In 2257, Gaynor petitioned for advancement to the second officers position aboard the Constitution but was passed over in favor of James T. Kirk, a lieutenant several years his junior, who had previously served aboard the USS Farragut. Despite the disappointment at being passed over, Gaynor still found it in himself to join the senior staff in the ship's lounge as they welcomed Kirk aboard.
A short time later, Gaynor's anger at Kirk flared in the rec room, when the young helmsman accidentally walked into him while carrying a tray of food, which then deposited itself down the front of Gaynor's uniform. Gaynor flipped Kirk's tray at the refuse aperture of the food slot, which missed and clattered to the floor. Refusing to pick it up he began to storm out, before being ordered back by Commander Akira Hirota who demanded he show more respect to the second officer and pick up the tray.
Gaynor later served at the weapons station on the bridge when the Constitution entered orbit of Sordinia IV to investigate the threat of six alien satellites that had appeared. When the Constitution came under attack by the satellites, Gaynor successfully disabled one of the satellites weapons before the starship was forced to withdraw. At the following briefing with the senior staff, Gaynor was the first of "Augenthaler's veterans" to support Kirk's and Borrik's plan to infiltrate the satellite they had disabled and take down the networked platforms from there, despite the risk of heavy damage.
With the approach of the alien mothership, Gaynor advised Kirk to take the Constitution out of range and leave Darick Lynch and Anita Jankowski behind on one of the satellites. However, Kirk disagreed and ordered Gaynor to send two of his security guards to the satellite to search for the remaining survivor. When the satellite was destroyed, killing both Lynch and the two guards, Park and Zuleta, Gaynor was outraged, and stated that he had lost complete faith in Kirk's command abilities.
Despite his misgivings, Gaynor continued to follow Kirk's orders when he was told to lead a second landing party to the mothership to defeat its ability to control the network. Whilst Lieutenants' Polcovich and Borrik worked on the ship's computers, Gaynor and security guards Chafin and Reboulet were charged with defending them, and was involved in combat with the aliens. When his team became surrounded, Gaynor contacted the Constitution and pleaded with Kirk to commence his attack at the cost of their lives, but Kirk refused, and the team were rescued although it placed the mission in jeopardy.
Safely back aboard the Constitution, Gaynor went straight to the bridge and punched Kirk in the face, causing Kirk to have him held in the brig on insubordination charges. However, Kirk later dropped the charges and they both decided to put past events behind them and forgave each other. Kirk later placed several commendations in Gaynor's personnel file. (TOS - My Brother's Keeper novels: Constitution, Enterprise)
Gaynor eventually left the Constitution just a few weeks after Kirk himself had departed, finally earning a second officers position aboard the USS Potemkin. (TOS - My Brother's Keeper novel: Enterprise)
|USS Constitution personnel|
|USS Constitution (22nd century)||La Forge|
|USS Constitution (prototype)||Augenthaler • Banks • Barton • Borrik • Carvajal • Chafin • Ferris • J. Gaynor • Herzog • A. Hirota • A. Jankowski • W.M. Jefferies • J.T. Kirk • Lidell • R. Likins • Livingstone • D. Lynch • Masefield • L.H. McCoy • Medina • G. Mitchell • Park • Polcovich • Rawitzer • Reboulet • Tomberlin • C. Velasquez • P. Waterston • R. Wesley • Wooten • Zuleta • unnamed personnel|
|USS Constitution (Galaxy-class)||J. van Osterlich • Solack • T. Soga • B. Spencer|
|USS Potemkin personnel|
|USS Potemkin (NCC-1657)||J. Armstrong • Arviela • S. Ascher • D. Bailey • T. Barrows • Callas • M. Cleary • D.M. Flinn • M. Garson • J. Gaynor • Gladstone • Jonesy • L. Kelso • Konstantin • R. Lonergan • D. Paris • M. Rahda • H. Takeshewada • Tutakai • N. Uhura • Yellowhorse|
|USS Potemkin (NCC-18253)||M. Bertrand • W. T. Riker|