When Luffy beats Kaido 1vs1,while having a much higher growth rate potential than Kaido
and all of Luffy's subordinates beat Kaido's subordinates
and take a large portion of the fodder with Tama
and prevent any new gifters through destroying SMILE
and gain the poneglyph meaning Luffy not only has Robin, a better navigator but 3 poneglyphs rather than 1
Then it is safe to say Kaido's aspirations of becoming PK are relegated to silver medalist status...
It's highly unlikely Kaido's imprisonments are since he's been holding Wano, and it's certain that the imprisonments haven't resulted in a thorough routing of his crew as is currently happening. Else one of the remaining scabbards would have tried to make a move already, if not the WB crew... But ignore those details as it doesn't fit your headcanon.