Lieutenant Bobby was a male Human Starfleet officer in the 23rd century. He served aboard the USS Enterprise from 2266 to 2267 under the command of Captain James T. Kirk, during the historic five-year mission. He often alternated between the command and operations divisions while he served as a maintenance technician, security guard, and transporter chief.
He and a sciences technician were chased in the ship's corridor by a rapier-wielding Lieutenant Sulu, who was under the influence of the Psi 2000 virus. Following the incident, he was among the guards who entered the engineering control room to apprehend the polywater intoxicated Kevin Riley, who had taken control of the ship through that station. (TOS: "The Naked Time")
During the Romulan Neutral Zone Incursion, when the Enterprise was attempting to outrun a plasma torpedo, Kirk signed off on his clipboard and handed it to Bobby, instructing him to "feed this into the space recorder and jettison immediately." (TOS: "Balance of Terror")
He later served as member of the ship's security. When the Enterprise was thrown back in time to 1969, Bobby was attacked by United States Air Force Captain John Christopher, who stole his phaser. (TOS: "Tomorrow is Yesterday", "Operation -- Annihilate!")