A Vision for a Better Tomorrow

The Bailey family has been deeply rooted in Winston-Salem for more than 100 years, with close ties to the neighborhood surrounding Reynolda Road and what is now Wake Forest University. Today, Wesley Bailey is celebrated for his esteemed career as a lawyer, but his legacy goes well beyond the courtroom. A true Winston-Salem man, Wesley is known for being one of the longest running members of the Moravian Easter Band in Old Salem, and a founding director of Arbor Acres Methodist retirement community where he now resides.

When Wesley began his private practice in 1955, lawyers were expected to oversee a variety of civil and criminal matters. Back then, it was typical for Wesley to have his hands in capital cases, business disputes, will caveats, or real estate transactions in a given week. After serving on the North Carolina General Assembly and the Judicial Council of the worldwide United Methodist Church, Wesley began to think differently about his practice, focusing more on his knack for forming meaningful relationships by helping people with their wills and estate plans.

"By partnering with The Winston-Salem Foundation, almost everyone can create a legacy and help make a bigger impact in their communities by pooling their funds with other."

Wesley’s partnership with The Winston-Salem Foundation began in the 1980’s, around the time when R. J. Reynolds tobacco company was bought out by a private equity firm. Many long-time Reynolds employees had company shares, and when the buyout happened, they sought guidance on how to handle the proceeds with care and intention. Wesley was pivotal in connecting folks with the Foundation, where they could explore charitable tools to fit their circumstances and benefit the community in the future. “I would help spark the idea for people and I could trust the Foundation to work out the details and make it happen,” said Wesley.

Since that time, Wesley has helped link millions of dollars to charitable causes through the Foundation. All the while, inspiring his own son, David, to follow in his footsteps. “Dad’s idea, which was a good one, was to help people live on through philanthropy,” said David. “People feel a great satisfaction and sense of accomplishment in knowing that a fund established at the Foundation will bear their name and support the community in perpetuity.”

David Bailey joined his father’s practice in 1982, where he developed a hands-on approach to working with clients, driven by a desire to really get to know the people he works with. “I like to say our clients are our friends, and our friends are our clients,” said David.

Though the charitable landscape has changed since his father’s heyday, David’s love of learning and connection keep him centered in finding the best solutions for his clients. “Back in the old days, only the wealthy could establish a charitable fund because of the high cost and expense of administration,” said David. “By partnering with The Winston-Salem Foundation, almost everyone can create a legacy and help make a bigger impact in their communities by pooling their funds with others.”

When David works with a client who has charitable intentions, but is unsure how to make a difference, he knows the team at the Foundation can help. “The Foundation’s strong reputation and local focus have been a huge draw for our clients. People want to see their giving applied right here in Winston-Salem—to support the causes they know and love.”

Thanks to Wesley and David, the Bailey family name will certainly live on through their intentional partnership with the Foundation and the charitable funds they’ve helped create for our community’s future.