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Frank Sinatra and Joe DiMaggio Tried To Catch Marilyn Cheating, With Disastrous Results

Ryan McLachlan
Photo Credit: Bettmann / Getty Images
Photo Credit: Bettmann / Getty Images

On November 5, 1954, Joe DiMaggio and Frank Sinatra teamed up to catch Marilyn Monroe cheating. After nine months of marriage, the Hollywood actress filed for divorce from the New York Yankees outfielder. DiMaggio clearly didn’t take this well, and he enlisted the help of his friend, Sinatra, and a private investigator named Barney Ruditsky to try and catch Monroe having a fling.

The plan would later be dubbed the Wrong-Door Raid, which saw them fail to catch Monroe cheating. It did, however, see the friendship between DiMaggio and Sinatra sour.

DiMaggio’s and Monroe’s relationship

DiMaggio and Monroe met through a mutual friend in 1952. Their relationship moved quickly, and despite coming from different worlds, DiMaggio being a sports star and Monroe a Hollywood actress, they were drawn together by their mutual admiration and affection for each other.

Marilyn Monroe and Joe DiMaggio having dinner at El Morocco, New York City. September 12, 1954.
Marilyn Monroe and Joe DiMaggio, September 12, 1954. (Photo Credit: Bettmann / Getty Images)

On January 14, 1954, DiMaggio and Monroe tied the knot in a low-key civil ceremony at San Francisco City Hall. The media frenzy surrounding their marriage made it challenging to maintain privacy and put significant strain on the relationship. Nevertheless, the couple tried to make it work and they genuinely cared for each other.

Their marriage faced many challenges, including the demands of their respective careers, public scrutiny, and tabloid rumors. The media’s constant intrusion into their personal lives took a toll on the couple, and after just nine months of marriage, they decided to divorce in October 1954.

Wrong-Door Raid

While going through their divorce, DiMaggio believed that Monroe was cheating. In an attempt to catch her in the act, he enlisted Frank Sinatra’s help as well as that of a private investigator. On November 5, 1954, while Sinatra and DiMaggio were having dinner at the Villa Capri restaurant in Hollywood, Ruditsky, DiMaggio’s private investigator, told him that Monroe had been seen with another man.

Joe DiMaggio and Frank Sinatra in 1949.
Joe DiMaggio and Frank Sinatra, March 8, 1949. (Photo Credit: New York Daily News Archive / Getty Images)

DiMaggio and Sinatra jumped into action and drove to the house at the corner of Kilkea Drive and Waring Avenue. They then reportedly kicked in the door while bearing a camera. To their surprise, Monroe was not there. Instead, it was a woman named Florence Kotz, who was unsurprisingly quite startled by the intrusion.

DiMaggio was reportedly mad at what had just happened; however, Sinatra saw the funny side and allegedly jumped up and down smiling.

Kotz sued DiMaggio, Sinatra, Ruditsky, and three others who were said to be accomplices. She was awarded $7,500 by Sinatra’s lawyer in an out-of-court settlement.

The aftermath of the Wrong-Door Raid

The damage done by the Wrong-Door Raid caused a rift between DiMaggio and Sinatra. DiMaggio was deeply embarrassed by the event and stopped talking to Sinatra. To make matters worse, in the early 1960s, Sinatra is rumored to have had an affair with Monroe after her marriage to Arthur Miller. This was around the same time that DiMaggio and Monroe reconciled.

Joe DiMaggio puts his head in his hands and wipes his eyes at Marilyn Monroe's funeral.
Joe DiMaggio and Joe DiMaggio Jr. at Marilyn Monroe’s funeral, August 8, 1962. (Photo Credit: Bettmann / Getty Images)

DiMaggio and Sinatra would never be friends again. DiMaggio and Monroe, however, remained close even after their divorce. Monroe’s death in August 1962 deeply affect DiMaggio. He planned her funeral, ensuring that it was a private and dignified affair. He even barred Sinatra as well as members of the Kennedy family from attending.

More from us: Is the Morbid Fascination With Marilyn Monroe’s Body Disrespecting Her Legacy?

After her death, DiMaggio remained a guardian of Monroe’s legacy and is said to have sent roses to her grave three times a week for 20 years.

Ryan McLachlan

Ryan McLachlan is a historian and content writer for Hive Media. He received his Bachelor of Arts in History and Classical Studies and his Master of Arts in History from the University of Western Ontario. Ryan’s research focused on military history, and he is particularly interested in the conflicts fought by the United Kingdom from the Napoleonic Wars to the Falklands War.

Ryan’s other historical interests include naval and maritime history, the history of aviation, the British Empire, and the British Monarchy. He is also interested in the lives of Sir Winston Churchill and Admiral Lord Nelson. Ryan enjoys teaching, reading, writing, and sharing history with anyone who will listen.

In his spare time, he enjoys watching period dramas such as Murdoch Mysteries and Ripper Street and also enjoys reading classical literature and Shakespeare. He also plays football and is an afternoon tea connoisseur.