In 1942, Romanoff met John Kirk during a "wild night in Moscow". Sometime later, Romanoff was one of two Russians who entered a German prison camp in Stalingrad during the great battle in the city. Disguised in German uniforms, they hoped to steal a Ju-52 transport plane which was needed to fly Commissar Nikita Khrushchev to Moscow. The two were caught by the Germans, and in the ensuing struggle Romanoff mistakenly shot the time-lost Pavel Chekov on the helmet, not realizing he was Russian.
Romanoff was incarcerated with Chekov and John Kirk. He was subsequently tortured by the Nazis and, erroneously thought to be dead, was left on a pile of unburied corpses. Crawling to a farmhouse, Romanoff convinced a group of laborers to begin sniping at the Germans, allowing him to rescue Kirk and Chekov. As Kirk began to take off in the Ju-52, Chekov pulled Romanoff on board the taxiing airplane, getting wounded in the shoulder in the process. Romanoff and the others on the plane safely reached the People's Hero airstrip in Stalingrad. (TOS novel: Home Is the Hunter)