Tbh i'm not with "Raid Fails' Squad, but i have a feeling that Kaidou will defeat Luffy.
Unlike all previous Major Villains that Luffy defeated, Kaidou has been Hyped for very very long time
Punk Hazard & then Dressrosa & then Zou & then WCI & then Wano First Two Acts
That's basically Hundreds of Chapters where everyone is waiting to see Kaidou's Final Fight
So Oda on purpose made this the Most Awaited 1 v 1 by Fandom (At least that's what he believes & tried to do)
That is when i remembered a Fight from Dragon Ball, which is Goku vs Jackie Chun (Who was actually Master Roshi)
There are many interesting details about this Fight
First of all, it was at the time, the most Anticipated Fight since Manga started (To see Goku vs Roshi who was like Strongest Character then)
Secondly, the Tournament is called "Tenka'ichi Budōkai", which means "Number One under Heavens"
Thirdly, during that Fight whom everyone were waiting for it's Conclusion, there was a "Full Moon"
Fourthly, Master Roshi used Drunken Fist during this Fight when he realized how strong Goku has gotten
And lastly, at the end of the fight, since they were matching each other blow for blow, the Refree told them that there can't be a Tie
And that whoever remains standing at the end & Smiles while declaring himself Winner, will be declared the Victor
Kaidou vs Luffy can indeed be considered a Fight Under Heavens, under Full Moon, where everyone is waiting for the Conclusion of this Fight, & Luffy is fighting the guy known as the Strongest, who also used Drunken Style after he got excited & both are smiling non-stop, even Kaidou hinted that whoever smiles more is better ... etc (+ Big Mom hinting at Kaidou's Unique Victory Cry)
Why am i doing this comparison & talking about all this?
Well, because Oda said that his Favorite Scene from Dragon Ball is this Fight of Goku vs Jacki Chun, because everyone was expecting Goku to win, but it was Master Roshi who won at the end, which Oda described as shocking to all readers at the time.
When Kaidou was introduced, his Intro Box said "In a 1 v 1, people say, always bet on Kaidou"
Ofc, as Readers, we don't expect this to apply on Main Character, but think about it
Since his Introduction, has Oda ever showed us a 1 v 1 of Kaidou against someone other than Luffy where that Statement about Kaidou was truly demonstrated? Never
He only fought Big Mom 1 v 1, but they decided to stop eventually
His other Fights were all against Group of Characters or Short 1 v 1 Clashes
Even Yamato Fight was interrupted & was mostly about stalling him
I believe all this time, Oda was building up for the inevitable outcome of Kaidou winning his 1 v 1 against Luffy
Literally everyone whether Characters or Readers are waiting for Luffy's Final Attack against Kaidou, but i honestly believe Kaidou will win
Oda wanted to Highlight that part where u should bet on him, & only gave him this 1 v 1 Fight against Luffy, so why aren't people betting on him?