The detective who was handcuffed to Lee Harvey Oswald as he was shot dead by Jack Ruby has died at the age of 99. James Leavelle died Thursday at a hospital in Denver. The former Dallas homicide detective was handcuffed to Oswald as he was led through a police station basement on Nov. 24, 1963, two days after the assassination of President John F. Kennedy. Ruby, a nightclub owner, stepped out of the crowd and fired a fatal shot at Oswald. The moment was captured in one of the most famous photographs of all time which showed Leavelle in his white stetson reacting with shock. Leavelle later recounted that he told Oswald moments before the shooting: “If anybody shoots at you, I hope they are as good a shot as you.” Oswald replied: “You’re being melodramatic.”