Lifestyle of the Rich and Famous: Steve and Tomisue Hilbert in the ’90s

A Monet over the mantel, his-and-hers Harleys, an indoor basketball court—how former insurance mogul Steve Hilbert spent Indy’s biggest paycheck.

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This article originally appeared in the November 1995 issue. Steve Hilbert

Imagine opening the mailbox and finding an envelope containing a gold-embossed invitation to Steve and Tomisue Hilbert’s Christmas party next month. Granted, unless one happens to be Stephen Goldsmith or Reggie Miller or Clyde Lee, the odds are about the same as winning a fistfight with Mike Tyson.

But suppose for a moment that it did happen.

First, understand that this isn’t the normal Bing-on-the-stereo, cheeseballs­on-the-kitchen-counter soiree—not when it’s hosted by Steve Hilbert. Hilbert is chairman, president, and chief executive officer of Conseco, Inc., the Carmel, Indiana–based insurance holding company that’s growing faster than Rik Smits in adolescence. In 1994 alone, he pocketed $117 millions in cash, stock options, and performance bonuses.

It’s easy to get a sense of where the money went when the big day arrives. Don’t even think of actually driving to the Hilbert’s sprawling, 36-acre estate. Instead, motor over to Conseco’s Carmel headquarters, park in the lot, and ease into one of the dozen’s of limousines Hilbert has retained to squire partygoers to his gala. The limo will drive five miles to his housing complex, worth an esti­mated $15 million and considered the state’s most expensive piece of residential property.

Once the guard houses (the 3,000­square-foot headquarters for the estate’s double-digit security staff) grants clearance, a massive Iron gate swings open, and guests travel along a winding, half-mile­long driveway bordered by trees illuminated with thousands of white Christmas lights. As the Hilberts’ three-level, 23,000-square-foot mansion looms ahead, one can almost hear Robin Leach launch into a spiel about “caviar wishes and champagne dreams.”

One step out of the limo prompts a collective greeting by a flock of officially attired staffers in the slate-covered courtyard. Don’t go through the front door, which opens to an expansive entryway featuring a marble floor from Italy, a crystal chandelier from France, and artwork from all over the world. Instead, walk through a foliage-bordered breezeway to the back of the home, where smiling staff members silently usher guests inside, take their coats and disappear into parts unknown. Interested? Well, join the club. More than a few people have wondered what goes on behind the stone walls of the Hilbert estate, especially after an assortment of recent Donald Trump–like events in his life. On the business side, he has cut several new million-dollar deals and vaulted to the top of Indiana’s salary list. On the personal side, he recently divorced his wife of many years, Louann, and wed a 23-year-old he met while still married to his first wife.

Then there’s the house, the most visible manifestation of his megabucks lifestyle. Built over several years by Hilbert and Louann, it embodies the sort of wealth that even some nations would envy (the Island Republic of Nauru, for instance, boasts a GNP of only $90 million).

Hanging over the fireplace in the formal living room is a painting of a Parisian bridge. Yes, it’s an authentic Monet. The house teems with such finds, including intricate tapestries from the 1600s and 1700s, a grab bag of street scenes by Edouard Leon Cortes, and, in the Hilberts’ massive first-floor master bedroom suite, large work by French impressionist Louis Valtat, featuring the artist’s wife in a garden.

Hilbert recently declined a request by the Musee d’Orsay, a Paris museum that asked to borrow the canvas for a Valtat exhibition. “Exhibiting it probably dou­bles its value, but we don’t have any plan s to sell it,” Hilbert says. “Plus, I don’t know what the hell I’d replace it with on that wall while they kept it for a year, so it’s staying here. We told them thanks, but no thanks.”

The d’Orsay’s staff needn’t worry about the painting, which resides in a setting as grand as any museum. Built by some of the finest American and European craftsmen, the estate includes every architectural amenity imaginable, such as castle-like archways, intricately carved wood moldings, and a cupola featuring painted scenes from the life of Alexander the Great, Hilbert’s favorite historical figure.

Tomisue, now 25, oversaw the furnishing of the estate under the tutelage of friend and decorator Suzanne Sams. “We didn’t want it to look so froufrou that it doesn’t even look lived-in,” says Tomisue. “Steve and I wanted something that was simple but elegant.” Elegant, yes. Simple, hardly. The three-story French-style abode features endless wings, all radiating from the center of the main level. The lineup includes two kitchens, a library with thousands of books perched in recessed oak shelves, and a dining room with an oak table that seats up to 24 guests. Those who glimpsed the Hilberts’ master bed­room have found themselves blinking in disbelief. Not only are its walls covered with beautiful impressionist oil paintings, but just beyond the bathroom are “his and hers” closets larger than most living rooms. “Tomisue’s closet looks like an old English store,” says a recent guest. “All of her things—her blazers, jackets, hats, shoes, purses—are neatly arranged. Nothing is out of place.”

