As the gates of incarceration swing open, freeing John "Duke" Anderson (Sean Connery) after a decade-long stint behind bars, he reignites his romance with Ingrid Everleigh (Dyan Cannon). However, he is soon confronted with the reality that Ingrid has been living a lavish life with her affluent patron, Werner (Richard Shull), among Manhattan's elite. With the exhilarating taste of freedom invigorating him, Anderson devises an audacious plot to rob the entire apartment building in a single, masterful operation, enlisting a seasoned crew of four to assist in his scheme. This eclectic ensemble features an aging ex-con, "Pop" (Stan Gottlieb), who coincidentally was released on the same day as Anderson; "The Kid" (Christopher Walken), a young and ambitious upstart; and Tommy Haskins (Martin Balsam), a clever antique dealer with a knack for spotting valuable treasures.
As Anderson meticulously lays out his plan, he inadvertently finds himself ensnared in a complex web of oversight from various government agencies. Werner's private investigator is keeping a close watch on Ingrid, while the Bureau of Narcotics and Dangerous Drugs monitors a recently released drug dealer. Concurrently, the FBI keeps tabs on Black activists and antique smugglers, and the IRS is investigating Pat Angelo (Alan King), the nostalgic Mafia kingpin funding Anderson's ambitious heist. Despite each agency's focus on different targets, they remain unaware of how these elements intertwine, blind to the approaching heist.
In the meantime, Anderson tasks Haskins with surveying the apartment building to pinpoint the most lucrative opportunities and gauge what they can take. Edward Spencer (Dick Anthony Williams) is enlisted as the getaway driver, while "The Kid" expertly manages the burglar alarms and phone lines. "Pops," eager to reintegrate into society, is given the green light by Anderson to join the crew. However, complications arise when Rocco "Socks" Parelli (Val Avery), a cold-hearted mobster, enters the mix with an ultimatum: Anderson must eliminate him during the heist, much to Anderson's dismay.
As Labor Day weekend approaches, the crew dons uniforms from Mayflower moving and storage, deftly cutting through phone lines and alarm systems as they ascend the building. With residents still in their homes, they methodically relieve each apartment of its valuables, while "Pops" takes on the role of an unofficial concierge, keeping the doorman locked up in the cellar.
Amidst the sweltering summer heat, Jerry Bingham (Scott Jacoby), a paraplegic and asthmatic resident, is confined to his air-conditioned refuge. Despite his limitations, Jerry's ingenuity shines through as he uses his amateur radio equipment to communicate with fellow enthusiasts across state lines. His distress signals finally reach the authorities, leading to a heated back-and-forth over who should cover the cost of their communication.
Meanwhile, the unsuspecting robbers continue with their heist, oblivious to the massive police presence building outside, ready to thwart their escape and dispatch a specialized unit via a neighboring rooftop. What follows is a tense and brutal shootout, with Anderson taking down "Socks" but sustaining severe injuries from law enforcement in the process. The remaining members of the crew face various fates, from capture to death.
As the chaos subsides, "Pop" ultimately chooses to surrender, shifting the blame to his deceased partner in crime. Having struggled to adapt to life outside the prison walls, he yearns for the certainty and safety that prison life once provided him.
In the wake of the tumult, police investigators discover an array of audio surveillance equipment that was left behind by the private detective monitoring Ingrid. As they trace the origins of this hidden surveillance, they stumble upon Anderson, who is in critical condition after a failed attempt to flee. To avoid the embarrassment of their oversight in failing to detect the heist and the legal issues surrounding the acquired recordings, each agency orders the destruction of their tapes, effectively erasing the evidence and any last doubts regarding their competence.
