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AP: Both scales to the same feat. However, Chopper has better showings for his strength. With Heavy Point he blocked Dosun's hammer swing, who could take a casual kick from Sanji. Chopper hurted his hand a bit but because he chosen a bad Point to counter a hammer, according to him. While Usopp one-shotted Daruma after getting enough preparation. Chopper can also increase his advantage with stronger Points, since Heavy Point is his standard human form.
Horn Point, Kung Fu Point and Monster Point are all upgrades to his regular AP.
Chopper takes the AP game.
Durability: Chopper also gets this. Even if they are comparable, Chopper has his amps available. Guard Point would counter a good amount of Usopp's gadgets and his Dura scales to Big Mom, so Usopp needs to use something like the Banana Shuriken or explosives to prevent Chopper's fur from absorbing the blunt force of the projectiles. And I think I remember Guard Point bouncing away from an explosion in Drum, but I might be wrong.
Range: Usopp hands down. No need to explain this.
Stamina: While both are pretty tough, Usopp is a monster in taking damage. Chopper would need to kill him in order to truly put him down if Usopp is determined enough in winning the fight. The sheer tenacity of the long-nose is something Chopper can't truly imitate.
Mindset: Both are cowardly and tend to panic quite easily, but Usopp is better at getting himself together and turning the tides of battle. He's also more tactical and once he calms down he gains more through sheer intelligence. And Chopper would fall for any bluff Usopp makes as seen in the manga quite consistently.
Chopper's no idiot however. He has shown tactic skills and he doesn't play around in a fight, since he knows how dangerous it could be if he loses his powers mid-fight. Added to the fact that he can come up with a plan if needed like in the Mirror World.
Abilities: Chopper has the skill in CQC. Usopp can't feasibly win if Chopper manages to get close enough to make him lose the range advantage. However, Usopp's versatility is by far superior to Chopper's. He has a lot of different gadgets to aid him in the fight.
Haki is not a factor. Usopp has only awakened it during a crisis and hasn't shown any proficiency with it outside of that unique instance, so he's not getting any advantage from it. If Usopp loses track of Chopper during the battle, the latter might be able to approach without being noticed. And Chopper has his nose to locate Usopp, unless the latter counters this like he did against Luffy with rotten eggs or similars.
How do I think this'd go?
They start at Usopp's range so he gets a big advantage at the beginning of the fight. Usopp is prone to hide and snipe, but he can't hide himself from Chopper's nose. He'd need to land a Egg Star in Chopper to mess with his nose. Any other option is useless since Chopper will locate him no matter where he hides.
Central Park is the battlefield here, meaning Usopp can and will use the trees and rocks to hide and snipe Chopper. The reindeer knows Usopp and will not let his guard down to give him any advantage. He will know where he's hidden and will go after him the moment the fight starts. He'll be cautios enough to watch out for any traps and tricks Usopp could pull off.
Usopp's best option here is to null Chopper's nose with Egg Star. Chopper would dodge, parry or block most attacks considering he's physically superior in every aspect (I forgot to talk about speed but it's an easy win for Chopper too). If Usopp lands it, he'll gain a massive advantage and will be able to set up traps for Chopper.
If Chopper gets close he'll pummel Usopp with ease, but if the latter sneaks a convincent lie (and with Chopper anything is convincent) to divert Chopper's attention he'll get the advantage to run away or land the Egg Star.
I firmly believe Monster Point is enough to put Usopp down, but it's a coin toss. Chopper would need to be sure about using it when Usopp couldn't run away. Otherwise, he might lose the form and will get incapacitated, losing the fight.
This comes down to who can gain the advantage first. Chopper is superior in every physical aspect, but Usopp is smarter, more resourceful and tougher.
Both know each other's skills to some extent. Usopp's full arsenal isn't known by Chopper, but he knows that in order to win he can't fall for a lie or let Usopp land something that'd null his biggest advantage. He saw the fight against Luffy. He knows how dangerous Usopp can be if given the chance.
I'm voting Chopper High-Diff. He's simply superior in stats and could anticipate Usopp's moves. Once he gets close enough he'll not leave him run away to gain the range because that'd be a terrible situation.
Actually, I think I'm going to vote Usopp for Calaca's reasons.
