"Honor among Thieves" (season six, episode fifteen; 23 February 1998): Wikipedia-link.
Commentary: I watched "Honor among Thieves" back in October 2024, but I cannot be certain of the precise date as I failed to record it then.
O'Brien must suffer. In this episode, the chief goes undercover for Starfleet Intelligence, to infiltrate the Orion Syndicate, who are in cahoots with the Dominion. He grows too close to his target, a human Syndicate operative named Liam Bilby, whom O'Brien must then betray to complete his mission. Bilby goes through with his assignment, which has becomes a suicide mission thanks to O'Brien's infiltration, in order to protect his family from Syndicate retribution.
This is the first mention of the Orion Syndicate, & virtually the first mention of Orions since The Original Series, though no Orion is seen on-screen. Later, Enterprise & Lower Decks would establish the Syndicate as the government of the Orions.
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