- John Cusack as "Buck" Weaver
- Clifton James as Charles "Commy" Comiskey
- Michael Lerner as Arnold Rothstein
- Christopher Lloyd as Bill Burns
- John Mahoney as "Kid" Gleason
- Charlie Sheen as "Happy" Felsch
- David Strathairn as Eddie Cicotte
- D. B. Sweeney as "Shoeless Joe" Jackson
- Michael Rooker as "Chick" Gandil
- Don Harvey as "Swede" Risberg
- James Read as "Lefty" Williams
- Perry Lang as Fred McMullin
- Gordon Clapp as Ray Schalk
- Jace Alexander as Dickey Kerr
- Bill Irwin as Eddie Collins
- Richard Edson as Billy Maharg
- Kevin Tighe as "Sport" Sullivan
- Michael Mantell as Abe Attell
- John Anderson as Judge Kenesaw Mountain Landis
- Studs Terkel as Hugh Fullerton
- John Sayles as "Ring" Lardner
- Barbara Garrick as Helen Weaver
- Maggie Renzi as Rose Cicotte
- Wendy Makkena as Kate Jackson
- Nancy Travis as Lyria Williams
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