In this engaging tale set against the backdrop of wartime intrigue, the story follows the adventures of Humphrey Bogart, known as Gloves Donahue, a prominent Broadway gambler with a penchant for imagining war scenarios with military toys. While enjoying a meal at a restaurant, Gloves is displeased when he receives a cheesecake not made by his favorite baker, Mr. Miller. His mother, Jane Darwell, expresses concern that Miller, who is missing, might have met with foul play, sensing that something sinister is afoot. Gloves investigates and discovers that Miller has been murdered, his body found in the bakery. In the aftermath, a young singer, Kaaren Verne, who was present, quickly departs upon hearing the grim news. Gloves’ mother believes that Leda Hamilton, a talented young singer, might possess vital information about the case, prompting her to track her down at a nightclub.
At the nightclub, tensions escalate as Gloves confronts Leda, who is upset and creating a disturbance over Miller’s death. The situation intensifies when Marty Callahan, a co-owner of the club, calls Gloves to assist in calming things down. During their interaction, Gloves shares a drink with Leda, but chaos ensues when her piano player, Pepi, Peter Lorre, takes her away to a back room, where unexpectedly, he shoots Joe Denning, a partner of Marty. Leda and Pepi then vanish in a taxi, leaving Gloves stunned and searching for answers. Before succumbing, Joe Denning raises five fingers, signaling Gloves to uncover who’s behind the murder, but Gloves inadvertently leaves one of his own gloves at the scene.
As suspicion grows and Gloves becomes a suspect in Joe Denning’s murder, he begins tracing the taxi to an antiques auction house operated by Hall Ebbing, played by Conrad Veidt, and his assistant, Madame. Gloves attempts to blend in by posing as a bidder but is soon recognized by Pepi. Trusting Leda initially, Gloves finds her at a secret location, but she soon knocks him out, leaving him tied up with Sunshine—an associate who was previously captured—inside a storage room. Later, Leda returns to free them, revealing a shocking discovery: they stumble upon a room filled with maps, charts, a short-wave radio, and a portrait of Adolf Hitler. The pieces of the puzzle come together as Gloves realizes that the captors are Nazi fifth columnists, the so-called “fivers.” Glimpsing at a notebook, Gloves uncovers that Miller and Leda share connections rooted in World War II atrocities, including references to Dachau and her original Jewish name, Uda Hammel.
With Leda’s help, Gloves and Sunshine narrowly escape, pursued into Central Park. Leda explains her situation—her work with Ebbing and the Nazi spies is a desperate effort to save her father’s life. Gloves fights off a Nazi as Leda reads a torn-out page, revealing her father is already dead, a fact that devastates her. The trio then seeks refuge at the police station, but authorities, skeptical of Gloves' story, attempt to arrest him. In a daring move, Gloves dives into the East River to escape, eventually reaching his lawyer’s apartment. However, his troubles are far from over as Marty and his gang invade, seeking vengeance for Joe Denning’s murder. After convincing them of his innocence, Gloves manages to unite the two gangs against the Nazi spies, turning the tide of the clandestine war.
The climax intensifies as Gloves, Sunshine, and Barney confront Nazi operatives at an underground meeting. Disguised as Nazis, they manage to infiltrate the gathering, capturing two of the enemies, and disrupt their plans. Ebbing attempts to escape, asking Pepi to join him in a reckless attack on a battleship in New York harbor, but Pepi refuses. Ebbing murders Pepi and proceeds alone, heading to the docks where Gloves follows him. Ebbing forces Gloves into a motorboat laden with explosives, steering it toward the battleship with a gun to his head. Demonstrating quick thinking and courage, Gloves manages to steer the boat off course and abandon it, causing the explosion to take Ebbing instead.
In the aftermath, Gloves and Leda learn that all charges against him have been dropped, and he is to be honored at city hall for his bravery. Meanwhile, his mother, Jane Darwell, reappears at the scene, worried about her missing milkman and expressing her ever-present feeling that something’s not right—highlighting her persistent intuition.
This longer, detailed journey underscores the themes of heroism, deception, and relentless pursuit of justice amid the chaos of wartime espionage, with a cast of compelling characters navigating danger at every turn.
