The dark history of Frank Sinatra’s mansion: The Rat Pack’s gambling and alleged encounters between Marilyn Monroe and John F. Kennedy

Poker was played there until the early hours of the morning, while million-dollar rounds of bourbon and French champagne were served. The host — Frank Sinatra — and famous guests, such as Dean Martin, Angie Dickinson, Sammy Davis Jr. and Joey Bishop, all partook in the activities.

Lucille Ball and the wealthy New York heiress Dora Hutchinson took a dip together in its pool. Paul McCartney and Miley Cyrus sang and played guitar in its gardens. Scenes from the TV shows Mad Men, Bewitched and Californication — as well as the movies Savages (2012) and Dreamgirls (2006) — were filmed in its luxurious rooms. Hermès dyed the house red for the presentation of its spring-summer collections two years ago. It also appears in music videos featuring top artists, including Rihanna, Beyoncé, Usher and Mariah Carey.

Furthermore — according to various (and not entirely confirmed) testimonies — Marilyn Monroe and John F. Kennedy would meet in the guest house of the Los Angeles mansion known as Farralone in the spring of 1962, before and after the Hollywood star sang an unforgettable “happy birthday” to the Democratic president.

It has been confirmed that Sinatra resided there intermittently between 1954 and 1963. In this corner of the San Fernando Valley — in the wealthy neighborhood of Chatsworth, at the foot of the Santa Susana mountain range — the singer found refuge during the days when he was divorcing Ava Gardner. During this period, he also lived out fleeting romances with Lauren Bacall and the British dancer and actress, Juliet Prowse.

Mystique had a price

These days, Farralone is in the news because it’s back on the market. This time, at a price of more than $8 million, less than the $9 million it was listed for last year, or the $21 million asking price in 2021. Its current owners claim to have obtained a profit of more than $750,000 from the villa by renting it out for film and TV shoots, but they clearly haven’t managed to prevent its further depreciation.

In a commercial maneuver that’s difficult to understand, the owners have even decided to change its name: it’s now called Byrdview (although the press continues to refer to it by that contraction of the words “far” and “alone” that made it famous). Indeed, the mansion was a perfect place to enjoy solitude, just half-an-hour from downtown Los Angeles. With 35,000 residents spread over a very large area, Chatsworth is one of the lowest-density suburban neighborhoods in the metropolitan area. Farralone sits atop a hill with restricted and discreet access.

Reports by outlets such as Architectural Digest suggest that the mansion may indeed be worth its price. For starters, the estate occupies an area of about three-and-a-half acres in the heart of the Chatsworth Nature Preserve, with splendid views of the San Fernando Valley, the Los Angeles foothills and the surrounding mountains. It has gardens, terraces and an outdoor pool.

The mansion — shaded by centuries-old trees — is a sleek, futuristic-looking building with more than 8,000 square feet of living space. It has four bedrooms, seven bathrooms and movable glass walls. It was designed in 1941 by the Portuguese-born architect William Pereira, who also did emblematic Californian buildings as the Transamerica Pyramid in San Francisco, the Theme Building at Los Angeles International Airport, the Geisel Bookstore in San Diego, the Pepperdine University campus in Malibu and the Disneyland Hotel in Anaheim.

This was the future in 1941

Pereira was a peculiar man. A fan of science fiction and motor racing, he advocated for a spectacular and accessible type of modernity. His vision was very cinematic, inherited from Art Deco. He was indebted both to Fritz Lang’s Metropolis (1927) and to the work of John Carter or Edgard Rice Burroughs.

The architect grew up in Chicago. His first works can be traced to various towns in the American Midwest. However, he ultimately settled in Los Angeles with his brother Hal — also an architect — in the 1930s and developed the bulk of his career in California. Hired by a real estate fund owned by the major studios, he became the unofficial architect of Hollywood. So much so that he was even offered the opportunity to work as art director on film noir classics, such as This Gun for Hire (1942) — Alan Ladd’s first film — or war movies, such as Since You Went Away (1944). With Reap the Wild Wind (1942), he won an Academy Award for Special Effects.

