Growing up in Ashland, Lester Jackson attended the Hanover County Training School (later John M. Gandy), where he organized the school’s first baseball team and doubled as player and coach. In 1933, eighteen-year-old Jackson started his professional career with the Jacksonville Redcaps in the Florida State Twilight League. He made it to the highest level a black player could in that era, playing for the Newark Eagles, the Mohawk Giants, and the Boston Giants. Jackson played with Satchel Paige, Jackie Robinson, and Josh Gibson.

Returning to Ashland, he worked as a scout for the Cleveland Indians from 1954 to 1974. He became supervisor for food services at Randolph-Macon College and was presented with the Honorary Alumnus award in 1984 by the Society of Alumni. Following his death in 1991, the Lester Jackson Scholarship was established by the college in his memory.