Behind the bounty
Behind this number sits an awkward fact: the Navy has already succeeded. Kaido has been captured eighteen times and sentenced to death forty times, with the procedure carried through to the end on more than one occasion. The blades broke, the ropes snapped, the drop did nothing. Seven defeats in a lifetime, none of them permanent.
What the figure covers is close to half a century of consequences. He was at God Valley as an apprentice, he survived the collapse of the Rocks Pirates, he watched Kozuki Oden stand for an hour in boiling oil before a crowd and then shot him, and he then ran an entire country as private property for twenty years, with twenty thousand men and an artificial Devil Fruit supply chain manufacturing his army on an industrial schedule. The World Government could observe the results and reach almost none of the causes.
There is a joke buried in the digits, of the sort Oda enjoys. Read the 110 in the middle as hyakuju and it becomes the hundred beasts of his epithet: the name of his crew written into the price of his own head.
The price never got in the way of business. While the World Government advertised the largest sum then on any living pirate's head, its own CP0 agents were in Wano negotiating for the weapons Orochi had the country manufacture on Kaido's behalf, and Kaido let them: he cared far more about the war than about whoever won it. On the night of the raid he took Orochi's head off — the man survived it, having seven more — and announced that he would put the whole country to work turning out more of them.

































