Short worked for the Chicago White Sox of Major League Baseball for over 20 years, including nine seasons as the team's general manager, from August 26, 1961, until September 2, 1970.
In his first off-season, he traded aging White Sox stars Billy Pierce, future Baseball Hall of Famer Minnie Miñoso and Roy Sievers to the National League for younger players.
After the 1962 campaign, Short swung one of the biggest deals of the off-season, sending Hall of Fame shortstop Luis Aparicio and outfielder Al Smith to the Baltimore Orioles for Aparicio's Baltimore counterpart, Ron Hansen, young third baseman Pete Ward, power-hitting outfielder Dave Nicholson and future Hall of Fame knuckleball pitcher Hoyt Wilhelm.
Wilhelm would be Chicago's bullpen ace for six seasons (1963–68) and compile an earned run average of 1.92 in 361 games and 675+2⁄3 innings pitched in a White Sox uniform.
Short also obtained left-handed knuckleball ace Wilbur Wood, who starred first in the bullpen and then, as a starting pitcher, won 20 games four times during his 12-season (1967–78) White Sox career.
[4] After an ownership transition from Arthur Allyn, Jr. to his younger brother John, and with the team's record at 49–87 and en route to a franchise-worst 56–106 finish,[5] Short was dismissed and replaced by Stu Holcomb on September 1, 1970.