Wynn / Encore Las Vegas

He had held Oscars before, had hoisted the golden trophies of Hollywood friends for a laugh—thinking always, it really is surprisingly hefty—but never had the presence of an Academy Award so resonated with Steve Wynn as the one that arrived in his office one afternoon last December. “I admit, I sat with it for a time—me, the Oscar, and a cigar,” Wynn says. “It’s not just what an Oscar represents, but what that one meant at that time. It was much more than an award; it was the beginning of the rest of a man’s life.”

I am envisioning this moment in Wynn’s office, and my imagination is adding dimmed lights and only one song in the background: “It’s quarter to three, there’s no one in the place, ‘cept you and me….” “One for My Baby (and One More for the Road)” is, of course, a song of reflection, and it seems fitting for a scenario in which Wynn would ruminate on this particular Oscar’s original owner: Frank Sinatra, who famously captured this Best Supporting Actor trophy for 1953’s From Here to Eternity, in what many still consider to be one of Hollywood’s most celebrated comeback performances. “It was legitimately one of the greatest moments of Sinatra’s life when he got that award,” Wynn says. “It’s a very rare thing when an object represents so much to a man. I was sitting in my office a few feet away from a couple of Picassos, but to me the most priceless thing in the room was the statue I was holding in my hand.”

That Oscar, joined by a Grammy and an Emmy, now resides in a shatterproof case within the tribute Wynn has crafted for the man he calls both friend and colleague: Sinatra, the fine-dining Italian restaurant among Encore’s slate of upscale culinary offerings. Sinatra is open for dinner only, but throughout the day you’ll routinely see groups gathered near the entrance to view the Oscar and other pieces of memorabilia, all on loan from the Sinatra family, including an assortment of photographs and gold records that lines the wall leading up to the restaurant. The dining room is adorned with oversize portraits of Sinatra in his younger years, while the restaurant’s soundtrack ranges from his earliest days with Dorsey on through to the iconic “My Way” and “New York, New York.”

But don’t think of Sinatra as a museum, because that isn’t at all what Steve Wynn had in mind: “It’s a place where the spirit and the mood of Frank can live on,” he says. “The marriage of Frank Sinatra and Las Vegas is probably the most successful single event in the history of this town, so the restaurant is meant to capture the feeling that he brought here. But more than anything else, I wanted to create a restaurant that Frank would have loved, a place where he would have wanted to hang out not only because he loved the ambience, but also because he loved the food.” (True to his über-meticulous reputation, Wynn also made a point of sitting in every seat at Sinatra prior to its opening, not only to get a sense of the various vantage points for his guests, but also because he wanted to figure out where Sinatra himself might sit: “I now know where that is, and that’s my table,” he says.)

Wynn had occasionally entertained the idea of a Sinatra restaurant over the years, and then his phone rang one Friday afternoon last November: It was Robert Finkelstein, longtime attorney for the Sinatra family, calling to get Wynn’s opinion on doing a Sinatra wine. “The conversation about the wine led to the restaurant conversation,” Wynn recalls. “And I told Bobby, ‘If you had a first-class Italian restaurant in Las Vegas, now you’re talking about authentic Sinatra territory.’”

Wynn was roughly six weeks away from opening his 2,034-room Encore, where a high-end Italian restaurant, helmed by executive chef Theo Schoenegger, was deep in the planning stages. Wynn realized he was experiencing a moment of pure serendipity. “I told Bobby, ‘We’ve got the perfect place,’ and he said, ‘I’ll be there Monday.’” Three days later, Finkelstein, joined by execs from Warner Bros. Records, which holds the rights to the Sinatra music catalog, were sitting in Wynn’s office, and the deal was struck.

“Steve is such a great idea person, and not unlike the pied piper,” says Nancy Sinatra from her Los Angeles office. “When Steve Wynn announces he’s going to do something, you know it’s not only going to be great, but also quite magical, and you want to get involved. And my dad had great affection for him; in my eyes, there was no one else who could do this.”

