Buddy Bailey

Welby Sheldon “Buddy” Bailey, 68, one of Minor League Baseball’s all-time winningest managers and most enduring figures, passed away on September 22, 2025, in Lynchburg, Virginia. Born on March 28, 1957, in Norristown, Pennsylvania, Buddy’s passion for baseball began in childhood and became his life’s calling.

He was predeceased by his father, Welby S. Bailey, Sr.; his mother, Lillian R. Kerns; and his brother, Brian Kerns. He is survived by his sisters, Nanci Woody of Lynchburg, Virginia, and Joanne Bailey of Madison Heights, Virginia; his brother, Bill Bailey (April) of Amherst, Virginia; nephews Chip Woody (Audelee), Michael Roberts (Mehgan), Brandon Terry (Lauren), Joshua Bailey (Susan), and Caleb Bailey; nieces Tracy Coleman (Eric) and Gwen Woody (Joe); and a host of great-nieces and great-nephews.

Buddy dedicated his life to the game of baseball as a player, coach, and manager. Over a career spanning over four decades, 11 cities, and three major-league organizations, he amassed 2,417 regular-season victories, five championship titles, and countless memories with the players he guided. Beginning with Little League Baseball, Amherst County High School, and Lynchburg College, Buddy realized his dream of professional baseball and went on to work for the Atlanta Braves and Boston Red Sox before finishing his career with the Chicago Cubs organization, most notably managing the Myrtle Beach Pelicans.

In the off-seasons, Buddy successfully managed Tigres de Aragua in Venezuela, earning respect internationally for his leadership and baseball knowledge. He was known as a gifted teacher, a steady mentor, and a friend to so many who shared his love of the game. His influence extended far beyond the diamond, shaping the lives of young athletes and colleagues alike.

Buddy’s passion and dedication left an indelible mark on Minor League Baseball and on the communities and players he served. He will be remembered not only for his historic number of wins but also for his kindness, humor, and unwavering commitment to the sport and people he loved.

A Graveside service will be held at El Bethel Church Cemetery (Allwood), 925 Buffalo Springs Turnpike, Amherst, VA on Friday, September 26, 2025 at 1:00 p.m. officiated by Pastor Steve Tyree.

In lieu of flowers, the family requests memorial contributions be made to Madison Heights Youth Baseball Association, P. O. Box 99, Madison Heights, VA 24572.