The big takeaway from chapter 1001 to me is that Kaido is no longer interested in breaking these “little monsters’” spirits and making them a subordinate – he’s had enough and he intends to kill them all.
The only exception is Nico Robin. That means this raid cannot end in failure – because if it does, then everyone except Robin will be killed. Maybe there is a round two within the battle (like with Luffy and Doflamingo’s fight) somehow, but there is no “they’ll lose here and come back later and win.” To lose is to die – Kaido has made the stakes explicit.
I think what’ll happen is that Kaido has them on the ropes and keeps “playing with his food,” but then Luffy sees that Onigashima is over the Wano mainland. Kaido then tells Luffy what he said to Big Mom – he’s going to drop it on the capital and kill everyone there.
Luffy has a flashback to when he failed to protect Tama, believes the same is soon to happen again (except this time she wouldn’t survive) because he doesn’t know she is actually on Onigashima, and that realization and desperation is what leads to his rapid growth moment in this battle.
Maybe he awakens his devil fruit and turns Onigashima into rubber so it bounces off the mainland when Kaido tries to drop it, and ends up landing in barren territory – and then realizes he can use this Awakening to “rubberize” Kaido’s scales and durable body, making it easier for Luffy to damage him with his Advanced Ryou.
Essentially his skin isn’t like steel, but like rubber – so it’s easier to penetrate with “break apart from the inside” Ryou and reverberate within him because Luffy is controlling what is/isn’t rubber.
What do you think?
*Theory by theschulk51