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This Day in History: WWII Pilot Gertrude Tompkins

On this day in 1944, an elite American female pilot climbs into a P-51D Mustang fighter. Gertrude Tompkins Silver was tasked with ferrying the plane to the east coast. She was never seen again.


Gertrude is the only member of the Women Airforce Service Pilots (WASPs) still missing in action after World War II.

Her path to the WASPs was unusual. Gertrude spent much of her childhood struggling with a stutter. She hated school because she was relentlessly teased, so she did just enough to scrape by. Books were her main escape.


Gertrude’s life would change forever in late 1940 or early 1941, when she was in her late 20s. By then, she was working for her father’s company. One night at a dance, she met Mike Kolendorski. He was an American pilot volunteering to help England against Germany.


The young couple had a necessarily short courtship because of the war, but they appear to have been in love. Unfortunately, Mike was killed in action in May 1941. Gertrude was distraught, but distracted herself with flying lessons.


When America began recruiting female pilots for the war effort, she volunteered.


Gertrude arrived at primary training in May 1943. The young woman had one challenge that others did not: She needed to control her stutter. Fellow WASP Mickey Axton believes that Gertrude may have sung her radio procedures to make sure she passed.


Singing had always stopped the stutter.


After graduation, Gertrude was sent to “top gun” training, an honor reserved for only the best pilots. She had a new beau during this time, pilot Duncan Miller.


“She had a great personality,” Duncan later said. “Really sharp girl. Any time off we probably spent together.” Gertrude’s life changed again when she was finally allowed to solo in a Mustang. It was an experience like none other! Several hours after she landed, Duncan noticed that her stutter was gone. It never came back.


“We think there was confidence when she was flying,” her sister mused, “and she overcame her stuttering.”


The happy, carefree time was unexpectedly interrupted.


Gertrude’s former landlord—a man who had long held unrequited feelings for Gertrude—asked her to marry him. His niece was an orphan, and he wanted to raise the infant with Gertrude. Her father supported the idea. Adoption, he thought, would prevent the stutter (which he shared) from being passed down to another generation.


“[Gertrude] was being asked to choose between loyalty to her father and a career in flying,” her biographer concludes. “Gertrude did not give Henry [Silver] or her father an immediate answer.”


She ultimately gave in.


Gertrude did not tell her friends that she was getting married. “The atmosphere was heavy with resignation and not happiness,” her sister said of the wedding. She believes Gertrude wanted out, but “obedience was the norm” for the sisters.


After the wedding, Gertrude returned to WASPs for a brief period. On October 26, 1944, she took off from Mines Field in Los Angeles, tasked with ferrying a P-51 Mustang to the east coast.


She took off toward the ocean. No one ever heard from her again.


Gertrude’s absence went unnoticed for days. Dozens of WASPs were flying all over the country, and the processes for keeping track of them were inefficient. Finally, her failure to report to her first stop was noted. Weeks of searches revealed nothing.


Was it mechanical failure? Pilot error? The heavy haze that day? Did she deliberately run away from her marriage?


Gertrude’s family is still working to solve the mystery.


“She overcame a lot to become a WASP, and then she wasn’t afraid to show intelligence and excellence,” her great-niece says. “She was just really proving what she could do.”


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