Wynn had met Frank Sinatra in what he calls a cursory way in the 1960s—“I was 25 years old and shook his hand briefly at an event, having been introduced to him by a friend of my father’s,” he remembers, and still recalls every moment of a Rat Pack performance at a Sands anniversary party on December 1, 1965. “Of course, Frank never called it the Rat Pack; he called it the Clan or the Summit or the Boys,” Wynn says. “Frank and Dean and Sammy ruled the world; they were masters of the universe and they knew it, full of mischief and hijinks and having a ball.”

Any witness to the latter half of the 20th century likely views Frank Sinatra as the quintessential essence of cool—Steve Wynn shares that opinion, though he went on to experience many sides of the legendary performer when he signed Sinatra to a somewhat famous contract in the 1980s to perform at the two Golden Nugget casinos Wynn then owned in Las Vegas and Atlantic City. “The contract wasn’t in writing, it was a handshake,” Wynn says. “And the first two weekends he did it without the contract and for no money just to see if my idea would work. I paid him $50,000 a show to perform in a 500-seat room, which meant that I would lose money, but having him was never about making money. We weren’t worried about tickets; it was about who would be in the room for this extraordinary experience.”

The playful side of Sinatra came out during the series of 14 commercials the pair filmed throughout Sinatra’s four-year stint with the Golden Nugget. The dynamic was always the same, Wynn says: Having just turned 40, Wynn was the young hotelier, “the kid,” while the 67-year-old crooner was still young enough to be “Frank Sinatra.” In the inaugural spot, Sinatra walks into the lobby and asks Wynn to point him toward the showroom; awestruck, Wynn complies, whereupon Sinatra pinches him on the cheek and says, “You’re alright, baby.” The line was an ad lib, and made it into the second version of the commercial as an alternative to the one featuring Sinatra alone that more closely followed the script; but upon viewing the rough cuts of both, Sinatra decreed the ad-lib version added the warmth and humor needed. “He was leaning against the back of a couch, wearing a sweater and an open-collar shirt,” Wynn recalls. “And he said, ‘It’s simple: The one with me is too cold; the one with the two of us is cute. Use that.’”

That first commercial became the template for many others—Sinatra was always game for more, telling Wynn, “Don’t let it get stale.” Subsequent spots show Sinatra mistaking Wynn for a bellman, tipping him and asking for more towels, or kick off with Wynn discussing the Golden Nugget as a “class act,” before Sinatra walks into the frame wearing a Groucho Marx nose-and-glasses. Wynn remembers what Sinatra told him early on:

“You know what’s good about the spots, Steve?”

“What, Frank?”

“That everyone’s in on the joke that it’s a little bit of a put-down; everyone knows it’s your joint, and when you have a self-effacing humor like that, it’s a sign of confidence. It puts both of us in exactly the right spot. We should stick with that.”

And stick with it they did for four years, in weekend jaunts on Wynn’s Gulfstream to and from Atlantic City performances, and also around the US and beyond for promotional parties thrown by Wynn’s satellite offices so VIP clients could meet Sinatra. “He liked that he had a stake in the success of the place,” Wynn says. “Frank didn’t want to be thought of as just the singer; he was a partner in what we wanted to do, and that meant something to him.”

The second year into his Golden Nugget stint, Sinatra asked Wynn if Dean Martin could join him for some performances. “He said, ‘You don’t have to pay him, I’ll pay him out of my own pocket,’” Wynn says. “And I said, ‘Of course I’ll pay him, Frank.’ And he said, ‘He doesn’t need a big suite, you can give him a small suite like me.’ Frank never took the biggest suite, he was happy with a regular suite; the only thing he asked was that his secretary, Dorothy Ullman, could ideally be placed in the room next door, because he didn’t like to answer his own phone. So that’s how Dean Martin was slotted in. Frank said, ‘It’ll be a party, we’ll have a great time and really whoop up the joint.’ And I thought, Frank Sinatra and Dean Martin in my hotel? It’s unbelievable.”

