The first season follows Blair Pfaff, an aspiring white stockbroker on Wall Street. Through a series of farcical events, he ends up working for Maurice Monroe, a veteran stockbroker. Blair endures workplace hazing and fights to prove he's tough enough for the high-stakes environment. Simultaneously, he tries to preserve his strained engagement to spoiled heiress, Tiffany Georgina. Monroe plans to use Blair to execute an underhanded business deal that involves buying out Tiffany's family company, Georgina Jeans. Dawn Darcy, the only woman among her coworkers, is running out of patience when it comes to Monroe's unwillingness to recognize her value in the workplace. Her husband wants to have children, leading to a crossroads in their marriage. Keith, an employee who takes interest in bullying Blair, is a closeted homosexual who carries on an affair with a Broadway performer. Monroe, meanwhile, struggles with the internal turmoil of reaching the high standards he sets for himself, as well as living under a false identity. The resulting backdoor deals, personal conflicts, and the journey of a particular pin create an increasingly convoluted mess as Black Monday approaches.