And that’s just the conventional stuff. The lower level, accessible by elevator, includes a large party room complete with full bar, dance floor, and big-screen TV—along with an original John Mellencamp painting featuring the artist with his hand. The vast lower level encompasses Hilbert’s wood-paneled home office and a pool room with an English billiard table constructed in 1703, along with a secret panel leading to a compact, temperature-controlled wine cellar.

But the Hilberts spend the balance their lower-level time in two workout rooms that contain enough weight-training machines, stair-steppers, and barbells to equip a spa; lockers, a changing area and a personal grooming center with an adult barber chair; a kiddie chair for the children, Christopher, 5 (Tomisue’s from a previous relationship), and the Hilberts’ new son, Thomas, 1-and-a-half; and an imposing manicure/pedicure chair. No trips to Supercuts for the Hilberts: Their personal stylists visit them as needed. Child-raising assistance comes from Tomisue’s mother and a fleet of nannies and nurses who stagger their shifts to the boys receive round-the-clock care. Several of the mansion’s elegant stairways are even blocked by baby gates.

It’s safe to say that personal fitness ranks as somewhat of an obsession for both Steve and Tomisue. “I’m up every morning at 6 a.m., doing the Stairmaster—7 a.m. on weekends,” says Steve. After 45 minutes  on the stairs, he showers and heads for the office between 7:30 a.m. and 8:30 a.m. Three days a week he comes home at 11 a.m. and works out for another 45 minutes under the supervision of his personal trainer, before showering and dashing back to the office at noon

Tomisue also hits the workout rooms at daybreak, then takes her daily saxophone lesson. The latter pursuit isn’t new: She tooted the instrument in marching at Ben Davis High School in Indianapolis, where she also played on the volleyball and basketball teams. These days her tastes run less to Sousa marches than to jazz, blues, and the pop stylings of Kenny G.

Next she takes a French class (she also wants to study Spanish), then attends to supervising the staff, decorating the house and, of course, watching the children. “I kid her sometimes,” says Hilbert. “I tell her that for her, living here is like going to camp.”

Certainly, the estate has much in common with a camp. When the Hilberts tire of doing reps on their weight machines, they can head out to the 7,000-square-foot “sports barn” at the rear of the property. The building includes a furnished bar area, a racquetball court, and two apartments (one decorated in Indiana University regalia, including a trash can that plays the IU fight song). Most important, it holds a full-size replica of the basketball court at Indiana University’s Assembly Hall—right down to an electronic scoreboard and duplicates of IU’s championship banners, made by the company that sewed the originals. Cincinnati Flooring installed a state-of-the-art basketball floor, a model so advanced that IU, after sending a contingent of staffers to examine it, ripped out Assembly Hall’s floor and replaced it with the new Hilbert surface.

The facilities certainly draw no complaints from the local and national celebs who sample them. Once or twice a month Hilbert holds weekend scrimmages. “We’ll have 15 or 20 couples over, and the guys will play basketball,” he says. “We have a scorekeeper, play seven­minute quarters, and alternate every quarter.” Longtime guests include Governor Evan Bayh, Mayor Stephen Goldsmith, Channel 8 sportscaster Mark Patrick, and WFBQ’s Bob Kevoian and Tom Griswold. Because he lacks the middle-age paunch that clings to most of his forty-something pals, the CEO himself generally performs respectably. “He’s good,” says Channel 6 news anchor Clyde Lee. “He’s got a nice jump shot, he’s in great shape, and he’s extremely competitive.” The best player ever to toss the rock there, however, was Pacer Reggie Miller, who worked out at the Hilberts’ in preparation for his service on the 1994 Dream Team.

“I’m a college dropout from Terre Haute,” says Steve Hilbert. “There’s no way on earth that I could have imagined being where I am today.”

