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By late 2499, Littlefield was in his early thirties. However, with iron-gray hair in long, unkempt strands, the faint grizzle of a beard, piercing dark eyes and a scarred and twisted face, he looked about a decade older.
- Littlefield reflects on his early service.(src)
Serving in the Confederate Marines, Littlefield obtained the rank of captain. His length of duty was extensive and, judging how no news of the destruction of Korhal reached him, isolated from Confederate space. However, due to executing operations in a style that did not mesh well with his superiors (along with PFC Fetu Koura-Abi and others under his command), Littlefield was bumped down to sergeant, losing his commissioned officer status.
In December 2499, Littlefield was serving in the 417th Confederate Marine Platoon. The 417th was deployed to Mar Sara to recon the settlement of Oasis and retrieve a piece of Confederate equipment. Littlefield was placed in command of Second Squad.
The platoon was heavily engaged when PFC Ardo Melnikov stumbled into an underground pit, uncovering the zerg that had infested Oasis. Once PFC Fetu Koura-Abi retrieved the psi emitter, Littlefield and Sergeant Jensen led the remnants of the platoon as they withdrew. Littlefield survived the nuclear destruction of Oasis and the trek through the Basin to arrive back at the now-near-deserted Confederate outpost they had started out from. Littlefield and Melnikov eventually became good friends.
Littlefield was killed when a group of mutalisks attacked the outpost. The zerg were drawn by the communications signal between the outpost's command center and Tegis Marz. When Marcus Jans negated the platoon's efforts to hide, Littlefield was picked up by a mutalisk. Littlefield fired at his assailant causing his armor to slowly dissolve from the acid spilling out from the mutalisk. He managed to kill the mutalisk but subsequently fell to his death.