https://archive.org/details/CharacterInsightEp227
Chekote first appears in Deep Space Nine in an episode where Bajoran extremists try to seize control of the station. The Admiral orders Sisko and his crew to leave the station, despite evidence that this faction was backed by Cardassians. His reasoning is that the Prime Directive applies and forces Starfleet to take a non-interfering position, which is one of the stronger interpretations on the Prime Directive seen on screen. He appears to be mournful of the potential loss of the wormhole and Bajor, but nevertheless, the order was given.
QUOTE - "Hell of a Turn" (The Circle, DS9)
The next time we see Vice Admiral Chekote, he appears as a supervisor to the Enterprise-D. Unlike his first appearance, where he is the usual unsympathetic admiral, in this appearance he allows Commander Riker to delay a mission and investigate a mysterious apparent death of Captain Picard. Of course, Picard turns out to not be killed in the archaeological expedition, proving the Admiral's instincts right on this occasion.
Chekote is one of only five characters to appear on Deep Space Nine before appearing on TNG. Of those characters, he is the only non-regular and non-regular recurring face on Deep Space Nine, giving this character a unique aspect different than all other such characters. He does not really have a unique story though, as we receive another typical jerk admiral story as mentioned before.
Nonetheless, it's good to see the overlap in these shows with overlapping timelines, even though the show writers did not take advantage of crossovers much. Would the shows have been better with more crossover? Definitely food for thought in view of this character.
Chekote is played by Bruce Gray, who still acts today and has been a prolific TV actor for four decades. One of his most recent appearances is in the movie My Big Fat Greek Wedding 2, because we needed another one of those.
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