Stories

Sterling Hayden: The Hollywood Star That Left the Silver Screen to Become a Spy

July 9, 2021

It almost sounds like a classic Hollywood screenplay: A handsome Hollywood leading man leaves fame and fortune behind to become a real-life spy.

During World War II, Sterling Hayden did exactly that. He left a promising career on the silver screen to join General William “Wild Bill” Donovan and the “glorious amateurs” of America’s first spy Agency, the legendary Office of Strategy Services (OSS).

A young Sterling Hayden at the beginning of his film career

From Sailor to Actor

Growing up in coastal towns throughout New England, Sterling fell in the love with the sea.
He dropped out of high school at age 16 and quickly got a job as a shipmate on a schooner. In the next few years, he learned the craft of sailing as he worked on various ships from New England to the Caribbean.

While on those ships, Sterling had two encounters that would change his life forever: A photo of him on the cover of a sailing magazine would prompt a Hollywood casting agent to offer him a screen test with Paramount pictures. Later, a chance meeting with Wild Bill Donovan on a sailing trip would lead to a lasting friendship between Sterling and the OSS spymaster.

The Role of a Lifetime: “John Hamilton” Joins the War Effort

In 1941, after starring in two films for Paramount, Sterling left Hollywood to join the war effort.

Taking advantage of his connection to Donovan, he asked to be sent to commando training in Scotland, where he became the only American—and novice—allowed to join the elite training group.

Sterling broke his ankle during a training parachute jump, however, and was forced to return to the United States.

Once he recovered from his injury, Donovan suggested he join the Navy, but Sterling chose the Marines instead and was sent off to boot camp in Parris Island, South Carolina.

Worried that his fellow Marines would not take him seriously because of his Hollywood fame, Sterling took the pseudonym John Hamilton—a name he would carry throughout his military and OSS career.

Sterling Hayden, aka “John Hamilton,” completes his Marine training and prepares to join the OSS

Once Sterling completed his training on Parris Island, he was recommended for Officer Candidate School. However, Sterling was more interested in pursuing a safer alternative to frontline combat, while also using his seafaring skills. He approached Donovan who put in the paperwork to transfer him to the Coordinator of Information, a precursor to the OSS.

The newly created OSS wasted no time in putting Sterling’s mastery of sailing to good use. It set up a secret shipping operation in Italy that would allow Sterling and his crew to bring weapons and supplies to agents behind enemy occupied territories in Eastern Europe.

A Most Daring Mission

On Christmas night in 1943, Sterling landed on the Yugoslav island of Korcula in Eastern Europe, aboard a broken-down motorboat in the midst of a German attack.

He had crossed the Adriatic Sea from Allied-held southern Italy to make contact with future-Yugoslavian President Marshal Josip Broz Tito’s communist rebels, drop off supplies, and perform reconnaissance on German landing forces to gage their strengths.

While on Korcula, the Germans attacked his jeep and killed his driver, forcing Sterling and his men to fire back and flea before being captured. They quickly fled to the island of Hvar, which was under attack by German Stuka dive bombers.

Sterling was able to complete his mission by supplying the Yugoslav rebels with collected intelligence and to secure a boat to get him back to Italy.

For that mission Sterling was awarded the Silver Star.

Interestingly, during his brush with Tito and the Yugoslav partisans, Sterling became briefly enamored with communism. He would later admit that he had been “duped” by communism.

A True Renaissance Man

After the war Hollywood came calling and Sterling, needing money to afford his love of sailing, answered the call.

For someone who had never taken an acting class in his life, Sterling was a natural born tough guy actor. He played everything from gangsters and cowboys to soldiers and outlaws.

Film director Stanley Kubrick would give him two standout roles: one in the classic film noir, The Killing, and the other as deranged general “Jack D. Ripper” in the dark comedy, Dr. Strangelove: or How I Learned to Stop Worrying and Love the Bomb.

Sterling, as General Jack D. Ripper, is ready to start a war with the Russians in Dr. Strangelove

The role he is perhaps the most famous for, however, is that of corrupt police captain McCluskey who gets shot by Al Pacino in, The Godfather.

Despite being a well-regarded Hollywood actor, Sterling would always mention in interviews that acting was just a way to play the bills.

He was at his happiest sailing his schooner, The Wanderer, which he would take on long voyages across the oceans: he did so well into his sixties.

Sterling turned to writing late in life and wrote two books: Wanderer, about his personal sailing experiences, and Voyage, a novel about the sea.

Sterling passed away from prostate cancer on May 23, 1986 at the age of 70.

Sailor, World War II hero, author, and actor is probably how he would have described his life, in that order. All in all, Sterling Hayden truly was a renaissance man.