As We See It

The loving dissolution of Mr. and Mrs. Wynn

Inside perhaps the most expensive - possibly the most civil - divorce ever

She’s my best friend”: Steve and Elaine Wynn remain amicable despite a costly divorce, he says.
SIPA via AP Images

Up to now, I had never asked. Sure, I’m as curious as anyone, but there are so many more important topics to discuss with both Steve and Elaine Wynn that, in my past interviews with them, it seemed ridiculous to waste precious time. But last week, for some reason, Steve was in a very giving mood. Early in our interview, he’d said two very kind things about the woman he officially divorced late last year, so I couldn’t help it.

“I have to ask, and if you don’t want to answer, I understand, but you clearly still have a very good relationship with Mrs. Wynn,” I said.

"She’s my buddy, she’s my best friend,” he intoned. “I love her.”

For many people—especially those of us who have endured ugly breakups that did not involve billions of dollars—this may seem baffling. Steve Wynn became involved with British divorcee Andrea Hissom while he was still wed to his wife of 46 years. He hardly even kept the relationship a secret, and within a year he and Elaine were divorced. Yet she remained on the board of Wynn Resorts, she took up residence in a different villa at their Wynn-Encore property—both paying rent to the publicly traded company, in fact—and life seemed to carry on.

In fact, a few months ago I found them eating together at the Sinatra restaurant at Encore during the week their divorce would be finalized. They seemed to be in intense conversation, so I didn’t say hello until I thought Elaine had departed. But then she returned, and I found they had precisely the same comfortable chemistry I’d observed in the past. When they left Sinatra, the visionary with the degenerative eye disease gripped her elbow for guidance as I’m sure he’s done thousands of times before.

In the intervening months, America baffled over the affectionate relationship of another prominent ex-couple, James Cameron and Kathryn Bigelow. As desperately as Us Weekly and that ilk wanted to gin up a feud between the Oscar-nominated directors, it fell flat, because they just kept being so darned caring toward one another in the press.

Yet Cameron and Bigelow have been divorced for many more years than they’d been married. And while they explained that they had just realized they weren’t suited for one another, Elaine and Steve Wynn were, in fact, perfectly suited for one another for nearly a half-century. They met as teens, built a family and more than one empire together. They’d even divorced once before, in 1986, only to remarry in 1991. At their second reception, Mr. Wynn quipped, “We regret to inform you, the divorce did not work out.”

So far this time, it did work out, and the Wynn dissolution offered up all the ingredients for a really dishy drama. And, had that happened, it would have been significant news, not only because of the prurient interest we all have in the tawdry affairs of the wealthy and famous, but because deteriorated relations could have had a real impact on the operations of the company. That, in turn, meant a bitter divorce could’ve harmed stockholders, tourists and Vegas itself.

Whether it went that way, then, depended on Elaine Wynn. Had she expressed anger or pain to the media or jabber-jawed to friends, it could’ve blown into a tabloid sensation. Instead, when I asked her during a February 2009 interview, offhandedly and essentially in code, whether she was “doing all right,” she knew precisely what I meant and replied: “Yeah, I’m doing great, I’m doing just great.” She went on to discuss her charity work—she’s the national chairwoman of the dropout-prevention nonprofit Communities in Schools—and concluded, just in case there was any confusion, that she was answering the unspecified divorce matter: “I intend to remain active in the company, and that won’t change.”

There’s a reason why you’ll have a tough time ever finding anyone who’s written a negative word about Elaine Wynn, and that’s because she’s all elegance and class. Steve Wynn wades jauntily into controversy and enjoys a good fight; his ex always prefers to do her work and be part of the team. The most controversial thing she’s ever done was to be a very early supporter of Barack Obama, and, even then, I don’t recall any right-wingers picking on her.

“How could you be with someone for 49 years of your life and not be deeply connected?” said Wynn, continuing his thought. “We have seven grandchildren. Elaine and I have shared everything from the time we were 18 to the time we were 67 years old. We’re still partners in the business, I respect and value and really covet her opinion on issues. She has a real feel for the business that’s terrific.”

Of course, in my head I’m saying, “Then what gives, sir?” But I didn’t have the guts to ask that. It’s not as though he dumped her for some Anna Nicole; Hissom is in her 40s and, so far as I understand, is far from the gold-digger type. These things happen. (I did ask if the Wynns’ notoriously bitter disagreements over Obama were related. He said no.)

“You know, Elaine Wynn is an item,” he said. “The last thing in the world I would want to do is lose, totally, that connection. So I’m doing whatever I can to keep us related in some fashion or another, and I’m enjoying the time I’m spending with her immensely.”

A few other things I learned: Elaine has never met Andrea. Andrea’s teenage sons socialize with Wynn’s grandchildren. Elaine got first pick of the couple’s considerable art collection, choosing a Manet and a few others from the Vegas holdings, as well as all the pieces in their Sun Valley home and Manhattan apartment. He kept Le Rêve, the 1932 Picasso that he put a hole in by accident in 2006, days before he was turning it over to a buyer. Steve Wynn has now bought another Sun Valley residence for himself and has bought some art for it as well.

I did try to get more about the settlement out of him, but there’s a confidentiality agreement in place, at Mrs. Wynn’s insistence, and they took advantage of the Nevada law that allows them to keep it private. All that has been said is that the two, together, remain in control of the resort company.

Still, it had been reported that the Wynn divorce could be the most expensive of all time. I asked if that were true.

“I would say so,” Wynn replied. “Rupert Murdoch and Jack Welch were two of the big ones.”

Had he discussed it with Murdoch or Welch?

A rueful laugh.

“It’s absolutely the Esquire magazine Dubious Distinction Award to ... whoever it is who has the largest divorce settlement,” he said. “It’s not exactly one of the great achievements of life.”

Pause for effect.

“Let’s put it this way. Elaine is a very wealthy woman. And no one deserves it more, and no one will use the wealth more intelligently, more compassionately than she will. She has a very definite attitude toward money that it should go to charity and to her grandchildren.”

With that, the subject was closed. I probably could’ve cajoled a little more out of him, but time with Steve Wynn is always finite and there were so many other topics—politics, art, casino development and more—to address. To hear that stuff, keep watch on my podcast site,

I don’t plan to ask him about it again. And ask her? I’m a cad, but I’m not that much of a cad.


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