Itachi vs Jiraiya:
This is not everything I think on this match-up and moreso a long summary - maybe sometime later I will edit it and add the details. For now this is a rough draft.
There's no direct evidence or statement that Itachi's statement about Jiraiya was a lie, just one people extrapolate from Itachi's reveal as a good guy. More importantly there is seemingly contradicting portrayal in that Itachi is > Orochimaru.
You see you can also argue Jiraiya > Orochimaru based on portrayal but it just seems like Jiraiya has been consistently portrayed as "on the same level" as Orochimaru, even if slightly superior. Kind of like Naruto and Sasuke.
1. the DB says Jiraiya is "on par" with Orochimaru in strength, "on par" is not the word I would describe Itachi and Orochimaru's power relationship.
2. Itachi is able to tell Orochimaru that "all his jutsu are useless before him", Jiraiya never had such portrayal to factually talk down to Orochimaru like that.
Basically the biggest issue in Jiraiya vs Itachi is Orochimaru, leading to Itachi-fans hyping Orochimaru in relation to Jiraiya (Orochimaru is > or = Jiraiya) and overrating the gap between Itachi and Orochimaru ("Itachi one-paneled Orochimaru twice as a kid!") Wh
ereas the Jiraiya-fans de-hype Orochimaru in relation to Jiraiya (i.e claim Jiraiya >>> Orochimaru) and underrate the gap between Itachi and Orochimaru ("Itachi needed Susano'o and Totsuka to seal Orochimaru so the gap must be small!")
Jiraiya has paralells with Itachi but he also has parallels with Orochimaru.
For me personally Itachi's superiority over Orochimaru has more statements and feats supporting it, not saying Jiraiya and Itachi's equality has no evidence for it just that Itachi's superiority over Orochimaru is emphasized more and therefore when two seemingly conflicting evidences co-exist I'd favor the one emphaized and repeated more.
The gap between Itachi and Orochimaru while not big, you can definitely make an easier case for the gap between Itachi/Oro to be bigger than Jiraiya/Oro. Just imagine if Jiraiya could tell Oro "all your jutsu are useless before me" or Oro emerging and then getting beat by SM Jiraiya swiftly who then smiles and says "is that all?" - most people would think the gap between the two Sannin is huge.
However, the statement still exists so it's a matter of abundance of evidence rather than lack of evidence on Jiraiya's part. I'd say Sick Itachi is at worst Jiraiya's equal and averagely superior to Orochimaru, and at best averagely superior to Jiraiya and decently superior to Orochimaru.
So basically I respect both those who believe Jiraiya = Sick Itachi and those who have Itachi > Jiraiya, but I think both sides need to be understanding that there are good arguments for both.
Then we get into Edo Itachi.
Edo are not brought back stronger than they were, in fact the opposite is implied. Yes Itachi didn't have his sickness but it's not like he was born with it, in fact the fact that Itachi is brough back without it means there was a time he wasn't sick while alive.
The point I'm trying to make is that Itachi at some point in his life could replicate everything his Edo self did (except Edo regen). Not only that, but Zetsu outright says on-panel that Itachi should have been "much stronger" than we've seen. The author would have also highlighted that Edo Itachi was at a level Itachi never achieved before, yet there was zero implication he was this reborn MS-spamming beast - and we're just left with previous ET regen hype as an advantage.
People will say "but Itachi probably didn't master MS back when he was healthy since he became sick while still learning to master it" but that doesn't matter since in the end Itachi at 13-15 years old was still portrayed as outright superior to Orochimaru meaning they're indirectly suggesting Itachi with no MS experience still embarrassed Orochimaru.
In fact the whole implication from "we don't know if Itachi mastered MS back then" is to suggest that Healthy Itachi might not be much stronger than Sick Itachi or not stronger at all since he might have traded health for MS experience, the problem is the manga directly shuts this down by stating Itachi should have been "much stronger" than his sick self.
So healthy Itachi does exist and he does have feats in the form of Edo Itachi and just because not every feat is 100% transferable doesn't mean we get to ignore Itachi was once healthy and stronger than what we've seen.
