Mr. Big


There is more to timeshare kingpin David Siegel than living fabulously large and being in charge. He says he is the ‘most misunderstood person in Orlando.’ We’ll leave that for you to decide.

The Reserve at Lake Butler Sound is an address for people with conspicuous wealth, but the homeowners in this enclave of fashionable Windermere don’t want their mansions on display for every-one to see. To enter the neighborhood means you either belong here or your name is on the list with the gatehouse guard.

Once waved through by the polite man in uniform, a visitor takes Bridge House Road past custom-built homes of Mediterranean, contemporary and English Tudor influences. Each is different from its neighbor, yet almost all the homes flow into a rhythm of size, proportion and curb appeal, with manicured lawns and palms, and brick-paver driveways.

On a mild, blue-sky morning in The Reserve, two young mothers dressed in active wear push strollers at a hurried pace while chatting at a similar speed. Just past Kirkstone Lane, a cul de sac off of Bridge House, they stop to answer a visitor’s inquiry about a distant blue-and-gray building that dwarfs all the homes around it, standing out in both size and architectural design.



“That’s Siegel’s house,” one of the women says. “We hate it.”

“Everybody hates it,” her friend adds.

“Siegel’s house” belongs to timeshare-resort mogul David Siegel. At a reported 90,000 square feet of living area, the home he is building contends as one of the largest—if not the largest—in modern America.

 While Siegel’s imposing new lakefront home on 10 acres doesn’t fit in with its neighbors, it does complement his reputation for living and succeeding at business on a grand scale. Siegel has made hundreds of millions of dollars over the years, and neither he nor his socialite wife, Jacqueline, has been restrained in spending it on themselves or their seven pre-teen children—or on charities and arts groups, for that matter.

The boxy Biltmore-esque residence—tentatively valued at $60 million by the Orange County Property Appraiser’s Office, more than 10 times the value of some homes in The Reserve—also serves as a fitting metaphor for how hard times are affecting even the super-rich.

As the economy worsened in recent months, Siegel cut 5,000 of his 11,000 workers nationally from his Orlando-based Westgate Resorts empire, the largest privately held timeshare owner-operator in the world, with 28 resorts and 10,000 units in 10 states. In keeping with his principle that business and pleasure are interwoven, Siegel followed his professional cuts with personal sacrifices.

Of course, sacrifices are relative to one’s station in life. So when Siegel halted construction on the three-story-tall, French-influenced estate mansion dubbed Versailles and laid off some of his wife’s household help, the impact of the economy hit him where he lived and where he hopes to live. He did not, it should be noted, cash a federal bailout check and then hop on his Gulfstream

G3 jet for a $12,000-a-night family vacation in Mexico while his former workers filed for unemployment. However, Jacqueline recently did take off on a globe-trotting trip while Siegel minded the store and their five nannies handled the kids, all with first names beginning with “J” or “D.”

 F. Scott Fitzgerald once wrote that the rich “are different from you and me.”

You can only imagine what the author of The Great Gatsby would have said had he lived among the Siegels.

David Siegel’s personal and professional excesses, not to mention some legal dramas related to a nine-year divorce settlement fight and lawsuits brought against him by former workers, may give the impression that he has a Mount Everest-size personality. He does not. A high school graduate who attended technical school and later operated a TV-repair shop in Miami, Siegel is big in confidence and in size, standing a solidly built 6-foot-1, but not in tone and gesture. Whether talking about Westgate’s operations, his young children or making what sounds like a sales pitch to a visitor described as a Saudi prince, Siegel uses his inside voice. He is calm, deliberate and always blunt.

But don’t mistake Siegel’s cool manner for passiveness. He is known as a shrewd and, critics say, ruthless businessman.

His sedate demeanor and casual dress—he prefers Tommy Bahama resort wear, bought on sale—stand in contrast to his wife’s ebullience. Jacqueline, a former beauty queen 31 years his junior, is as bubbly as a glass of Cristal. If she were a wallflower she would still stand out on looks alone: long, blond hair and toned legs that rise from designer stilettos past designer hemlines. At black-tie charity functions, Siegel wears open-collar tux shirts while buxom, 5-foot-7 Jacqueline pops out eye sockets with plunging necklines.

Like her husband, she is direct in replying to questions, such as: What makes David tick?

