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Admiral Matthias W. Jefferies was Chief of Starfleet Operations in 2264. He authorized the recommissioning of three Daedalus-class starships for use by the Starfleet Corps of Engineers. (Star Trek Magazine Issue 162: "Blast Off!")
In 2265, Admiral Mattea Hahn served in the capacity and was partly responsible for a refit program to several Constitution-class vessels, such as the USS Constellation, USS Defiant and USS Enterprise. (TOS - Crucible novel: The Fire and the Rose)
In 2270, newly-promoted Rear Admiral James T. Kirk was made Chief by Admiral Heihachiro Nogura in the wake of the Rittenhouse Scandal and other difficulties over several years. Kirk remained in the post until 2273, when he regained command of the USS Enterprise during the V'Ger crisis. He was reinstated in 2283 after his brief retirement from the service. (TOS novel: The Lost Years, TOS movie: Star Trek: The Motion Picture, TOS novel: Elusive Salvation)
In 2319, Admiral Los Tirasol Mentir served as Chief of Starfleet Operations. Admiral John Harriman, the Admiral-at-Large stationed at Helaspont Station, reported directly to Admiral Mentir. (ST - The Lost Era novel: One Constant Star)
By December 2385, the post was occupied by Admiral Philip Herthum. He was the one who issued Captain Benjamin Sisko and the USS Robinson (NCC-71842) new orders of an upcoming multi-year exploration assignment into the Gamma Quadrant. (DS9 novel: Ascendance)