Positions: officer, owner
Team: Homestead Grays
Died: March 6, 1949, Pittsburgh, Pennsylvania
When Homestead Grays' owner Cum Posey had financial difficulties during the Depression years, he turned to Jackson for assistance, taking him in as co-owner. Posey handled the responsibilities of general manager, while Jackson served as the president and treasurer for the team.
Jackson's money came from two primary sources: the piccolo business and the numbers racket. He supplied the money and Posey supplied the organizational skills during the Grays' glory years. When Mexican officials began raiding the Negro League teams, Jackson was almost arrested because of an altercation when they tried to lure away some of his players.
After Posey's death, Jackson ran the team himself, winning the last pennant in Negro National League history in 1948. The following season, the Grays toured as an independent team, but the attrition of players had reduced the team's quality, and their years of greatness were gone, never to return.
Source: James A. Riley, The Biographical Encyclopedia of the Negro Baseball Leagues, New York: Carroll & Graf Publishers, Inc., 1994.