“His No. 1 hobby is work,’’ Jacqueline says, adding almost innocently, “and his No. 2 hobby, he would say, is sex. He doesn’t need Viagra. He says I’m his Viagra.’’

Hobby No. 2 has led to the birth of three boys and four girls in the 10 years the Siegels have been married.

“I thought the best birth control was to keep her pregnant,’’ jokes Siegel, who has six adult children from previous marriages. Two of his grown sons are top sales executives for his company. A niece of Jacqueline’s also lives with the couple.

As much as his schedule can allow, Siegel tries to be a doting father, attending his kids’ school and sports activities.

“He’s looking at this as an opportunity to raise a family,’’ Jacqueline says. “He learned from the first time what he’d be like the second time around.’’

 The siegels’ current 34,000-square-foot home is on a stately, four-acre private peninsula in Isleworth, the gated community best known as Tiger Woods’ home base. In keeping with a privilege reserved for the ultra-rich, the home has a name: Seagull Island. But that is where the pretentiousness ends. Inside, football and baseball jerseys hang on the backs of dining room chairs, unopened boxes of toys are piled in the theater room, and stuffed animals and kids’ drawings are displayed in a large second-floor cabinet. Glade candles and a real casino slot machine sit on a hallway table. Kitschy slogans you find in bargain décor centers like the nearby HomeGoods can be found in a sitting room just off the foyer. One, set on a buffet, reads “Faith Family Believe.”

“It’s a very lived-in home,” Jacqueline says.

Christmas apparently is such a large-scale affair that it takes the kids months to get to all their presents. In mid-April, several gifts, including a Cinderella phone and Stars Wars Lego set, remained in their packaging. A Guitar Hero drum set looked untouched. “They get a lot of presents,” Siegel says in a deadpan tone while sitting in the theater room. Behind him hangs a life-sized portrait of him wearing a tux with tails, looking like an early 20th century industrialist. The painting was a gift from a sales executive who has made it big with Siegel.

“He gets me all these things I wouldn’t get myself,” Siegel remarks about Jim Gissy, Westgate’s executive vice president of sales. Gissy also bought his boss the Rolls-Royce parked in the portico.

Just inside the foyer near the Wizard of Oz-sized double doors are snapshot-quality framed photos of the Siegels with Arnold Schwarzenegger, taken during the filming of Terminator 3. Jacqueline got a bit part in the movie and spent some quality time with its star.

“The ‘Governator’ is a friend,” says Siegel, referring to the current governor of California, for whom he hosted a Republican fund-raiser in 2005.

A financial supporter of Republican candidates—“we’re not in politics but we’ve gotten a lot of politicians elected,” he says—Siegel takes credit for putting George W. Bush into office.

“The biggest impact [I made] on the world was getting George W. Bush elected” president the first time, he says as plainly as if he were talking about the balmy weather outside. “I got him 2,000 votes in Florida.” Bush won the state by 537 votes to beat Vice President Al Gore in the controversial election settled by the U.S. Supreme Court.

Pressed to explain how he personally delivered the winning margin, Siegel doesn’t give specifics, only saying, “It was legal.” But he acknowledges now that he has some remorse for helping Bush become president. “I feel bad for it now.”

Describing himself as a 24/7 businessman, Siegel has little time for maintaining friendships. He works from home before he goes into his Westgate office near Universal Orlando Resort late in the morning, and he stays there well into the night. “I am a dictator. I’m the last word on everything,’’ Siegel says of his management style.

“I tell people I have a board of directors meeting every morning when I shave.”

Privately held, Westgate is not required to report its earnings and revenues, yet the dictator gives a reporter a graphic showing Westgate’s sales reached nearly $900 million last year. That would be yet another record amount for the company. Vacation Ownership World, a timeshare trade publication, gives credence to Siegel’s chart, reporting that in 2007 Westgate pulled in an estimated $875 million. The magazine’s editor, Scott Burlingame, says Westgate ranked third in overall timeshares sales two years ago. Wyndham Vacation Ownership ($2 billion) and Marriott Vacation Club ($1.33 billion) were the leaders in the $10 billion-a-year industry.