The sports barn is just one of the numerous outbuildings dotting the Hilberts’ expansive—and growing—compound. The property, complete with flawlessly manicured lawns and professionally tended plantings (including a recently installed 1.5-acre formal garden), boasts so many structures and interconnecting roads that it seems more like a village than a single-family dwelling. There’s the requisite tennis court, along with a six-car garage filled with all things automotive. The lineup includes a yellow Ferrari convertible (Tomisue’s favorite summer car); Hilbert’s Ferrari Testarossa; a couple of Mercedes, and even his-and-hers Harley-Davidson motorcycles. Hilbert, who serves on the board of directors of the motorcycle maker’s finance company, got his as a gift and bought Tomisue a matching model for Christmas. They tend to admire the bikes more than ride them. “We’ve ridden from the garage to the gate and back a couple of times,” Hilbert says. “I love looking at them and feeling macho, but every time I get on one, I’m scared to death.”

The centerpiece of the grounds is a two-tiered swimming pool with a 13-foot waterfall. Adjoining the pool is the 1,300-square-foot pool house, equipped with men’s and women’s locker rooms, a full kitchen, and a living room with a fireplace and a big-screen TV.

The cluster of outbuildings surrounding the pool also includes a massive, freestanding catering kitchen—solid testament to the massive gatherings the estate regularly hosts. Though the facility handle meals for 1,500, the Hilberts’ guest list for everything from charity functions to pre–Indy 500 and Brickyard 400 parties usually doesn’t exceed 500. Fair-weather functions often take place at tables surrounding the pool area, while last year’s Christmas party brought hundreds of people indoors. “We had 275 people inside the house, and you wouldn’t have known,” says Hilbert. “We could have had 500 easily.”

The Hilberts regularly throw large parties, but also stage more intimate get-togethers. Randy Foxworthy, executive vice president of the Simon Property Group and a friend of Steve’s for 10 years, says the CEO enjoys small gatherings more than mega-bashes. “Sometimes the four of us—Steve and Tomisue, plus my wife Jenifer and I—will just spend a quiet, relaxed evening together, either going to a restaurant or having dinner in one of our homes,” says Foxworthy. “I think he likes socializing on a smaller scale because he can get away from the spotlight and just be himself.”

Hilbert says he and Tomisue schedule dinners with friends once or twice a week. And though they employ a personal chef, they also occasionally venture out to Amalfi, the Skyline Club, the California Café in Circle Centre, and Deeter’s. “Deeter’s is our favorite,” says Hilbert. “It’s casual.” Still, they don’t often eat out. “We’re kind of stay-at-home people,” he notes. “When we’re in town, we like to chill out, enjoy our family and enjoy our home.”

Actually, the Hilberts spend about a third of each month out of town, either at their Beaver Creek, Colorado vacation home (usually in winter) or in New York City on business. They recently put their New York condominium up for sale, however. The Fifth Avenue residence, which occupies the 46th and 47th floors of the tony Olympic Tower building (and was purchased from Iran-Contra arms dealer Adnan Khashoggi), was simply more than they needed for quick business trips. “We don’t want to keep a staff in New York, and I don’t want to get up in the morning and fry eggs, either,” says Hilbert. “Staying in a hotel makes more sense.”

But few hotels can compare to their Colorado home, purchased in November 1993. “The home had just been built, but never lived in,” Hilbert recalls. “We bought it and gutted it, even tore out the fireplace and put in a new one. It took over a year to complete.” The couple spends perhaps 30 days there each year, a good deal of that time on skis.

On the opposite end of the climate scale, the Hilberts think they may some day purchase a house in the Caribbean, which they visit four or five times each winter. The problem is that one can rent a tropical home, complete with staff, for such a reasonable rate that buying doesn’t make sense—unless, of course, they find the absolutely perfect location. “I’m positive we’ll   something, but I don’t know when,” says Steve.

Skiing in Colorado and island hopping in the Caribbean constitutes a major lifestyle change for the former Tomisue Tomlinson, a westside-Indianapolis native who attended private elementary schools, graduated from Ben Davis, and worked for several years at a Key West antiques shop. Her mother, Suzy Tomlinson, is a French expatriate who now lives a few minutes from the Hilbert estate. Her father,  Harold Tomlinson (who died when she was 14) was a real-estate developer who owned westside residential and business properties.

Hilbert says the two of them met on July 17, 1993, shortly after Tomisue returned   to Indiana, when they were introduced at a party by a mutual friend, Sunshine Promotions vice president Steve Sybesma. “I hate to talk a whole hell of a lot about how I met her, because I was married at the time,” Hilbert says. “We started talking and spending some time together. I was married at the time, but once I met Tommy, I knew that wasn’t going to last long. We fell in love, and the rest is history.” The couple married on February 19, 1994, and had their son, Thomas, on July 17, 1994—exactly one year after their introduction.