After such weekends, on the private jet back to Palm Springs on Sunday nights, Wynn says Sinatra would make him have a vodka while he would settle in with his trademark Jack Daniels and Martin would nurse a Scotch, “and I’d get them to start telling stories. I’d say, ‘Hey, do you guys remember when you made Sergeants 3 or Ocean’s 11 or Robin and the 7 Hoods?’ and they would talk about Harry James and Tommy Dorsey and shtick with the movies and the women. Oh, the stories they had.”

Of course, there were also jaunts to restaurants, such as a late-night visit to Rocky Lee’s, a now-defunct restaurant on New York’s Second Avenue, a spontaneous stop because Wynn remarked on a trip from New Orleans that he was craving pizza. “You want the best pizza in New York? C’mon, we’ll go for the best pizza in New York,” Sinatra said, and with that he was calling Rocky from the jet and asking him to “keep the joint open, we’ll be there by midnight.”

“If he liked you, that’s how he treated you,” Wynn says. “He’d serve you a drink, or he’d say, ‘You gotta try the veal scallopine, it’s the best veal scallopine you’ve ever had.’ And he knew about wines, about white Burgundies and reds—he knew about Pétrus before anybody else did.”

The menu at Sinatra likewise reflects this love. It’s notable that the restaurant was originally to be called Theo’s, after executive chef Schoenegger, who most recently had overseen Patina in Los Angeles. What did he think of the switch to Sinatra? “It was a surprise but also a very interesting development,” Schoenegger says. “The idea that you could pair a great place and great food with a legend, that definitely sparked my interest. We had to change direction a little, because from the beginning we had been in discussions for a very seasonal, farmers’-market-driven establishment; and now with this icon as the spirit of the restaurant, we had to delve into our cookbooks a little to tie the two together.”

The core menu that resulted, Schoenegger says, is intended to put people at ease. “There’s a lot of comfort food, such as a veal Milanese, a favorite of Sinatra’s, and also an osso buco, but an updated version with no flour,” he notes. “And there are a lot of pastas because Sinatra loved pasta, and everything is handmade using the best possible ingredients.”

During Encore’s opening weekend in December, guests included Nancy, Tina, and Frank Sinatra Jr., and a dinner at the namesake restaurant celebrated the idea that, to borrow yet another title from the Sinatra oeuvre, the best is yet to come. “I remember thinking to myself, You’re the eldest, you have to make a speech,” Nancy says. “It was a beautiful evening, and we toasted what Steve had achieved with this beautiful place and the great friendship between him and my dad that brought us all together for that moment.”

In Wynn’s mind, such an homage is only appropriate for a man who taught him so much. “I had the time of my life with Frank Sinatra, and he was the most generous guy I ever knew,” Wynn says. “After he died [in 1998], my first tribute to him was a deal I made with the county to give him a road behind the Strip; I talked Circus Circus into paying for half of it, because it was half their road as well. Part of the deal was that it had to have an exit from the interstate, and I told Nancy and Tina and [Sinatra’s wife] Barbara, ‘Now everyone traveling on the Interstate through Nevada, when they go through the middle of Las Vegas, they’ll see Frank Sinatra Drive.’ I’ve been true to my gratitude and my memory of this remarkable character, and it means a great deal to me to have a second opportunity with this restaurant, which is so much more alive than a road. For as many seasons as I’ve got left, to keep that charisma alive—well, that’s my salute to my friend.”

Nancy Sinatra has another take on it. “Steve’s a dreamer,” she says. “And my father was a dreamer, also. These are two men who share something very special. Frank Sinatra is responsible for the early success of Las Vegas; and what he was then, Steve Wynn is now. He’s the only one who could be the keeper of the flame.”