Chicago, Illinois in the early fall of 1919. A couple of kids get tickets and run to go see the White Sox play the final pennant game to get into the World Series. In the press box, sports writers Ring Lardner (Director John Sayles) and Hugh Fullerton (Writer Studs Terkel) are passing around comments to one another about the players. Entering the room is "The Old Roman", Charles Comiskey (Clifton James), the owner of the White Sox along with a group of sports writers and press agents into a nice banquet room with hors d'oevre's and champagne with Comiskey bragging about his ballplayers and them winning. While he is talking about them, we get glimpses of the star players of the White Sox on the field, to include Chick Gandil (Michael Rooker), pitcher Eddie Ciccotte (David Strathairn), Eddie Collins (Bill Irwin), Swede Risberg (Don Harvey), Hap Felsch (Charlie Sheen in a small role), Buck Weaver (John Cusack), Ray Schaalk (Gordon Clapp), and the legendary Shoeless Joe Jackson (D.B. Sweeney). While the game is going on, small-time gamblers Sleepy Bill Burns (Christopher Lloyd) and Billy Maharg (Richard Edson) are in the stands evaluating players who they think could be part of a plot to throw the World Series for some cash, since Comiskey grossly underpays most of his ballplayers compared to most other teams. They do not want Eddie Collins or Ray Schaalk to be part of it, since Collins is a college-educated man that gets paid well and Schaalk is too temperamental to even be considered part of it. Eddie Ciccotte is the key player they want because of his pitching record and nearing retirement in his late 30's.
The White Sox win the pennant with Hap Felsch having caught the ball of the player in the outfield. The team wins and enters the locker room with Comiskey's secretary Harry Grabiner (Jack Merrill) giving them champagne for having won. They are delighted at having it, but it turns out the champagne is their bonus for having won instead of cash and all the team are disappointed. Their manager Kid Gleason (John Mahoney), tries to encourage them, but cut off and assured he's not part of their beef. Even more disappointing is the champagne turns out to be flat. Whereas Comiskey and the press agents are enjoying expensive champagne and hors doevre's giving him cheers. The team all poses for a group photograph.
That night, many of the players are celebrating in a local gin mill. The illiterate Joe Jackson is having his wife read the paper to him about the day, Felsch, Risberg, Weaver, and utility player Fred McMullen (Perry Lang) are hanging around the bar area, and Chick Gandil is hanging out with a couple of ladies and a shady gambler, Sport Sullivan (Kevin Tighe), explaining his ordeal and Sullivan assures him he could get 6-7 men in to throw the World Series, but doesn't believe Gandil could engineer it, but Gandil reminds him of the cheapskate they work for. Burns and Maharg are also in the gin mill overseeing the conversation between the two with Burns believing Sullivan is just trying to get inside information about them.
Gandil and Risberg are in the men's room using the urinals with Gandil explaining what he wants to do and McMullen overhears their conversation. Fearing exposure, Risberg lets him in on the projected fix the men will have on the World Series. After leaving the men's room, Burns and Maharg approach Gandil wanting to have a part in the bet presumably unaware that Sullivan already beat them to it. Gandil doesn't want to have more than one party, but Risberg facetiously asks "what will they do, call the cops"?, if they have all of them.
Back at his home, Ciccotte is having his wife rub balm on his arm to help get it prepared for the World Series. And Buck Weaver is going home from the gin mill with local boys wanting to play a little catch with him.
Ciccotte is dismissing Gandil's idea about throwing the World Series that he has a secure income, but Gandil insists his time is running out. Ciccotte goes to visit Comiskey for his $10,000 bonus for winning 30 games, but Comiskey denies it to him that he won only 29, even though he was benched for 2 weeks. Ciccotte approaches Gandil at a depot requesting $10,000 in cash before the first game and Gandil is delighted he's in on the fix.
At horse race tracks in New York City, Burns and Maharg approach former boxing Champion Featherweight, Abe Attell (Michael Mantell), since he's an alleged messenger for powerful gangster Arnold Rothstein. Abe brushes them off at first thinking they're just small-timers.
Risberg is at pitcher Lefty Williams' (James Read) home trying to convince him to join the fix to throw the World Series, since they now have Ciccotte, and he concurs.
We are introduced to Arnold Rothstein, a shrewd, aloof, impersonal businessman and one of the most powerful mobster figures in the country. Attell is at his home trying to convince Rothstein to be the man for the fix to throw the World Series, but he denies he's interested without hesitation because he knows how these people work and how this type of people tried to bring him down when he was a kid. Attell leaves and Rothstein gets an operator on the phone to get someone to come see him.
Attell lies and tells Burns and Maharg at a bar that Rothstein is interested, but not to let any of the information to leak out unless they want the deal off.
Rothstein is having dinner at his lavish home and Sport Sullivan enters telling Rothstein that he can get eight men in on the fix, to include Ciccotte, but Rothstein tells him to just wait and not say or ask anything more for the time being. Sullivan leaves.
