25 Years Later: A Look Back at Frank Sinatra’s Life in Palm Springs

Commemorating the icon's death with a remembrance of his time in the desert he fondly considered home.

Michael Arkin Arts & Entertainment, History

Sinatra kicks back at home in Palm Springs with his dog Ringo and a centerpiece of cigarette boxes on the coffee table. 

An orange, gibbous moon hung over Southern California on the evening of May 14, 1998. Its color, a curiosity to most, took on greater meeting for the family and friends that gathered on the eighth floor of Cedars-Sinai Medical Center in Los Angeles. Perhaps it was a sign from the husband and father who had just passed that he would always be with them — and us. That man was Francis Albert Sinatra, and orange was his favorite color.

He embodied sophisticated cool. Although Gay Talese’s definitive profile, “Frank Sinatra Has a Cold,” for the April 1966 issue of Esquire, never revealed his signature scent — Agua Lavanda Puig — Sinatra himself had no problem telling those close to him what they shouldn’t smell like: garlic. And no matter how beautiful the dame, perfume. Most importantly, regardless of who you were, you’d better be on time; he famously left Elizabeth Taylor behind when she couldn’t pull herself out of the bathtub in time for a flight. Sinatra noticed what you were wearing, whether your shoes were shined, and if your suit was pressed. Elavil helped tame his mood swings and mercurial temper, which often fueled his inclination to “hate like a Sicilian.”

Hailing from Hoboken, New Jersey, the only child of Martin and Natalie “Dolly” Sinatra, the legendary crooner epitomized the archetypical swinger. He owned houses in Beverly Hills, Malibu, and New York, but Palm Springs, which his pal, composer Jimmy Van Heusen introduced him to, was the place he called home. Like a generation of stars before him, he considered the desert a sanctuary where he could escape the spotlight. Just before Christmas 1947, he moved into Twin Palms on Alejo Road with his wife, Nancy, and their children, Nancy and Frank Jr. Their daughter Tina was born six months later. Designed by E. Stewart Williams, the estate, with its piano-shaped pool, became a model of midcentury architecture.


Sinatra tickles the ivories for the Palm Springs police captain and a lovely dame. 

Sinatra’s career hit the skids in the early 1950s, about the time he started an affair with Ava Gardner. His marriage soon crumbled. Sinatra had a weakness for beautiful women, and Ava, whom he married in 1951, was the most beautiful of them all. Their relationship was stormy; frankly put, if they weren’t fornicating, they were fighting. A bathroom sink at Twin Palms still bears a crack from the Champagne bottle he threw at her. 

After they separated in 1954, he took solace hanging out with the boys. His inner circle included Ermenegildo “Jilly” Rizzo, the brother he never had; his “crowd disperser,” Ed Pucci; Brad Dexter, who saved him from drowning; Leo “The Lip” Durocher; Jerry “The Crusher” Amaniera; Tom Dreesen; and Tony Oppedisano, better known as Tony O, whose vivid memoir, Sinatra and Me: In the Wee Small Hours, details his deep and abiding 26-year friendship with Sinatra. There was no shortage of pinky rings among the guys he watched Monday Night Football with at Dominick’s; crammed into a corner booth alongside at Ruby Dunes; drank with at Melvyn’s; chowed down with at D’Amico’s; or drove aimlessly around town with, often till dawn.

Not an early riser, Sinatra welcomed audiences by bidding them good morning, excusing himself for finishing his breakfast while they finished dinner. In fact, he wielded the ultimate power in Hollywood by dictating what time production began. For him, it was noon. Unlike Vegas, where there were no clocks, Palm Springs, where the bars closed at 2 a.m., was an early-ish town. Not for Sinatra, who thought nothing of making a pot of spaghetti at 3 a.m. and having Jilly round up a crowd. He liked having it his way, which meant “putting it in the bag” (as he called going to sleep) sometime around daybreak.


Restaurateur Mike Romanoff and Sinatra advertise the Palm Springs Police Show Dance. 


The crooner chats with Peter Lawford.

