The Toby Webb award is made possible through the generosity of gifts from individuals and companies to an endowment fund now managed by the NCHSAA Foundation and annually recognizes two outstanding coaches. The award is in honor of Toby Webb, a member of the NCHSAA Hall of Fame who was an outstanding coach as well as principal and superintendent. He helped turn Albemarle into a football power and posted a brilliant 103-18-6 mark as a head coach there.

To be eligible for the award, a coach must be nominated by school personnel at the NCHSAA member school where he or she coaches, have coached a minimum of 10 years, and have made major contributions to the success of high school athletics at the school, in the community and beyond. Winners receive the award and a $2,500 cash stipend.

The winners of the 2023-24 Toby Webb Outstanding Coach Award are Richard Bailey from Scotland High School and Brian Carver from Enka High School.

Bailey has been the Head Football Coach at Scotland High School for 12 years, following 12 years at Jack Britt High School. His previous posts include coaching baseball at Pine Forest and Andrews High Schools. In 2024, he was named Carolinas Head Coach of the Shrine Bowl and was an assistant in 2011. He was Head Coach of the East-West All-Star Game in 2017 and an assistant at the US Army All-American Bowl in 2017. Bailey was the North Carolina Representative to the NFL-USA Youth Football Summit in Canton, former president of the NC Football Coaches Association, and committee member to hire the Southeastern Football Regional Supervisor of Officials in 2013 and 2022. 

Bailey has a career record of 240-71 on the gridiron. 

“His teams continually make deep runs in the state playoffs, and his players are always meeting the demands of balancing football and classroom expectations,” noted a former principal and superintendent, highlighting his ability to maintain high athletic and academic standards.

He also has made a significant impact through his educational seminars for athletes and their parents and he has presented at multiple clinics both around the state of North Carolina and at universities in the southeastern United States. 

Coach Bailey is also heavily involved with middle school and local youth sports organizations as well as the Kiwanis, Rotary and Optimist Clubs and the Fellowship of Christian Athletes.

“Coach Bailey instilled in all of his players the idea that they were students first and foremost,” said former player Jon Boyd. Cory Satterfield, a former colleague, said, “Richard is a caring person whose genuine concern for others has earned him the popularity of his peers and the respect of the community,”

Carver has been the Head Basketball Coach at Enka for the last 22 years and Athletic Director for 21 years. He has also coached golf and been an assistant football coach in his career, which has spanned over 30 years and three schools.

He is very active at the state level as he is an executive board member for the NCBCA, a Board Member for the NCCA, on the high school counsel for Coaches vs. Cancer, and a member of the NCHSAA Board of Directors. He was awarded the 2022-23 NABC Coaches vs Cancer Nation High School Champion Coach of the year and in 2024 he was both the Head Coach of the North Carolina All-Star Team at the 2024 Carolinas Classic and given the Athletic Director of Excellence award from the NCADA.

Carver created the NCBCA Coaches vs Cancer Shootout in 2013 and has since raised over $175,000 for cancer research. He also created the Catamount Clash of Conferences, which is a two-day event held at Western Carolina, modeled after the ACC/Big 10 Challenge. His basketball teams participate in Operation Christmas Child and they provide gifts for a family to open on Christmas as well as meals.

He has success on the court as well as he led Enka to consecutive 20-win season for the first time.

“We had a coach that cared about us beyond the game and made the playing experience memorable. Coach Carver helped me achieve my goal of playing collegiate basketball as I went on to play two seasons at Piedmont College,” said former player Jake Smith. “Coach Carver has had such a huge impact on my life. Because of him, I decided to pursue coaching myself and recently just finished my third year as an assistant coach at Watauga High School.”