In many scenes, players toss their gloves down on the field near their positions before they head to the dugout. Until the 1950s, players frequently left their gloves on the field while at bat. Because of the danger of players stepping on or tripping on them, and batted or thrown balls bouncing off them in odd directions, Major League Baseball requested, then demanded, players to take their gloves with them to the dugout. They finally complied after a rule change and fines.
Initially, John Sayles envisioned himself in a minor role as a member of the Chicago White Sox squad. However, after working over a decade to turn the script turned into a movie, he was too old to convincingly portray a ballplayer when filming started, where, instead, he cast himself as newspaper sportswriter Ring Lardner as Sayles bore such a striking resemblance to Lardner.
Director John Sayles was contractually obligated to a running time under two hours. To inspire the cast to talk fast, he showed them the film City for Conquest (1940). The final cut of the film is 1:59:48.
John Sayles said he cast Charlie Sheen and John Cusack because of their ball playing experience and abilities.
A child in the movie utters the famous quote, "Say it ain't so, Joe!" In real life, a Chicago reporter was standing close by when a boy said something to the effect of "Say it didn't really happen, Joe." The reporter took creative license, and created the "Say it ain't so, Joe!" quote, to give the story more emotional impact.