I wonder happened to the Drake Pirates between the time of arriving on Kaido's to them not being seen Post Timeskip at this point. WW and Sasaki were called out for having had their Own Crew once, but Drake did as well. It seems a little fishy, but maybe they just returned to the Marines if he was going solo.
I will say though while I thought Wano was going to be an Capone 2.0 arc as far as Drake went but with success, Oda throwing Kid, Killer, and Hawkins in there was certainly unexpected, but adds more interesting elements overall.
I thought Drake's story / role was going to open up more when he began to show up more frequently in Wano, but it still seems with everything going on at this point, we're still building up to get more info on him eventhough his role as an ally has now been solidified.
Drake could've tried harder in the short fight against Sanji in the anime, but he didn't, and while we know Sanji is pretty strong, calling Drake's defeat that a "low diff" is silly. He's clearly more of a challenge, and that's all I've got to say.
It's not looking great atm for Drake to be heading up to the roof himself to get in on the fighting like I had hoped, but I guess there's still a chance. I still think he deserves to confront and fight Kaido in any case.
Drake has been knocking on Kaido's door since pre-timeskip basically. I really hope he does have a hand in actually fighting Kaido. He literally said his and Luffy's goals line up and the defeat would benefit him as well. Don't count Drake out just yet, is my opinion.