Kaido fought Roger and primebeard after he became a solo pirate.
It explains why he knows about Roger and Wb pOwerlevel and character, that's why he was comparing Oden to them 20 years ago
Even now
Same way he also fought wb, bm, xebec during Rocks time
It explains why he knows about Roger and Wb pOwerlevel and character, that's why he was comparing Oden to them 20 years ago
Even now
Same way he also fought wb, bm, xebec during Rocks time
Edit: I doubt that they fought for real like oden did. Oden wanted to kill Kaido, if Roger or WB would had the intent to kill him, there would have been victims at the crew.