Billionaire and trophy wife move into dream mansion, with sad results

Four years ago, I wrote a glowing review of a documentary, Queen of Versailles. Can’t imagine what brought this to mind.

…The second-most-astonishing aspect of this film is even sadder. I tuned in expecting to see the usual diverting reality-TV real-estate porn. Yet the wealth generated and consumed in this film just provides very little value or real enjoyment to anyone.

David Siegel runs Westgate Resorts. He made his money by selling people timeshares they really can’t afford. For a time, Westgate generates great opulence for the Siegel family. But what comes of that wealth? Unlike (say) Steve Jobs, David Siegel doesn’t create beautiful and useful innovations that make our lives noticeably better. Unlike Bill Gates and Warren Buffett, Siegel has no philanthropic vision to channel his wealth for worthy purposes.

Unlike millions of prosperous, albeit less cosmically-wealthy Americans, the Siegels don’t seem to use their wealth to make people close to them safe and happy. David Siegel’s checkered history with his adult son exemplifies things. Their relationship is strictly business. Then there is Jackie’s high school best friend. She’s a single mom who ends up in foreclosure. Jackie sends her $5,000 in an apparently unsuccessful effort to forestall the foreclosure. If I had the cash to construct a $100 million mansion, my best friend wouldn’t lose her modest home.

The Siegel family’s spiritual emptiness—I don’t know how else to say it– is rather heartbreaking. The Siegel children don’t seem to be turning out very well –except perhaps for his teenage daughter who in one scene rightly and righteously chews Siegel out for being a jerk to the rest of the family. [Heartbreaking post-script: This young woman subsequently died of an accidental drug overdose.] It’s hardly surprising that the kids are irresponsible and bratty, given their father’s narcissism and plain meanness.

Jackie Siegel is a beautiful, sweet, and vacuous trophy wife. She accumulates warehouses full of expensive junk for what is expected to be America’s biggest mansion. She has too many kids, too many toys, too many rooms, animals, too many nannies and servants. She even has too many inches on her bustline after (what I assume to be) ludicrous surgical enlargement shown off through her correspondingly ridiculous cleavage-displaying wardrobe.

Her husband treats her with blatant disrespect. When she turns forty, he jokes that he will replace her with two twenty-year-olds. Or maybe when she’s sixty he will replace her with three twenty-year-olds. He comments on camera that being married to her is like having another child.

Westgate teeters on the edge of collapse when it’s hit by the financial crisis. Both Siegel and his adult son protest that the banks got them hooked on cheap credit and are now trying to take over the jewels of their empire. Truthfully, though, everyone seems to lose in this story. The banks don’t get their principal back. The huge mansion is last seen as an unfinished and unsold construction project. Westgate teeters on the edge of ruin. Employees are laid off. Timeshare owners are foreclosed or left holding the bag for an over-valued properties.

We get to know two responsible adults in the entire film. The first is the limo driver (himself a failed real estate speculator). We also watch a heartrending interview with their Philippine nanny who relaxes in a big former playhouse of the Siegel children and who sends money back to her real family overseas.

I take it from later news that Siegel eventually landed on his feet. I guess that’s good. During the 2012 campaign, he got public attention as one of those crazy entitled CEOs who threatened to fire his workforce if Obama won reelection. In the end, Siegel didn’t go through with it.

I take it that he’s back on top again. He’s restarting construction on his 90,000 square-foot palace. It’s an old story, though. This man remains a pitiful figure.

Author: Harold Pollack

Harold Pollack is Helen Ross Professor of Social Service Administration at the University of Chicago. He has served on three expert committees of the National Academies of Science. His recent research appears in such journals as Addiction, Journal of the American Medical Association, and American Journal of Public Health. He writes regularly on HIV prevention, crime and drug policy, health reform, and disability policy for American Prospect,, and other news outlets. His essay, "Lessons from an Emergency Room Nightmare" was selected for the collection The Best American Medical Writing, 2009. He recently participated, with zero critical acclaim, in the University of Chicago's annual Latke-Hamentaschen debate.

4 thoughts on “Billionaire and trophy wife move into dream mansion, with sad results”

    1. More generous to whom? His wife? Did she need even larger boobs, but he said "Sorry, can't, taxes too darn high"? Is he generous because he cares about the welfare of Filipinos so much that he hires them instead of Americans? Or because he lets her stay in a playhouse good enough for his kids, so it must be really luxe for someone from a poor country?

      Or perhaps he's being generous the way Jesus asked his followers to be. You know, when he said "blessed are the rich who keep everything to themselves instead of hurting the poor by giving them money. For truly I say unto you, it is harder for a poor person to get into heaven than for a camel to pass through the eye of a needle, because they can't afford the cover charge, and even if they could, have you seen the rags they wear? Give me a break. Behold the lilies of the field. Those suckers are expensive, and only rich people can afford them, but Solomon in all his glory was not dressed as beautifully as they are. You gotta have much bigger bucks than some old king to get the the most important things in life, which can only be purchased with money. Maybe if Solomon, wise as he was, could have figured out to scam people into buying timeshares, he'd have had the bucks, but he spent all his time dispensing wisdom for free and writing about sex, which would have made him rich too, if he had monetized it."

  1. Ultimately, I can't hold it against a man because he's born a sociopath, someone without a conscience, or empathy. At least he didn't turn to serial killing. But to paraphrase Jesus, I think that the sociopaths will inherit the earth, not the meek. The sociopaths have all the advantages in selling things – they can lie without fear or remorse, they don't care about who may get hurt in the course of getting what they want. Their inability to reach billions of people at the same time is the one thing that slowed them down before. Now, we have even fewer defenses against them, and the people are still unable to discern them.

    1. The sociopaths will inherit the earth, but they won't like it. Too many sociopaths.

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