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Norfolk Academy mourns the passing of former Board President and Trustee John O. “Dubby” Wynne ’63, who passed away on October 26, 2023. Mr. Wynne was a passionate Bulldog and the epitome of selfless service. He was known and admired as a business leader whose work as President and CEO of Landmark Communications Inc. had a transformative impact on the nation’s media landscape. He was an active philanthropist in myriad organizations, particularly educational institutions. He loved NA, the values it stood for, and the teachers who instilled those values — above all, Headmaster J.B. Massey Jr., who inspired him as a student and became a lifelong mentor to him.

Mr. Wynne was a mighty force in all he undertook, and he had tremendous, far-reaching impact in his work and his philanthropy. After graduating from Norfolk Academy, where he served as captain of the football, basketball, and tennis teams, he went to Princeton University and from there to University of Virginia Law School, interrupting his time in law school for active duty in the U.S. Army Reserves. He worked as a lawyer for Willcox Savage, then in 1974 went to work for Frank Batten Sr. at Landmark Communications Inc. He was involved in many of that company’s pioneering initiatives, including The Weather Channel. Throughout the decades, Frank Batten and Wynne forged a successful business partnership and a close personal friendship. Wynne retired as President and CEO of Landmark in 2001, and he continued to serve on the Board of Directors for many years after his retirement. 

Mr. Wynne had a passionate commitment to community service and philanthropy. Amid all of his involvements, Norfolk Academy remained a lodestar. He and his wife Susan, who served for some years as a fifth-grade teacher and as a Trustee, loved the school. There was nothing Dubby would not do for Norfolk Academy, and he traced it back to his formative years and to the profound gratitude he felt to Mr. Massey for inspiring him to become a serious student. Dubby joined the Board of Trustees in 1980 and served as President from 1986-89. The period of his presidency was a time of rapid accomplishment, including the construction of the Vaughan Aquatic Center, the expansion of the Slover Science Building, and crucial strategic planning initiatives. He championed the cause of student diversity and a competitively compensated faculty. He was a leading force in the establishment and growth of the school’s endowment. At the dedication of the Wynne-Darden Stadium in 2017, Board President Tom Alberico spoke about the friendship between Dubby and the late Joshua P. Darden ’54, who was a close friend and like Dubby, a past Board President and philanthropic force at the Academy.

The 1997 Board resolution signed by Richard Burroughs upon Dubby’s retirement noted, “From earlier days, when ‘Number Ten’ led Bulldog teams to his leadership today, Dubby Wynne has demonstrated a devotion, judgement, and strength of will second to none.”  It also called him “a community leader and fundraiser without peer” and “a Trustee’s trustee.”

Head of School Travis Larrabee spoke about Mr. Wynne during Upper School Chapel on October 30, calling him a servant-leader.

The Virginian-Pilot wrote a front page news story highlighting Mr. Wynne's lifetime of service. Services will be held on November 3 at noon at Galilee Episcopal Church in Virginia Beach. 

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