Semi-related, but I'll offer my thoughts here...
First, let's compare Judge to Kaido. They both had few things in common;
--- 1) Both had children.
--- 2) Both of them wanted an alliance with Big Mom.
--- 3) Both are fucking assholes.
In Judge's case, he treasured his sons so much that he didn't want to offer any of them for marriage, even though he wanted the alliance so badly, so he painstakingly went out of his way to find the dud - Sanji - and get him to marry one of Big Mom's daughters, just so he could achieve this partnership.
Next is Kaido.... tbh, it's getting pretty evident that Kaido hardly even cares for his son, and doesn't even view him as how other parents view their children.... Kaido calls his son an "idiot", and the fact that he's getting him to Onigashima to marry a Charlotte shows that Kaido just sees him as an item.... a means to achieve his selfish desires and get this alliance to work.... similar to Judge.
His son also coincidentally "disappears" at such an important time... it's clear the dude just doesn't want to get married.... being married just so his father can go on little pirate games?? Utterly ridiculous. Yamato is basically Kaido's "dud" here... someone the latter hardly cares about other than to just sell him off like a prostitute, and someone who doesn't want anything to do with his dad..
So yeah... I don't think his son is necessarily "spoiled" or "being a rebel"...
I think it's more to do with Kaido being a selfish little cock, and being a really shit dad.
Black Maria says it's a difficult task!
WhoWho says "bring him in peace."
You dont send 6 strong dudes to fetch a Weakling
Yamato is a prodigy who has CoC ,
Yamato ~ Calamities
It doesn't necessarily mean Yamato is strong, really...
1) It's the urgency of the situation. Kaido needs his son present to secure the alliance with Big Mom.. No son, no alliance.. Kaido sending the 6 guys ensures this will be accomplished efficiently, with no hassle. It'll be quicker to find him, and quicker to get his ass back to Kaido's crib.
2) Black Maria says it's a difficult task because Kaido needs his son alive. If he's dead, the alliance is dead... and everything ruined... Kaido sending 6 dependable guys to track his son and beat him up to "convince" him to get married shows that Yamato could just be a weak ass dude....
Hell, why not Jack and King if Yamato is really as strong as calamities?
You don't send 6 inferior guys to fetch a rebel who can just beat them up and continue being a rebel...
You need to send guys who can beat that bastard up and make him not be a rebel.
3) Why would Kaido give up a son who is supposedly "as strong as calamities" to marry one of Big Mom's daughters and hence, effectively lose a really huge firepower in his arsenal?? Doesn't make sense, tbh.
Even Black Maria said that bringing him safely is a very difficult task
