The Last Castle (2001)

Lieutenant General Eugene Irwin (Robert Redford) is brought to a maximum security military prison to begin a ten-year sentence for his decision (in violation of a presidential order) to send U.S. troops on a mission in Burundi, resulting in the deaths of eight soldiers. Colonel Winter (James Gandolfini), the prison's commandant, is a great admirer of the general but is offended by a comment he overhears: Irwin criticizes Winter's much-prized military artifacts collection, calling it something no actual battlefield veteran would ever have.

Winter, who has never seen combat, resents the remark. He then takes exception to what he perceives as Irwin's attempt to change the attitudes of the prisoners, his admiration for Irwin fading fast. On one occasion, Irwin is punished harshly after stopping a guard from clubbing a prisoner, Corporal Ramon Aguilar (Clifton Collins, Jr.), who had made the mistake of saluting Irwin in the prison yard.

Continuing to observe acts of cruelty, Irwin attempts to unify the prisoners by building a "castle wall" of stone and mortar at the facility, which in many ways resembles a medieval castle. Envying the respect Irwin is clearly receiving, Winter orders his guards to destroy the wall. Aguilar, directly involved in its construction, takes a stand before the bulldozer. Winter orders a sharpshooter to fire a normally non-lethal rubber bullet directly at Aguilar's head, killing him.

After the wall is destroyed, Irwin and the inmates pay final respects to Aguilar in formation. Winter later tries to make amends with Irwin, who calls him a disgrace to the uniform and demands his resignation.

The prisoners begin to behave like soldiers around Irwin, using code words and gestures, infuriating the commandant. Winter reaches out to an anti-social prisoner named Yates (Mark Ruffalo), a former officer and Apache helicopter pilot convicted of running a drug-smuggling ring. Yates is bribed to inform about Irwin's plans in exchange for a reduced sentence.

Irwin organizes a plot to throw the prison into chaos. His intent is to show a friend, Brigadier General Wheeler (Delroy Lindo), the commandant's superior officer, that the commandant is unfit and should be removed from command under the Uniform Code of Military Justice. During a visit, Winter receives a letter threatening the kidnapping of General Wheeler by the prisoners. After ordering his men into action, Winter discovers that the scheme was a fake. Irwin orchestrated it as a way to detect how prison guards would react during an actual uprising.

Yates becomes the key to their plan, tasked with stealing a U.S. flag from the warden's office and seizing a Bell UH-1 helicopter used by guards. The inmate revolt begins.

Using improvised weapons -- some resembling medieval ones, such as a trebuchet -- and the tactics of a military unit, the prisoners capture an armored vehicle and the helicopter. The prisoners place a call to Wheeler's headquarters and inform him of the riot. Winter has little time to regain control before Wheeler will arrive to see the prison under siege. He orders the use of live ammunition against the prisoners.

Winter knows from Yates that Irwin's ultimate goal is to raise the American flag upside down, a classic signal of distress. Irwin's men create havoc but ultimately are confronted by overwhelming numbers of guards, all armed with live ammunition. Knowing further resistance would only mean a massacre, Irwin orders the prisoners to stand down. Winter has successfully halted the uprising, but Irwin nonetheless elects to personally hoist the flag.

Unable to make him stop, Winter orders his men to open fire on Irwin before the upside-down U.S. flag is flown. They refuse to do so on the orders of Winter's second-in-command, Captain Peretz. The colonel cannot persuade anyone else to follow his command, so he proceeds to shoot Irwin fatally himself.

Peretz places the commandant under arrest. The prisoners salute the flag and Winter now sees that Irwin has actually raised the flag in the correct manner. It flies above the prison's walls as General Wheeler arrives and Colonel Winter is led away in handcuffs. The story ends with the inmates building a new wall as memorial to their fallen comrades. Aguilar's and Irwin's names are among those carved onto the castle's wall.