Commodore Stone from TOS "The Court Martial"

Played by Percy Rodriguez.

Commodore Stone was the portmaster of Starbase 11 and oversaw the court martial of James Kirk over the death of Lieutenant Commander Benjamin Finney after the latter faked his death during an ion storm and altered the Enterprise's logs to show that Kirk had jettisoned the ion pod Finney was "in" prematurely. Interestingly, Stone didn't want to convene a court martial against Kirk at first. Instead, he offered to sweep the incident under the rug, but only if Kirk gave up starship command and accepted what amounted to a desk job in return. Jim Kirk refused, obviously and the court martial was convened to either clear or damn his name. Naturally, the end result was the former.

What I think is amazing about Commodore Stone is that he was black and outranked Jim Kirk. "The Court Martial" originally aired in 1967, so having a white character being subordinate to a person of color was pretty damn bold for the time.

This episode was also notable for featuring an Indian or South Asian Starfleet captain named Chandra, but that's another post for another day.

Picture via Memory Alpha.