Harry Stewart Jr. Dies at 100; One of Last Tuskegee Airmen to See Combat

His boyhood dream to be an adventurous pilot was fulfilled thanks to World War II. But, as a civilian, racial prejudice kept him out of the cockpit.


Harry Stewart Jr. in 1944. During World War II he flew 43 missions — almost one every other day — between 1944 and 1945. via Stewart Family

By Alex Traub
Feb. 5, 2025

Harry Stewart Jr., a decorated former combat pilot who was among the last surviving Tuskegee Airmen, the all-Black unit of the Army Air Forces in World War II, and who, after being denied a civilian career in aviation, made a late-life return to the skies, died on Sunday at his home in Bloomfield Hills, Mich. He was 100. ... The death was confirmed by Philip Handleman, who collaborated with Mr. Stewart in writing his biography, “Soaring to Glory: A Tuskegee Airman’s Firsthand Account of World War II” (2019).

Mr. Stewart was one of a tiny handful of still-living Tuskegee pilots who saw combat in the war. He flew 43 missions — almost one every other day — from late winter 1944 into the spring of 1945. ... On one mission, to attack a Luftwaffe base in Germany, Lieutenant Stewart and six other American pilots were baited into a dogfight with at least 16 German fighter planes. Firing his machine guns and performing risky aerial maneuvers, he downed three enemy aircraft in succession, fending off a potential rout.

He was awarded the Distinguished Flying Cross, cited for having “gallantly engaged, fought and defeated the enemy” with no regard for his personal safety. ... Four years later, in a southern Nevada desert known as Frenchman Flat, the military held its first aerial gunnery competition for both jet and propeller-plane pilots, a contest of precision bombing, gun firing and flight maneuvers of the sort later made famous by the 1986 movie “Top Gun.” Lieutenant Stewart and three other Tuskegee Airmen won the first-place trophy in the propeller-plane category. ... In that contest Lieutenant Stewart earned a perfect score in “skip bombing,” in which a low-flying plane drops bombs that hit the ground and roll into a target.} ... Months later, he was mandatorily discharged from the military. He soon discovered that, as a Black pilot, he would have no further chance of a career in the skies.

Harry Thaddeus Stewart Jr. was born on July 4, 1924, in Newport News, Va. His father, whose grandparents had been born into slavery, took a job as an assistant galley cook on a passenger liner and made his way to New York City, where he became a postal worker in 1929, right before the Depression. He was soon joined by his family, who settled in the working-class Corona section of Queens.

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Mr. Stewart in 1939 when he attended the dedication ceremony of New York Municipal Airport (now known as LaGuardia). via Stewart Family

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Mr. Stewart, fourth from the right in the front row, with his Tuskegee class at the school’s airfield in Alabama. His class started with 75 cadets and ended with 26 graduates. via Stewart Family

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Lieutenant Stewart in 1949 with his wife, Delphine Friend, at and Delphine on the ramp at the Lockbourne Air Force Base in Ohio. via Stewart Family

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Alex Traub works on the Obituaries desk and occasionally reports on New York City for other sections of the paper. More about Alex Traub