From Orphan to Icon: Mama Ann Bailey Celebrates 100 Years of Strength, Grit,and Grace

Ann W. Bailey, affectionately referred to as “Mama Ann” throughout North Carolina, will turn 100 on June 21, 2025. For most people, living to be 100 years old would be a significant achievement, but for Mama Ann, it’s just another milestone in a life characterized by fortitude, foresight, and unwavering resolve.

Heartbreak was the starting point of her path to become Nash County’s first female business owner. Ann, who was born during the worst of the Great Depression, lost her father to TB when she was just two years old. Her grandfather and mother passed away within a few years of one another. When she was eight years old, she was placed in the Oxford Orphanage, where she discovered that perseverance may heal—or at least sustain—a broken heart.

“I cried for a solid week,” she once recalled. “I felt like I was thrown away.”

However, Ann’s spirit was indestructible even as a little child. She developed the intense work ethic that would ultimately characterize her legacy by giving her responsibilities her whole attention.

When Ann was eighteen, she met Clyde Bailey, Sr.—a calm watch repairman with blue eyes, black hair, and a starched white shirt—on the eve of starting at Atlantic Christian College (now Barton College). They got married in Goldsboro, where they spent their honeymoon on cots in the trainmen’s quarters after their romance started over boardinghouse dinners. It wasn’t glitzy, but it belonged to them.

Clyde and Ann established Bailey’s Fine Jewelry in Rocky Mount’s downtown in 1948. She worked alongside Clyde, learning how to run a business and repair watches, and was a full-time working mother, which was uncommon in those days. They didn’t go on holidays. They didn’t seek assistance. One component at a time, they merely constructed something.

Then tragedy happened once more.

At the age of 46, Clyde unexpectedly died, leaving Ann a widow at 36 with two little children and a company that many believed could not thrive without a man running it. The men in town even wagered on the closing time of Bailey’s. However, as Ann famously stated:

“They don’t know this girl!”

Mama Ann wouldn’t fold. She worked in the store six days a week, and on Sundays, after church, she handled the books. She established the company, reared her kids, and subtly disproved all the skeptics. She gradually expanded Bailey’s from that tiny, 11-foot-wide storefront to become one of North Carolina’s most well-known family-run jewelry companies, now employing close to 300 people across five sites.

Ann never stopped moving—even when she eventually took a lunch break for the first time in her life in 1978, marking her official retirement. She visited the Taj Mahal, took a cruise to Alaska, and explored national parks on her global travels. She liked to say that sleeping was a waste of time. She frequently joked that:

“Go” was her middle name.

Many people have praised her narrative and accomplishments. In 2017, Mama Ann garnered standing ovations for her stirring speech and was given the Triangle Business Journal’s “Women in Business Award.” She has been honored by the Nash County and North Carolina Business Owner Halls of Fame, and she has been highlighted in Our State Magazine. But she never lost sight of her beliefs or her heritage.

Mama Ann, a dedicated member of The Eastern Star and a founding member of Edgemont Baptist Church, attributes her longevity to continuing to be active, taking care of herself, and maintaining her faith in God. Her favorite quotes, which are reflected in the walls of every Bailey’s store, reflect her wisdom:

• “If the Lord gives you a good day, you better not waste it.”

• “I’ll sleep when I’m dead.”

• “You can’t sell from an empty wagon.”

• “It doesn’t pay to underestimate some women.”

The third generation of Bailey’s is still being run by her children, Clyde Jr. and Cindy, and their offspring, with the same zeal and dedication that Ann instilled in them from the beginning.

On June 19, from 4 to 6 p.m., Bailey’s Fine Jewelry will throw a party in her honor at the Rocky Mount store to commemorate her 100th birthday. All are welcome to join in the celebration, eat cake and ice cream, and pay tribute to the woman who made it all possible—including friends, family, loyal customers, and admirers.

Mama Ann’s journey from a young child left behind during the Great Depression to a trailblazing businesswoman who contributed to a community’s transformation is not merely one of survival—it is one of triumph. She didn’t simply keep moving forward; she continued to create, give, and shine.

And her legacy’s light is stronger than ever now, a century later.