In chapter 944 Kaido mentioned “But rather in death, that humans truly attain perfection.” This is probably his core principle in life which explains his desire for a place to die.
Kaido wants to die in an epic way as well, just like how Whitebeard, Roger and Oden did. This also explains why he admires Oden so much for having one of the most epic deaths in One Piece and deep inside, he is jealous of the fact and so he wants also to die as honorable as Oden or Whitebeard.
This is also why in chapter 933 Kaido mentioned to Scabbards “I don’t mind if you kill me here…. however your cuts are too shallow, you could not do it”
I like that Oda is showing us that Kaido is looking up to the greats of the generation before his, but for the wrong reasons. He admires Whitebeard and Roger, not for how they lived their lives but for how great their deaths were. He tries to force his idea of greatness by wanting to start a great war even though he doesn’t have a clear motive for doing so. He has a strong army but it’s full of bootleg abilities that look like abominations. He wants to have a great death so that he is remembered as a great pirate, but he’s just a bloodthirsty tyrant.
Kaido referenced Oden, Roger, and Whitebeard, all men who achieved greatness with death and put the idea in his head. I can’t help but feel Kaido fails to realize those deaths were glorious not in the way they went down but by passing on a will or legacy to be carried on by the next generation. That’s why their deaths, in addition to their lives, had meaning.
What does Kaido hope to pass on with his death?
Looking at that I can 100% understand why Kaido feels the way he does. He is still alive, basically unkillable and he has achieved nothing with his life.
He conquered Wano through deception, not strength. No matter how strong he becomes he is still unable to find the One Piece.
When he looks at his life I’m sure he feels extremely disappointed and inadequate. Not to mention we still don’t even know what happened with him in Rocks Pirates. Can’t wait for Kaido’s flashback!