Kirk's middle name was due to his grandfather's interest in Latin studies, but Kirk was embarrassed by it while in school and hid it from his classmates. Kirk had one sister, who by 1942 worked for the U.S.O. and was engaged to a man named Capelli; their father was dead by that year. Like his famous descendant, Kirk enjoyed a good time. He became acquainted with a Russian soldier named Ivan Romanoff during a "wild night in Moscow".
In October 1942, after being shot down while ferrying lend-lease P-39s, Kirk was incarcerated in a German prison camp in Stalingrad during the great battle in the city. His cellmates were Romanoff and the time-lost Pavel Chekov, who had been sent into the past by the omnipotent being Weyland. Kirk and Chekov were shot at with blanks by a Nazi firing squad as a form of psychological torture, but Romanoff rescued them as the Russian army began shelling the camp. Kirk, Chekov and Romanoff escaped in a Ju-52 transport plane, which Kirk flew to the People's Hero airstrip in Stalingrad, where it was needed to fly Commissar Nikita Khrushchev to Moscow.
Kirk subsequently left for London, but returned to Russia in November 1942 to fly Averell Harriman to London aboard a Consolidated B-24 transport. Chekov's Red Guard squadron escorted Kirk's plane. When the convoy was attacked over the Baltic Sea by German planes, Chekov abandoned his plans to escape to Sweden, fighting to save his captain's ancestor. Even after he lost a wing, Chekov urged Kirk to escape with Harriman. Kirk proceeded safely toward London, but Chekov bailed out into the ocean.