It's obvious that Kid, Luffy, Drake, Law, and Hawkins are going to be all facing off against Kaidou and Big Mom at some point, them being the only good guys here for pirate captains of the worst gen, and them being the exact 5 shakky mentioned as the top 5, that was literally oda building up for this exact war. Say what you want about power levels or not (your power scales are prob shit), but we're talking about narrative build up. So yeah, Drake, Law, and Hawkins will be joining Kid and Luffy up there soon.
My guess: Luffy, Kid, Zoro, and Killer try to fight, get trounced. They'll do a little damage to Kaidou but it'll be Kid and Luffy standing after they were hit down. (surpassing their old self)
Eventually the 5 end up there, and it ends up with those 5 supernova (maybe zoro and killer too, but that's less likely), and probably Marco teaming up against Kaidou and Big Mom (Marco hard counters big mom and is too powerful not to be involved here)
Hawkins bolsters the party with his coin flip power up stuff, Law plays support as well, the two still do some damage via hawkins spawning creations and swordsmanship of his own, and law doesn't just teleport people around and stuff, he'll drop buildings on kaidou and stuff too, and do air cuts and all that. While Awakened zoan Drake, G4 Luffy, and Kid with his pillow filled with pennies will be the hard damage dealers.