Star Trek has only hinted at the events of Admiral James T. Kirk (William Shatner) and the crew of the USS Enterprise's "lost years". In Star Trek's timeline, the 5-year mission of Captain Kirk and the Starship Enterprise seen in Star Trek: The Original Series took place from 2265-2269. Star Trek: The Motion Picture picked up in the 2270s, and the rest of the Star Trek: The Original Series movies follow a relatively tight chronology from 2285-2293, when Kirk and his Enterprise crew permanently go their separate ways.
Star Trek's 23rd century is well-documented overall. Although the events of the first four and a half decades of the 23rd century are largely unrecorded, between Star Trek: Discovery seasons 1 and 2, Star Trek: Strange New Worlds, Star Trek: The Original Series, and the first six Star Trek movies, there is a clear picture from the mid-2250s to 2293. However, in the years between Star Trek: The Motion Picture and Star Trek II: The Wrath of Khan, there are big question marks about what happened to Admiral Kirk and his USS Enterprise crew.
Admiral James T. Kirk and the Starship Enterprise share "lost years" that span about a dozen years between Star Trek: The Motion Picture, which happened somewhere around 2273, and Star Trek II: The Wrath of Khan in 2285. It's established canon that after the five-year mission of Kirk's Enterprise in Star Trek: The Original Series, he was promoted to Rear Admiral and made Chief of Starfleet Operations. Kirk returned to Captain the Enterprise in Star Trek: The Motion Picture.
It's possible Admiral Kirk commanded the Starship Enterprise on a second five-year mission after Star Trek: The Motion Picture. Star Trek Generations established that Kirk retired from Starfleet, moved to a mountain home in Idaho, and met a woman named Antonia. Kirk gave a peaceful life of horses and homesteading on Earth the old college try, but the lure of outer space adventures was irresistible. At some point before Star Trek II: The Wrath of Khan, Kirk left Antonia and returned to Starfleet.
Star Trek has only revealed tidbits about how Admiral Kirk's Starship Enterprise crew spent the lost years from the 2270s to 2285. Spock (Leonard Nimoy) returned to Starfleet after Star Trek: The Motion Picture and was promoted to Captain of the Enterprise. The Vulcan became an instructor at Starfleet Academy, and the USS Enterprise became an Academy training vessel under his command. Enterprise crew members Dr. Leonard McCoy (DeForest Kelley), Hikaru Sulu (George Takei), Scotty (James Doohan), and Lt, Uhura (Nichelle Nichols) remained aboard.
Meanwhile, Pavel Chekov was promoted to Commander and became First Officer of the USS Reliant under Captain Clark Terrell (Paul Winfield). At some point, Sulu had a daughter named Demora (Jacqueline Kim), who eventually became helmsman of the USS Enterprise-B. Admiral Kirk last saw Demora 12 years before Star Trek Generations' prologue, set in 2293, which would be 2281. It's unlikely Star Trek movies and TV will further explore the events of Kirk and the Enterprise's "lost years," but perhaps the fact that the Enterprise and his crew remained in action was what pulled Admiral Kirk back to space.
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