Suggested by Destroyer Jack Sparrow is a pirate who gets by on a luck a lot of the time but his skills will usually leave you feeling rather skeptical. Even with his temporary immortal form I don’t see Jack being able to do much against the Kraken. This monster’s physical abilities will just be too much. He can effectively squash Jack or just chomp him to bits. Jack can dodge his attacks for a little while but with no real way to counter he is finished in the end. Kraken wins.