Honestly I don't see the raid itself failing. I don't see it being all happy fun rainbows and banquets afterward, either.
I was listening in parallel to doing other things so I may have missed it but he didn't seem to address CP0. He seems to fall back a lot on "X happened for a reason so that's why Y will happen" but Lucci's whole discussion with the agents on Onigashima was very relevant and represents a fork in the plot; It could go that Kaido wins, CP0 backs off their battleships and commences trade negotiations with New Onigashima, or Kaido falls and they step in to annex Wano into the WG system as a directly managed subordinate country. I don't see how you can say "Yamato is going to disarm bombs because Onigashima IS going to fall" but not "CP0 has battle ships in tow because Kaido IS going to fall."
I think Marco's theory on the raid "failing" is a bit more fleshed out and less "I want this to happen so it will happen."
Here is that video. I haven't watched in in a hot minute but I can try to summarize it. Basically he outlines that the island that Drake landed on during the time-skip (where Scotch was, Kaido's "favorite Island") and where Caribou's side-story happened, is actually kaido's original base, and where Onigashima originally came from. He notes that the island is being "built" artificially - everything from trees to mountains. He also notes that Law and Robin found poneglyphs but not THE poneglyph, thus Kaido might have it stashed away in another location. Marco was correct about Kanjuro way before the reveal ever happened, too.
I wouldn't be surprised if we see Kaido "defeated" here, but it's not a pure defeat of a Yonko by Luffy in that it doesn't equate to Luffy being able to go toe to to with say, an undamaged / unfatigued Yonko, and defeat them. It went from 1v9 to 2v5 to 1v1 to 1v1 to 1v1. Kaido's gone through a gauntlet of very strong fighters and is weakened / roughed up for Luffy now. What I could see happening is Kaido DOES get some level of a whoopin' from Luffy while also realizing CP0 is closing in, and his alliance is flipping. I could see him gathering his core group (TF6 and Calamities) to "regroup" on his "home island", with plans to move back in on Wano. This would shift the battle over to Luffy & Alliance vs. CP0. Perhaps BM will even call a temporary truce to avoid her own capture, then head back to WCI stating how things aren't settled with Luffy and that she will destroy him eventually.
So in summary: I could see Kaido "losing" but a soft loss. Not knocked unconscious and arrested like Doflamingo. He dragons up and takes his core group out. The alliance is winded enough and has CP0 to deal with so he takes advantage of the situation knowing he can likely retake Wano if he goes and collects his strength and performs a more pointed attack. Wano gets liberated under Momo after CP0 is "repelled" and flies Luffy's flag over it as his territory now, which would mean Luffy likely has Uranus (Momo could potentially be Uranus) and Poseidon on his side for the final war. Drake will probably be less into the whole CP0 doing Tenryuubito's bidding, and thankful for Luffy's help in saving his life and flip him a bonus letting him know where Kaido likely retreated to. The SHP recognize they still lack a Road Poneglyph and regroup to go take on Kaido in a more traditional OP arc fashion. Luffy vs Kaido, Sanji and Zoro rematched vs King and Queen, and the whole group getting their own battles instead of what we've thus far experienced. Luffy takes the Poneglyph from Kaido and defeats him 100%, cementing himself as a yonko level fighter who can compete with Blackbeard, Shanks, and BM.
I also think the final Road Poneglyph is either in Blackbeard's possession or the WG (likely the former).
