Lupton was on the ground floor at the start of operations for the Frederick Keys (High Class A; Carolina League), Bowie Baysox (Class AA; Eastern League), Delmarva Shorebirds (Low Class A; Sally League), Lancaster Barnstormers and Southern Maryland Blue Crabs (both independent; Atlantic League).
Prior to getting into professional baseball, Lupton was in radio broadcasting in Winchester, VA where he served as a DJ, manager, play by play announcer, and syndicated sports show host with WHPL. He owned the Winchester Royals in the summer-collegiate Valley Baseball League in 1979, 80, and 81. The Royals won three consecutive league championships with 35 players drafted by Major League organizations under Lupton’s tutelage.
Lupton got into professional baseball as an associate scout. While he was thought to have a good eye for baseball talent, an emerging company in Western Maryland also saw Lupton’s abilities in the business end of Minor League Baseball. Initially hired with the startup Hagerstown Suns of the Carolina League in 1981, Lupton worked for what would later become Maryland Baseball and later, its partner company, Keystone Baseball and Opening Day Partners. He was quickly promoted to assistant general manager, a position in which he remained for seven seasons. Then, when the company opened an operation in Frederick, MD in 1989, he was named general manager of the Frederick Keys and served in that position until 1993.
After winning the Carolina League Championship in 1990 he was selected by the Carolina League as General Manager of the Year. In 1992 he was again named General Manager of the Year by the Carolina League. In 1993 Lupton was promoted to the Double AA Bowie Baysox, an Oriole affiliate and he was once again named General Manager of the Year, this time by the Eastern League. The Delmarva Shorebirds began playing in Salisbury, Maryland in 1996. With his success in the start up of Frederick and Bowie, Lupton was once again chosen to head the start up operation in Salisbury. In 1997 Lupton picked up his fourth General Manager of the Year Award with the South Atlantic League.
Following the 1997 season, he was promoted to Senior Vice President of Maryland Baseball and worked with the Lancaster Barnstormers in Lancaster, PA and with the Southern Maryland Blue Crabs in Waldorf, MD. He was named by Major League Baseball as President of the Maryland Fall Baseball League. The National Association of Minor Leagues named Lupton National General Manager of the Year. He was named Executive of the Year by the Major League Scouting Association in 1999.