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Admiral Saylor was a Starfleet flag officer, not native to Earth, who served in the 23rd century. By the 2260s, Saylor was serving as commanding officer of Starbase 33 and sector commander of the surrounding area.

Circa 2263, Saylor was attending a Starfleet function in San Francisco, when he met Captain James T. Kirk for the first time. A couple of years later, the USS Enterprise under Kirk's command was assigned to Saylor's sector. Around stardate 1312.4, Saylor contacted the Enterprise and ordered Kirk to take her out to the edge of the galaxy and, if possible, probe beyond.

Fifteen days later, the Enterprise arrived at Starbase 33 so that Kirk could be debriefed about the ship's findings. Although Saylor would normally perform such a debriefing, Starfleet Command assigned Captain Francis Damion to lead, but allowed Saylor to sit in. As Kirk reported about the Enterprise's discovery of the SS Valiant's flight recorder and the encounter with the galactic barrier and its affects on some of Kirk's crew, Saylor found himself starting to believe that Kirk was being colorful with the truth, but Kirk's logs backed him up and Damion pressed for the debrief to continue. (TOS - My Brother's Keeper novel: Constitution)

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