Given their similar backgrounds, his first wife, Nancy Barbato, may have been thebest-suited for Sinatra and the great love of his life. But with four daughters-in-law to choose from, Gardner appears to have been Sinatra’s mother’s favorite. She’s the one who gifted Dolly a luminous strand of pearls, stayed in touch with her, and remained a topic of conversation even after Gardner and Sinatra split. Mia Farrow, whom he married at 50 when she was 21, was more than a midlife diversion. Recalling their first time, Farrow told Howard Stern that Sinatra invited her to a screening, where they held hands the whole time. Afterward, he was flying back to Palm Springs and wanted her to join him. She couldn’t because she had a cat at home that needed to be fed. He offered to send his plane for her the next day. Thinking he was great looking, she accepted, bringing the cat with her. After setting up the litter box, he took her into another room and undressed her. She has admitted that he was the great love of her life and “possibly” the father of her son, Ronan.

Many say that Barbara, who was still Mrs.Zeppo Marx when she met Sinatra, was Dolly’s least favorite. According to Oppedisano, her dislike of the former Vegas showgirl was so strong she refused to fly on the same plane with her, opting to take a later flight from Palm Springs to Las Vegas for her son’s opening at Caesar’s Palace in January 1977. That flight never arrived. Three days later, the wreckage of her plane was discovered at 9,000 feet on snowcapped San Gorgonio Mountain. Despite that, their marriage, his fourth and her third, proved to be the most enduring for both of them.


The crooner contemplates his $100,000 kitchen upgrade over a sandwich, circa 1965.

Sinatra and his Rat Pack — Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop — made audiences feel that the party they were witnessing onstage was continuing offstage as well. But their onstage antics were native to a different desert — Las Vegas — and even though Martin, Davis, and Lawford owned homes in the Vista Las Palmas neighborhood, there were only a handful of occasions they performed together in Palm Springs at venues including The Riviera and The Purple Room, or to raise money for Desert Hospital (now Desert Regional Medical Center). Despite the Rat Pack’s place in local lore, their clowning wasn’t really a part of his life in Palm Springs — the life he considered private and didn’t want to talk about. In some ways, he was more like the “Harvard Boys,” as he called the mobsters he was often alleged to be affiliated with: the guys who vacationed in Palm Springs but didn’t “work” there. 

In 1954, he purchased a house on Wonder Palms Road (later renamed Frank Sinatra Drive) along the 17th fairway of the predominantly Jewish Tamarisk Country Club in what was then the wilderness of Rancho Mirage. His neighbors included Jack Benny, Danny Kaye, and all four Marx brothers. Over the years, he expanded the property to 2½ acres and proceeded to turn it into his 8,000-square-foot dream house, where he named each room for one of his songs, except for The Train Room, which housed his beloved electric train sets. The compound had everything, even a green parrot named Rocky, who according to Oppedisano, had a penchant for jumping down from his perch and biting Sinatra, who would threaten, “One of these days you’re going to find yourself in an oven surrounded by potatoes and onions!”


Sinatra with his daughter Tina (front) at the Chuck Connors Charity Invitational Golf Tournament in 1969. 

In anticipation of hosting John F. Kennedy, whom he worked tirelessly to get elected, Sinatra added a four-bedroom, four-bath guesthouse with a private pool and helipad. That presidential visit never came to be. Serving as his attorney general, Kennedy’s brother, Bobby, quashed the trip due to Sinatra’s alleged ties to the mob. Citing security issues, Kennedy wound up staying at Bing Crosby’s desert home, leaving Sinatra deeply wounded. 

According to The Way It Was: My Life With Frank Sinatra, the book by his former manager, Eliot Weisman, Sinatra blamed fellow Rat Packer (and Kennedy’s brother-in-law) Peter Lawford for not doing enough to influence JFK’s decision, asking Lawford on a call, “Can you hear me, Peter?” When Lawford replied, “Yes,” Sinatra slammed down the phone. Oppedisano maintains that Sinatra was more disappointed than hurt and disputes the myth that he never spoke to JFK again. Lawford was quoted as saying that after he received the news that Kennedy wasn’t coming, Sinatra went outside with a sledgehammer and chopped up the concrete helipad.

