Worstgen
Cinera
@Veku, @comrade, @Light D Lamperouge.
comrade
Kaido was mad at Doffy because all of his dreams were shattered with Doffy's downfall. I mean Kaido will fall to those same weaklings as well. As for Jack recapturing Doffy, well, Doffy was wrapped in a ton of Kairoseki. For this you don't necessarily need a Doffy level character to guard him. But Kaido sending Jack to fight an admiral + Ex Fleet Admiral isn't a smart move either
Cinera
It's possible Kaido wasn't aware of the force that was guarding Doffy. His intelligence gathering operations haven't been hyped like BM's.
Finalbeta
Just two words: G4 overpowered healthy Cracker and Cracker only put somewhat of a better resistance than GK'ed Doffy did
Healthy Doffy >> Healthy Cracker > GK'ed Doffy is a good guess to me
Healthy Doffy >> Healthy Cracker > GK'ed Doffy is a good guess to me
Finalbeta
Also Doffy was playing around with G2/G3 Luffy before being GK'ed. Then things changed very visibly