As for what the 25-year-old former mom single and the 49-year-old magnate (with three grown sons and a daughter) have in common, Hilbert can rattle off a list. “We enjoy each other,” he says. Also, they both love sports and physical activity, and he admires her ability to cope with    last-minute trips, parties, and guests he throws at her. “Not one time have I ever heard her complain or say, ‘Do we have to do it tonight?’” Hilbert says. “She has been such a spectacular asset to me.” Recently, he marveled while Tomisue personally greeted more than 300 guests for a charity function. “I like people, but I know I don’t have the patience to do that, “ he says.

A New York finishing school helped polish her image. She now dresses in classic conservative style, converses with corporate moguls and highbrow socialites, and can explain the particulars of their art collection. Because she doesn’t have to so much as boil an egg (the Hilberts’ 20-plus staff attends to such matters), Tomisue has plenty of time for shopping, traveling, and entertaining. Her favorite shopping venue is New York City, where she rubs shoulders with Hollywood celebs in the city’s most exclusive dress shops. Not long ago, friends say, she strolled out of one such shop’s changing rooms garbed in a summer dress, only to see actress Linda Evans in the same outfit, studying herself in the mirror.

But it’s not all a fairy tale. To be sure, Tomisue is discovering (as her husband has known for years) that unfathomable wealth has its drawbacks. The Hilberts rarely go anywhere without bodyguards, and their home crawls with security personnel. And because of safety concerns that range from burglary to kidnapping, the Hilberts live behind a 10-foot-high brick-and-stone fence, augmented by state-of-the-art surveillance equipment, including searchlights, motion-sensing alarms, and video cameras. They decline to allow interior photographs of the home, and the guard house even scans incoming mail with an X-ray machine.

Tomisue is also learning to deal with the meltdown heat generated by the residual friction from Steve and Louann’s divorce—as is almost everyone else in the Hilberts’ social circle. “It puts us in a difficult situation,” says a friend. “If you accept an invitation from Steve to go skiing in Colorado, you will likely run into Louann, because she has a place there, too. But if he sees you being friendly to her, he’ll never speak to you again.”

Nevertheless, Hilbert’s friends say Tomisue has transformed him emotionally and physically. He’s undergone radial keratotomy surgery on his eyes, enabling him to discard his clunky glasses; and he’s thrown himself into an exercise regimen that has melted more than 40 pounds from his  5-foot-9 frame. He religiously adheres to a low-fat diet and does weight training three times a week with personal trainer Steve Hoffacker, a muscle specialist whose clients Include John Mellencamp and Tony George.

When Hoffacker began working with Hilbert three years ago, the Conseco czar tipped the scales at 200-plus pounds. Today he’s a chiseled 158. “I’ve been doing this for 10 years, and I know no one, other than professional athletes, who’s made improvement as significant as Steve has,” says Hoffacker. “He’s made amazing improvements in body composition, muscle tone, and weight loss. He looks 15 years younger.”

Of course, his company, too, is amazingly healthy, especially given the humble roots of its founder. “I’m a college dropout from Terre Haute,” Hilbert says. “There’s no way on earth that I could have imagined being where I am today.” The son of middle-class parents (his mother was a telephone operator, his father a maintenance man), he bootstrapped his way to the top, dropping out of Indiana State University at age 19 to sell encyclopedias, then working for several insurance companies during the ’70s before launching his own firm in 1979.

Hilbert spent three long, lean years soliciting everyone from farmers to golfing buddies for the necessary startup capital. His former wife, Louann, even worked for free as a company secretary. Of course, some of the investors who helped finance his brainchild have cashed in on their foresight: In 16 years, Conseco’s assets have risen from $10,000 to $10 billion.

Barring an economic collapse, the world is still Hilbert’s oyster. However, it’s a world he views differently than he did a few years ago. On the business side, his strategy remains what it’s always been—ever forward. But his personal life has a new goal: to live as long as possible so he can watch Thomas and Christopher grow up.

That, more than anything else, is what gets him out of bed and onto the Stairmaster at 6 a.m. “I was becoming somewhat jaded,” he recalls. “I didn’t think there were any happy married people. But I can assure you there are, and I am definitely one of them. Having money doesn’t make you happy. Being content with your life and your family and your surroundings makes you happy.”

 

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