It's very unrealistic and bordering on corny fan fiction, but I still love the idea of it.I think about this a lot. I think the honest answer is no. William Shatner won't ever play James T. Kirk...
But if I were to imagine how, I'd say assuming there were a few more movies beyond... BEYOND, then have the last one be a story about time travel and the consequences of time travel. Unite all the survivng original cast members. Shatner, Takei, Nichols, Koenig.
Ignore the events of Generations. The alternate timeline changed the fate of Kirk and the Enterprise B. Set the story in the year 2319. This would make Captain Kirk approximately 86 years old, and it would correspond to the ages of the original series actors. Have them for whatever reason send someone to go back in time to the five year mission and whatever year it takes place in (after the events of ST:B). Have the cast of the new movies Pine/Quinto etc headline the movie, with occasional cues and flashbacks/forwards to the older guys. Address the death of Spock in the JJ-Timeline somehow. A funeral on new Vulcan, with Shatner's Kirk in attendance. Wrap up the adventure of the movie with the older actors riding off into the sunset. That's how I'd give them a true send-off. It'd be a logistical mess... but if there was a nice mix of the casts with some sweetness and action, it could be very successful. The 60's cast is still so beloved, and it could bridge the timelines and bring them back together. Everyone wins.
One question, how does the alternate timeline change the events of Generations? I don't think that makes sense.
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