#then something/someone brought him back to starfleet and then carol and david were brought back to his life

[lenievi]

I thought about it, and I decided that I’m actually really happy about Antonia existing in Kirk’s life and him having a chance at happiness for like two years.

[lenievi]

I think the galaxy owes me one. All right, ...I was like you once ...so completely blinded by duty and obligations that I couldn't see anything past this uniform. And in the end, what did it get me? An empty house (Kirk, Generations)

I still haven’t watched Generations, but I have thoughts anyway

I know that we all have our own interpretation, and mine is “Kirk has always yearned for home, love, the simple life, even family” but his duty held him back. His orders, his obligations, his ship, his crew – those were always the most important. He could never give any of his partners his all, he could not even promise his friends not to send them to death – he killed Gary, he send Spock on a suicidal mission, he sacrificed Spock in Return to Tomorrow, he would do the same with McCoy if the script demanded it. His uniform was everything.

I’m going to assume that after TMP, Kirk was still doing stuff in space, missions, surveys, but more and more he had to just sit behind a desk and do nothing. And suddenly he had a lot of time to think, and when he couldn’t go out to space and make a difference, maybe he could try what he always wanted - the simple life. So he packed up to Idaho to ride horses. And there he met Antonia.

He was almost 50, and he was offered a chance at what he’s always wanted but could never have. He bought a house, got a dog, and for two years, lived with Antonia. And I like to imagine that for a time, he was happy. After a long time, he got a chance at happiness and he enjoyed it.

But then something or someone dragged him back to Starfleet (or rather, to Starfleet Academy where he would oversee new cadets). And he knew that if he went back, he would hurt Antonia sooner or later, because he would never be able to be with her the way he could for the last couple of years. So he broke up with her, but it was something he regretted. But he buried it deep, and continued with his life. Celebrated his 52th birthday. 

And suddenly another of his regrets was thrown back into his life - Carol and David, his son.

And then Spock died. And then he was brought back, but David was killed and the Enterprise destroyed. Then TFF and TUC happened. He spent seven years wallowing in what ifs and “my son I never knew”, and he couldn’t deal with the world moving on, moving forward. But he could at least still be out there making a difference.

But then they retired him for good. They decommissioned the Enterprise, and he stopped being the captain. And a few months later they told him to give his blessing to a new ship. Enterprise-B. With a new crew. The first starship Enterprise without James T. Kirk in command in thirty years.

And he sacrifices himself and gets stuck in some time anomaly and is presented with the last time when his life was simple. When he was happy. And he wants to stay. Badly. But it’s an illusion. It doesn’t matter. It isn’t real, and it’s long gone. An empty house. 

An empty chair, he truly yearns for.

He’s not the Captain anymore.

So he leaves the “paradise” and makes the last difference, and dies to help the Captain of the Enterprise. 

This vessel, I give, she takes. She won't permit me my life. I've got to live hers. (Kirk, The Naked Time)