Jack Sparrow vs Captain Kirk
Suggested by Sonic Jack Sparrow is a skilled pirate but his swords won’t be doing much against Kirk’s energy blasters. While a bullet would be enough to take Kirk out like anyone else, Jack is definitely not the most skilled guy out there and I’ll take a fancy sci-fi gun over a normal pistol any day. Jack can do his best to try and stay ahead of the curve here but he is ultimately doomed no matter how you slice it. Captain Kirk wins.