#CeaselessDevotion: Diane Wynter ’74

Monday, January 27, 2020
Diane Wynter ’74

During Family and Alumni Weekend 2019 at a celebratory dinner for the 30th anniversary of the Black Student Union, the Mercersburg community honored Diane Wynter ’74, the first black female graduate of Mercersburg Academy. Tonya Rutherford ’90, founder of the BSU, read the inscription on the award: “With our deepest gratitude, we stand on your shoulders. Thank you for coming before us and laying the groundwork for excellence.”
Wynter wonders why she would receive such attention, but as she demonstrated that night, she is a trailblazer whose story needs to be shared. “I came to Mercersburg with wounds,” she told her audience. “These wounds were voices in my head that said that I’m not smart enough, and I’m not good enough. Mercersburg is a magical place. It really is … but when you are walking around with wounds, it is possible that you are not soaking up all of the goodness. Unfortunately, sometimes what happens is in this environment, those wounds are amplified.”
Wynter was born in Jamaica, and grew up in Manhattan. “I don’t have a recollection of a nuclear family,” she says. “I have a recollection of my mother being a single parent, working in the night.” During her grade school years, she lived with her mother, brother, aunt, and three cousins in the Washington Heights neighborhood. For her junior-high years, her mother moved the family to the lower east side to an area called Alphabet City, and Wynter attended the High School of Fashion Industries.
Wynter’s background qualified her to take a test with A Better Chance, a nonprofit organization that helps talented young people of color attend high-achieving schools in the United States. She passed the test and was accepted to Mercersburg. “I was thrilled,” she says, “and as preparation, they had all of the ABC students go to Carleton College in Minnesota for two weeks of training to help us get used to being in an academy.”
In Minnesota, she met students from all over the United States and bonded with some who would be her future classmates, including Earl Dawson ’75 and Royce Sisk ’75. Wynter describes the preparation at Carleton College as helpful, but it did not mitigate the culture shock she experienced when arriving at Mercersburg.
“I learned about sports that I had never heard of in my life like squash and lacrosse,” she says. “What was that? I was exposed to so many things that I never would have experienced on the lower east side, but it was definitely a challenge. I started feeling the tugs of being academically disadvantaged pretty early on, and I tried my best to keep up.”
A highlight of her academic career, Wynter remembers a creative writing assignment for Karl Reisner’s English class where she had to describe how the moon looked: “It was something so simple, but he went crazy over this thing, and it was just so enchanting to be appreciated in some academic way along my journey.”
Mercersburg is known as a college-preparatory school, but for Wynter, her path did not lead immediately to a college degree. As she told her audience at the dinner, “I felt like a failure because I was not able to go right from high school, from Mercersburg into college. I carried this around for a long time. I had a college adviser who knew nothing about providing a scholarship student with financial aid, so even though I got accepted into college, I was already getting bills for dorm fees, and my parents, unfortunately, had nothing to contribute.”
When she graduated from Mercersburg, she began working full time and attending Bronx Community College. During her first semester, on her way home from class one night, someone followed her off the subway and mugged her at knifepoint. That was the end of her first college attempt. It would take her 19 years, four colleges, and four majors to ultimately secure a bachelor’s degree, but she didn’t stop there. As she told her audience, “The bottom line is that I did get my bachelor’s. I just took the scenic route, and life happened in the interim. Three years after that, I got my master’s.”
Along her journey, she became connected with Toastmasters, an international organization that promotes public speaking and leadership skills. Her talent, self-confidence, and poise were clearly evident as she spoke at the BSU dinner, a speech that was—in a way—45 years in the making.
Her return to Mercersburg for Family and Alumni Weekend was the first time she had been back on campus since graduation: “One of the most wonderful things that I did was I sat outside on the dining room balcony for a couple of hours and [watched the campus go by]. It was delightful to sit there and think about the old days and think about how far it’s come.”
From her own experience, she is keenly aware of the importance of students finding and reaching out for help and support along the way and also the importance of communities being vigilant to find those individuals who may need help but not even know where to look for it or how to ask.
“In a few of my Toastmaster speeches, I have told my public that my theme in life is ‘If you need help, get help,’” she says. “When I was in Mercersburg, I was not particularly religious, so going for walks in nature in that beautiful campus helped soothe my mind, and sitting in the Chapel helped soothe my mind.” She returned to the Chapel when she came home to Mercersburg.

Tonya Rutherford ’90 and Diane Wynter ’74

As Wynter reflected on her journey, she told her audience at the BSU dinner that “what seemed like I had academic challenges when I was here, when I got to college, [it was] smooth sailing. It was effortless as I made the dean’s list every semester and graduated magna cum laude. All of that was ingrained in my DNA while I was here. So, today I say, to all of those voices in my head that said that I’m not smart enough, I’m not good enough, I say, ‘Shut the heck up!’”

View this video of Wynter’s speech at the BSU dinner.

Wynter is also quick to add, “I am most grateful to Tonya Rutherford ’90, the BSU, and Cecil Swift ’73 for bringing me back home to Mercersburg.”
Looking forward, Wynter will be raising her voice in support of Mercersburg’s conversations surrounding diversity, equity, and inclusion, and she will be a frequent face at regional events in New York City, nearer to her home in New Jersey. As she said in her speech, “I’m so glad … to come back here after 45 years of being away, and now you might be seeing me regularly.” We hope we do.

Editor’s Note: Diane Wynter ’74 is one of several Mercersburg community members featured in the Winter 2020 issue of Mercersburg Academy magazine. To meet other members of the Mercersburg community and enjoy all the content of this issue, visit mercersburg.edu/magazine