O'Brien goes undercover in an Orion crime syndicate.
Starfleet Intelligence sends O'Brien undercover to Farius Prime as a down-on-his-luck repairman to infiltrate the Orion Syndicate. He wins the trust of the local operator Bilby by fixing his crew's broken equipment, and Bilby vouches for him with his boss Raimus. O'Brien uncovers the Starfleet officer working for the Syndicate, but discovers that the Syndicate is now working with the Dominion, and his handler Chadwick asks him to stay on.
A Vorta orders Bilby to kill a Klingon ambassador with Klingon disruptors, a plot to make the ambassador a martyr and weaken the Klingon alliance with the Federation. Starfleet plans to let the Klingons kill Bilby's crew. Unable to bear betraying a friend, O'Brien tells Bilby the truth, but Bilby goes to his death anyway to protect his family from the Syndicate, leaving O'Brien his cat. The sixth-season episode explores the human cost of espionage and O'Brien's divided loyalties.