Flint was one of 12 pilots incorporated into the nascent Jewish state's first air squadron. He served alongside Ezer Weizman, who would later go on to become the head of the air force, and eventually the seventh president of Israel.
As the Cessna aircraft took off from Sde Dov airport in north Tel Aviv, it was hard for the veteran pilot to hide his excitement.
"We did what we needed to do, and since then, the State of Israel has only become stronger. Israel can defeat any enemy," Flint said.
While the plane was initially supposed to be flown by pilot Eli Inbar, Flint couldn't resist and took over the controls. "When I was flying, we were flying fast and under fire. Now, it's really a pleasurable experience. This is a great aircraft," he said.
A group of Jewish pilots form various English speaking countries came to Israel under the Mahal framework during the Israeli War of Independence. Mahal is a part of the Israeli Defense Forces comprised of volunteers from outside of Israel.
Flint first served as a combat pilot for the US during World War II. After he saw what had befallen the Jews in Europe and the breakout of war between Jews and Arabs in what would become Israel in early 1948, he decided to go and contribute to the new state's air force as a Mahal soldier.
At the beginning of the War of Independence, Flint and his colleagues flew in German aircraft captured during WWII. The Nazi insignia which were painted on the planes were covered up by Stars of David.
These volunteers performed a crucial role in the war, and laid the foundation for the establishment of the Israel Air Force as it is seen today.
"Israeli Independence Day proves to me that we succeeded in doing what we needed to do," Flint said after he landed the plane. "I remember times which were a lot more difficult. Now, things are a lot better. The most important thing is that the State of Israel can now take care of itself, and has the ability to deal with and conquer any foe."
A movie about these foreign volunteers who helped establish the Israel Air Force in 1948 is currently being filmed, and is expected to be released in 2017. The movie, Angels in the Sky, is based on these pilots' stories, including Flint's.
The movie is being produced by Flint's son Mike, and the screenplay was written by Robert Roy Paul, who was also the screenwriter for "Armageddon."