The Galactic High Commissioner in The Galileo Seven
I don't think I've despised a character more in all of Star Trek.
Forgetting his fashion choices which include an ascot and a bizarre half cape, all he does is annoy Kirk and says nothing of value.
He just reminds Kirk how difficult his task is or admonishes him for sending them out in the first place or reminding him how they'll have to abandon the search.
"You don't think you'll have any success, do you?"
How did this a-hole become a Galactic High Commissioner by saying stuff like this?