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Leonardo (4Kids) vs Samurai Jack

Actually Samurai Jack's sword CAN HURT good people/good beings; It was used to sleigh that one warrior who was turned into a rock monster so Jack could send him to valhala.

Plus, even if you argue that Jack's sword can't hurt Leonardo, Jack has shown capable of using Bow and arrows + Hand to hand combat. Plus, what's to stop Jack from using his sword to shatter Leonardo's swords, which he could do with ease?

Jack has many more years experience, and more feats of strength and durability by comparison.

Once Leonardo's sword have been shattered by Jack's, it comes down to hand to hand combat. Keep in mind that Leonardo is more acustomed to fighting with his sword than hand to hand/martial arts and has rarely triumphed with out a weapon, where as Jack has actually fought and beat people hand to hand on more than one occasion and has mastered various martial arts from around the world.

This is no stalemate: Jack destroys Leonardo's sword with his own, and then he destroy's Leonardo's body with his fists.
 
@Marcman Jack is not strong enough to hurt Leonardo. He is only Large Building level against good things while Leonardo is Town level. However Jack has Mountain level durability with his best feats, meaning Leonardo can't hurt him. It's a stalemate.
 
@ God-King Superman77 Leonardo is only town level with the Gunshin Sword, a weapon that Jack can easily destroy with his own sword. Leonardo's attack/striking strength is at small town level, while Jack is at Mountain level in terms of durability.

Plus Jack was able to hurt Aku who's Large Country level with his BARE HANDS. Leonardo's durability is small town level.

Besides, Jack can literally fight for days with out resting, while Leonardo has never demonstrated that kind of stamina. If you insist they can't hurt each other, then Jack still beats Leonardo via outlasting him in combat. The moment Leonardo starts to get whoozy, tired, and fatigued from the battle lasting too long, Jack can either finish him off by grabbing him and snapping his neck, or grabbing Leonardo's swords and using them to slice Leonardo to bits since they don't have the same "can't cut good people" thing that Jack's sword does.

The front of Leonardo's shell was EASILY peirced by Karai with a regular sword, Jack could impale Leo with his own swords and tear his shell wide open the moment Leonardo gets too tired to fight back.
 
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