James T. Kirk/Key dates/2280s

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|-| 2281=Retires from Starfleet.
|-| 2282=Meets Antonia and enjoys a romantic relationship with her until choosing to resume his Starfleet career instead of marrying her — a decision he later regrets.
|-| 2284=Returns to Starfleet as an instructor at Starfleet Academy.
|-| 2285=
* Assumes temporary command of the Enterprise during a routine training mission, engages [[Kahn Noonien Singh] in the Battle of the Mutara Nebula.
* Deserts from Starfleet later that year to retrieve body of Captain Spock from Genesis Planet.
|-| 2286=
* Returns to Earth to face court martial charges.
* Subsequently, saves the planet in the Whale Probe incident.
* Demoted to captain for disobeying orders of Starfleet Commander Morrow and assigned to command the USS Enterprise-A.
|-| 2287=Takes the Enterprise-A to the center of the galaxy after Vulcan renegade Sybok hijacked the ship.
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