Sullivan is at a train depot telling Jimmy (Phillip Murphy) an employee of his, about Rothstein's home. An employee of Rothstein's, Monk (Stephen Mendillo), steps in and tells Jimmy to leave. Monk drops $80,000 in cash telling him that the fix is on, Rothstein is in and Ciccotte is to hit the first ballplayer at bat to signal that the fix is on. He's also instructed to not in any way connect Rothstein to the fix. Sullivan wants Jimmy to take some of the cash and place bets elsewhere and that some of the players will get money, nevertheless.
The ballplayers and sportswriters Lardner and Fullerton are all on a train to Cincinnati for the first game. Hap Felsch is now being summoned to be part of the fix, but refuses unless Joe Jackson gets in. Buck Weaver overhears the conversation and is outraged that the men are talking about a fix. Sullivan is on board as well offering them a drink of champagne. Risberg visits Jackson in his dark quarters with Jackson doing an old wives tale of staring at a candle with one eye covered to make his batting eye better. Risberg tells him about the fix and the simple-minded Jackson can't understand why they're doing it or want him part of it, but he's intimidated by Risberg and concurs. Weaver is troubled by the men's arrangement in this proposed scandal.
The men are now in Cincinnati and Gandil is visiting Attell with other ballplayers thinking the man is a bluff in it because of the lack of cash. Ciccotte is secretly asking Gandil about the cash and he's told to just look under his pillow, compliments of Sullivan.
Buck Weaver is at the empty ballpark practicing for the series and Kid Gleason approaches him. He almost decides to tell Gleason about what he's heard, but declines.
Ciccotte is looking out his hotel room at the commotion of a street crowd opposing the White Sox. He then goes to his bed and finds $10,000 in cash under his pillow.
The first game is about to begin. Kid Gleason tells Lardner and Sullivan that he hears rumors all the time about a fix and denies his players would be part of it. They pretend to believe him and both secretly agree to keep separate score cards for any player they feel is not performing up to par and to compare afterwards. Jackson, feeling guilty about what he now knows, tells Gleason he doesn't want to play, but Gleason angrily tells him he will. Gleason gives a lecture to his club before the game to give it all they have.
Game One begins. Arnold Rothstein is at a conference room in New York where the game is being transmitted into Morse Code for the audience. Ciccotte hits the first player with his ball and Rothstein leaves the room knowing the fix is on. Cicotte's pitching is not up to par, catcher Ray Schaalk is frustrated at Ciccotte, the Red's keep scoring, and Buck Weaver is giving 100% into the game. At the end of the game, the Red's have won. Risberg approaches Weaver inquiring about his playing abilities and Weaver tells him he will have no part in the fix and take no money.
Cicotte visits Lardner in his hotel room with Lardner trying to tactfully question him if there is anything going on or a fix, but Ciccotte denies it and Lardner reluctantly believes him.
Joe Jackson is sitting on the bed in his hotel room with McMullen entering and placing a small sum of cash on the dresser drawer. Jackson simply accepts it and does not get up.
Game 2. Lefty Williams is pitching. He is messing up constantly and Schaalk even more outraged than the previous game. A small aeroplane drops a dummy onto the field mocking the ballplayers. Game 2 has been lost and Schaalk angrily attacks Williams for his incompetence on the field with Gleason and Weaver breaking them up. Gandil is laughing and joking with other players and Gleason is angered at his jovial attitude thinking he's trying to deliberately lose and attacks him being broken away.
Outside the ballplayers hotel, an effigy of the White Sox is being burned by fans of the Reds and there are numerous trips being made in between hotel rooms. Comiskey is awoken by Gleason to come to another room to straighten out the situation and Burns and Maharg go to Attell's room demanding cash to bet on the third game and given $10,000. They are being stiffed, but have no other way. Newcomer Dickie Kerr is being summoned to be the pitcher for the third game.
Game 3 of the World Series. Chick Gandil gets to first base, but another player makes a hit and he deliberately slows down to get thrown out at second base and the sportswriters know right away he did it on purpose. Dickie Kerr (Jace Alexander) makes his first pitch and throughout the entire game pitching a no-hitter. Burns and Maharg are very upset, since all the $10,000 was placed on them losing the game.
Buck Weaver is sitting on the front porch of his home with his wife (Barbara Garrick) coming out to talk to him. He tells her of the fix and tells her he wanted no part of it, but she supports him for what he's doing on his part.
Game 4 is poorly played once again with Weaver upset at Ciccotte's bad pitching.
Games 5 and 6 of the World Series the players are performing up to par again, but the gamblers are all outraged, despite their disappearance in the fix and Gandil being unable to contact them. Feeling they've now been abandoned, the ballplayers go back to their top performance. Arnold Rothstein is informed by an employee of his while he's at the barber shop at the end of game 5. At game 6, Monk pays a visit to Sport Sullivan in the stands for failure to live up to the gamblers expectations. Kid Gleason is being interviewed and insisting that all along his players all gave their best. Sullivan, by the orders of Monk and Rothstein, has a man dispatched that threatens to have Lefty Williams' wife killed if he does not lose the 7th game.
