The film opens on a rainy night in a local Chinese restaurant situated in southern Brooklyn, New York City. Here, we meet Sheldon 'Shelley' Levene, an experienced real estate salesman, who is anxiously trying to reach a doctor via a phone booth to gather updates on his daughter, currently hospitalized due to a serious illness. Nearby, Dave Moss (played by Ed Harris) struggles to sell properties at Rio Rancho Estates. After a round of complaints about their dubious leads, they both return to their office, Premiere Properties, where they encounter a domineering figure named Blake (Alec Baldwin), sent by their company owners, Mitch and Murray. Blake's harsh demeanor is on full display as he chastises the sales staff for their lackluster performance and lays down a high-stakes contest: the top seller earns a Cadillac, while the worst performer is unceremoniously fired.
Blake holds out hope for the coveted Glengarry Leads—prime prospects capable of purchasing the properties—designating them for the most successful agents. This intensifies the competition among the men. However, when office manager John Williamson (Kevin Spacey) distributes outdated leads instead, Levene becomes increasingly agitated. In a desperate plea, he lays bare his dire financial situation and his daughter's health challenges, imploring Williamson for access to the Glengarry Leads. When his pleas are ignored, Levene resorts to threats, bribes, and emotional appeals, yet Williamson takes advantage of his urgency, asking for $50 per lead along with 20% of his profits—a sum Levene cannot afford.
Meanwhile, Dave Moss and his colleague George Aaronow (Alan Arkin) face their own frustrating day, compounded by the portrayal of their boss as uncaring. Moss hatches a daring plan to stage a burglary and sell the Glengarry leads to a rival agency, Jerry Graff, but finds Aaronow reluctant to join him. Over at the bar, Ricky Roma (played by Al Pacino) engages a timid customer, James Lingk (Jonathon Pryce), in conversation, spinning a narrative of opportunity that leaves Lingk entranced.
The following day, shocking news greets the sales team: the office has been burglarized. As police interrogate the salesmen, Roma finds himself on the wrong side of luck—he was banked on the Glengarry leads for his Cadillac dream. Just as Levene triumphantly announces a hefty $82,000 sale, the tension mounts when Lingk arrives to retract his investment due to his wife's objections. Roma desperately attempts to salvage the deal, employing deceit and misdirection, only to be thwarted by Williamson's careless remarks.
As the chaotic interrogation progresses, Levene inadvertently reveals his knowledge of details only the burglar might know, leading Williamson to confront him about his involvement in the crime. Despite attempts at humor, Levene’s facade crumbles as he confesses to breaking in alongside Moss and betraying their trust for personal gain. Levene’s grand illusion of success is shattered when Williamson declares that the buyers from his big sale are financially unreliable. In a final bid for sympathy, Levene invokes his daughter’s plight, yet it does nothing to soften Williamson, who swiftly decides to report him.
In a poignant scene, the paths of dreams and despair intertwine, as the office dynamics shift once more, leaving Levene to confront the consequences of his actions and the brutal reality of his profession.
