Ocelot later witnessed Volgin's torture and killing of Aleksandr Leonovitch Granin, after the latter was accused of enemy espionage. Ocelot berated Volgin about his practices, but to no avail. When Volgin's lover Tatyana arrived, he noticed the smell of motorcycle gasoline on her, and made his suspicions known to her by threatening her with a crossbow and commenting on the state of her boots (which were biking boots instead of officer boots).

After Snake was captured while infiltrating the fortress, Ocelot again bore witness to Volgin's brutal torture, but developed an appreciation for it, calling it "the ultimate form of expression." He also attempted to expose EVA in her disguise as Tatyana after she objected to Volgin ordering the The Boss to gouging Snake's eyes out, subjecting her tohis Russian roulette. However, Snake, desperately trying to protect EVA, got between the two of them, resulting in Ocelot accidentally discharging his gun in Snake's face, costing him his right eye, an act which earned Ocelot a violent slap from The Boss. Volgin, however, satisfied with the outcome, left the room. With Volgin gone, Ocelot covertly picked up the transmitter that The Boss had earlier placed on Snake's body, and replanted it on him while hitting him in the back. After Snake escaped, Ocelot hunted him down in the sewers and was about to shoot him with the bullet from their first meeting, until Snake evaded him by jumping from a waterfall.

When Snake was again caught infiltrating Groznyj Grad, Ocelot expressed his desire to settle the score with