By the time Lester Jackson (1915-1991) joined Randolph-Macon College’s cafeteria staff in 1946, he had already spent a decade playing alongside some of baseball’s all-time greats in the Negro Major Leagues. But Jackson’s athletic prowess was well-known in his native Ashland long before he left town to play with the pros. 

With a friend, Jackson started his own baseball team in 1929 while still a student at Hanover Country Training School. At the time there was no varsity team, coaches, uniforms, or means of transporting players to games. As one of two player-coaches, Jackson persuaded his teammates to raise the necessary funds themselves, traveling to games in New Kent, Fredericksburg, and Manassas in a truck owned by the store one of the team members worked at.

Jackson tried out for the Florida State Twilight League in 1933, where another friend had been playing for the Jacksonville Redcaps. The 18-year-old made the cut as a pitcher and outfielder, and it wasn’t long before a scout signed him to a professional contract with the Newark Eagles. Jackson played two seasons with their farm team in Winston-Salem before trades sent him to the Mohawk Giants in 1935 and the Boston Giants in 1936. He returned to Newark in 1938, where he stayed until the end of his playing career in 1941, having faced legends like Jackie Robinson, Josh Gibson, “Cool Papa” Bell, and Don Newcombe.

The highlight of his career came in a base hit he scored in spring training, knee-deep in snow, against Satchel Paige, the first Black pitcher to join the American League and recently ranked #41 on ESPN’s list of the all-time greatest baseball players. 

“Oh, he struck me out several times,” Jackson once told a reporter with the Hanover Herald-Progress. “But I did get one hit off him.”

Jackson never batted below .321 in any season, and he won 21 games as a starting pitcher over the course of two seasons with Boston. He later channeled that success into a lengthy 20-year scouting career with the Cleveland Indians from 1954-1974. During that time he signed several players to major-league contracts. All the while, Jackson never lost his sense of home in Ashland.

His Yellow Jacket career began in the newly opened College cafeteria, and over the next four decades he assumed the roles of staff supervisor and assistant manager. Jackson’s presence in the cafeteria put him in contact with countless students at mealtimes. Even as graduating classes grew, Jackson was famous for his encyclopedic knowledge of the students who passed through Randolph-Macon, and reportedly could recall them by face and name.

“He got to the point where he probably knew as many alumni as anyone,” former RMC athletic director Hugh Stephens ’41 once said. “He said he never forgot any of the students. Many of the alumni would ask if Les was still there.”

Mark Person ’78 remembered in a written reflection on Jackson’s legacy that it was only after he befriended Jackson that he learned he “played a little ball.” Person—whom Jackson invited to play on the Brown Grove Spiders, a Hanover-based freelance baseball team—remembers Jackson’s steady presence at RMC sporting events and expansive sports acumen.

“Lester would often be in attendance at many of the RMC baseball games and he would talk with many from the RMC community,” Person wrote. “He was one of those folks that knew everyone and always made you feel good about yourself.” It was only after knowing him for years that Person learned the extent of Jackson’s Negro League career.

The impact Jackson had on the campus community was evident from his early days working just across the street at the Henry Clay Inn and continuing over the course of his life. In 1976, Jackson was awarded a Distinguished Friend Award from the Society of Alumni. The award letter praised Jackson as a friend who “served our college students, faculty, and the alumni family both with unselfishness and love.” Then, in 1984, he was presented with the Honorary Alumnus Award.

“To a great many of us, Lester Jackson and Randolph-Macon are synonymous,” wrote the late James L. “Jim” Miller ’52. “Les, you are probably a more loyal ‘alumnus’ than any of the rest of us could ever be.”

Up until the time of his death in 1991, Jackson was respected by everyone who got to know him, and his reputation lives on today. In 1993, the Lester Jackson Scholarship was established by the College to honor his legacy as a “friend and ally to generations of Randolph-Macon students,” and is given on the basis of financial need.

“Lester Jackson was one of those people you meet in life who has a positive impact on you and your ethic and approach to other humans simply by his presence and what I will call his life witness,” wrote Jay Pace in his reflection on Jackson’s life for the Hanover Herald-Progress. “Compassionate. Interested. An example I could follow but never duplicate.”

In other words: the consummate Yellow Jacket.