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After earning a B.A. in political science in 1984 from Sewanee, the University of the South, in Sewanee, Tennessee, Wakefield received an M.B.A. from the University of South Carolina in Columbia in 1985. That is when he moved back to Spartanburg and launched his full-time career at the Dealership owned by his father, the late John William Wakefield, Jr. Wakefield greatly valued his father's mentorship.

Over the years, Wakefield operated multiple automotive franchises, including Pontiac, GMC, Cadillac, and Suzuki. Through his experience and expertise as an industry leader, he was tapped by the South Carolina Automobile Dealers Association, where he served on the Board of Directors as President, Vice President, and Treasurer throughout his Board tenure.

A staunch advocate for the retail automotive industry, Wakefield worked tirelessly on behalf of fellow Dealers. He fought to protect franchise laws at the State House and hosted regional meetings with his peers to share ideas and gather feedback in an effort to fully and fairly represent the interests of Dealers throughout the State.

In the area of community service, Wakefield was also a leader. He founded the Eastside Vikings Youth Lacrosse League in 2010 to introduce the game to local children, and, according to his wife, Jenny, he was coaching and organizing schedules up until the last day of his life.

He was also a devoted member of the Boy Scouts of America and was an outdoor wilderness leader for Troop 1 in Spartanburg, leading groups into the Great Smoky Mountains National Park and along the Appalachian Trail. In recognition of his positive impact on young people, Wakefield received the Dr. George Dean Johnson Leadership Award for scouting.

As a longtime resident of Spartanburg, Wakefield was actively involved in the community he loved. He was a graduate of Leadership Spartanburg and Leadership South Carolina, two organizations that foster civic involvement, volunteerism, and community engagement. He served the state chapter of the American Red Cross, Mobile Meals of Spartanburg, the Episcopal Church of the Advent in Spartanburg, and the Spartanburg Development Association, to name a few.

Wakefield is survived by his wife, Jenny, and their three children, Anne Townsend, Walker, and Brownlee Wakefield. He was nominated for the TIME Dealer of the Year award by E. Simmons Floyd, Jr., Executive Vice President of the South Carolina Automobile Dealers Association.