Bilby: Good. It's the most important thing.
The annual "O'Brien Must Suffer" episode. Chief O'Brien is sent to infiltrate a branch of the Orion Syndicate, the Star Trek version of the Mafia. (No, it's never explained why an engineer and family man from a space station that's critical to the defense of the Federation is sent on a dangerous spy mission.) He presents himself as a down-on-his-luck mechanic, which gets him a job fixing technology, especially weapons, for Bilby, the local crime boss. He finds himself becoming friends with Bilby and doubting his mission, but also discovers that the Orion Syndicate is working for the Dominion. He gets pulled into a plot involving Klingon weapons, and tries to find a way to foil the plot and get himself out of harm's way, without getting Bilby killed by his bosses.
This episode contains examples of
- Arc Words: Bilby repeatedly tells O'Brien that family "is the most important thing."
- Bittersweet Ending: The assassination attempt is foiled, thus preserving the Federation/Klingon alliance, but O'Brien is devastated by Bilby's death.
- Blatant Lies: O'Brien gets off easy with a lot of convenient lies that would not pass any serious investigation.
- Blofeld Ploy: Ramius and Gelnon announce that one of Bilby's cell is a traitor. The Vorta picks O'Brien...then Ramius executes Flith, who was Gelnon's second choice.
- Equal-Opportunity Evil: The Orion Syndicate, despite its name, is surprisingly lacking in Orions. Even Raimus who is a high-ranking capo is of a different species.
- Even Evil Has Loved Ones: Bilby, through and through. He will kill a betrayer in cold blood, but he loves his family and is completely loyal to those he trusts.
- Going Native: O'Brien ends up sympathizing too much with Bilby, forgetting he's a ruthless criminal who would gladly have helped the Dominion to win the war.
- I Lied: Chadwick (O'Brien's Federation contact) never had any intent of building a legal case against Bilby. Chadwick lied because he could tell O'Brien was Going Native.
- Informed Ability: The Syndicate's skill at sniffing out infiltrators is what's supposed to justify O'Brien's involvement. They then let a number of ridiculous tells go past without asking any questions like "how does this guy nobody's ever heard of the only person in the underworld with ready access to obscure Klingon weapon parts", and the explanations he does give them are so obviously made up on the spot that he would have been found out if they'd looked into them at all.
- Irony: Bilby reflects that he's going to lose his operation and life because of a Starfleet operation that wasn't even targeting him directly.
- Kindhearted Cat Lover: Bilby is devoted to his cat, Chester.
- Last Request: Bilby asks O'Brien to make sure Chester is looked after.
- The Main Characters Do Everything: Seriously, why does Starfleet Intelligence recruit an engineer and family man from a space station that's critical to the defense of the Federation for a dangerous spy mission? Especially since the episode clearly shows that without his constant tinkering, the station immediately starts falling apart.
- Make an Example of Them: The reason Bilby willingly walks into the Klingon trap after O'Brien reveals himself to be a undercover Federation agent: if he tried to run, the Syndicate would kill his family.
- My God, What Have I Done?: O'Brien is deeply shaken by the end of the episode.
- Noir Episode: With gangsters, back-stabbings, and poorly-lit alleys, this is a very unusual look and feel for Star Trek.
- Oh, Crap!: O'Brien fears he has been found out as a traitor when Raimus and the Vorta arrive unexpectedly. Doubly worrying is the Vorta agent guesses him as the traitor. Thankfully another Orion agent is not paying his fare and the real reason Raimus is there.
- Reasonable Authority Figure: O'Brien's Federation contact doesn't report O'Brien assaulting him to warn Bilby.
- Seduction-Proof Marriage: The local Orion Syndicate boss offers the undercover O'Brien a prostitute as a gesture of Sacred Hospitality. However he's satisfied with this explanation for refusal.
- Shout-Out: The plot is pretty much Star Trek's Donnie Brasco.
- Sympathy for the Devil: It's damn near impossible to not hope Bilby somehow got away in the end, even though he's probably a murderer - at the very least he has no qualms about murdering someone for a reward and/or to prove his loyalty.
- Tragic Keepsake: O'Brien takes in Chester in the end.
- Villainous Valor: Bilby shows his love for his family by going to die knowing he is walking into a trap in order to save them from reprisals from the Syndicate.
- Visionary Villain: The Dominion target the Klingon Ambassador to Farius (who opposes the alliance with the Federation) and intend to make it look like fellow Klingons did it. According to the featured Vorta, this would cause a diplomatic crisis that would call the Klingons to pull out of the alliance and leave the Federation at a severe disadvantage against the Dominion.