In prohibition-era Chicago, the corrupt sheriff and Guy Gisborne, a south-side racketeer, knock off the boss Big Jim. Everyone falls in line behind Guy except Robbo, who controls the north side. Although he's out-gunned, Robbo wants to keep his own territory. A pool-playing dude from Indiana and the director of a boys' orphanage join forces with Robbo; and, when he gives some money to the orphanage, he becomes the toast of the town as a hood like Robin Hood. Meanwhile, Guy schemes to get rid of Robbo, and Big Jim's heretofore unknown daughter Marian appears and goes from man to man trying to find an ally in her quest to run the whole show. Can Robbo hold things together?
| Directing | Gordon Douglas | Director |
| Writing | David R. Schwartz | Writer |
| Production | Frank Sinatra | Producer |
| Camera | William H. Daniels | Director of Photography |
| Sound | Nelson Riddle | Original Music Composer |
| Costume & Make-Up | Donfeld | Costume Design |
| Art | LeRoy Deane | Art Direction |
| Editing | Sam O'Steen | Editor |
| Production | Howard W. Koch | Executive Producer |
| Production | William H. Daniels | Associate Producer |
| Art | Raphael Bretton | Set Decoration |
| Sound | Everett A. Hughes | Sound |
| Sound | Vinton Vernon | Sound |
| Directing | David Salven | Assistant Director |
| Directing | Lee White | Assistant Director |
| Costume & Make-Up | Gordon Bau | Makeup Supervisor |
| Costume & Make-Up | Jean Burt Reilly | Hair Supervisor |
| Sound | Gil Grau | Orchestrator |
| Crew | Charlie Picerni | Stunts |
| Costume & Make-Up | Robert J. Schiffer | Makeup Artist |
| Directing | Michael Daves | Second Assistant Director |
| Art | Richard Lawrence | Art Designer |
| Art | Bill Gold | Art Designer |
| Art | Mentor Huebner | Production Illustrator |
| Crew | James J. Casino | Stunts |
| Crew | Roger Creed | Stunts |
| Crew | Joe Gray | Stunts |
| Crew | Chuck Hicks | Stunts |
| Crew | Boyd 'Red' Morgan | Stunts |
| Crew | Victor Paul | Stunts |
| Crew | Al Wyatt Sr. | Stunts |
| Sound | Jack Baker | Music Score Producer |
| Sound | Sammy Cahn | Songs |
| Sound | Nelson Riddle | Conductor |
| Sound | Jimmy Van Heusen | Songs |
| Sound | Sally Stevens | Vocals |
| Directing | Doris DeHerdt | Script Supervisor |
| Directing | Dolores Rubin | Script Supervisor |
| Crew | Thom Conroy | Dialogue Coach |
