-> '''Bilby''': Back home, wherever that is, do you have a family?\\
'''O'Brien''': Yeah.\\
'''Bilby''': Good. It's the most important thing.

O'Brien is [[DeepCoverAgent undercover]] in a BadGuyBar on Farius Prime eavesdropping on three members of the [[TheSyndicate Orion Syndicate]]: Flith, Krole, and their human boss Bilby. When trying to hack a food terminal, Krole gets "spiked," and O'Brien rushes to save him. Impressed, Bilby orders O'Brien to fix Krole's dataport to prove himself. The chief leaves and meets with his Federation contact, Chadwick, who assures him that as soon as he can infiltrate the syndicate enough to find out who their mole is in Starfleet Intelligence, he can go home.

O'Brien returns with the fixed dataport. Bilby has researched O'Brien's cover identity, a down-on-his-luck fix-it man named "Connelly," and shares a little about himself. It turns out he's a rather affable guy who lives with a cat and sends all his money back to his family. "[[EvenEvilHasLovedOnes Family is the most important thing]]," he states. Bilby has another job for Connelly: fix some faulty Klingon disruptors. O'Brien does so and accompanies his men to confront the gun runner who sold them to him. The chief is quietly horrified when Bilby guns down the gun runner with a repaired disruptor. Later, the gangster offers to bring O'Brien into the syndicate and reveals that the syndicate's mole used to operate the weather controls on Risa about a year ago. Mission accomplished!

But Bilby's capo demands an immediate meeting to pick up the guns, so O'Brien has to tag along. Shockingly, a Vorta accompanies Raimus. Bilby officially vouches for O'Brien to Raimus during the handover. When Chadwick learns that the Dominion is working with the syndicate, he tells O'Brien that the new priority of the mission is to figure out what they're up to. O'Brien gets in good with Bilby and his goons, hacking a bank in the process. Bilby and O'Brien take to each other, and the gangster even buys a floozy for him, which O'Brien politely declines. The chief grows increasingly uncomfortable with the knowledge that betraying Bilby will cost him his life for vouching for a spy.

Raimus and the Vorta arrive unexpectedly to announce that there's a spy among Bilby's crew. The Vorta guesses that O'Brien is the traitor, but it's Flith who's executed for lying about a side hustle. With that out of the way, the remaining crew receive their mission: use the Klingon disruptors to assassinate a Klingon diplomat. O'Brien realizes that they need the Klingon guns to implicate someone else, and the Vorta confirms that the blame will fall on Gowron so that a wedge is driven between the Klingon Empire and the Federation. O'Brien reports all this to Chadwick and laments that Bilby will get killed by the syndicate once the gig is up. Chadwick tells O'Brien not to worry about it, but O'Brien knocks him out with a punch and rushes off to warn his gangster buddy.

Upon hearing O'Brien's confession, Bilby says he should have known that "Connelly" was too good to be true. O'Brien suggests that he hand himself over to the Federation to save his life, but Bilby knows that the syndicate would go after his family. Their only hope is if it looks like he died before ever knowing about Connelly's duplicity. Bilby asks that O'Brien take care of his cat. Before leaving to meet his fate, Bilby learns that O'Brien really does have a family after all and says approvingly that family is the most important thing.

Back on the station, O'Brien is still wracked with a giant guilt trip. Bashir tries to ease his mind but fails. After the doctor leaves, O'Brien sits down to brood while stroking Bilby's cat.

