I just thought this up while looking through pages of the DS9 characters' 1950's personaes on Memory Alpha. Kirk would be experiencing visions like those of Sisko's in "Far Beyond the Stars" and "Shadows and Symbols." Kirk becomes "Boston Legal's" Denny Crane, and TOS characters would be BL characters.
McCoy: Alan Shore
Spock: Carl Sack
Janice Rand: Shirley Schmidt
Chekov: Jerry Espensen
McCoy: Alan Shore
Spock: Carl Sack
Janice Rand: Shirley Schmidt
Chekov: Jerry Espensen