Through the Kenneth T. Whitescarver III Memorial Scholarship, a young man’s commitment to service reveals the lasting impact of one community leader’s generosity.
Sometimes the most meaningful connections in a community are the ones we never expect.
When Jack Schaffer applied for the Kenneth T. Whitescarver III Memorial Scholarship through The Community Foundation of the Rappahannock River Region, he shared a deeply personal reflection about the experiences that shaped his character, his commitment to service and the lessons his mother taught him about generosity.
Among those experiences, he mentioned a local program called Kenny’s Closet, a resource he had come to know through his mother’s work at Mary Washington Healthcare.
For Rosalind “Rozzie” Whitescarver, who established the scholarship in memory of her late husband, Kenneth “Kenny” Whitescarver, that mention carried special meaning.
Kenny’s Closet was named in honor of her husband following his passing from cancer in 2012.
It was an unexpected connection between a young man’s journey of service and the legacy of someone who had devoted much of his life to caring for others. And it offered a beautiful reminder of how generosity can continue to influence lives long after someone is gone.
Where a Commitment to Giving Begins
For Jack, the importance of helping others was something he learned long before he understood the meaning of philanthropy.
His mother, Gin Schaffer, built a career in healthcare and served as the Integrative Medicine Coordinator at Mary Washington Healthcare’s Regional Cancer Center. She was also a cancer patient herself.
When Jack was just six years old, his mother’s cancer returned. During a time when Gin was facing her own difficult medical journey, she continued helping others who were navigating similar circumstances.
Rather than shielding her children entirely from the realities of illness, Gin wanted them to understand the importance of compassion, dignity and community support. She believed that giving back was not simply something to talk about, but something to practice.
“My mother instilled in me the importance of love and generosity very early in my life,” Jack wrote in his scholarship application. “I was 6 years old when her cancer returned and I watched her help others with cancer while she was fighting it herself.”
Through his mother’s work and his own experiences as a junior volunteer at Mary Washington Healthcare, Jack saw firsthand how meaningful it could be when someone took the time to help another person.
He also learned that not everyone facing illness has the same access to healthcare, resources or support.
Those early lessons inspired Jack to find ways to give back himself.
As a child, he organized a Valentine’s Day gathering where participants made cards and collected items for St. Jude Children’s Research Hospital. His family then rented an RV and traveled to Memphis to deliver the donations.
“I will never forget that experience and I have been dedicated to helping others, especially children ever since,” Jack shared.
As he grew older, his commitment to service grew with him.
Jack became involved in Vacation Bible School as a leader, mentor and volunteer. He organized friends to participate in food bank initiatives, including a Canstruction project that collected diapers and wipes for families in need. He also participated in the Community Foundation’s Youth in Philanthropy program, gaining a deeper understanding of community needs, charitable giving and the responsibility young people have to make a difference.
But Jack’s character was shaped by more than his volunteer experiences.
During his sophomore year of high school, his family was displaced by a house fire. Living temporarily in hotels and other people’s homes taught him lessons about gratitude, resilience and self-reliance.
He credited his parents with helping him navigate those challenges while continuing to succeed academically and as a student athlete.
Through each experience, Gin and her family reinforced a simple belief: circumstances may change, but the way we treat others and respond to adversity is a choice.
Those are the very qualities the Kenneth T. Whitescarver III Memorial Scholarship was created to recognize.
Honoring a Man Who Believed in Taking Care of Others
Kenneth “Kenny” Whitescarver was a beloved Fredericksburg community leader whose life reflected an extraordinary commitment to family, friendship and service.
A graduate of James Monroe High School, Kenny went on to earn degrees from the University of Richmond and the T.C. Williams School of Law. He served in the United States Army, practiced law and built a successful career in banking, eventually retiring as Senior Vice President at StellarOne Bank.
Yet those who knew Kenny remember him just as much for his generosity as for his professional accomplishments.
He was an active community volunteer and leader, serving on the Board of Governors of The Community Foundation of the Rappahannock River Region and supporting organizations including Rappahannock United Way, the Fredericksburg Rotary Club, Boy Scouts, the Chamber of Commerce and numerous other civic initiatives.
For Kenny, community service was not an occasional obligation. It was a way of life.
He was raised in a family that emphasized community involvement, and he carried those values into his own relationships and leadership.
Kenny and Rosalind were high school sweethearts who shared a joyful and fulfilling life together. Friends and family remember him as a devoted husband, an avid outdoorsman and someone who was always willing to lend a hand.
Following Kenny’s passing in July 2012, Rosalind established the Kenneth T. Whitescarver III Memorial Scholarship Fund at the Community Foundation to ensure that his values would continue to inspire future generations.
Each year, the scholarship recognizes at least one graduating senior from James Monroe High School who demonstrates hard work, self-sufficiency, love, generosity and strong personal character.
More than an award for academic achievement, the scholarship celebrates young people who understand that good citizenship is contagious and who lead by example.
For Rosalind, Jack’s application reflected those values in a particularly personal way.
His experiences volunteering, his mother’s influence and his resilience spoke directly to the qualities Kenny had demonstrated throughout his life.
And his mention of Kenny’s Closet connected those values to another part of Kenny’s enduring legacy.
Kenny’s Closet: A Dream That Became a Lifeline
Before Kenny passed away, he had expressed a desire for a local resource dedicated to supporting individuals who needed ostomy supplies.
An ostomy is a surgically created opening that allows waste to leave the body following certain medical procedures, often related to cancer or other serious health conditions. People living with an ostomy require specialized supplies for everyday care, and those products can be costly, particularly for individuals with limited financial resources or inadequate insurance coverage.
Kenny understood the importance of making those supplies accessible to people who needed them.
In January 2013, just six months after his passing, that vision became a reality.
Kenny’s Closet opened through the collaborative efforts of friends, healthcare professionals, volunteers and members of the Fredericksburg Area Ostomy Connection Support Group, working alongside Mary Washington Healthcare.
Among those instrumental in bringing the program to life was Barbara Kane, who has remained an active volunteer and leader since its beginning.
The program collects donated, unused ostomy supplies and distributes them free of charge to individuals throughout the greater Fredericksburg region and surrounding counties. Kenny’s Closet remains under the United Ostomy Association of America (UOAA) and its 501c3 charitable designation.
What began as a small community initiative has become a meaningful source of practical assistance and personal support for people managing complex medical needs.
From 2013 through 2025, Kenny’s Closet recorded approximately 2,845 visits, serving 705 individuals. These figures represent far more than supplies distributed. They reflect thousands of moments when someone facing a medical challenge found help, reassurance and a community willing to care.
Even during the COVID-19 pandemic, Kenny’s Closet never completely closed. Volunteers and healthcare partners adapted their operations to ensure individuals could continue accessing necessary supplies.
The program is volunteer-driven, demonstrating what can happen when community members recognize a need and work together to address it.
In a written account documenting the program’s beginnings, founding volunteer Gail Erickson described Kenny’s Closet as a collaboration of friends carrying forward Kenny’s philanthropic spirit.
That spirit remains at the center of the program today.
Kenny’s Closet is also an example of the interconnected network of care throughout the Fredericksburg region, where healthcare providers, nonprofit organizations, volunteers and neighbors work together to make resources accessible to those who might otherwise go without.
It is a testament to Kenny’s belief that caring for others should never depend on whether someone has the financial means or personal connections to find help.
A Legacy That Continues Through Others
When Jack learned he had received the scholarship, he had the opportunity to meet Rosalind and hear more about Kenny’s life, including his own years at James Monroe High School and his dedication to the Fredericksburg community.
For Jack, it was an opportunity to better understand the person whose values the scholarship represented.
For Rosalind, it was an opportunity to see those values reflected in a young man preparing for his next chapter.
And for Gin, whose commitment to philanthropy helped shape Jack from childhood, the recognition affirmed the importance of teaching the next generation to care for others.
Their stories are different, but they share something fundamental.
Kenny believed in helping people, whether through professional leadership, charitable involvement or the simple kindnesses that define a person’s character.
Gin believed in teaching her children those same values, even while navigating her own health challenges.
And Jack has taken those lessons into his own life, finding ways to serve, lead and encourage others to give back.
As Jack prepares to continue his education at the University of Massachusetts Amherst’s Isenberg School of Management, where he plans to study finance or business management, he carries with him the experiences that shaped his understanding of community and service.
The scholarship will help support his educational journey, but its meaning extends beyond financial assistance.
It connects a young person committed to making a difference with the memory of a man who spent his life doing the same.
That is the lasting power of philanthropy.
A scholarship established in someone’s memory. A medical supply program created from a community leader’s dream. A mother who teaches her child to care for others. A young man who carries those lessons forward.
Individually, each represents an act of generosity. Together, they demonstrate how a community becomes stronger when people invest in one another.
Kenny Whitescarver’s legacy is not measured only by the organizations he served or the accomplishments of his lifetime. It lives on through the people who continue to benefit from his generosity and through young leaders like Jack, who are carrying those values into the future.
Because the greatest legacy we can leave is not simply what we give, but what we inspire others to give.
The Kenneth T. Whitescarver III Memorial Scholarship Fund is one of the many charitable funds administered by The Community Foundation of the Rappahannock River Region, helping preserve the legacies of generous individuals while investing in the next generation of community leaders.