// SHEPHERD FAMILY LEGACY // by David Proffitt

A Simple ‘Thank You’ Led to a Family Legacy — and Turned $1K into $2MM

It was January of 2018, and I was working from home during a freak snowstorm in Virginia Beach, VA, calling our donors to thank them for their recent contributions. I came across Mrs. Barbara Shepherd and a $1,000 gift she recently made to support our Nightingale Air Ambulance. 

I made the call and introduced myself from the Sentara Foundation and thanked her for her recent contribution.

I asked her, “Do you mind me asking, what influenced your gift?” She began to tell me that her daughter (also Barbara “Bobbi” Shepherd) had been a nurse executive at our Sentara Williamsburg Regional Medical Center until she was in a terrible car accident. Our Nightingale (an air ambulance service) responded to the accident and flew her to Sentara Norfolk General Hospital, our regional trauma center.

The family had to drive 60 minutes to reach her bedside. They arrived with just enough time to say goodbye as she passed away. Mrs. Shepherd continued to say, “I’ve always been so grateful to the air ambulance service because it gave us the ‘gift of time’ to keep her alive just long enough to reach her bedside and say goodbye.” I told Mrs. Shepherd that her story was so compelling that I would love to personally meet her. She replied by saying, “What day are you coming?”

Roughly two weeks later, I arrived  at Mrs. Shepherd’s home. She warmly greeted me and invited me into her sitting room. It was full of photos and memorabilia from around the world. I learned that she and her husband were personal concierge staff at a high-end resort in the U.S. Virgin Islands before moving to raise a family in Colonial Williamsburg, Va. We began to talk about her daughter Bobbi, and she asked me If I’d like to see her “memory box.”

As I leafed through the box, I came across the program for her funeral service. I noticed the date of the service and realized that in one month, it would be 10 years since her passing. I asked Mrs. Shepherd if she would be willing to let me make a few phone calls to the Williamsburg hospital to see if I could find some staff that previously worked with her daughter. Perhaps I could arrange a meeting? She was very interested in the opportunity.

I reached out to the current nurse executive at the Sentara Williamsburg Regional Medical Center and mentioned the idea. She immediately recognized the name and knew of several staff that would remember working with Bobbi Shepherd. So almost 10 years to the day of the funeral service, we invited Mrs. Shepherd and her son, Winston, to a catered lunch in Administration to meet the staff that had once worked with Bobbi Shepherd. Over a chef-prepared lunch of grilled salmon and roasted potatoes, the staff spent the next hour conveying wonderful stories and positive memories of Mrs. Shepherd’s daughter (pictured).

As I was walking Mrs. Shepherd and her son Winston to their car following the luncheon, I thanked Mrs. Shepherd again for her generous contribution to support our Nightingale Air Ambulance, but I asked if she would ever consider creating a scholarship to support the nurses at the hospital who would like to advance their careers. A $5,000 donation would allow us to “name” the scholarship in memory of her daughter to support her legacy of giving back to the community. Mrs. Shepherd said, “You’ve given me a lot to think about today—give me 30 days and follow up with me.”

In the meantime, I received the nicest handwritten note from Mrs. Shepherd thanking me for the luncheon and the afternoon of remembering her daughter through all the staff that loved working with her. She was deeply touched by the time spent.

Roughly three weeks later, I called Mrs. Shepherd. I made multiple efforts to connect with her, but there was no response. On the last attempt, her son Winston answered the phone and said how glad he was to hear from me. He began to tell me that in the weeks following our lunch together, all he heard his mother say was how grateful she was for the time spent at the hospital. Unfortunately, one recent afternoon Mrs. Shepherd was working in her garden, tripped on a stone, hit her head and had been in a coma for the last several days. He asked if I would come visit her in the hospital. I replied, “What day am I coming?”

I took Mrs. Shepherd a framed photo of the luncheon group to place at her bedside. She was awake now and resting in bed, but extremely limited by the injuries she had suffered. She fluttered her eyes as she heard my voice and squeezed my hand—but that was the extent to which she could respond. A week later, Mrs. Shepherd passed away. Her son, Winston, followed up with me to say he wanted to make the $5,000 donation for the named nursing scholarship in memory of his sister and in honor of his mother.

I followed up weeks later with Winston to establish the “Bobbie Shepherd Nursing Scholarship” for nurses who want to continue their education and certification at Sentara Williamsburg Regional Medical Center. In one of our conversations, I asked him how he was doing with settling his mother’s estate and, realizing he was the last member of the family, asked if he had established his personal estate plans. He told me the question was perfectly timed, as the issue was keeping him awake at night. He was gathering documents and bank accounts and estimated his family estate was worth roughly $500,000.

I told him I had some resources we could share through the Foundation to assist him and that he might consider a gift through his estate plans, to further support his sister’s nursing scholarship. I mentioned to him that estate gifts would qualify him to join our Sentara Legacy Society; a group of like-minded individuals who desire to give back to the community, well-beyond our lifetime. We would recognize his name on the donor wall at each of our nine hospitals throughout our region. He was quite enthusiastic about the idea as he wanted his family name remembered in the community. Roughly nine months later, Winston forwarded me the formal documentation and confirmation he had finished his estate plans. He had allocated $150,000 from his estate to support the nursing scholarship at the hospital.

Within the year, Winston Shepherd prematurely passed away from an unfortunate illness. A few weeks later, I received notification from the Executor of his estate letting me know that Winston had named the Sentara Foundation to receive $150,000 to support nursing care at the Williamsburg hospital. He went on to say that besides a few other small donations, Winston had indicated the Sentara Foundation would be the “residual beneficiary” of the estate. Meaning, once all debts, disbursements and expenses had been paid, the Foundation would receive the final balance of the estate. The Executor explained that Mr. Shepherd’s estate was worth far more than he anticipated. His mother had left several trusts associated to the deed of her house. The final worth of the entire estate that would be paid out to the Foundation was roughly $2 million dollars.

The Shepherd legacy gift will establish an endowment to support nursing scholarships in memory of Bobbi Shepherd that will give back to the community well beyond our lifetimes. The Shepherd family and their generous demonstration of philanthropy will always be remembered in our community. The experience was truly a rewarding one for me, and reminds me every day of the importance of developing strong relationships and, as a development officer, understanding the heart of our donors—for you never know where that might lead!

Barbara “Bobbi” Shepherd
Barbara Shepherd and her son, Winston, at a luncheon with her daughter’s coworkers.

David Proffitt is the Corporate Director of Development & Community Engagement for the Sentara Foundation, a division of Sentara Healthcare, a nonprofit organization serving Virginia and northeastern North Carolina. His story on the left demonstrates the power of stewardship — and it’s the perfect example of the magic fundraisers can work by using the planned giving power words “thank you.”

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