The Night Frank Sinatra & Joe DiMaggio Tried To Catch Marilyn Monroe Cheating Only To Fail Epically

Frank Sinatra and Joe DiMaggio allegedly once ideated a wild plan to attempt to catch Marilyn Monroe cheating on her then-husband but it failed miserably. It was November 5, 1954 and the Hollywood icon had just filed for divorce from DiMaggio after 9 months of marriage in October but he was clearly still struggling with his split from Monroe. According to The New York Times, the poorly executed plan would also cause irreparable damage to The Yankees Clipper’s friendship with another Italian-American star — Sinatra.

The Times reports that the two were dining with friends at the Villa Capri in Hollywood when they suddenly left the restaurant after getting word from a private investigator, Barney Ruditsky, that Monroe was seen at a residence with another man. Sinatra and DiMaggio drove to a little apartment house at Kilkea Drive and Waring Avenue.

Without naming names, the Times alleges that a door was kicked in on one of the apartments but the intruders, using a flash camera, happened upon a frightened woman in her night gown. Monroe was nowhere to be found. The woman was Florence Kotz, an office secretary who later sued DiMaggio, Sinatra, Ruditsky and three others alleged accomplices that she identified. Kotz was awarded $7,500 in an out-of-court settlement brokered by Sinatra’s lawyer.

Years later, a California state senate panel examining the ethics of private investigators would hear from Kotz’s landlady, Virginia Blasgen, who recalled peering out of her window that night and seeing an argument between a “mad” looking DiMaggio and an oddly bemused Sinatra seeing — Blasgen reportedly claimed he was “jumping up and down and looking at me, smiling.”

It wasn’t until two years after the failed plan that the rest of the world learned about it after Confidential magazine published an article about what then became known as “Wrong-Door Raid.” The story becoming public knowledge reportedly embarrassed DiMaggio so much that he stopped speaking to Sinatra, despite the singer having been on his side the whole time. Of course, in the early 1960s Sinatra and Monroe were rumored to have had a fling so DiMaggio likely never put the feud to bed.

Sinatra and Monroe’s rumored fling, after her marriage to Arthur Miller broke down, also occured around the same time that Monroe and DiMaggio reportedly reconciled — the two maintained that they were just friends. When Monroe passed away in August, 1962, DiMaggio took control of planning her funeral and even reportedly barred Sinatra from attending.