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Sydney Bailey, a writer and NHHS theater teacher, dies at age 35


Sydney Katherine Bailey, a brilliant writer, beloved high school theater teacher and courageous survivor, died on Sunday, May 14, after a six-and-a-half-year battle with brain cancer. She was 35.

She was a brilliant writer, a beloved theater teacher, the absolute best nephew aunt, and above all else, an amazing mother.

Born in Miami, Sydney spent most of her childhood in Hendersonville, where her parents were intimately involved in the Flat Rock Playhouse. Her late mother, Wendy Wilkins Bailey, performed all along the East Coast for the first eight years of Sydney’s life, primarily jumping between Disney World and Flat Rock Playhouse, where she was a crowd favorite and her husband, Bruce Bailey, worked as a production manager and set designer. Having been raised by thespians certainly helped shape her craft, but the simple truth is that Sydney was born to be an artist.

She knew more loss in her life than most young people. She was just 11 years old when her mother succumbed to cancer in 1999, and 27 when she lost Bailey, her adoptive father, who died in 2015 at age 60 when his heart stopped suddenly.

Sydney attended New York University’s Tisch School of the Arts, where she received her degree in dramatic writing in December of 2009. Sydney had the effortless ability to write what she knew and turn it into something beautiful. Sydney’s inherent wisdom was rare and the kind that will live on forever in her words that she so generously left behind.

In the fall of 2013, Sydney became the theater teacher at North Henderson High School, where she left a legacy. She was involved in her students’ lives more deeply than as a teacher alone. She was a confidant, mentor, safe space and friend. The fact that Sydney was responsible for changing children’s lives was abundantly clear. Some of them went as far as to say that she saved their lives.

In addition to Wendy and Bruce Bailey, Sydney was preceded in death by her grandparents, George and Teal Wilkins; uncle, George Wilkins, Jr.; and cousin, Christopher Wilkins.

She leaves behind the light of her life, her daughter, Hayes Wilkins Bailey; loving husband, Jeffrey Thompson; father Riccardo Hernández; Bonus Mom Julie E. Smith; siblings Katie Bailey, Molly Bailey, Teo Hernández and Lucas Hernández; brother-in-law, Andrew Sigmon; nephews, Luke Collazo, Jude Collazo, Callum Bailey Enzor; countless wonderful aunts, uncles and cousins, lifelong friends, students, Hot Dog Queen Gretchen Weiners and Fairy Godmothers Allison, Amycoco and Kk.

A special place will always be held for Dr. Navin Anthony. The family will never forget the care and kindness he and his team provided for our Syd.

There will be a celebratory gathering to honor Sydney’s life in the near future.

In lieu of flowers, the family suggests memorial contributions be made to The Preston Robert Tisch Brain Tumor Center at Donations can also be made by mail. Checks should be made payable to the Tisch Brain Tumor Center and sent to The Preston Robert Tisch Brain Tumor Center, DUMC Box 3624, Durham, North Carolina 27710. Donations may also be made to the Hayes Wilkins Bailey education fund at: