With her infectious smile, indefatigably sunny demeanor and characteristically musical Mid-Atlantic diction, Jean Winston is taking Downtown South Boston by storm.
Her presence throughout the district — whether via her daily walks or at any given public event — is so ubiquitous that some have taken to calling her “the Duchess of Downtown.”
“She really is the Duchess of Downtown,” said friend and Factory Street Brewing Company proprietor Lisa Francisco. “It just fits her so perfectly!” she exclaimed.
Winston said she has “fallen in love” with downtown since she began venturing in that direction five years ago. It all began with her favorite pastime of walking.
“I love, enjoy and live to walk everyday,” Winston related. “I have always walked; as a matter of fact, all my life, even — thank God — now.”
It was through these daily walks that Winston seized the opportunity to get to know her hometown better after a decades-long tenure in New York City.
“South Boston is such a wonderful and beautiful small town,” she said with adoration. “Quiet, things to do, places to go, people to meet and greet, no matter where you may go.”
Winston inspires locals as much as her beloved downtown inspires her.
“She brings such a different perspective on her life and the things that she’s done, and she’s made me realize that nothing is unattainable,” said Mark Shawn Anthony, a local artist and friend of Winston.
Winston especially loves volunteering at The Prizery — an activity that gives her opportunities to stay connected to the arts as well as community members.
“I am excited beyond words when I volunteer at The Prizery,” she shared. “It gives me wonderful pleasures of welcoming, greeting, assisting and serving beautiful people who come through the doors for entertainment—a fabulous way to spend an evening!”
Melanie Jannotta, of The Prizery, is impressed by Winston’s dedication.
“She is very welcoming. In fact, she has such a great personality that a lot of times we use her as a greeter at the front door,” Jannotta stated. “She really has an amazing spirit for the community, and she is so supportive of not just The Prizery, but of all the local events that are happening.”
Winston also shares her talent with the community by singing in the First Baptist Church (Main Street) choir.
“I am so thankful to God that He allows me to use my voice at First Baptist Church,” she stated with gratitude.
Through this activity, Winston gets to use her craft of singing — which she honed during her years working in show business in New York City.
‘A city girl’
Winston did not choose to move to New York; rather, the adults in her life made the decision for her, so that she could live with her mother.
“One day, I was told that I was going to live in New York,” she recounted. “I don’t recall exactly how I reacted. I didn’t fuss about it.
“All I knew was that we were going to be with mama,” she continued.
Winston then lived with her mother and siblings in the Bronx, New York.
She made a “clean break” from her life in Halifax upon moving.
“When I left all that I knew as a child to go to my new home in New York, I put away the old,” she shared, specifying that she did not write or call childhood friends. She was ready for new adventures and the opportunity to pursue her dreams.
A natural-born creative, Winston knew that these dreams would lie in the limelight of show business.
“I knew I wanted to be in show business,” she confessed.
Even as a child growing up in South Boston, Winston loved to sing most of all.
“I always sang in the glee clubs at schools and churches, all in the four parts of the natural voice,” she elaborated.
Her desire to succeed in show business propelled her to study the performing arts and communication skills to hone her craft in a highly competitive industry.
“I studied voice, elocution, diction, acting, dance,” she listed. “The elocution was one of my favorites because I could not speak clearly to be understood. It was the nasal southern accent.”
Winston often experienced speech correction due to her accent, and this motivated her to learn proper diction and to speak “the King’s English.”
Winston studied standard English diction and elocution with Alice Hermes at New York’s H.B. Studio, and she studied privately with Madeleine Marshall, who taught singers voice control at the famous Julliard School of Music.
“I moved to change my speech pattern. It soon must have shown up, because I no longer heard speech correction,” she explained.
Upon adopting her Mid-Atlantic diction, Winston said many reacted to her strangely, as though surprised to witness an African American woman communicating in the traditional elevated style.
She recounts an episode in which Hermes defended her to classmates.
“My teacher Alice Hermes lovingly explained to the class that it was because I was born in Virginia — the 13th colony — that I was able to speak the King’s English so easily,” she recalled. “It was proud news to my ears.”
To this day, people react in various ways to Winston’s unique style of elocution. These days, many will ask if she is of Caribbean origin, assuming that this accounts for the melodic difference in her speech.
These and other false assumptions do not bother Winston, as she learned resiliency by working in show business in New York.
“Well, because I was in show business, it taught me strength in rejection,” she explained.
She offers astute counsel to others who face rejection in life: “Continue to try as though you have not been rejected. Go for it as if you have won.”
Winston’s hard work and dedication paid off, as she worked successfully as a singer and performer for many years. How many years exactly is something that she keeps to herself, for fear of offering clues to her most tightly kept secret — her age.
“I sang in night clubs, acted on stage, sang Gershwin on the cruise ship The Rotterdam. I fell in love with ‘Rhapsody in Blue,’” she fondly recalled.
Her life and career afforded her opportunities to travel to England, Paris, Copenhagen, Sweden, Spain, Mexico, Nassau, Bahamas and Bermuda.
Winston is especially proud that famous jazz critic John S. Wilson, of The New York Times, appreciated her singing, comparing her to Ella Fitzgerald in one of his coveted reviews.
Overall, her time in show business taught her confidence, poise and how to assert a presence.
“I knew early on that I belonged wherever I wished to be,” she continued. It is this attitude that inspires her to seek diversity, novelty and joy no matter what the context, or how “different” she may appear within it.
Winston ultimately left the showbiz scene in New York due to a religious conversion, which precipitated perceptions that the industry was morally corrupted and no longer something that she wanted to be part of.
“Somewhere along the way, there was so much missing in life, and I began to search for Jesus,” she revealed.
Winston explored several avenues seeking spiritual fulfillment before learning about the Christian faith from Harold Camping of Family Radio.
Finding Christianity prior to moving back to the Halifax area was undoubtedly helpful to her, as so much of the local cultural offerings revolve around church life. Still, Winston had quite an adjustment to make when she returned home from “the Big Apple.”
“It has been and was a culture shock, returning to South Boston,” she admitted.
Coming out of her shell and finding purpose
Although known for her gregarious extraversion, Winston did not immediately begin participating in the downtown scene when she first moved back to the area from New York upon her retirement. She regretfully admits that this was in part due to fears that stereotypes about racism in the South were true.
“When I first moved here, I had been told that white people were prejudiced,” she revealed. “And I never sought to find out on my own, and I was never sure,” she continued.
Winston shares that, though she lived in South Boston when race relations were much more strained in her youth, her life in New York was so different in that she was surrounded by diversity.
“I had worked with people from all over the world,” she related.
In such an environment, Winston’s race became a non-issue — especially in the creative circles that she preferred to occupy.
“When I realized I was going to come back to live here, I didn’t think about all of a sudden I would be with only one race of people,” she expounded.
Winston largely stayed with her family and within the familiarity of Black spaces when she first moved back.
She further reports that the COVID-19 pandemic pushed her deeper into self-isolation.
“With COVID, I think I just sat around and actually did nothing and thought, and I guess wondered, ‘What do I do, what did we do?’” she recounted. “We really didn’t go anywhere, couldn’t go anywhere, were afraid to go anywhere.”
As a means of keeping her sanity, Winston continued her lifelong habit of walking. However, by this time, the psychological toll of the pandemic catalyzed her to finally venture downtown to see “the other side” of South Boston.
She began hanging out at places like The Busy Bean and Factory Street Brewing Company and getting to know shopkeepers and passers-by throughout the downtown district. She was surprised by how well-received she was.
“All the long it didn’t matter, but I didn’t know because I had listened to others,” she lamented.
In some ways, Winston made her local “big debut” earlier this year at the dedication of the Diamond Hill monument to slaves who worked at the Berry Hill plantation — an event that coincided with Juneteenth, an African American holiday celebrating the end of American chattle slavery.
A descendant of Lucy Alderson — one of the best-known Berry Hill slaves — Winston gave remarks at the event.
“It is with much love for my ancestors that I am here at Diamond Hill today,” Winston orated. “It is so marvelous to be the great-great granddaughter of Lucy Alderson.”
Winston is proud of her heritage as well as the depth of knowledge that she has gained through researching her ancestry. She hopes that more African Americans will follow suit and learn about their heritage.
Winston also hopes to see more local Black folks involved in the downtown scene, particularly during community events.
A true “crossover personality,” Winston frequently finds herself being “the token” Black person at events or at informal gatherings. It’s a moniker that she accepts without grief, as she feels that she is doing her part to help integrate the community.
“A ‘token’ for me is to be especially trustworthy, being the first and only one different from others and not fearful,” she explained.
Winston sees herself as forging a path for others to follow, and she hopes that her own experiences with crossing the divide will help to deconstruct outdated lines of separation.
“They believe that white people are prejudiced. But, all white people are not prejudiced,” she explained matter-of-factly. “There may be some, but those you just overlook. You recognize it’s there, but you move on with your own life,” she elaborated.
She acknowledges, however, that the history of racism and prejudice in the Halifax area continues to manifest as de facto or voluntary self-segregation in this generation.
“I suppose they probably have been through more than I will ever go through, because I left this place, and I became free when I went to the city,” she emphasized. “I was able to go anywhere I wanted to go and do what I wanted to do.”
Winston feels that prejudicial attitudes have largely shifted in a region that is increasingly diversifying, but that the behavioral pattern of self-segregation remains in large part due to tradition and old habits.
“I believe that that’s what the [Black] people believe in their hearts, and they won’t let go,” she said, speaking of racism.
Winston has greater hope that the younger generations of local African Americans may follow in her footsteps to create a truly integrated community.
“I hope that the young people see in time as they grow, when they become young adults or even teenagers, and will want to do what I’ve done,” she shared with a sparkle of optimism.
For people of all demographics, the Duchess of Downtown has sage counsel.
“It’s our old town. Love it, enjoy it — it’s your town. See you soon!”
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