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Kaido would still remember though so until he realized she didn't know anymore I think he'd still be nervous.

She did mention that he owes her a big one in one of the earlier chapters. I'd be shocked if his attitude towards her didn't have to do with said favor.

Yes given the context of the page before. 1547995560 On the topic of the stress factor let's not forget the Manga explicitly said 1v1 -> Kaido it also explicitly said he's been captrued by Marines AND Yonko before. What we saw being set wasn't a 1v1 so yes there is a very real possibility...

Probably because of this They lost their captain.

Where did it say that? Her and Kaido were on the same crew until Garp beat their captain(rocks or locks or whatever the translation ended up being) I don't recall it saying when either of them got the title let alone who got it first.