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Can't see Kirk ever giving in to the dark side, but Sisko or Janeway...
Sisko was firmly a Gray Jedi. Always on the side of the Light, but sometimes one has to get their hands dirty to move things along.
The Sisko was Mace Windu before Mace Windu was Mace Windu.
I've had it with this monkey-fighting war for this Monday-to-Friday quadrant!
Janeway: "I will never allow -"
Sith: "We have coffee."
Janeway: "I'm going to personally tuvix the shit out of any je-die I find, the women and the children too."(Garack voice: especially the women and children...)
Aeronmelon is right about Sisko, and Janeway was forced into a desperate survival situation while still doing her best to maintain the ideals of the Federation.
Kirk and Riker wouldn't comprehend (nor bother to) the force, they would just gravitate towards where the hot women at.
"Set course to the nearest sith bikini planet, we need to perform ... erm, like emergency plasma polarity manifolds maintenance or something.
Pink alert!"