Big Jim Stevens, the undisputed boss of Chicago’s underworld, is celebrating his birthday when his ambitious lieutenant Guy Gisborne orchestrates a trap that shoots him down before his guests. Gisborne seizes control and declares that every gangster in town must pay for protection, while stubbornly insisting the motto remains All for One. The brutal shift in power unsettles Jim’s ally, Robbo, and soon a gangland war lights up the city.
Robbo answers the challenge by assembling a lean, capable crew. He brings in Little John, a pool sharks’ ace who can also belt out a tune, and the quick-draw Will, along with a handful of others. They are formidable but still outnumbered by Gisborne’s growing reach. The town’s corruption is underscored by the presence of the crooked Sheriff Sheriff Octavius Glick, who works on Gisborne’s payroll, complicating every move Robbo makes.
Into this volatile mix arrives Marian Stevens, the refined daughter of Big Jim, played with poise by Barbara Rush. She asks Robbo to avenge her father’s death, wrongly blaming the sheriff for the violence. Robbo refuses the notion of vengeance, and Gisborne wastes no time removing Sheriff Glick to cement his hold on the city. Marian, convinced Robbo had acted as she asked, offers him a fortune and invites him to dinner, hoping to lure him into allying with her. Robbo refuses the money, yet Marian pushes the plan forward by sending the funds to Robbo’s under-repair gambling club, a gesture that Robbo turns into a symbolic gift to the city’s orphans.
The orphanage angle is given a public-facing boost by Allen A. Dale, the director of the orphanage. Dale notifies newspapers about Robbo’s charitable deeds, turning the gang’s image into a Robin Hood legend. Robbo leans into this perception, inviting Dale to run the charitable front and build a public-relations machine around the “foundation.” The Robbo Foundation grows into a network of soup kitchens, free clinics, and shelters for orphans, even handing out green hats and symbolic gear to the children — a calculated move to win the city’s heart. The pair even talk through public relations tips, with Robbo and his allies offering Dale advice on how to polish their image, a process the film presents as a kind of performance of virtue, highlighted by the moment of genuine community support.
Robbo’s joint reopens and becomes an instant sensation, drawing the ire of Gisborne. The new sheriff, along with Gisborne, stages a raid, but Robbo has anticipated the move and has dressed the club as a mission, complete with hymnals and tambourines as the raid unfolds, a moment the crowd interprets as a spiritual stand against vice, often remembered through the number Mr. Booze as part of the spectacle.
Soon Robbo is framed for Sheriff Glick’s murder. In the courtroom drama that follows, Gisborne and Potts push the idea that Robbo planned the crime, while Dale tries to teach the orphans to see the setback as a lesson, a moment the film frames with the line Don’t Be a Do-Badder. The jury, however, finds Robbo not guilty, and he responds with a public thanksgiving, wearing a green suit and declaring to the city, My Kind of Town. The moment crystallizes Robbo’s mythic status in Chicago, even as the city’s power dynamics continue to shift around him.
The treasure of Robbo’s charitable facade soon reveals a darker undercurrent: his supposedly benevolent acts become the front for a counterfeit operation. The soup kitchen becomes a corridor for fake bills smuggled across state lines, exposing a more cynical edge to the Robbo persona. Robbo discovers Little John living at Marian’s mansion, and Marian proves she would rather run the town alongside Gisborne than see Robbo hold the reins. Robbo’s contempt for Marian’s ambition comes through in his decision to walk away, with Little John reluctantly following.
Marian allies with Gisborne again, but Robbo proves more cunning and ruthless, killing Gisborne and forcing Marian to reassess her grip on power. In a final, destabilizing turn, Marian frames Robbo for the counterfeit scheme, and Potts becomes her reluctant partner in crime. Outmatched by a mob’s outrage, Robbo and his men flee the city, their glamour fading. The trio — Robbo, Marian, and Dale — retreat into anonymity, even as they continue to perform their public-facing roles, reappearing later as Santa Clauses who solicit donations, their bells ringing through the streets as Marian steps from a car with Dale, who quietly tips a fund, while the two walk away together.
What remains is a portrait of a city where power, spectacle, and charity blur into one messy, compelling story — a modern parable of a gangster who becomes a symbol of compassion, and a community that can be swayed by spectacle as easily as by justice.
