View all newsletters
Have the short, sharp Spear's newsletter delivered to your inbox each week
  1. Wealth
June 4, 2013

Meet the Timeshare Tycoon and Former Swimwear Model Building the Largest House in America

By Spear's

The timeshare tycoon, the former swimwear model, the Florida home that’s bigger than the White House – and the documentary that led to a lawsuit. Ivan Lindsay asks David and Jackie Siegel about trouble in paradise

The timeshare tycoon, the former swimwear model, the Florida home that’s bigger than the White House – and the documentary that led to a lawsuit. Ivan Lindsay asks David and Jackie Siegel about trouble in paradise

IT’S A WARM, sunny evening in central Florida. The Spanish moss hanging down from the oaks and cypresses gently rustles in the breeze. Inside Seagull Island, a spacious 26,000 sq ft home which sits on Lake Isleworth, are Jackie and David Siegel, Florida’s richest and most colourful couple — and lately the most notorious, too.

Twenty-six thousand square feet was evidently not enough, however, for timeshare magnate David and his wife, a former beauty queen, as viewers of The Queen of Versailles will have seen. That documentary, directed by Lauren Greenfield, showed their attempt to build the largest private home in America — Versailles, at 90,000 sq ft — and how it stalled during the recession. The success of the film has elicited diverse reactions from the couple, with David suing the producer and Jackie enjoying the red carpet.

Now the Siegels have thrown themselves back into Versailles. They invited Ivan Lindsay over for dinner to set the record straight — in separate interviews.


David Siegel is a well-built man in his late seventies with the seasoned air of one who has seen most things. He is alert and friendly with a quick humour delivered in a deadpan voice.  

Is it true you started out as an actor?

Content from our partners
How Flygreen is ascending into the future of private aviation
Stoneweg, Icona, and CBH Strengthen Partnership with Cromwell Acquisition, Adding €4 Billion AUM to Stoneweg
Why investors should consider investing in nature

Yes. A girlfriend jilted me and I thought it was because my boxing made me very thin. I started weightlifting and became Florida champion at twenty. I kept getting stopped in the streets and being asked if I was Rock Hudson, so I took off to Hollywood to be a movie star.

I found Rock Hudson’s photographer and asked him to do my portfolio, but he told me I looked too similar to Rock and you could never have two stars looking like each other, so I ended up working as a lineman installing power lines in Malibu.

How long were you there for?

Only a year, but the important thing was that I saw Disneyland opening in Anaheim in 1955 and the explosive growth in the surrounding orange groves.

When Disney opened in Orlando in 1971, I knew what was going to happen to real estate values but the Floridians had no idea. That was the basis of my success. I arrived in Orlando in 1970. 

What did you do?

In Miami I had several TV repair shops, but in Orlando I went into real estate and everything I touched turned to gold. By 1975 I had two vintage hotels, two apartment complexes, the Mystery Fun House tourist attraction and 80 acres of orange grove next to Disney. I was making about $1 million a year, had $5 million in the bank, and thought about retiring.

Why didn’t you?

A guy turned up and tried to buy ten acres of my orange grove for a timeshare resort. I had never heard of this concept, but I researched it and decided to do it myself. That was the beginning, and now, 33 years later, I have 10,000 units in 27 resorts spread over eleven states. 

Were there roadblocks along the way?

Of course. Timeshare sucks capital and I nearly ran out of money in 1983, only three years after I started. However, my biggest problem came later in Las Vegas, and this gets coverage in the recent documentary.

In 2005, I decided to build the largest timeshare resort in the world in Las Vegas at 1.5 million sq ft. I put in all my spare cash — $260 million — and the bank put in $400 million. I made $500 million of sales there, was paying them off ahead of schedule, and my mortgage was not due until 2015, but they ran into difficulties in the recession and pulled the loan with no notice.

