yes, it will happen. right after elbaf to be more precise. matchups are:
luffy vs akainu
sabo vs greenbull
zoro vs fujitora
sanji vs kizaru
hancock vs doll
jinbe vs strawberry
franky vs lacroix
robin vs onigamu
brook vs cancer
chopper vs urban
nami vs hina
usopp vs django & fullbody
cavendish vs...
Super Sommers will get a kill within the next few chapters... shamrock will lose to loki in a close fight, garling will lose to cavendish in a close fight etc. they are villains, aren't all villains "jobbers" to some extent? holy knight doflamingo will get some hype i am sure, before sanji defeats him.
yes i would. look how underwhelming he performed against law. many consider him the final villain. as he is now, he wouldn't be a good next villain. all his titanic captains, apart from kuzan (who will leave anyway), need powerups. i think teach will get orochi's df. his goons will get df weapons.
I think it will be:
Buggy vs Usopp
Mihawk vs Zoro
Doflamingo vs Sanji
Crocodile vs Nami
Weevil vs Chopper
though 2 of those haven't joined Crossguild yet
battle of the weather manipulating loan sharks who punch their captains
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