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!!This episode contains examples of
* AffablyEvil: He may be a murderous gangster working for the Dominion, but Bilby is a [[FriendlyEnemy very friendly]] and sociable person who takes a shine to O'Brien, [[EvilVirtues sends his earnings to support his family]], and takes very good care of his cat Chester. This is why O'Brien can't bring himself to betray him.
* AnthropicPrinciple: The episode actually gives a few reasons for why O'Brien was selected for this mission, but ultimately it's because the episode wouldn't happen otherwise.
* ArcWords: Bilby repeatedly tells O'Brien that family "is the most important thing."
* BaitAndSwitch: It looks like O'Brien is going to be murdered, but it's Flith.
* BittersweetEnding: The assassination attempt is foiled, thus preserving the Federation/Klingon alliance, but O'Brien is devastated by Bilby's death.
* DeepCoverAgent: O'Brien is undercover and has a fake identity created for him by Starfleet.
* EqualOpportunityEvil: The Orion Syndicate, despite its name, is surprisingly lacking in Orions. The local outfit on Farius is mostly composed of Farians.
* EvenEvilHasLovedOnes: 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.
* FamilyValuesVillain: Not only does Bilby have a family he loves dearly, and who at least seem to be part of why he's in a life of crime (to earn money to support them), when O'Brien is reluctant to make use of the Farian call girl and claims to have a girlfriend, Bilby completely understands (even wanting to meet said girlfriend) but urges O'Brien not to hurt the call girl's feelings, leading O'Brien to [[PlatonicProstitution let her down easily, politely paying her and claiming he'll contact her at a future date]].
* FatalFamilyPhoto: Almost as soon as Bilby brings O'Brien back to his apartment, he shows him a large framed picture of his wife and children while telling him [[ArcWords "family is the most important thing."]] Despite the mission just being about finding out who the Starfleet spy for the syndicate is, this practically guarantees Bilby will be dead by episode's end (even though we never get to actually see it happen).
* GoingNative: 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.
* HeroicSacrifice: Well, not "heroic", but this is what Bilby ends up doing. Knowing that he'll be killed if he gives up O'Brien to the Orion syndicate since he witnessed for him, and if he goes into protection under Starfleet they'll just go after his family instead, he decides to go along on the mission and get killed walking into the trap he knows is coming, because it's the only way that both O'Brien and Bilby's family will be spared reprisal from the syndicate.
* ILied: Chadwick never had any intent of building a legal case against Bilby. Chadwick lied because he could tell O'Brien was GoingNative.
* InformedAbility: 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 in the underworld have ready access to obscure Klingon weapon parts", and the explanation that O'Brien gives for where he got them, ''and'' why he tried to avoid answering at first, are obviously made-up on the spot.
* {{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.
** Part of O'Brien's cover is as a guy who has suffered so much in life that he's convinced the galaxy has given him perpetual bad luck. O'Brien states that he hopes getting to know Bilby will improve his luck, which causes Bilby to counter that it's his luck he hopes will improve thanks to their relationship. Sure enough, while O'Brien doesn't die, he does end up having to betray Bilby, who does die by episode's end.
* KindheartedCatLover: Bilby is devoted to his cat, Chester.
* LastRequest: Bilby asks O'Brien to make sure Chester is looked after.
* LethalChef: Bilby's wife's cake is apparently so bad that O'Brien risks pissing off a gangster and maybe even blowing his undercover operation to avoid having to eat it.
* TheMainCharactersDoEverything: O'Brien, a hot-headed space station engineer, is sent on an undercover mission to infiltrate gangsters. This is justified by the fact that Starfleet Intelligence has been infiltrated, so they need someone outside the agency, and as an engineer, his skills will make him highly prized to his targets.
* MakeAnExampleOfThem: 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.
* MyGodWhatHaveIDone: O'Brien is deeply shaken by the end of the episode.
* NoirEpisode: With gangsters, back-stabbings, and poorly-lit alleys, this is a very unusual look and feel for ''Franchise/StarTrek''.
* OhCrap: 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.
* OneLinerNameOneLiner:
-->'''Sisko:''' The Chief can take care of himself as well as anyone I know.
-->'''Bashir:''' You're right about that, sir. You're right about that.
* ReasonableAuthorityFigure: Chadwick doesn't report O'Brien assaulting him to warn Bilby, and doesn't object to O'Brien being late to a meeting because he was spending time with Bilby. Chadwick mentions he's been undercover himself, so he understands what it's like to get close to a target and become friends with them.
* SecretTestOfCharacter: Bilby insists on his men eating his wife's cake, [[LethalChef which is disgusting]], and enjoys watching them pretend to love it. He's impressed when O'Brien actually tells him the truth.
* SeductionProofMarriage: O'Brien won't even let possibly blowing his cover get in the way of upholding his marriage vows.
* SympathyForTheDevil: It's damn near impossible to ''not'' hope Bilby somehow got away in the end, even though he's a murderer.
* TragicKeepsake: O'Brien takes in Chester in the end.
* VillainousValor: 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.
* VisionaryVillain: 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.
* WholePlotReference: The episode's entire plot is lifted straight from ''Film/DonnieBrasco''.
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