Viola Gentry: The Flying Cashier (1894-1988)
By: Jennifer Bean Bower
Viola Estelle Gentry was born in Rockingham County, North Carolina, in 1894. In her early years, she endured a strained relationship with her stepmother and a monotonous job in a cigar factory. At the age of 16— to break free from the two—Gentry ran away from home and attempted to join a circus in Greensboro. When the plan failed, she and her young boyfriend eloped.
Because of Gentry’s age, the marriage was dissolved, and she was sent to live with family members in Florida. There, without permission, Gentry took her initial jaunt through the clouds. For the first time in her life, Gentry felt alive—free from Earthly burdens—and she became fascinated with flight. Her interest, however, was suppressed rather than nurtured. When Gentry landed, she received a “sound spanking” for the escapade and soon after returned home.
A few months later, the United States entered World War I and Gentry was sent to live with friends in Connecticut. To support the war effort, Gentry found work in an ordnance department and sold Liberty bonds. When the war was over, she volunteered with the American Red Cross, traveled to San Francisco, California, and witnessed the event that changed her life.
On a pivotal day in July 1920, Gentry watched in awe as a stuntman landed his airplane on the roof of the tallest hotel in San Francisco. In one breathless moment, her destiny was revealed.
Gentry recalled how she had felt in the air and declared that she would part the clouds.
And soon after, she did.
Gentry’s appetite for all things flight-related became insatiable. She attended lectures, read books and saved money to take a flying lesson. When she had the amount needed, Gentry arranged to meet an instructor. But her enthusiasm to fly was dampened—albeit not extinguished—by the words of her male flight instructor who said: “A woman should not fly, but should stay home, get married and raise a family.”
Of course, Gentry did not agree with his sentiments, so she packed her bags and headed to New York. She was convinced that the East Coast offered better opportunities for women interested in aviation and—at least in her regard—she was right. In 1924—while working two jobs—Gentry learned to fly. The following year, she soloed; and in 1926, she flew underneath the Brooklyn and Manhattan bridges. The stunt was front page news and Gentry—who the press dubbed “the flying cashier” because of her position in a local restaurant—was an instant celebrity. Not everyone was impressed with her aerial achievements. According to a relative, Gentry’s parents felt her “activities were so unladylike that…she had disgraced the family.”
Although Gentry was likely disheartened by her family’s opinion, it did not stop her from flying; and in 1928, she set the first officially recorded women’s solo endurance flight record. That same year, she also became the first federally licensed female pilot from North Carolina.
Gentry soared in the spotlight of an admiring nation and sought to achieve even greater feats. In 1929, she and John W. Ashcraft endeavored to set a new refueling endurance flight record. The two intended to fly 174 hours or longer, but fog and an empty fuel tank sent them to the ground.
Ashcraft—who was at the controls—died instantly. Gentry survived, but her injuries were so severe that she remained in a hospital for more than a year.
Throughout her recovery and in the years that followed, Gentry married; became a charter member of the Ninety-Nines; laundered clothes for Harold Gatty and Wiley Post when they flew around the world; supported women’s rights in aviation; presented lectures; and welcomed Amelia Earhart back to New York after her famous flight across the Atlantic. She competed in air races; helped preserve the history of early aviation; received numerous awards; and continued to fly until cataracts permanently grounded her in 1975.
On June 23, 1988, at the age of 94, Gentry folded her wings. When she died, there were no large gatherings or grand speeches from famous men and women. No words could have defined her life better than two sentences printed in the Danville Register & Bee.
In her death notice, the author proclaimed that Gentry “wanted to fly airplanes. And fly she did.”
Jennifer Bean Bower is an award-winning writer, native Tar Heel and graduate of the University of North Carolina at Greensboro. While working as the associate curator of photographic collections at Old Salem Museums & Gardens, Bower researched local tragedies and composed the book Winston & Salem: Tales of Murder, Mystery and Mayhem.