O'Brien gets sent to a dark corner of the Alpha Quadrant, a forgotten industrial park of a planet called Farius Prime where law and order come from the barrel of a phaser. His assignment leads him to a bar that a local chapter of the Syndicate call home. Waiting for an opportunity, he sits atop a bar stool and diligently works on various gadgets from day to day. Starfleet Intelligence has given him the cover of a "fix-it-man" hard on his luck, knowing full well that the Syndicate is actively recruiting people with such skills.
Opportunity strikes and Miles makes the most of it: he gets noticed by saving one of the master criminals who was attempting to hack into a computer belonging to a local restaurant. The criminal is not seriously hurt, but his expensive equipment is damaged. Miles offers to fix it and his relationship with Liam Bilby, the leader of the group, grows from then on.
An unexpected meeting in the middle of the night from Bilby's boss, Raimus, leads to the former "witnessing" for Miles, making the new recruit's relationship with the organization official and taking responsibility should anything go wrong. Raimus comes to the meeting joined by a Vorta, implying that the Orion Syndicate and the Dominion are working together towards their mutual gain.
The Vorta later explains to Bilby that three Klingon disruptors are needed to assassinate the local Klingon ambassador. Unlike Chancellor Gowron, this Klingon is deeply opposed to the Klingon alliance with the Federation. By having the ambassador killed by Klingon disruptors, it will appear that his assassination was ordered by Gowron. The Dominion believes that he will be branded a martyr, furthering his cause and therefore weakening the alliance from within.
O'Brien later informs his contact with Starfleet Intelligence of the assassination plot. Rather than arrest the men involved, he opts to alert the Klingons and let them deal with it. At this point O'Brien has gotten close to Bilby, as instructed, and hates the idea of being responsible for his death. He decides to break with Starfleet Intelligence and tell Bilby the truth. Broken with the news, Bilby has little option but to head straight into the trap as there is no running from the Syndicate. By dying before it becomes obvious that O'Brien is working for Starfleet, he hopes that Raimus will spare his family. Before leaving, he asks O'Brien to deliver a birthday present to his daughter, and to take care of his pet cat Chester.
This show is significant in that it shows a side of the galaxy rarely seen in most Star Trek series and episodes. Gene Roddenberry's vision of the future showed that cold blooded murder, treachery, gambling, prostitution, drugs, poverty, and crime are no longer characteristic of humans but they all play a prominent role in this episode. This continues the Deep Space Nine tradition of bringing reality to a franchise built on utopian grounds.