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I'm 50/50 on if Who's-Who fights Brook. I think there are factors that suggest it will happen, but they're not conclusive. I won't lie, I would consider it bullshit writing if Usopp and Brook don't fight a 5% Page One and Who's-Who. This is the Straw Hats' biggest glass ceiling yet, bigger than...

Who's-Who to complete the pair-up. Page One <-> Usopp Ulti <-> Nami Black Maria <-> Robin Sasaki <-> Franky Who's-Who <-> Brook Drake <-> Chopper (but they're allies)