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The term cowboy diplomacy was used by Jean-Luc Picard to criticize Spock's unauthorized participation in the Romulan underground movement in 2368. Picard claimed that Spock's attempt to foster the peaceful reunification of Vulcan and Romulus was an action that had significant consequences to the Federation, thus the Federation Council should have been consulted first. (TNG: "Unification II")
In 2369, this term was used by Stefan DeSeve as a code word given to him by Spock in order to prove to Picard that his request to move the USS Enterprise to the Kaleb sector was legitimate. (TNG: "Face of the Enemy")