Buckle up. This story has more plot twists than a Hollywood blockbuster. Speaking of blockbusters, English actor Leslie Howard was in plenty of them, including the 1939 epic, Gone With the Wind, in which he played Scarlett O’Hara’s crush, Ashley Wilkes, as shown in these colorized photos.

This Golden Age of Hollywood leading man, however, traded in his acting career to return to England and devote himself to the war effort. This is where things took a turn. A civilian airplane with Howard and a handful of others on board was shot down by the Nazis and crashed into the ocean, never to be seen again. Was Leslie Howard targeted by the Nazis? Was he a spy? Were the Nazis out to get one of the other passengers? Well, we don’t know the answers to these questions, but there are some theories.

A Brief Background on Leslie Howard

Leslie Howard’s father was a Hungarian Jew, and his mother was a British Christian. As a young man, and after a brief stint in World War I, he dropped his Jewish-sounding given name, Steiner, and began to use his middle name as his last name when he entered show business. Howard started as a stage actor but found greater success when he moved to New York City and performed on Broadway. Hollywood came calling. In 1934, he starred in The Scarlet Pimpernel. He took the role of Henry Higgins in the 1938 film adaptation of Pygmalion. The next year, he was cast as the Southern gentleman, Ashley Wilkes in Gone With the Wind.

By this point, Leslie Howard was a bona fide movie star, but he was dissatisfied with the entertainment industry. And war was brewing in Europe. Even worse, there were reports that the German Nazis were systematically exterminating Jewish people. Howard felt compelled to help stop the Nazis. The problem was, he had a studio contract.

In 1939, Howard used his savings to buy himself out of his contract. Breaking his contract meant that he would have to sacrifice his royalties for Gone With the Wind. 

Through his well-connected family, Leslie Howard had met Winston Churchill in the past. Back in Britain in 1939, he contacted Churchill and offered his services. He appeared in several propaganda films put out by Britain’s Ministry of Information. He also directed and starred in two independent anti-German films that he initiated himself. Both of these films, Pimpernel Smith and The First of The Few, greatly angered Joseph Goebbels, the Nazi Party’s chief of propaganda. Howard also recorded broadcasts aimed at the then-neutral Americans to encourage them to join the war. In short, he was a public face on the German’s radar. 

After his death, rumors swirled that Leslie Howard was engaging in espionage for the British, for the Germans, and possibly both as a double agent. During what was labeled a “lecture circuit” tour to Madrid and Lisbon, Howard, a known womanizer, spent time with two questionable women, which fueled the espionage rumors. One was a beautiful Argentinian woman named Countess Lila Miranda and the other was Baroness von Podewils, who was employed at the Ritz Hotel in Madrid where Howard was staying. The countess was definitely working with the Germans. As for the baroness, it is most likely that she was assigned by the British to get close to Howard and keep an eye on him. Howard made a last-minute decision to switch his flight, leaving Madrid a day ahead of schedule, and he let both women know this. What they did with the information is a matter of speculation.

Leslie Howard’s Flight

When Leslie Howard announced his plan to leave Madrid early, it posed a problem. The flight was already full. He used his famous name to get two of the passengers bumped from the flight. They were two teenage heirs to the Vanderbilt fortune who were trying to fly back to London from their Swiss boarding school. Getting bumped from the flight saved their lives.

Others on the civilian flight were not so lucky … and they were an interesting collection of people. There was Ivan Sharp, a mining engineer who was involved in activities that made it difficult for the Germans to get the raw materials they needed for the war effort. Also on board was Tyrell Shervington, the CEO of Shell Oil who may have had ties to the Portuguese secret service. And then there was Wilfrid Israel, an heir to a prominent Jewish family in Berlin. It was her work with the Kindertransport that inspired Howard to make the film, Pimpernel Smith, which was about the work being done to rescue Jewish children from Nazi concentration camps.

Joining Howard on the flight was his agent, Alfred Chenhalls. Short, bald, pudgy, and with a perchance of wearing top hats and smoking a cigar, Chenhalls’s resemblance to Winston Churchill was uncanny. From a distance, it was hard to tell them apart. 

Leslie Howard’s plane took off on June 1, 1943, en route to Bristol, England, from Lisbon when it was shot down by a Luftwaffe C-6 maritime fighter plane over the Atlantic Ocean. All 17 passengers aboard the plane, including Leslie Howard, were killed. Their bodies and the wreckage of the plane have never been found.

The Theories

The civilian plane was clearly targeted by the Nazis, but why? Was Leslie Howard the reason the plane was shot down? With his propaganda films, Pimpernel Smith and The First of The Few, Howard made an enemy of Joseph Goebbels. In fact, after the crash, it was Goebbels himself that wrote the headline accompanying the article in the German newspapers. It read, “Pimpernel Smith made his last trip.” Perhaps Goebbels ordered the plane to be attacked.

Until his dying day, Winston Churchill felt guilty about the incident. He felt sure that he was the intended target and that a Nazi spy mistook Chenhalls for him. Several of the other passengers could also have been on the Nazis’ radar. To date, the mystery has not been solved, yet the outcome of the attack was the loss of a great Hollywood legend, Leslie Howard.