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Luffy (Post-Haōshoku Advancement and has access to Gear 5) vs Kaido (no restrictions)
-Both start in base.
-Knowledge of each other gained during their canon fight is restricted.
-Battle takes place on a grounded Onigashima.

One of the criticisms about Kaido during his fight was that he was attacked by multiple people, was holding up Onigashima most of the time, and Luffy was able to rest and recover between the times he lost. Would he would have been able to beat Kaido 1v1 if he had Gear 5 from the start and Kaido only had to focus of fighting him?
 
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