Not long after the end of World War I, with aviation fever surging, a school opened in Long Beach to train the next generation of pilots and aerial stuntmen. Among the earliest recruits was Wesley May, a young wingwalker who would pioneer several firsts, including cranking a propeller midair, synchronized wing walking, and most famously “air to air” refueling. On Nov. 12, 1921, May hopped from one biplane to another with a five-pound can of fuel strapped to his back and poured the fuel into its gas tank, a historic moment captured in the photo above.

The following spring, May joined a traveling “flying circus” created by the showman Ivan Gates. During an event at San Francisco’s Crissy Field on May 21, 1922, he performed his “bullet-drop,” which involved a delayed parachute release using a newly developed self-contained pack. Until then, parachutes were released by fixed cords, so spectators thought they were watching a man fall to his death. On this day, they were. May opened his chute successfully, but winds sent him careening into a tree. As he unbuckled, a tree limb snapped and he fell 50 feet to the earth, killing him. He was 24.

May’s odds of survival were never good. Deaths were so frequent that Gates stopped using the names of his stuntmen on his posters to avoid the cost of reprinting when they died. In a span of six years starting in 1922, more than half of the 48 pilots and stuntmen who performed for the circus died, according to the aviation historian Claudine Burnett. In 1932, Gates himself joined them: Said to be despondent over health and money troubles, he jumped from the 6th floor window of his Manhattan apartment, without a parachute.

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