But Westgate, parent company Central Florida Investments and other Siegel-related enterprises beat their closest timeshare competitor in customer complaints over the past three years, with 717 to Marriott’s 69, according to the Better Business Bureau of Central Florida. Siegel dismisses the complaints as a relatively small number filed by “unreasonable” customers whose beefs could not be resolved. In the last six months, Westgate and CFI have been dinged by legal challenges related to sales tactics: a $1 million jury award for punitive damages to 15 people in Utah who said Westgate never delivered on free-travel vouchers in exchange for attending timeshare pitches, and a $900,000 settlement with the Federal Trade Commission over unauthorized phone calls to people on the nation’s “do not call’’ list. Siegel and company officials denied any wrongdoing and blamed problems on third-party vendors or “gray areas” of the law in both cases.

He also is fighting two federal labor lawsuits brought by nearly 100 ex-sales employees of Westgate and other Siegel companies who allege they were denied overtime. Siegel’s attorneys say the workers were independent contractors and therefore not entitled to overtime. Siegel says he will countersue the plaintiffs, claiming they owe him money.

Being the target of lawsuits comes with the territory of being rich and successful, Siegel says.

“You can’t fire anyone without getting sued. When you’re in business today, you have to expect to get sued.”

Siegel has been involved in so many legal clashes that he probably could sell timeshares in courthouses. He has sued neighboring businesses, competitors, former employees and, almost routinely, Orange County Property Appraiser Bill Donegan’s office over real estate assessments.

“He doesn’t mind overassessing me and I don’t mind suing him,” Siegel says. “We’re cordial in public.”

Donegan calls Siegel a friend, joking that the multimillionaire is intentionally delaying the Versailles project so the 69-year-old property appraiser won’t be around when it’s time to deliver the hefty tax bill. (For the record, Donegan’s office tentatively lists Versailles as having only 62,317 square feet of living space, a much smaller home than is widely reported.)

Getting others to talk on the record about less-than-positive dealings with Siegel isn’t easy. Fearing loss of potential business with Siegel or being sued by him for making unflattering comments, sources dry up as soon as the notepad and pen come out.

Last year, Siegel lost a sexual harassment lawsuit in Orlando federal court. The trial was Page 1 of the Orlando Sentinel and led TV news broadcasts. A salacious sex scandal that played out in court for four years, it was the Orlando version of  Indecent Proposal. Dawn Myers, who was fired after working 14 years for Westgate, claimed Siegel offered her $1 million for sex and that Jacqueline propositioned her for a ménage a trois. Myers also alleged that Siegel sexually harassed and groped her repeatedly in the 1990s and 2000 while she dated one of his sons.

Siegel denied the allegations in court, but the jurors sided with Myers, awarding her $5.4 million. Afterward, Siegel complained they ruled against him because he was a “wealthy guy.” The judge later reduced the award—to $610,000. Both sides are appealing.

Whatever the final amount, it will be a pittance compared with the price Siegel paid after a protracted divorce fight with his second—and third—wife, Bettie.

Theirs was a divorce battle and corporate breakup for the ages.

High school sweethearts in Miami, David and Bettie married in 1970 after their first marriages ended. The new union lasted only a few months. In 1973, with Siegel living in Orlando and selling real estate, they tied the knot again. And this time they clicked.

Together they built Central Florida Investments, a holding company that owned dozens of businesses, apartments, office buildings, the Mystery Fun House attraction and Hotel Royal Plaza. They launched Westgate (originally Westgate Vacation Villas) in 1982. Westgate took off, climbing from about $7 million in sales its first year to $300 million in 1997, when Bettie filed for divorce.

Siegel backed out of the initial divorce settlement offer totaling about $45 million in cash and real estate. The divorce-settlement fight, appeals and related cases lasted nine years. The dispute featured a sideshow involving Siegel suing several top former executives—who later formed their own rival timeshare company—for allegedly giving him bad financial advice about the value of his company during the divorce.

Bettie ultimately won perhaps the biggest divorce settlement in U.S. history—cash and real estate valued at more than $200 million, including the 36,600-square-foot mansion they built on Lake Butler. The settlement actually cost Siegel $300 million, with taxes. It stifled Westgate’s growth in the late 1990s because profits went to pay Bettie, Siegel says. (Since remarried, Bettie Whitaker didn’t respond to requests for comment for this story.)

Bettie’s divorce attorney, Mayanne Downs, says her client wanted out of the marriage because she grew tired of living on the edge.

“He always pushed his chips to the center of the table,” Downs says of Siegel’s business style. “His entire life was a crapshoot. She is free from the situation David is in now. She wanted security.”

