Sure, Sauron has the One Ring. But, Kirk has the resourcefulness of a planet killer killer.
I give the edge to Kirk, since he’s got both a dark side and a good side.
Here is some diologue for your pleasure:
Kirk: Sauron, you bloodsucker. You’re gonna have to do your own dirty work now, do you hear me? Do you?
Sauron: Kirk. You’re still alive, old friend.
Kirk: Still, “old friend.” You’ve managed to kill everyone else but like a poor marksman, you keep missing the target.
Sauron: Perhaps I no longer need to try, Admiral.
[beams the One Ring away]
Kirk: Sauron… Sauron, you’ve got the Ring, but you don’t have me. You were going to kill me, Sauron. You’re gonna have to come down here. You’re gonna have to come down here.
Sauron: I’ve done far worse than kill you, Admiral. I’ve hurt you. And I wish to go on hurting you. I shall leave you as you left me, as you left her: fingerless for all eternity in the center of a dead planet, buried alive. Buried alive.
Archer: Grrrr…snarl…I’m in a crappy mood that’s lasted since “The Expanse” and I’ve alienated every one of you. I wish to go on…alienating you. All I do anymore is yell, complain, furrow, push, grab, shove and threaten. Even my dog doesn’t want me around anymore. I’m psychotic and I don’t care who knows it.
I–
Crew plus Porthos: All right, that’s enough. We’re airlocking you and blowing your grouchy ass out into a perpetuatizing reflective anomaly so you’ll have to spend eternity staring at your own sour face.
Sauron could send the Nazgul, or an army of 10,00 orcs, none of which Kirk could defend himself against. Or, if he regained the ring, Sauron could just do to Kirk what he did to Elendil.
Sure he can. All he needs to do is find naturally-occuring deposits of sulpher, saltpeter, and charcoal, and an improvised lathe.
But let’s look at this mathematically.
Torn-Shirt Kirk > Picard
Picard = Patrick Stewart
Patrick Stewart = Professor X
Professor X > Magneto
Magneto = Ian McKellan
Ian McKellan = Gandalf
Gandalf > Sauron
Kirk would just talk Sauron into blowing himself up. If he could do it to Nomad and Norman and that city-controlling computer in “Return of the Archons”, he could do it to Sauron.
(And besides, Sauron doesn’t even have the One Ring. It’s currently in the hands of Balok from “The Corbomite Maneuver.”)