In conclusion; Healthy Itachi is at worst averagely superior to Jiraiya and decently superior to Orochimaru and at best decently superior to Jiraiya and massively superior to Orochimaru.
Deidara is a level below Hebi Sasuke
Jiraiya can't beat the three paths without Frog Song
Kakashi is much weaker than Itachi. 3T Itachi would mid-diff 3T Kakashi.
3T Itachi is on the same level as the mid-tier Akatsuki generally speaking, whereas Base Jiraiya is a level above them.
Shoten Itachi was jobbing against Naruto & co
All of Hebi Sasuke's feats/portrayal are by far the most undermined in the NBD.
Gai needs the 7th gate to beat Kisame.
Kisame is weaker than Base Jiraiya.
A Doton cannot overcome Daikodan.
A boss summon is decently smaller than the waterdome.
Kisame has a chance to beat A3 who's a tier above him due to match-up, if A3 is assumed to be like V2 Bee (but it's not concrete).
Jiraiya needs frog song and a favourable location to beat the Preta, Animal and Human Paths.
Jiraiya can step up to Muu and can beat him.
Jiraiya having Katas and sensing doesn't make him stronger than what he was already portrayed.
Jiraiya is stronger than Prime Hanzo.
Jiraiya is stronger than A3.
Base Jiraiya would beat WA Kakashi.
Gama the toad is somewhere in the low-Jonin level.
Katsuya's combat strength is at best on Manda and Gamabunta's level and may be weaker than them.
Ribcage-Susano'o Sasuke is easily stronger than Raikage 1v1 in a fair fight.
Gengetsu vs Mū:
They probably started in CQC, Gengetsu with water gun and Muu with his blades. Gengetsu manages to get the upper hand and set up a water pistol, only for Muu to sense it and evade last minute. Taken aback by this, Gengetsu leaves himself open for a sword slash by Muu, which goes through his water body leaving him undamaged.
Both Kage fall back praising each other's defenses. Muu then taunts Gengetsu as he goes invisible, to which Gengetsu responds by summoning the clam, taunting back that Muu isn't the only one who can hide.
Muu, who's invisible, notices the appearance of several Gengetsu bodies on the battlefield. He contemplates whether they're bunshins or an illusion, but since he can't sense any disturbance in his chakra he presumes it's the former and proceeds to re-appear several feet in the air and charge Jinton which he concluded was the perfect way to deal with their numbers. Gengetsu realizes that Muu can't use Jinton while invisible. As the Kekkei Totai beam obliterates the battlefield and the dust clears, Muu sees the doubles are still there, much to his chagrin, before narrowly dodging another water pistol ambush.
Muu starts to rethink things, whether the doubles are real or not, whether it's an illusion or a powerful ninjutsu that Gengetsu possesses. He decides to use Jinton again, and pay more attention to the doubles, as close range combat would leave him more open than being on the air.
After a bit, the battle reaches a stalemate, where neither seems to find the other. Muu concludes that whether this is an illusion or a ninjutsu, as his sensing powers can't break him out, the only way must be to find and destroy the clam. The invisible Muu goes to the ground, and walks between the doubles unhindered. He decides to re-appear and charge a big Jinton beam to destroy the ground, instead of the doubles, and hits the mark. The doubles disappear, and Muu attempts to sense Gengetsu's whereabouts, and he does so successfully. Although the Jinton and invisibility took a chunk of his chakra.
Gengetsu, hiding behind a distant rock pillar, congratulates Muu on figuring out his clam jutsu, and tells him he's got more under his sleeve. Gengetsu then summons Joki Boi. The imp quickly launches himself at Muu, who decides to not risk a Jinton to conserve chakra, and attempts to go invisible, barely making it in time due to Joki Boi's unexpected speed.
As an invisible Muu closes in on the imp, he senses an usual buildup of chakra inside the imp's now bigger body, and barely manages to dodge the range of its explosion with minor injuries.
