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> Usopp goes against Luffy's decision, then leaves the crew and challenges him in a fight, betraying crew;
> Drake, an enemy, one of Tobi Roppo, who burned Tama's village, jumps outta nowhere then demands an alliance.

What should Zoro say here? "Okay, doesn't matter if he is one of the main headliners of enemy's crew, let him join, yeah."
Dont go into the bait
 
I rather want him to face the dukes again, but yeah, at this point your matchup is on.
Oda will for sure make Inu and Neko fight Kaido along with the rest of the Scabbards, which is a fight that they will inevitably lose (probably a little before chapter 1000 so that Oda can have Luffy vs Kaido start on chapter 1000). So the Dukes won’t be able to have a re-rematch with Jack unless they’re for some reason the only Scabbards not knocked out, which would be really contrived
 
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