User blog comment:Fliu/Chapter 929: Jurassic Wano/@comment-77.218.255.231-20181230190240/@comment-24850639-20190102212039

Drake is the only Supernova to date aside from Bege to ally with a Yonko willingly. Bege did it as part of plan to eventually take Big Mom's head - we're given no reason to believe that he couldn't have escaped if he truly wanted to the way Kid & Urouge did. Until we hear the reason from Drake/Oda himself why he decided to ally with Kaido, his intentions in doing so will always be scrutinized.

We have seen that the Supernova for the most part have their own grand ambitions, and serving under a Yonko tends to not be one of them. None of them also seem to feel that they absolutely need to sail under a Yonko's flag in order to be safe in the New World, as this wasn't the first thing any of them sought out when they entered it - the exception of course being Drake. So until we're given explicit reason to believe there isn't, there will always be an expectation that he has ulterior motives. The Worst Generation developed a reputation as starry-eyed youngsters looking to do something big, it's doubtful that being a pawn for someone much stronger is what any of them had in mind.