Charlie Winters: Smuggling B-17s to Israel

War History Online proudly presents this Guest Piece from Christopher Stuttard

Prior to and during 1947, the Jewish paramilitary group, the Haganah (precursor to the Israeli Defense Forces), had been procuring weapons in the build-up to the “Declaration of the Establishment of the State of Israel,” otherwise known as Israeli independence from Britain and Palestine.

Under the leadership of Israel’s founding father, David Ben-Gurion, the underground operatives of the Haganah had been manufacturing and stockpiling small arms in what Benny Morris dubbed: “a massive, covert arms acquisition campaign in the West.”

By late September 1947, they had an arsenal of rifles, sub-machine guns, mortars, and light machine guns. These weapons numbered in the thousands. However, the problem the fledgling force faced was a distinct lack of heavy weaponry, aircraft, and armored units.

Haganah ship Jewish State at Haifa Port (1947)
Haganah ship Jewish State at Haifa Port (1947)


Enter the curious case of Charles “Charlie” Thompson Winters. Born February 10, 1913, in Brookline, Massachusetts, Charlie Winters procured four B-17 Flying Fortresses with the bold plan of retrofitting them and delivering them to the newly created Israeli AirForce.

Along with Al Schwimmer and Herman “Hank” Greenspun, Winters was essential in the creation of the Israeli Air Force and a major contributor to the course of the first Arab-Israeli war in 1948.

Al Schwimmer
Al Schwimmer

In 1948, Winters was running a freight service between Miami, Florida and the Caribbean, mainly transporting fruit and vegetables. He used his piloting skills and export license to deliver three B-17 bombers to Israel.

Taking off from Miami, the B-17s refueled in Puerto Rico as they would do in a normal produce delivery.

Then, instead of heading to the Caribbean with their usual cargo, the heavy bombers were piloted to the Azores and then to Žatec in former Czechoslovakia. Winters flew one of the aircraft himself.

B-17F of the 305th Bomb Group “Flyin Hobo” 42-30015 1943 in flight
B-17F of the 305th Bomb Group “Flyin Hobo” 42-30015 1943 in flight

The planes were retrofitted with the components necessary to make them effective heavy bombers.

At the request of the US government, one of the B-17s was apprehended by Portuguese authorities in the Azores, but the other three successfully made the flight of over 6200 miles to their destination.

B-17 on a bomb run.
B-17 on a bomb run.


Once in Israel, the three B-17s were the basis of the 69th Hammer Squadron of the Israeli Air Force. Before they had even landed in Israel, the newly equipped bombers were tasked with bombing the Royal Abdeen palace in Cairo and el Arīsh in Egypt.

The palace was hit, but el Arīsh proved too difficult to locate, so the settlement of Rafah was bombed instead. The Egyptian air force station at el Arīsh was bombed the following morning.

In the months that followed, the B-17s of the 69th helped to turn the tide in the war for air superiority.

Israeli B-17s in flight, 1953
Israeli B-17s in flight, 1953


In the aftermath of WWII, the USA had a vast surplus of military assets. However, as the country had passed strict laws regarding the sale of arms and US neutrality, the actions of Winters, Schwimmer, and Greenspun led the trio into legal trouble.

In 1950, Schwimmer was convicted of violating the neutrality acts. He was stripped of his voting rights and fined $10,000.

Hank Greenspun was fined $10,000 for violating the neutrality acts and supplying aircraft components and small arms.

1958 passport issued to Al Schwimmer which he used on his official trips as head of the IAI.
1958 passport issued to Al Schwimmer which he used on his official trips as head of the IAI.

However, it was Winters who received the brunt of the punishment. For his active part in the transport of the aircraft, he was convicted by the US attorney in Miami. He was fined $5,000 and was sentenced to serve 18 months in prison.


Of the three men convicted under the 1939 Neutrality Act, all three received presidential pardons in the following decades. Greenspun was pardoned in 1961 by President John F. Kennedy.

Schwimmer received his Presidential pardon from Bill Clinton in 2000, and Charlie Winters received a posthumous pardon from George W. Bush in 2008, becoming one of the few people in US history to be pardoned after their death.

The campaign to recognize Charlie Winters as a hero and to pardon him posthumously gained significant momentum after Steven Spielberg joined the campaign for his recognition. In a letter to President Bush, the film director said:

“There are probably many unsung heroes of America and of Israel, but Charlie Winters is surely one of them.

While a pardon cannot make Charlie Winters whole, and regrettably he did not live to see it, it would be a fitting tribute to his memory and a great blessing to his family if this pardon is granted.”

Steven Spielberg
Steven Spielberg

Read another story from us: Last of His Crew – Flying Fortress Captain Tells his Story

Half of Winter’s ashes are buried in a Christian cemetery near the Jewish cemetery of the Knights Templar in Jerusalem. The other half have been scattered at the summit of Mount Tabor in Israel.

Charlie Winters, born on the outskirts of Boston, made himself a criminal in the eyes of his government for over 50 years because he had the courage to act on his convictions.

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