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Since Usopp didn't get to fight a CP9 member pre-timeskip and these two are the weakest or least impressive...
Round 1 - Sogeking vs. Nero
Round 2 - Usopp (PostSkip) vs. Nero
Round 3 - Sogeking vs. Blueno
Round 4 - Usopp (PostSkip) vs. Blueno
Round 5 - Usopp vs. Nero & Blueno*****
All the fights take place on a fully restored Eneis Lobby
They can go to any cannonical place that was visited in the island from the gates, the towers, the various buildings, the bridge of hesitation.. ect...
*****Round 5 Usopp has been told about their abilities by Luffy and Franky...
For each fight he has his entire arsenal...
Well, ussop did take on that fishman guy who was using those pills so I think ussop can handle his post time skip fights. The pills were a huge boost and ussop has shown enormous versatility when it comes to his seeds and several of them actually do have some serious firepower. Nero in particular should not be a big deal. Blueno is a lot stronger but I think ussop could manage.
Post-time skip Usopp would be able to handle these two with relative ease. Nero isn't particularly dangerous, and Blueno shouldn't be too problematic. Usopp's firepower and versatility should be more than enough to handle Nero and Blueno.
Well, a normal fishman is supposed to be about ten times stronger than a regular human. The regular human stands at about 10 doukiri if I recall. In that regard each of hodi's underlings had at a bare minimum 100 doriki. Now, as far as we saw hodi's crew members were well above your standard fishman though. In this regard a mere 250 doriki which is not much would already mean uppop fought and bested someone at least as strong as nero as a single pills would double that. For that matter, it would be weird if hodi's men had easily well over that physical strength considering they were indeed fighters. Pills allowed them to easily best the princes who were supposedly quite strong and perhaps even haki users. The doriki thing does not actually consider fighting technique however I do think it gives us some perspective in regards to to the physical capacity of a guy ussop could potentially fight.
There is also the part where ussop did take out one of doflamingo's men alongside nami. The two of them were not particularly strong but they were also not that weak either, even franky (who should be well stronger than a pacifista) took a dent from them.
I guess the issue is that ultimately we don't know how much ussop grew, he has yet to fight someone who can push him to the limit. In the end there is no particular reason for him to be well stronger than pre time skip luffy or lucci. Neither of them were worth a sliver of a damn before the timeskip in the grand scheme of things and ussop and nami are supposed to be able to contribute something to the crew in the new world. Nami just gave us an indication that she can create medium sized storms with relative ease, even in her case it wouldn't be strange if she had the firepower to take on someone of pre time skip lucci's caliber... Luffy went from o to what he was before the timeskip in between 6 months and one year, it wouldn't be that strange if the other strawhats actually exceed pre time skip luffy by quite a bit. Heck, even pre time skip ussop put up a fight against luffy at the time (although luffy did not use gears but still). To be honest I am of the idea that currently even the weakest strawhat exceeds pre time skip luffy by quite a bit though, that should be the bare minimum for all of the strawhats to have a position among the crew of the current pirate king.
That post is wrong on few levels imo, dont take it personally- in short I will say that Luffy pre-time skip was stronger than his crewmembers are right now, beside monster trio of course and maybe destructive power of Franky as he is now(Beams and Shogun).
When it comes to matches I would say that post time skip Ussop would have chance of defeating Blueno. Nero would be easily defeated by "all Ussops". Pre-timeskip Ussop would get trashed by Blueno. Thats all from me.
Well, as far as the strength the crewmembers should have I think the ability to take out a pacifista is a good measure. Pre time skip luffy was at large fodder to a pacifista. If franky can take on a pacifista on his own then he would naturally also be capable of giving pre time skip luffy a clobbering with ease. I am of the idea that brook is the one that follows franky in terms of strength among the strawhats so it wouldn't really be weird if he could do roughly the same. Ultimately all of the strawhats should be able to do that to pre time skip luffy at large. The main strawhats necessarily must be seen by the government as something like shank's main crewmembers or WB's commanders if luffy wants to have a small chance at being pirate king and that can only be achieved if even the likes of nami, chopper and ussop acquire power comparable to at least the weaker members of said groups.
I can't see any way for Usop to beat Blueno even post time skip.Not only Blueno has the door door fruit, but he is also really fast with his Soru. I can't see any way for Usop to dodge his first attack,and a couple of well applied shigan would make him unable tp use his kabuto. Usop's ability stand for other things, but I can't see him win this...