While building Farralone, Pereira was assisted by a young architecture student of exceptional talent: one Frank Gehry. The mansion was commissioned by Dora Hutchinson, heiress to the Manhattan Chase Bank fortune. In the months leading up to the United States’ entry into World War II, Hutchinson had grown tired of what she considered to be the decadent and provincial high society of New York. She was looking for a place in the Los Angeles area to host grand parties with her new friends from the Hollywood elite.

Her Fourth of July celebrations — with fireworks displays that were hardly unprecedented in the area — became legendary and attracted the attention of illustrious figures, such as Ava Gardner and Judy Garland. Garland would end up marrying Vincente Minnelli in the Farralone Gardens (which, at that time, was still called “Fox Gardens”) on June 15, 1945, in a ceremony attended by the top brass of Metro-Goldwyn-Mayer. This gave rise to one of the most tortuous marriages in classic Hollywood, burdened by infidelity and drug use.

From Lucille to Marilyn via Frank

Years later, Dora hosted a close friend — Lucille Ball — for several months. She was then going through a marital crisis with her husband and co-star in I Love Lucy, the Cuban actor Desi Arnaz. In 1954, Hutchinson grew tired of drinking margaritas by the pool and decided to return to New York. She rented the house to Frank Sinatra, who had just been left alone in Palm Springs after his wife — Ava Gardner — moved to Madrid. This brought an end to three years of legendary marital squabbles, crowned by the occasional clandestine affair and an overdose of barbiturates.

Sinatra celebrated his return to bachelorhood by turning Farralone into the official headquarters of the Rat Pack’s poker games. During these alcohol-fueled gatherings, huge fortunes changed hands in the blink of an eye. The parties usually ended with guests swimming in the pool at dawn. The card games at the Chatsworth mansion between Sinatra and Dean Martin would end up consolidating the men’s passion for gambling: in 1960, they would buy Cal Neva, a casino-hotel on the shores of Lake Tahoe. This is where, in later years, the Kennedy brothers — Jack and Bobby — would host their legendary orgies.

By this time, Sinatra had already welcomed Marilyn Monroe as a regular guest at Farralone. So much so that the actress ended up renting the guest house. It was there that — in theory — the never-confirmed encounters between Monroe and Kennedy took place. Monroe was then working on what would end up being her last film — the unfinished Something’s Got to Give (1962), directed by George Cukor — and struggling with serious problems with alcohol and amphetamines.

One of the actress’s biographers — Jason Spada — claims that Marilyn and JFK had known each other since 1954, but the definitive connection between the two occurred in 1962. This was allegedly at the request of Sinatra, who was more than accustomed by then to acting as a pimp for his illustrious friend. The paradox of this story is that the first time the lovers spent the night together wasn’t at Farralone, but at a mansion in Palm Springs owned by another singer — Bing Crosby — who was a supporter of the Republican Party.

Sinatra had offered to host Kennedy on his official trip to Los Angeles, as he had done on his frequent private visits. He even made renovations to his residence to accommodate the presidential escort. But the FBI recommended that Kennedy not be seen in public with Sinatra, whose friendship with the notorious mafia leaders of the Genovese crime family was already public. Hence, Crosby ended up being the official host of the president. So, if Kennedy’s encounters with Monroe at the mansion on the hill really did take place, he would have had to have gone to Farralone incognito.

Marilyn died in strange circumstances on August 4, 1962, shortly after her (alleged) spring of love in the guest house. Kennedy was subsequently assassinated in Dallas on November 22, 1963. Sinatra soon got rid of the mansion, which perhaps brought back terrible memories for him.

Over the last 60 years, Farralone has continued to have prominent tenants and high-class visitors, who have contributed to its mystique. Paul McCartney attended one of the parties organized at the property and ended up picking up an acoustic guitar to give an improvised concert. Miley Cyrus chose the gardens of the Pereira estate as the setting for one of her famous Backyard Sessions. And Beyoncé apparently asked about the property, although she ultimately decided against buying it.

The question remains: why is a place with so much history currently selling for a third of what its asking price was in the middle of the pandemic? Whatever the answer may be — as in Sinatra’s poker games — those interested in winning the hand will still have to be willing to put a lot of money on the table.

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