Why Frank Sinatra’s Attorney Advised Against Marrying Marilyn Monroe

Frank Sinatra and Marilyn Monroe were once involved in a romantic relationship, but their love story took an unexpected turn.

Despite planning to marry Monroe, Sinatra's lawyer intervened and prevented the union from happening due to a devastating reason.

The friendship between Sinatra and Monroe blossomed in 1954 when he was still married to actor Ava Gardner.

Over the course of several months, they developed a close bond, even though they were seeing other people at the time.

According to Charles Casillo, author of “Marilyn Monroe: The Private Life of a Public Icon,” their relationship could be described as a modern-day “friends with benefits” arrangement.

However, Sinatra's feelings for Monroe went far beyond casual.

In an episode of “The Killing Of Marilyn Monroe” podcast, Casillo explained that Sinatra was enchanted by Monroe and treated her unlike any other woman.

He was fiercely protective of her, recognizing her inherent vulnerabilities.

Despite being deeply enamored by Monroe, Sinatra was aware of her dark side.

Casillo reveals in his autobiography that while Sinatra adored Monroe when she appeared glamorous and radiant, her deep-rooted problems often led her to rely on alcohol and pills to cope.

This aspect of her personality frightened Sinatra.

Nevertheless, Sinatra found Monroe's vulnerability captivating, and she touched him in a way no other woman had before.

He wanted to shield her from harm, drawn to her damsel-in-distress quality.

As Sinatra's love for Monroe grew, he reached a point where he wanted to spend the rest of his life with her.

However, something troubling came to light, causing him to change his mind about marrying the Blonde Bombshell.

The exact details of this revelation remain undisclosed, but it had such a profound impact on Sinatra that his attorney forbade him from marrying Monroe.

Though the specifics are unknown, it is evident that whatever Sinatra discovered raised serious concerns and made him reconsider the idea of a lifelong commitment.

In the end, Sinatra heeded his lawyer's advice and did not go through with marrying Monroe.

Their relationship continued to evolve, but the dreams of matrimony were shattered due to the shocking revelation Sinatra had uncovered.

The story of Frank Sinatra and Marilyn Monroe remains one of the most captivating tales in Hollywood history.

Their love, albeit short-lived, was filled with passion, turmoil, and ultimately, a heartbreaking decision that forever altered the course of their lives.