How many successful diplomatic missions has either of these captains been on? Before that question is asked, we have to recognize the individual personalities of both captains. Kirk is a self-confessed soldier not a diplomat, yet he has found himself on many successful diplomatic missions despite this assertion. Picard is actually a better diplomat, but on the eleven diplomatic missions Kirk was assigned, he succeeded every single one of them. Granted, the cowboy diplomatic approach may have been the most unsubtle and overt approach to its success, but regardless, Kirk succeeded. Compared to the amount of recorded Picards diplomatic missions there must be about two or three in comparison its amazing that despite Picards natural aptitude, its remarkable that Picard hasnt been in more successful ones. In fact, in Star Trek: Nemesis, Picard claims to have been involved in 27 first contact missions, but there is no way to actually discern the level of his involvement. Whereas in Kirks recorded missions he has a 100% success rate in over ten missions compared to Picards two or three. The nod has to go to Kirk in this category.