[4] He was a top player for Wendell Phillips Academy High School and also played in his freshman season at the City College of New York, although he dropped out before his second year.
[2][4] A 6 feet 3 inches (1.91 m), 205 pounds (93 kg) center, Jackson played independent basketball starting in 1925 with the Chicago Giles American Legion Post team.
[7] He was renowned for his handling abilities, being described by The Montana Standard as "one of the greatest ball handlers in the nation today" and by The Minneapolis Journal as playing "as though he were born with a basketball in each hand".
[8][9] He was also known as having introduced comedy and showmanship to the Globetrotters, previously a regular team: team founder Abe Saperstein named Jackson the most important Globetrotter of all time and Charley Eckman credited him with having been "the guy who transformed the Trotters from a bunch traveling around playing basketball like everybody else to the great show they are.
[1][13] He was the team captain for much of his tenure with Harlem and helped them win the second World Professional Basketball Tournament in 1940, towards the end of his career.