Its plainly obvious that Kirk is a tactical genius. He can beat a Vulcan at chess, can out-bluff a variety of alien species while facing overwhelming odds, and can demonstrate tactical versatility at a variety of levels, ranging from the small squad level to starship combat. As we see in Star Trek II: TWOK, Kirks ability to out-guess his opponent trumps Khans superior intellect. Time and time again, Kirk demonstrates his capacity to adapt to his environment and emerge triumphant. If we remember his confrontation with the Gorn in 'Arena', Kirk creates a make-shift, rudimentary gun-powder weapon out of nothing but base elements and bamboo. Oh, and of course, the Kobiyashi Maru scenario speaks for itself. In terms of war games, what matters is winning, not somebodys concept of fair game, and Kirk gets that. While Picard is no slouch in the starship combat department (The Picard Maneuver, anyone?), he's more of a grand strategist. He likes to look at the big picture and make the overall decision at that level. In Redemption, Pts 1 & 2, Picard is appointed as commodore of a blockading task force. While he is able to position his starships in a fleet-worthy formation with a hole big enough to lure a Romulan force through and entrap them, unfortunately, the Romulans are able to easily detect this stratagem and are able to counter it. It is Data, commanding one of the ships of the task force, who is able to perceive the counter at the tactical level and respond effectively, saving the day. Picard just isnt a front-line captain when it comes to combat. He even loses the Enterprise to an attacking Klingon force at one point, even if it is only in an alternative timeline. The only time Kirk lost the Enterprise was to save his crew, rescue Spock and he STILL managed to capture the enemy ship. Winner? Kirk.