Williams pitches a pathetic and painfully bad first inning and taken out of the the series by Kid Gleason. Joe Jackson hits a home run, but it does nothing to alleviate the losing score of the White Sox' game. They lose the 7th and final game of the World Series. By the end, Fullerton has five of the players circled on his list, with only Jackson, McMullen (who played only briefly at bat) and Weaver.
Within the next year, sportswriters Lardner and Fullerton have interviewed Schaalk, Maharg, and maybe others about an alleged fix and now there is a $1,000 reward being offered by Comiskey for any alleged gambling. Weaver and Jackson are made aware of what's going on through the newspapers.
Eddie Collins visits Comiskey at his office telling him he believes there might have been a fix, but does not want any reward money. Comiskey begrudgingly accepts Collins' suggestion and tells his secretary Grabiner to get his lawyer on the phone.
Comiskey's lawyer, Alfred Austrian (Michael Laskin), tells Comiskey he wants to help him clean up the game, but business reasons will not help the players be found guilty in a court of law if they are guilty of gambling.
Comiskey enlists a federal judge, Kenesaw Mountain Landis (John Anderson, the used car salesman in Psycho), to act exclusively in the interest of baseball and to be the Commissioner of Baseball to clean up the gambling elements of the sport, announcing it to a group of powerful lawyers and sportswriters Lardner and Fullerton of his enlistment of the man.
Arnold Rothstein and Sport Sullivan are leaving the country by boat and train to flee the trial and Abe Attell is shown at a train station with a broken nose trying to read a newspaper in Spanish.
Ciccotte is with lawyer Austrian at the Cook Co. courthouse to testify before a grand jury and waiver of immunity tearfully regretting his crookedness at what's happened. Jackson does the same too, not knowing what's going on, but assured that they just want to get rid of the gamblers and not the ballplayers. He reluctantly signs an "X" mark. Joe leaves the courthouse with a child in the crowd pleading "Say it ain't so Joe". Lardner now circles Joe as one of the suspects in the fix.
Austrian tells the eight indicted players to simply cooperate and that they have the best lawyers to defend them. Weaver dismisses him that he's being paid off in this, but Austrian tells him as long as he doesn't know what's going on, he's better off.
Austrian meets with Rothstein's lawyer that Comiskey and Rothstein both indirectly, but mutually agree to do away with the signed confessions.
The ballplayers have their first day in court. Fullerton and Lardner are present with Fullerton telling Lardner it depends on where the ball rolls on what the verdict will be. They are all told before the testimonies they have conspired to commit a confidence game from a Charles Nims, possibly a pseudonym for Arnold Rothstein.
Comiskey testifies that he only suspected them throwing the game, Burns testifies he was approached and did not profit at all from the fix, and Maharg testifies all of the players associated with the exception of Jackson, due to his confession before the grand jury. The judge (Dick Cusack, John's father), asks it to be brought forward, but the confessions were "stolen", more than likely paid off by Rothstein or Comiskey from the meeting their lawyers had.
Ciccotte is home with his wife (Maggie Renzi) that night telling her his plans for her and the kids if he goes to jail and tells her of all the injustice with the powers that be and that they are the conspiracy.
The next hearing, Collins takes the stand telling the lawyer he didn't know about it because of his limited association with the players due to personal differences, but only suspected it, and Weaver has an outburst with the judge because he refused to take part of the scandal and gave it his all.in the games.
Jackson is with his wife at his home telling her he just wants to go back and play baseball and doesn't know what he'll do if he doesn't.
At the next hearing, their manager Kid Gleason testifies his years in baseball defending them that people make mistakes in life and are human, but declares his ballplayers are the best he's ever had.
Buck Weaver is out hanging around the brownstones in his neighborhood with the local kids and tells them not to be so hard on the players and about how hard life gets when you're older assuring them he will be on the field next year playing his heart out.
At the final hearing, the ballplayers are all found not guilty in court. They all cheer, but Comiskey is outraged that he will make them pay for all this. That night, they have a lavish welcoming dinner for them at a hotel.
Judge Landis is making a statement before the sportswriters, to include Lardner and Fullerton, that no ballplayer that gambles or hears anything about gambling and doesn't inform anybody, will never play baseball again. This is a private sector decision made the courts are not able to do anything about.
In New Jersey in 1925, a young trio of baseball fans watching a minor league team are sitting in the stands wondering who this guy Brown is who's playing so well. It's Shoeless Joe Jackson and one of them knows it's him, but one denies it and another one doesn't know who Joe Jackson is. Buck Weaver is in the stands watching as well and tells them Joe Jackson was the best ever, but that's not the man on the field.
After "Brown" being cheered for his playing, it's announced on the screen that Joe Jackson and the other banned players never played professional baseball again and that Buck Weaver tried to clear his name until his death with his appeals denied.