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O'Shea was serving as an officer in Starfleet, with the rank of lieutenant, when he took an assignment as an undercover agent in the 2290s decade, posing as Romulan officer named "Berza". Serving in this guise aboard the ChR Talon, O'Shea learned of the existence of Romulan Star Empire sleeper agents within Starfleet. In order to obtain their identities, O'Shea sabotaged the Romulan ship, then assisted Captain John Harriman in secretly bringing Tal Shiar High Examiner Rokan aboard the USS Enterprise and staging an interrogation of Harriman. (ST short story: "Shakedown")