the word: “Not in my vocabulary.”

She says now, of men like Ivan, “some of these men are extremely insecure—they focus on something they can do well, they excel at it to the point where the world sees them as hugely successful while failing at personal relationships and in so many ways that they’re not happy.”

She also says that her ex and his new wife are dear friends and that they spend many holidays together. “I was able to go back to the man I knew and loved and let go of all the things I disliked and forge a relationship for the sake of my children.”

The meeting with the contractor wraps up. Boesky dangles the prospect of other projects in front of him, parcels she wants to develop, maybe subdivide: 119 acres here, 350 there. Maybe, too, this man, who is a devoted hunter, can hunt deer on some of her land when the season opens. She is cultivating him. He will charge her for his services but maybe at a rate lower than usual in hopes of securing future business.

During the fall and spring, when the Westchester charity circuit is busy, Boesky will be too. She chaired a capital campaign for the Boys & Girls Club that raised $7 million in four years and still works closely with the group, wrangling rich friends and neighbors to the cause.

Today, though, all she has to do is write. For more than a decade she has written a column, “Seema Says,” for the Wag, a society magazine. She writes in the chatty, slightly breathless style of an old-time gossip columnist, minus the gossip. Instead, she gives tips on parenting or entertaining or escaping from Nantucket during a rainy summer weekend when, she wrote in her column, she had talked her way onto a private plane bound for New Jersey and surprised the plane’s owner by asking him to put out his cigarette and suggesting he divert to White Plains.

“He broke out laughing and from then on we had a terrific flight. In the end, he insisted on taking me to the Westchester County Airport. I offered to pay for the entire flight, which he refused—so the cost of my travel was a bottle of Champagne, a tin of caviar, and a friend for life.” She thinks today’s piece will have something to do with weeding what turned out to be a bed of poison ivy. “I think I’m jinxed,” she says.

Later, her boyfriend, lover, companion—when both parties are north of 40, none of the old words for it seem to work—will come over for dinner. After her divorce, she went on more than 200 dates with men recommended by friends, friends of friends, and computer dating services. Some of the computer daters had lied about their appearance or their jobs; some seemed decent enough but drab.

She was sure she would spend the rest of her life alone before she met Kent Karlsson for coffee in the Mount Kisco Coach Diner, at the insistence of a real estate agent they shared.

The consensus among her friends is that he is a dead ringer for singer Kenny Rogers. He is a white-haired, jeans-and-sandals-wearing real estate lawyer who took Seema to her first ever rock concert—Bruce Springsteen—a few years back.

“He’s the perfect man,” she says. “At least, he’s the perfect man for me.” He is funny and handsome, interested in her projects. They see most of the shows on Broadway. Sometimes they go out to eat, at the Kittle House or Ladle of Love. Most nights, though, she cooks. He does the dishes. Then they play Scrabble or watch a movie. And every Wednesday at 5 o’clock, she gives him a massage, and vice versa.

“I don’t like pampering,” she says. “That’s the extent of the pampering.”

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