of course lol they have to meet because of jinbei
If that's true, then it should be Drake who should be fighting Kaidou as he attacked one of his territory before the timeskip, as far as I recall. I'm not sure if SHP would earn respect from Fishman Island if they're not the ones who beat Big Mom. Wouldn't that mean the island would be recognized as Kidd's, instead? If he knows about the territory, he can lay claim to it. Neptune might only accept the stronger crew, and since Kidd would have beaten Big Mom, he'd likely accept Kidd, though that depends.That's why I had thought he and Law would fight Big Mam, not Kaido. Challenging her, then fighting a different Yonkou leaves some awkward plot strings, at least for now. Kid's goal also is to take down a Yonkou. I'm not sure the point of him saying it so explicitly, if he does not actually fight one himself, and win. Luffy is going to fight Kaido. Big Mom seems like a natural for Kid, since he already sunk two ships in her fleet. The Fishman Island issue, and Jinbe, can be dealt with even if Kid, not Luffy, is the one to actually fight Mom one on one. Once Kaido is defeated, Neptune could renounce his alliance with Mom, accepting Luffy's protection instead. Jinbe also could join the Strawhats at that point. That would entangle Luffy in the war against Mom, ensuring the Strawhats are actually involved in the arc.
We don't really know Drake's status right now. He's an active, notorious pirate, re Brownbeard's speech, beyond that we don't know any details. He went to that Winter Island seeking Kaido's attention, but we don't know what happened since. He may have spent the last two years conducting minor raids against Kaido. he might have been seeking an alliance. Drake could become an ally of Luffy, later in the saga. He could end up being an enemy. Kid's intentions have been explicitly stated to the audience. We know he will try and defeat one of the Yonkou, and not necessarily the same one as Luffy and Law.If that's true, then it should be Drake who should be fighting Kaidou as he attacked one of his territory before the timeskip, as far as I recall. I'm not sure if SHP would earn respect from Fishman Island if they're not the ones who beat Big Mom. Wouldn't that mean the island would be recognized as Kidd's, instead? If he knows about the territory, he can lay claim to it. Neptune might only accept the stronger crew, and since Kidd would have beaten Big Mom, he'd likely accept Kidd, though that depends.
At some point yes, I think they will team up. Out of necessity, but not permanently. Maybe more than once, over the course of the series. I think they also will fight a few times, in between alliances. They already have fought side by side once, at Sabaody. It could happen again. Kid also seems to respect Luffy, though he sees him as a rival, not a friend.We could also see Kidd and Luffy team up. Maybe the Worst Generation could be the first bunch of crews that really work together to overhaul the world.