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I don't think Kaido took it personally. Sure he was annoyed because it screwed up his plans but in fact he probably respected Luffy for it - you either try to fight your way to the top in order to live freely just like Kaido himself did or you surrender and live under the tyranny (of Orochi and...

He wasn't perfect but he actually did do good by many King - uplifted his spirits, made him King, gave him shelter, never sold him out Queen - gave him shelter, made him #3, gave him funds for research, experiments and prostitutes Jack - pushed him to become great, stepped in when it was too...

Kaido was very brilliant at what he did. He recognized strength and built his forces brick by brick, crew by crew. Even kept Ashura Douji alive for 20+ years in the hopes of one day recruiting him. I'm not afraid to say I'm a lesser man that would have given up many years ago in that spot.