User blog comment:Kaido King of the Beasts/Chapter 800 Prediction/@comment-142.51.164.228-20150915151928/@comment-67.204.208.3-20150916235426

I think wanting to die is more of an exaggeration than an explicit goal. The way I see it, he wants to challenge himself and find something that will bring him close to death, not necessarily literally die. That's why something as sure as drowning would hold no appeal for him. Jumping off a sky island just to see what would happen is a thrill because of the risk that he might not make it. Jumping in the ocean and just letting himself sink would be mundane and more than a little unpleasant.

That's why any situation that increases danger is one that he would view favourably.

Fighting WB: big danger.

Starting a war that would involve the whole world: big danger.

Gathering an army to wage war on one guy that he doesn't like: even if that guy's a Yonko, still not so much danger.

You'll notice that he doesn't want to "win" the biggest war this world has ever seen, he just wants to "start" it. He doesn't have a goal, he just wants danger; he wants chaos. He's basically the Joker.

That's why I think it's unlikely that he would recruit someone that he had just met, solely on the basis that they share one common enemy.

Also, given that he's been fighting WB and ruling the New World since before the start of the series, someone who just got famous 2 years ago is definitely a newbie in his book.