Downs says Siegel has a knack for finding great business deals and talented executives to work with him. But, she says, he often gets in his own way.

“I always said David was an idiot savant. He has a genius for the deal. It’s not because of his qualities. It’s in spite of them.”

Siegel says Downs was “very tough” on him in the litigation but she did a “great job” for his ex-wife. He and his lawyers have since referred clients her way.

That doesn’t sound like the behavior of a ruthless dictator.

“People say I’m ruthless. I’m not ruthless,’’ Siegel says. “Some say I’m litigious. And I’m not litigious. I’m not any of the things people say who don’t know me,” he says. “I’m the most misunderstood person in Orlando. I like to build things and try to help people.”

Altruism may not be what comes to mind when Siegel’s name is mentioned, but he is a big giver. Siegel says his Westgate Resorts Foundation and company employees have helped raise about $10 million for dozens of groups since 2001, and his David’s Dollars Foundation has assisted numerous needy employees and their families. IRS records show the Westgate foundation itself distributed more than $4.2 million to various charities from 2001 to 2007.

In 2007, the foundation contributed to 65 organizations. The biggest recipient was the Orlando Ballet, which received $200,000. Siegel gave more than $325,000 out of his pocket to the foundation that year.

“I think his charitable work is downplayed,” says Jill Schwartz, an attorney and board member of Hospice of the Comforter in Altamonte Springs. “He’s always responded with a big heart.”

Says Orlando attorney Michael Marder, a close friend and Siegel legal adviser: “My hope is that when time judges him, he will be judged kindly for what he did and the kind of person he is.’’

This Fall, Siegel, true to his gambler mentality, moves his chips to the center of the table in—where else?—Las Vegas. The $1 billion Planet Hollywood Towers by Westgate Resorts, a twin, 52-story, timeshare Shangri-la, is Siegel’s grandest endeavor. A cynic would say the resort, slated for a September premiere, will open at the wrong time and in the worst location in the current economy—a tourism market that thrives on free spending and self-indulgence. But Siegel is unfazed.

“I’ve been through oil embargoes, recessions, 21 percent interest rates, Gulf Wars, 9/11, everything that could possibly happen,” Siegel says. “We’re the only industry I can think of today where demand is strong.”

Company officials say Siegel has done well in the timeshare industry because he’s fanatical about quality and service to his 400,000 customers. Locally, Siegel is an impact player in the economy, employing thousands of people and luring tourists  here each year to spend money.  

Still, he says his economic contribution has gone largely unnoticed and unappreciated. “People don’t know what I’ve done for Central Florida,” he says.

They do know about the blond wife, the army of children with nannies, the fleet of luxury cars and, of course, that gigantic house in The Reserve. Versailles is a now an idle construction site, a symbol of Siegel’s newfound restraint. When “times were great, people asked why was I building such a big house? ‘Because I could.’ And why did I slow down? ‘Because I had to,’” says Siegel.

The timeshare tycoon says he doesn’t know when Versailles will be ready for occupancy. But when it is, will his family be the ones occupying it?

“Everything’s for sale in this economy,” he says on a day in mid-April when two well-dressed young gentlemen—one identified by Siegel and his wife as a Saudi prince—visit the couple’s Isleworth estate. The visitors, who wait for more than an hour to talk with Siegel, apparently are here to learn a bit more about Versailles and its 15 bedrooms, 30 bathrooms, 11 kitchens, roller rink and bowling alley.

Siegel says Jacqueline met “Prince Joseph” while on her recent world travels. Jacqueline says the prince may be interested in buying Versailles or their current home, but she politely declines to give any details on the prince’s familial link to Saudi royalty.

Siegel seems torn about the prospect of letting go of his dream home. “I really don’t want to sell it,” he says.

But while talking with the visitors, he can be overheard describing in a low-key sales pitch the home’s various amenities. “The windows all cost $4 million. Everything was done right,” he says to the prince, who strikes a debonair figure in a blue double-breasted sport coat with baby blue handkerchief flowing upward from the pocket. “The way the economy is right now, it’s hard to justify a big palace while I’m laying off 5,000 people,” Siegel says to the prince.

Whoever ends up in “Siegel’s house,’’ its creator insists the neighbors—even the stroller-pushing moms—will thank him because their property values will rise.

“They’ll love it when it’s finished,’’ he says. “My house is going to put my neighborhood on the map.’’

 It already has.

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