I understand your point; Maybe that's in fact what Oda has in mind, but I strongly disagree with that position.
Kaidou has already defeated Luffy multiple times on his own, and Luffy is the one who has been escaping death and having more chances to get another try thanks to the help of others, all while Kaidou is weakened with the accumulated damage from Luffy's previous tries and all the other people who fought and ran away after failing to beat him.
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Oda is being sly here. On one hand, the courageous/macho stance is "pirates don't care about cheating".
Then he has all these hangups with Kaido and Oden/Luffy, and Katakuri doing this
Exactly. There's always a double standard when it comes to whether or not it's a praiseworthy thing to receive help from others in a fight.
If the villain receives help from someone else in a fight, then it's a cowardly attitude.
But if the protagonist receives help from other people in a fight, then it's considered the protagonist's merit for having friends, and he even lectures the villain about the power of friendship and about how it's the villain's own fault that he lost for being alone.
Oda is not the only one with this problem; This is a very common thing among authors of shounen manga.