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Shanks vs Rayleigh.

First, something that should be clarified: is this prime Rayleigh or current Rayleigh? Cuz the current Rayleigh has much less stamina and is weaker than his prime self, which would play a big factor in the fight.

Rayleigh's clearly got impressive skill and Haki, since he taught Luffy all three types of Haki and has been capable of holding back Admirals such as Kizaru. At the same time, Shanks is an emperor who was capable of clashing evenly against Blackbeard and could duel against Mihawk, the World's Greatest Swordsman. His Conqueror's Haki has been enough to impress Whitebeard, was potent enough to terrify Admiral Ryokugyu, and was referred by Jinbe as "monstrous." Furthermore, both Blackbeard and Akainu chose not to fight him, even though both of them had no problems fighting against Whitebeard before. Honestly, based on reputation and the feats he's displayed thus far, Shanks should take this with difficulty, regardless of whether this is Prime Rayleigh or Current Rayleigh. So the cabinboy beats the first mate.
 
Shanks scales somewhere around old Whitebeard with one arm. Shanks was ready to throw down with all of Marineford including the Admirals with his crew. I can't see Rayleigh beating Shanks.

Since this is prime Rayleigh, I think Shanks still takes this high difficulty.
 
Rayleigh is implied to be comparable to Roger who even Kaidou knew to respect and fear and even complimented his Haki, so I don't think Shanks would take this easily but he should win at a high diff.
 
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