"Starfleet Intelligence recruits Chief O'Brien to infiltrate the Orion Syndicate to find a Starfleet informant."
What is up with Starfleet sending random people into dangerous situations. They never use security people to do this stuff, it's always an Engineer or Doctor. So in this one O'Brien goes under cover to infiltrate the space mob. Now I have seen a handful of Biographies about FBI undercover agents and actually this one plays out rather realistically. O'Brien slowly gains the trust of the Boss and then they become good "pals". O'Brien uncovers a plot to kill Gowron, which he reports to Starfleet. He also discovers that the mob boss will soon be killed, he actually feels bad for the guy so he reveals everything to him. The mob boss still decides to walk into his own death, but before that he gives Miles his cat to take care of. In the end Miles feels bad about the entire ordeal.
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This is an awesome episode (all O'Brien episodes are awesome, which is weird because on paper he's the most boring), but you're right. Why does Starfleet send the weirdest people on these super high risk missions?
"Should we send Donnie Brasco or Serpico to infiltrate the mafia this time?"
"Nah... let's send my mechanic."
"Brilliant!"
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