Bessie B. Stringfield, intrepid motorcyclist and storyteller
Herb Boyd | 7/11/2019, 6:55 p.m.
Gertrude Hadley Jeannette, a theater maven, was 103 when she died in 2018. Mainly remembered for founding the Hadley Players, she distinguished herself earlier when she learned to drive and became the first woman in New York City to obtain a motorcycle license.
Several years after Jeannette got her license, Bessie B. Stringfield was using her skills on the motorcycle as a civilian dispatch rider for the U.S. Army. Even more daring she often performed stunts on the Wall of Death at carnivals.
Her daredevil feats and roaring through the streets of Florida on her Harley-Davidson earned her the title of “Motorcycle Queen of Miami.”
According to her—and she had a reputation for dressing up her life with fabulous tales—she was born in Jamaica to an interracial couple and left motherless at an early age. Later, she claimed to have been abandoned by her father on a street in Boston and subsequently adopted by a benevolent Irish Catholic woman. The woman was compassionate and kind-hearted, so much so that when Bessie turned 16 she was given a motorcycle.
All of this, however, about her biography must be taken with a grain of salt since there are conflicting stories about her background. New York Times reporter Nikita Stewart summarized some of the problems related to her life, citing varying accounts from people who knew her, including Robert Scott Thomas, who said that Bessie never told him a lie. But Esther Bennett has another version. “She lied. Her mother’s name was Maggie Cherry. Her father was James White.”
Bennett, Bessie’s niece, said Bessie’s parents were both Black Americans who lived in Edenton, N.C. Records confirmed her account. “I don’t know anything about Jamaican,” Bennett related to Stewart. “She was never adopted.” Her niece’s memory of her aunt was confirmed by Bessie’s death certificate when she died in 1993, noting that she was born in March 1911 in Kingston to James Richard White and M. Cherry, “a conclusion drawn by an attorney for her estate, according to a Social Security index, she was born in March 1912,” according to Stewart’s story.
Bessie’s biography may be in dispute—and she was apparently a mistress of reinvention. Some of her motorcycle legend is verifiable, so much so that nearly 10 years after her death she was inducted into the Hall of Fame of the American Motorcyclist Association in 2002. Again we turn to Stewart’s profile, in which in Bessie’s tales, “she always came out on top by proving herself or by finding common ground. She told people that she won over a white Miami police officer by demonstrating her riding skills. She told people that she was followed through back roads by an angry white mob, yet she outran them and then found a kind white gas station owner who allowed her to fill up her tank free. There was also folklore passed from one generation of relatives to the next that Stringfield had worked for the Federal Bureau of Investigation, and perhaps, she had disappeared to protect them. The stories were outrageous enough to ring true. Only Stringfield knew if they really were.”