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What happens between TMP and WOK?

Time to make stuff up!!!

Feeling young again after TMP, he starts acting that way and successfully completes a second 5 year mission, and after a mandatory year off, signs up for a 3rd, but soon thereafter, the ship is nearly destroyed and he is severely injured in hand to hand combat that he is convinced his younger self would have won.

Despite this, he, the crew and the ship miraculously survive yet again - thanks this time to the heroics of Spock instead of the severely injured captain who wasn't even conscious to save the day.

Facing the prospect of nearly losing their most celebrated commander in recent memory, he is forced by the top brass at Starfleet to either accept desk duty or retirement. They aren't willing to ship him or the Enterprise to the far reaches of the Federation any longer. Kirk is convinced that by his failure that he simply is no longer the man that he used to be and is afraid - not that he'll get himself killed, but that he'll get his crew and ship killed because he just doesn't have it anymore. He won't admit it to anyone else. He must project confidence. Retirement would be giving up the only life he's ever known, and admitting defeat, so he accepts desk duty.

When he takes the ship out for the first time since re-assignment, for a training cruise in TWOK, his carefully constructed demeanor begins to crack with snide comments about gallivanting around the universe being a game for the young... catching all his long-time friends completely off-guard. The prospect of being on the ship again, even on a training cruise brings back bad memories.

There. There's the made up Chimp version, on the spot! Worth nothing, but fun for me to write.
 
Not bad, a nice summary of what probably happened. My head cannon is the events in the novels happened, and your theory that the ship almost had a bad ending fits with that. Pick any one of a number of said stories and there is your ending point.
 
After the shakedown cruise, he never commanded the Enterprise again, beyond the emergency situation shown in The Wrath of Khan. No open ended five-year missions. He bounced from desk job to desk job. Even after getting the Enterprise-A, he was kept on a relatively short leash.
 
I'm more interested in my Kirk left starfleet after the five year mission and did nothing until TMP. Was he trying to do something else in his life and it just didn't work out? At least he had a career between TMP and WOK even if it was just a desk job. And seems like he kept in touch with everyone. Between TOS and TMP they all went there separate ways, Spock tried to get rid of his emotions, ultimately failing, McCoy became some hippi guy and Kirk I guess just did nothing. Both gaps are interesting to think about.
 
My take? Kirk docks at Spacedock Earth at the conclusion of TOS, in 2270, and gets promoted to Commodore and given a desk job. He gets more of those, and a further promotion to Rear Admiral, in the following seven years. He next spends seven days flying around in his old ship at Captain rank during and after ST:TMP, then returns to his desk job after being told that any other course of action would result in immediate dishonorable discharge. He spends the next five years at various desks again (including that of Academy Commandant), at his regular Rear Admiral rank he reverted to after his joyride week, achieving little. One weekend, he considers the drastic step of taking extended leave, perhaps even a whole month's worth of it, but then reconsiders and tells Antonia he will be going back to the office on Monday after all.

And then comes ST2:TWoK.

Timo Saloniemi
 
I'm more interested in my Kirk left starfleet after the five year mission and did nothing until TMP.

I take it you missed the beginning of the movie? Kirk is in an Admiral's uniform and brings up being Chief of Starfleet Operations for two-and-a-half years.

The Motion Picture said:
KIRK: Two and a half years as Chief of Starfleet Operations may have made me a stale but I wouldn't exactly consider myself untried. They gave her back to me, Scotty.
 
2273-2285. A twelve-year gap during which Kirk commanded the newly-refitted Enterprise on his second five-year mission of deep space exploration, returning in 2278 after which he relenquished command to Spock, who assumed the captaincy of the Enterprise for its tour of duty as a Starfleet Academy training vessel docked in Earth orbit.

Kirk gradually weaned himself away from Starfleet over the next three years, retiring for the very first time around 2281 when he met Antonia and the two of them settled on his uncle's farm in Idaho to pursue a relationship. In 2284 the call back to duty and his Starfleet uniform became too strong to ignore and he chose returning to duty with a promotion back to the rank of Admiral over proposing marriage to Antonia and continuing their life together. About a year later the Reliant and Genesis Device incidents happened and the second and third films take place in the timeline.
 
Captain Morgan Bateson's girlfriend was seduced by Kirk and the two of them filmed a notorious holoporno without Bateson's knowledge. He didn't know what to do about them tossed salads and scrambled eggs.
 
He uses the Guardian of Forever to live in 1970's Earth and becomes a writer who commits murder but is caught by a clever police officer named Columbo. However the jury finds him not guilty, after the trial he changes his name and becomes a radio host who commits murder because he is secretly in love with his adopted daughter who wants to leave home with her boyfriend. Once again Columbo catches him out. Kirk decides life in the 1970's is too unfair so he asks the GOF to take him back to 23rd century Earth since a boring desk job at Starfleet is much better than a 1970's jail cell.
 
Kirk decides life in the 1970's is too unfair so he asks the GOF to take him back to 23rd century Earth since a boring desk job at Starfleet is much better than a 1970's jail cell.

But not before the GOF lands him a Lt Colonel's gig in the United States Air Force, where with the assistance of Lt Kyle, he investigates the decades old crash of a long lost WWII bomber, hoping to find Lokai.
 
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