In 1998, NYPD Detective John Shaft II (Samuel L. Jackson), a relative of legendary private investigator John Shaft I (Richard Roundtree), is called in to investigate the grievous assault of Trey Howard (Mekhi Phifer) outside a restaurant. Shaft arrests Walter Wade Jr. (Christian Bale), the son of a wealthy real estate tycoon Walter Wade Sr. (Philip Bosco), after noticing blood on him and Wade claims he acted in self-defense. However, Trey's friend tells Shaft that when she and Trey entered the restaurant, Wade racially harassed him. Trey humiliated Wade in response and left the restaurant, and Wade followed after him. Shaft notices a waitress, Diane Palmieri (Toni Collette), eyeing Wade and tries to coax a statement from her but she claims to have not witnessed anything and disappears from the scene. When Wade mocks Trey after he dies on the ambulance stretcher, Shaft punches him and is suspended and transferred to another precinct. Later, Wade phones Shaft to taunt him that because of the punch, he was granted bail (for $200K) on the homicide charge and has fled to Switzerland.Two years later, Wade returns to the country and Shaft rearrests him. Shaft's friends throw him a celebratory party where the elder Shaft appears and warns him that Wade's wealth puts him at an advantage to beat the case. While temporarily detained at police headquarters, Wade befriends Peoples Hernandez (Jeffrey Wright), a Dominican drug lord who Shaft previously arrested (they were both put in the same cell). At his bail hearing, the judge makes Wade relinquish his passport in exchange for being released on bail again (for $1 MM); frustrated, Shaft resigns from the police force, promising to bring Wade to justice on his own terms. Worried that Shaft might find the missing eyewitness, Wade hires Peoples to find and kill her first.Shaft continues searching for Diane, enlisting the help of his friends Detective Carmen Vasquez (Vanessa Williams) and taxi driver Rasaan (Trevor Smith Jr.). Shaft gets Diane's location via her colleague Terry (Lanette Ware), who was at the restaurant that night. Diane spots Shaft and manages to escape. While visiting Diane's uncooperative mother, Shaft and Carmen realize they are being followed by officers Jack Roselli (Dan Hedaya) and Jimmy Groves (Ruben Santiago-Hudson), whom Peoples has promised a cut of the payment (of $40K) to follow Shaft and get to Diane.Disguised, Shaft and his former colleague, Detective Luger (Lee Tergesen), rob Wade of the money he had gathered to pay Peoples' off by selling some of his deceased mother's 'exclusive' jewelry. Now, without any cash, Peoples forces Wade to be his distributor to high end customers for 16 months, in exchange for finding Diane. Shaft and Luger plant the money on Roselli and Groves to make Peoples think he is being double-crossed (they call Peoples and tell him that the cops have the money under their car seats as they robbed Wade). However, Roselli and Groves spot Shaft fleeing the scene and realize they are being set up and resume tailing Shaft.Shaft traces a number Diane's mother called and finds Diane being protected by her brothers Mike (Ron Castellano) and Frank (Richard Cocchiaro). Before they can talk, Peoples' Gangbangers attack them. In the shootout, Shaft kills Peoples' younger brother and Mikey is injured. Shaft, Diane, Rasaan, and Frank take shelter at Rasaan's apartment, secretly followed by Roselli and Groves. While at the apartment, Diane admits seeing Wade murder Trey. Wade then made her keep silent in return for a payoff from Wade's father. Meanwhile, Peoples angrily attacks Wade over his brother's death.Peoples and his Gangbangers arrive at Rasaan's apartment, but Shaft engages and kills most of them in a shootout and everyone flees through the fire escape. Roselli and Groves try to kill Shaft, but Carmen comes up behind them and she kills the corrupt officers at Shaft's command. The shootout spills into the city streets where Shaft and Carmen kill the Gangbangers but Rasaan's cab crashes alongside Peoples' vehicle. Peoples takes Diane hostage with an ice pick. Shaft puts his gun down and convinces Peoples not to do Wade's dirty work and instead to fight him individually. Peoples releases Diane and drops his ice pick, then feigns preparing to fight Shaft before drawing his gun from his back; Shaft pulls his backup gun and kills Peoples first.Wade's trial finally arrives. Shaft tells Trey's mother, Carla Howard (Lynne Thigpen), that the trial will have a new judge, the D.A. as prosecutor, and an eyewitness. However, before the trial can begin, Carla guns down Wade on the courthouse steps and she is arrested. In the police station, Shaft reiterates to Carmen that he prefers to be a private detective. A woman arrives, asking Shaft for help filing assault charges against her abusive boyfriend. Shaft is initially reluctant, but when he sees her injury, he decides to help her via his methods. Shaft, along with John Shaft I and Rasaan, go together to confront the abusive boyfriend.