In 2268, Black Jack Nova had half of a map showing the location of a stolen dilithium shipment. Starfleet, having acquired the other half, assigned USS Enterprise officers James T. Kirk, Spock, Leonard McCoy and Montgomery Scott to go undercover as pirates, contact Nova and recover the shipment. They found him in a tavern on Tortuga VI, where they impressed him by starting and winning a fight his crew. Afterwards, they showed him their half of the map and he hired them as crewmembers, promising to split the profits with them while secretly planning to kill them. Later, Nova made Spock and Scott walk the plank after Kirk told him that they were Federation spies, ejecting them from an airlock in spacesuits so that they would die slowly as their oxygen ran out.
Upon arriving at Taos IV in a shuttlecraft, Nova and his crew followed the map to the location of the buried dilithium, but when they dug there they found nothing. Nova accused Kirk of finding it first and tried to shoot him, but was stopped by Spock, who had been rescued by the Enterprise earlier. Nova fled into the jungle, fought off the pursuing Kirk, and made it back to his shuttle. However, it had been damaged when Kirk threw his sword at it, and when Nova took off, it crashed and exploded, killing him. (TOS comic: "The Flight of the Buccaneer")