Tony Rome Frank Sinatra is a former cop turned private investigator who lives on a powerboat in Miami, a place he calls Straight Pass and that feels like a floating home base for a man with a cheeky, gambling-tinged streak. His old partner, Ralph Turpin, comes to him with a job: bring home a young woman who was left unconscious in a hotel room. The case soon widens as Tony learns the woman, Diana Pines (Diana Kosterman), is the daughter of a wealthy Kosterman family and is connected to Rita Kosterman, Diana’s stepmother Rita Kosterman. Diana and Rita hire Tony to figure out why she’s been acting so irrationally since waking up and to locate a missing diamond pin she wore the night before.
As the investigation begins, Tony is knocked out by a pair of thugs, and the very next day Ralph Turpin is found murdered in Tony’s office. The Miami police, led by Lt. Dave Santini, arrive on the scene and press Tony for information, testing their old friendship against the murk of the case. To help him navigate the tangled family dynamics and the danger now closing in, Tony enlists the aid of Ann Archer Jill St. John, a divorcee with her own complicated motives and connections.
The plot thickens as someone makes an attempt on Kosterman’s life and a jeweler is murdered, pushing Tony deeper into a web of deceit. He discovers that Diana has been quietly selling her stepmother’s jewels and sending the money to Lorna, her biological mother Lorna Boyd. Meanwhile, the pin itself proves to be a fake—the real gem having been mailed to Tony by Turpin after a failed fence—but the motive behind the struggle for the jewels becomes clearer as the trail backtracks through lies and theft.
Following the clues, Tony uncovers that Rita’s dead ex-husband, Adam Boyd Adam Boyd, an abortion doctor whose license had been revoked, ordered Kosterman’s killing in the belief that Diana would inherit the family estate and, in turn, provide for Rita. The revelations bring the case to a close, with Tony resolving the motive and the impostors behind the scheme.
In the aftermath, Tony contemplates a getaway for two with Ann on his boat, but she ultimately decides to return to her husband, choosing a different path rather than the romance a private eye might offer. Through the twists of blackmail, inheritance, and a once-trusted friendship, the case remains a portrait of a man who thrives on reading people even as they try to hide their true selves.
Along the way, a mysterious man with a gimp leg—known as Catleg Shecky Greene—drifts in and out of the story, adding a final layer of menace and intrigue to the Miami-night atmosphere that surrounds Tony’s investigations.
