Luffy’s ceiling aka kaido’s top 5 all represent men luffy will surpass. Not just in strength but actually succeeding in places they weren’t able to
Luffy surpassing oden: off the bat it already happened both in strength and goal. Oden wanted to defeat kaido and open the boarders of wano. Luffy succeeded where oden failed by actually taking Kaido down and liberating wano. He might’ve not opened up its boarders but he gave momo the ability to do it whenever he pleases
Luffy surpassing shanks: more likely than not the next to happen. Both luffy and shanks are emperors who strive to get the one piece. Both are the closest things that resemble successors to roger. Luffy becoming pirates king will be him doing something shanks failed to do
Luffy surpassing xebec: luffy doesn’t want to be king of the world at all but I don’t think it’s all that unlikely he’d be seen as the king of kings despite not doing anything with it. With luffy actually being able to overthrow imu and the world government. That being something xebec dreamed of doing before falling
I think luffy will also surpass him when it comes to being able to lead multiple conquerors. While they aren’t part of the main crew I think characters like Katakuri, Yamato, Hancock, maybe weevil, etc will in some way work together under/for luffy. Xebec’s crew didn’t respect him and were very dysfunctional. Under luffy the rocks kids likely wouldn’t have that issue despite how many conquerors there are
Luffy surpassing whitebeard: Whitebeard achieved his goal of creating a family so it wouldn’t have anything to do with that. Plus luffy and the strawhats are already a family
I think it could just be as simple as luffy becoming the actual world’s strongest man. Due to the existence of imu wb most likely wasn’t the strongest in reality so luffy will be
Maybe it can also tie into why Newgate joined rocks in the first place instead
Luffy surpassing roger: luffy will obviously become pirate king achieving the same status of wealth fame and strength. On top of that he is also going to achieve their shared secret dream post becoming pirate king whatever it is. Again doing something Roger couldn’t
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