12 Most Heart-Breaking Star Trek Moments Ever
6. Picards Interrogation - Chain Of Command Pts 1 & 2 - TNG

A clandestine sabotage mission goes awry and Captain Picard is captured by the Cardassians to obtain information about the defences of Minos Korva, a tactically significant planet. He is tortured by the sinister Gul Madred through a combination of humiliation, sensory deprivation, pain infliction, and starvation and deception techniques. One particular attempt to break Picards will involves the assertion that there are five lights when in reality there only four in front of him.
During the interrogation, this is a recurring battle. Picard is able to constantly maintain that there are four lights even after the point where he actually believes he can see five. While his spirited resistance is a noble thing to behold, it is also a saddening thing to see the sinister Madred humiliate and bring down a heroic captain like Picard.
The use of torture as a military practice is a despicable and loathsome one. While it is a non-human delivering the torture, this episode is a clear indictment of the act and a reminder of the cruelties of war. This is a truly sad moment and one that cant help but elicit sympathy from a viewing audience. Cruelty is a heartbreaking thing to witness.