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.
John Sayles said he cast Charlie Sheen and John Cusack because of their ball playing experience and abilities.
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 Dois Contra uma Cidade Inteira (1940). The final cut of the film is 1:59:48.
D.B. Sweeney, who is right-handed, played the left-handed hitting "Shoeless" Joe Jackson. He initially suggested filming his hitting scenes in reverse, a process used in Ídolo, Amante e Herói (1942). John Sayles didn't have the budget for such effects. Sweeney arranged to work out with a Class A Minor League Baseball team to learn how to hit left-handed. Sweeney came to feel that the conditions and atmosphere around Class A ball were comparable to those around big league baseball in 1919.