I believe that intelligence gap to be much more valuable than the AP gap here. This is for two reasons. The first is that Chopper has seen Usopp fight, so while he may be able to operate off of that knowledge, him not knowing all of what Usopp has can be more detrimental to him. As working off of old, somewhat outdated information is often times worse than working off of no information at all. Secondly, Usopp's intelligence has allowed him to defeat physically superior enemies before, so I don't see why it would be any different with Chopper. Especially since Chopper is much more gullible than those previous opponents.
It simply seems that Chopper will have an incredibly hard time getting in. And by the time he does, Usopp can lie to get away. And getting in, even just a second time, will be all the more difficult. And by the time he does get in, he'll likely be rather worn down. Usopp's stamina is certainly greater than Chopper's, so he can keep up the range game for longer than Chopper can stand it. Especially if Usopp gets clever and uses the egg star to give himself a particular stench, while also using other egg stars to place that very same stench throughout the city. And his versatility would force Chopper to stay on his toes, and make it that much more difficult to get in. Every time Chopper has to stop and block is another point for Usopp.
It will be high diff because at some point, Chopper will get in. It comes down to what he will do once he gets in. But, since Usopp can take loads of damage, and can also lie his way back into the long range where he has advantage, I can see him taking it a bit more often that not.
While it's true that intelligence is also fundamental in this fight, the stat is probably more noticeable.
Usopp hasn't deal any true damage to notable characters at this point. His fight with Daruma shown that he can deal with that level of fighters with enough time (and likely using the Impact Dial), while Chopper can match someone arguably stronger than Daruma with one of the weakest forms. Not to mention Guard Point would render most attacks useless by sheer durability alone.
It's an interesting tactic the one you brought up. However, there's a difference: Usopp isn't stationary, unlike the spots he might impregnate with rotten eggs. Chopper would be able to tell where Usopp is based on the fact that one of those eggs is moving and by judging the path the projectiles come from.
Chopper can no sell most of Usopp's weapons and he might be able to detect the Pop Greens too if Usopp sets a trap.
I suppose. Though Usopp also hasn't gotten a lot of screen time in a while. Same with Chopper.
That tactic is just one of many Usopp could come up with. Additionally, he could cause the spell to become ubiquitous through the use of explosions to blow the smell around. Or if it's a windy day the smell would spread regardless. It's certainly something that can still be useful. Plus, if Chopper is closer to a stationary source than the moving source, it would be significantly harder for him to tell the two apart. As he would primarily be smelling the stationary source.
Him detecting the Pop Greens is certainly speculation. But Usopp has other things like his smoke grenades, chalkboard and such. Additionally, I'm fairly certain he has a way of putting Chopper to sleep from long range, which, if combat applicable, seems more likely than Chopper dealing enough damage to Usopp once he gets in.
All this aside, if/once Usopp finds a way to seal off Chopper's primary means of finding him, Chopper will be left with the incredibly difficult task of finding Usopp, let alone getting close enough to do enough damage. Usopp seems to have the intelligence to come up with a strategy to do this. It'll be a long battle since Chopper is indeed quite durable, but it's certainly doable.
Chopper detected Wapol's smell back in Drum during a blizzard and at a few km of distance. He can detect Usopp anywhere going by this.
The sleep gas is a possibility. But it also is Chopper smelling the PG. Plants have particular essence and animals detect these.
The stat difference makes much easier for Chopper to find Usopp and defeat him. He's faster, stronger, more durable and more agile, on top of being able to detect Usopp's weapons and traps.
I said this is a high-diff for Chopper because of Usopp's versatility and field advantage, because he dominates in a physical fight. Usopp has defeated people stronger than him, alright, but they didn't know about his weapons and couldn't locate him with ease, added to the fact he was able to deal damage in the end. Chopper would get too little damage based on the scaling and the amps to get notable damage.
The battle sounds like a game of cat and mouse. With the mouse being able to attack at long range.
Also, I took a look at the link on his page. For the sleep manipulation. The AoE is massive considering that he put multiple giant kids to sleep. It's also unclear whether or not they had to smell it, or if they just had to breathe it. But I very much doubt that Chopper could get out of that sleep gas without taking at least a single breath. Especially if it catches him off guard. Guard point doesn't exactly help with that.
The point on speed and durability is well made, however. This is an in verse match, so in verse comparisons apply here rather than just the general statistics. Usopp would have to hit Chopper with quite a few attacks to leave any lasting damage (Or use an impact dial if he has any more of those. But that requires him to be up close).