No matter how cool he was, the desert was sometimes too hot, even for Sinatra. In 1967, he built Villa Maggio in Pinyon Crest, 4,200 feet above the desert floor. Named for his Oscar-winning role in From Here to Eternity, the eight-bedroom midcentury compound is where he hosted both Hollywood and European royalty, including Britain’s Princess Margaret and his former co-star, Princess Grace of Monaco.

Everyone knew he drank Jack Daniels, but only those close to him knew of his acts of everyday philanthropy. He would scour The Desert Sun for stories about someone down on their luck and anonymously send them a check to pay their medical bills or their kid’s tuition. His valet would fold up $100 bills like origami, which he’d stuff in his pockets to hand out to the waitstaff at restaurants or throw under the table, so the cleaning crew would find them.  


Guests enjoy Sinatra's piano-shaped pool. 

More visible acts of his altruism include the dedication in his father’s name of the Martin Anthony Sinatra Medical Education Center at Desert Hospital, and the Barbara Sinatra Children’s Center Foundation at Eisenhower Medical Center (now Eisenhower Health), for which he, Dean Martin, Sammy Davis Jr., and Liza Minnelli performed at a $10,000-a-table benefit. In 1988, he and Barbara founded the Frank Sinatra Celebrity Invitational Golf Tournament to benefit the center. He also made numerous contributions to St. Louis Catholic Church in Cathedral City, where his mother worshipped twice a week.


In 1970, he broke ground for the Martin Anthony Sinatra Medical Education Center at Desert Hospital. 


Sinatra with his fourth wife, Barbara, at a 1985 benefit. 

Barbara Foster remembers her husband Bill, then mayor of Palm Springs, receiving a call from Sinatra just as they and 18 guests were sitting down to Thanksgiving dinner in 1978. His friend Irwin “Ruby” Rubinstein, owner of Ruby Dunes, had died that morning, and “Sinatra had notified hundreds of people that the funeral was going to be at Temple Isaiah on Monday.” The only problem was that the temple was closed on Mondays. Sinatra wouldn’t take no for an answer. So, Foster called the rabbi and asked, “How badly do you want $1 million?” The rabbi purportedly responded, “For $1 million, I’ll open the damn grave myself!” While temple officials refute the story, Sinatra did donate $1 million, and Rubinstein was buried that Monday. 

It seems that almost everyone who was around back then has a Sinatra story, including Vince Costa, whose father, Johnny, often served as Sinatra’s private chef and whose eponymous Palm Springs restaurant features The Sinatra Room. His tale involves Sinatra’s chauffer. Eager to get somewhere, Sinatra urged his driver to go faster. Having gotten a number of speeding tickets driving him around town, the chauffeur said he couldn’t risk getting another one. Sinatra snapped, “Pull over, I’ll drive.” They switched places, and not surprisingly, with pedal to the metal, Sinatra soon got pulled over. When the perplexed cop saw who was driving, he called his captain. “I got this limo, but I don’t know if I should give him a ticket.” 

“Well, who’s in the back?” the captain asked.

“I don’t know, but it must be somebody really famous. Frank Sinatra’s driving.”  

While The Godfather paints the Sinatra-inspired Johnny Fontaine character as a weak but talented cry baby who left all the women at Connie’s wedding swooning, Sinatra only seemed to appear weak in his final years. That’s when he struggled to remember lyrics, as he did during his last performance at a February 1995 fundraiser in the ballroom at what is now the JW Marriott Desert Springs Resort & Spa in Palm Desert. A few months later, his wife convinced him to sell his beloved desert compound and move to Beverly Hills. “That was a fatal turning point,” Oppedisano claims.

In the end, it seems fitting that he died from a massive heart attack, having given so much of his own heart to the world. His final words were, “I’m losing.” But that night, under an orange moon, it was the world that lost.