In the glamorous world of Hollywood’s golden era, two iconic stars, Marilyn Monroe and Frank Sinatra, captivated the hearts of millions with their extraordinary talent and charisma. As their paths crossed, fate had much more in store for them than just mere acquaintances. Over time, their bond evolved into a genuine and enduring friendship that withstood the tests of fame and personal struggles. In this blog post, we delve into the captivating journey of Marilyn Monroe and Frank Sinatra, from their early acquaintance and the infamous “Wrong Door Raid” to their cherished friendship in 1961, which included shared moments and a thoughtful gift that left a lasting impact.

Acquaintance Blossoms into Friendship

Marilyn Monroe and Frank Sinatra’s paths likely crossed at the beginning of the 1950s, Joe DiMaggio, who was a close companion of Sinatra. Some biographers suggest that they were introduced to each other on July 15, 1953, at the premiere of “Gentlemen Prefer Blondes,” or at the Fox studio towards the end of 1953 when they were being considered for potential collaboration in “Pink Tights.” However, the project did not come to fruition as Marilyn prioritised projects that aligned better with her vision and independence.

The Wrong Door Raid: A Pivotal Moment

In November 1954, a quiet West Hollywood-adjacent Street became the setting for an infamous incident known as the “Wrong Door Raid.” Florence Kotz, a 39-year-old secretary who lived alone, woke up to the sound of someone breaking into her kitchen door. In the darkness, she could only scream for help as intruders breached her sanctuary.

The raiders, hoping to catch a sexy blond actress in a compromising situation with her vocal coach, were instead faced with the sight of Florence in her curlers. Realising their blunder, they hurriedly retreated, breaking glasses in the kitchen during their escape.

The incident was initially investigated as an attempted burglary, but it soon faded from memory. However, nearly a year later, Confidential magazine published an account of the raid, introducing it to the world and linking it to three of the most famous people on the planet: Marilyn Monroe, Joe DiMaggio, and Frank Sinatra.

In the weeks preceding the raid, Marilyn’s divorce from Joe head become headline news, leaving the ex-Yankees slugger in distress. He was rumoured to be struggling with his jealousy and convinced that Marilyn had left him for someone else.

To track Marilyn’s every move, Joe enlisted the services of private detective Barney Ruditsky, who, in turn, brought in Phil Irwin. On the night of November 5, 1954, they spotted Marilyn’s car parked near Sheila Stewart’s apartment at 8120 Waring Ave, leading them to believe she was having an affair with Hal Schaefer, her, and Sheila’s vocal coach.

Convinced that they had caught Marilyn with Schaefer, DiMaggio ordered Ruditsky to stage the raid, hoping to obtain compromising photographs. However, the raid went awry, and no evidence was obtained. The incident remained relatively unnoticed until Confidential magazine published its scandalous version in September 1955, causing a media frenzy.

The aftermath of the raid saw conflicting testimonies, with Sinatra and DiMaggio denying any involvement, while Irwin, Ruditsky, and other witnesses told a different story. The incident triggered investigations and hearings, leading to the infamous criminal libel conspiracy trial against Confidential. In the end, the magazine agreed to stop reporting Hollywood stars’ intimate secrets, and its success eventually dwindled.

Florence Kotz, now Florence Ross after marrying, sued DiMaggio, Sinatra, and others for $200,000, eventually settling for $7,500.

A Cherished Friendship

The year 1961 marked a turning point in the friendship between Marilyn Monroe and Frank Sinatra. She told her masseuse Ralph Roberts, “I play his records, as you know, constantly on set. He helps me get in the mood for acting. Frees me. Frank was interested in seeing me some years ago, but I refused. Maybe the second time around.”

In March 1961, Marilyn met with Frank again at Waldorf Towers with Ralph Roberts dropping her off, apparently with her nervous and shaking beforehand.

At the time, Frank was busy with his music career, often going on tours to perform for adoring fans across the country. Despite his demanding schedule, he made sure to open the doors of his home to Marilyn whenever she needed an escape from the relentless public eye. Marilyn had left New York and needed to find refuge back in Hollywood, as per Joe DiMaggio’s advice to be closer to work (they had agreed to see each other again as well as others if it so suited them)

Frank’s home became a shelter for Marilyn, a place where she could seek sanctuary and find comfort away from the chaotic Hollywood scene especially after her divorce from Arthur Miller and mental health struggles. With the keys to his residence, allowing her to enjoy the tranquillity and privacy it offered until she could find a new apartment of her own.

Marilyn and Frank were happy to spend time together in public. On his return from tour in September 1961, Frank invited Marilyn to Romanoff’s for a large party in which Pat Newcomb found the perfect dress – a Nile green, sequined Norell gown (which she would also wear in her November 1961 Kirkland photoshoot and the 1962 Golden Globes, pictured). For this date, Frank would present Marilyn with emerald earrings

Frank Sinatra also took the initiative to whisk Marilyn away for brief breaks on occasions. One of these memorable getaways was where they enjoyed the soothing embrace of the sea while savouring each other’s company as well as many of Sinatra’s friends. She would also spend time with members of The Rat Pack and their wives at the home of Peter and Patricia Lawford.


Another retreat was at the Cal-Neva Lodge, a resort casino situated on the shores of Lake Tahoe. The lodge was a favourite destination for Frank, and he welcomed Marilyn into this exclusive haven in 1962 (she had also visited with the cast of The Misfits in 1960). Here, amidst the breathtaking beauty of nature, Marilyn would have her final weekend, relaxing amongst friends.

A Friendship That Endured

Despite the 1954 drama, an open dating scene and occasional rumours and speculations, Marilyn and Frank’s friendship endured.

One rumour that has been ongoing is that Frank contemplated marrying Marilyn to protect her from constant public scrutiny. However, Frank’s own engagement with Juliet Prowse puts these rumours to rest.

In August 1962, tragedy struck when Marilyn passed away. 

According to Marilyn’s business manager Inez Melson, Marilyn had wanted a small memorial to be held so co-stars and  Hollywood circles were not invited to the service, including Frank which apparently had upset him greatly.