I was going to make $2 billion from the resort but I eventually lost around $440 million. I had to cut off my arm to save my body, even though there wasn’t anything wrong with the arm.

What did you learn from this?

Firstly, I never realised that the banks, for whom I had been making money for 25 years and who I thought were my friends, pulled loans which were performing well. I have changed Westgate’s business strategy.

We are lean now and I am neither giving any more personal guarantees nor borrowing money and, although our sales at $500 million are about half what they used to be, we have never been more profitable.

How did you come to let Lauren Greenfield make The Queen of Versailles? 

I wanted someone to document the building of the house. She met Jackie and offered to do it. Then she became a friend and part of the scenery. I thought it would just get a single showing on HBO on television, but it turned into a worldwide sensation and was released in cinemas.

have sued her because it implies I lost my house, my company was in trouble and I live in squalor, all of which are untrue.

Do you think you were naïve, because surely a documentary maker is out to make a film as entertaining as possible and the truth is often lost in the mix? 

Yes, I was naïve, but we all make mistakes.

Do you think it is ironic that your wife Jackie loves the success of the film and goes to all the premieres while you are locked in litigation with the producers and director? 

Yes, it is a bit odd, but you can call Jackie an axe murderer and she will be happy, as long as you spell her name right.

What do you say to people who make fun of your building such a huge house? Ten kitchens and 30 bathrooms… The great hall is 160ft long.

It is not my first big house. I gave my ex-wife our old house, which was 63,000sq ft. Also, I have three children with my first wife, three with my second wife (including two stepchildren) and seven with Jackie, plus my niece, Jonquil.

That’s fourteen kids plus their friends, plus the four dogs and the staff, and we like giving charity parties. I need a big house and it’s money that I made, so why can’t I spend it how I want? 


Jackie Siegel is a tall, statuesque blonde in her mid-forties, a former Hawaiian Tropic model and Mrs Florida. As the face of Don Q rum, she once adorned 10,000 billboards across America. Wearing high heels and a tight leopard-print dress, she has a warm personality with an easy, infectious laugh.

Where are you from?

I was born in Binghampton, New York, and went to college in Rochester, New York.

What did you study at college?

I got a BSc in computer engineering.

How was that?

I quite enjoyed it, but I didn’t have much time as I paid my way with three jobs. I couldn’t even have a boyfriend because I worked as a waitress at Red Lobster until 10pm and then as a cocktail waitress until 2am. Any free time in the day I taught aerobics. 

After college, I worked at Citibank in New York. When my modelling took off, I went into that full time. I did a lot of swimwear as I was smaller in those days [she giggles and looks down at her cleavage].

Why did you move to Florida?

I was married to a Wall Street banker and he didn’t like me modelling, so he moved me into the Everglades to get me away from it all. We got divorced after nine years.

How did you meet David?

I became Mrs Florida and then I ran the competition. One of the competitors threw a party in Orlando and I met David there.

What was David doing there?

Apart from his work, David’s major hobby is looking at and judging beautiful women. We started dating and then David told me he couldn’t do it long-distance any more. I thought he was going to break up with me and prepared myself — but he drove to Miami. I was having a shower and I came out to find him cleaning out my closet and loading my clothes into his car. I couldn’t think what he was doing but he said, ‘You are coming with me.’ And that was that.

People have said you are a gold-digger…

I know, but he chased me, not the other way round. He had given his ex-wife all his money [$200 million, at the time the largest divorce settlement in US history]. We lived in a modest three-bedroom house on Conroy [Avenue, in Orlando]. He only had three resorts then, and I did all the cleaning and cooking in our house. 

I didn’t marry a billionaire, but he became one within eight years. He took five years to pay off his wife and the settlement was more than his company was worth at that time. He told me that we would have to start from scratch again. He is older, of course, but he is funny and wise. He was the one who wanted to get married and I had had three children with him already before we married.

What is it like being married to him?

