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He served on the ONI spyship Apocalypso long enough for Melissa, the ship's AI, to become protective of him. When the ship picked up the Deep-Space Artifact, McKaskill tried to send a message to Herzog about it. Melissa, however, recognized the act as treason and halted it at once to keep her crew member safe from capital punishment.
After the ship crashed in Lunar orbit and Major Standish acquired the artifact, Standish attempted to eliminate every former crew member including McKaskill. The brakes of his Hog were cut, but he was able to survive. He went dark after that, taking James James' black taxi across the country.