Snake into bringing about an insurrection on Shadow Moses Island, along with the other serving members of FOXHOUND and the Next-Generation Special Forces. In addition, Ocelot used his influence to gain his old comrade Sergei Gurlukovich's support, providing military hardware to the Sons of Big Boss.

Early in the insurrection, Ocelot tortured ArmsTech President Kenneth Baker and broke his right arm, resulting in Baker divulging his detonation code for Metal Gear REX. Ocelot then killed the DARPA Chief Donald Anderson during a supposedly botched torture session. By doing so, he intentionally deprived Liquid of the necessary launch codes for Metal Gear, though the real reason was that Anderson recognized Ocelot as not truly working for the terrorists.[18][19] He was later reprimanded by Liquid for this action, which, compounded withPsycho Mantis' inability to read Anderson's mind due to cranial implants designed to prevent mind-readers to detect the pass-codes, had them restrategize by tricking the arriving force to activating REX for them.[20] They made Decoy Octopus disguise himself as Anderson to talk Snake into the act.

Ocelot later challenged Solid Snake to a gunfight. But midway through the duel, his right hand was cut off by the Cyborg Ninja, and he was forced to flee, taking the amputated hand with him. Ocelot later vowed to kill Snake during a conversation with Vulcan Raven, expressing irritation when the latter reminded him of his defeat. Later after Psycho Mantis's death and Sniper Wolf captured Snake, Ocelot interrogated Snake, electrocuting him via his torture device, with orders from Liquid to not kill