My ambition growing up was to live in a $100,000 home. Now I spend that on household expenses alone per month. When David really started to make money I worried a lot about what a rich wife was supposed to do and be like. 

What did you do?

A lot of shopping.

And what else?

I did charity events and tried to learn how to be a rich man’s wife, but there is no manual. I joined the tennis team and, because I was so bad, became the captain. We bought this home just to live in while we built Versailles.

I started Thrift Mart in the recession, where we sell off all the Westgate surplus for next to nothing to try to help people in need, and the Westgate Foundation gives and raises lots for charity.

An article compared you to Lady Diana the other day.

That was very flattering… I suppose I am shy like her. 

How did The Queen of Versailles come to be?

I met Lauren Greenfield at the opening of the Versace shop in Rodeo Drive in LA. She offered to do the film about the construction of the house for free, and David loves free. 

We didn’t realise a documentary could be shown in cinemas all over the world. And we were astonished by its success. It opened the Sundance Film Festival, was introduced by Robert Redford and won the best director for Lauren.

That was fun for me because I directed most of it [she laughs]…Lauren is going to kill me for saying that. Lauren did a great job with the editing, filming and the music and everything, but most of the ideas in the film came from me. [No doubt Greenfield would disagree.]

David regrets making it and has sued them, but you seem
to be enjoying it?

Yes — I was a model and always wanted to be a movie star, and I love the red carpet and the interviews. I have been to the documentary’s premieres all over the world.

I was on the Today show last week and [CNN presenter] Anderson Cooper called today to make an appointment. I understand David’s annoyance because it exaggerates his company’s demise when it was only one resort out of 27 we lost and now he is doing really well again, and Lauren didn’t let us know what she was planning.

And do you really need 90,000 sq ft?

We do have a big family and we want to make a beautiful and elegant home. David has made all his money in property and he wants a showcase for his company and his success. 

We are not so different from rich people before us. The Vanderbilts and Hearsts all built massive homes and no one made fun of them, did they? It’s an American tradition.

I am concerned, though, that due to delays in the recession it might not be finished until the kids go off to college and then we are going to echo around by ourselves. Maybe I will just have to fill it with my friends… Do you want a room?

What was your best decision?

Moving to Orlando and believing in a future with David. I wanted love, found it, and then this fantasy life followed, a life I could never have imagined, let alone believed I might live one day. My husband was so romantic the way he single-mindedly pursued me. No man had ever behaved like that with me before and he made me laugh.

And your worst decision?

Staying in my first marriage for far too long. It was abusive.

How do feel being Florida’s most famous couple?

Well, there is always Donald [Trump] in Palm Beach… but I suppose we are now. I still find it a bit odd being recognised everywhere, but I don’t mind. It’s actually quite good fun, although it’s strange the way people think they know me. Strangers are always asking me about my kids and what’s happening with Versailles.

And the future?

David was in shock for about five months after the film came out and wouldn’t let me do anything. Now he is supportive and realises I need a new challenge after the seven children. I want to do some more television under my own supervision and I would like to make some of my own money. I have got all kinds of ideas and would like to do a line of jewellery, clothes and furniture.

And finally, when will Versailles be finished?

I don’t know… I guess we will have to watch the next film to see how it all pans out! 

Select and enter your email address The short, sharp email newsletter from Spear’s
  • Business owner/co-owner
  • CEO
  • COO
  • CFO
  • CTO
  • Chairperson
  • Non-Exec Director
  • Other C-Suite
  • Managing Director
  • President/Partner
  • Senior Executive/SVP or Corporate VP or equivalent
  • Director or equivalent
  • Group or Senior Manager
  • Head of Department/Function
  • Manager
  • Non-manager
  • Retired
  • Other
Visit our privacy policy for more information about our services, how Progressive Media Investments may use, process and share your personal data, including information on your rights in respect of your personal data and how you can unsubscribe from future marketing communications.
Thank you

Thanks for subscribing.

Websites in our network