The battle continues with Muu withholding his Jinton for a perfect moment, finally managing to outsmart the imp by throwing his blade and distracting the imp (similar to base Bee doing something similar to Kisame in a pincer attack with his thrown blades), reappearing outside of the imp's line of sight, and charging a huge Jinton to cover for the imp attempting to dodge as Muu has witnessed first hand how fast the imp was. The Jinton manages to tag the imp, destroying it.
Muu's chakra with that last Jinton was below half, so he couldn't use Jinton anymore, and was running low on reserves and getting fatigued. Gengetsu, despite barely engaging directly, is also drained from the passive usage of his clam and Joki Boi summons.
They engage in a last ditch effort CQC scuffle that, despite Gengetsu having a slight skill advantage, Muu being able to go invisible gains the upper hand. Although to no avail as Muu has no way of winning unless he can outlast Gengetsu's water body.
Eventually both Kage succumb to their death in CQC after running out of chakra, ending a glorious battle.
Kakashi vs Orochimaru:
Orochimaru wins, probably low difficulty.
Kakashi can't do much to hurt Orochimaru as his offense is easily handled by Orochimaru's passive defenses ala WSP and Kamui will be needed to even survive a lot of Orochimaru's arsenal. Manda and Orochimaru attacking Kakashi together will overwhelm him pretty quickly and Yamata isn't needed.
Without Kamui, Kakashi was so far below Orochimaru he didn't even dare face him, and Orochimaru literally mocked Kabuto for being only as powerful as Kakashi. Kakashi improved his non-Kamui arsenal slightly throughout PII, but nothing to really make a difference as we saw he was praised for mastering his MS instead rather than his jutsu or physicals. So Orochimaru no-low diffs 3T Kakashi and low-mid diffs unrestricted Kakashi.
Kisame vs Mei:
Kisame already defeated a Yoton user, and Mei's suitons can be countered by Kisame's suitons which are bigger and can be spammed more. Hidden mist isn't an issue for Kisame because he is a swordsmen of the mist (Kakashi stated Zabuza is making the other swordsmen "dangerous" in the mist, rather than restricting them or holding them back) and because Mei isn't a master at silent killing. The only reason she might opt for the mist is so she can cast acid mist in conjunction with it, but not only is the acid slow to take effect, Kisame can just dive underwater in his lake to avoid the effect and have his 1000 sharks swarm her (Asa Kujaku stalemated a bijuu's attack in aoe but failed to match 1000 shark's aoe). Worst for Mei she has no reliable answer for Daikodan and/or Waterdome.
Kisame losing in CQC to acid mist is unlikely for several reasons. It is not guaranteed that he wouldn't start with ninjutsu. He started with ninjutsu against team Gai and 6G Gai on turtle island, only starting with CQC against Bee and Asuma so it's a 50/50. Even then in both cases we could argue that either he was told not to use big jutsu by Itachi or that he was maximizing Samehada's effect on the Jinchuriki cloak. Furthermore Kisame doesn't have to start the battle offensively with suitons, summoning his lake and then engaging in CQC is still relatively safe for him as he can go underwater. This is assuming Mei will go for acid mist when he's charging her and that Kisame will not retaliate by using ninjutsu (Kisame used ninjutsu twice in the midst of CQC against Gai and Asuma, and his clone interrupted Neji and Lee's ambush with ninjutsu, yes they are not strong but they are fast and skilled in CQC). Kisame also should have knowledge on Mei's abilities, probably.
Based on portrayal, Mei doesn't have anything that definitively puts her above Kisame. She is a Kage, but Kisame was matched closely with Gai as his long-time rival and needing his trump card to be finished off by him; Gai is relative to Kakashi who an arc earlier was confirmed as Kage-level when he was considered for the hat. So Kisame is also Kage-level. Furthermore, she was portrayed as performing the worst against her Susano'o clones, a liability to Gaara, outperformed by Tsunade who has the title of the strongest kunoichi instead of Mei; so Kisame being weaker than Gaara/Onoki/Tsunade/A4 doesn't mean much, because Mei also is.
Kisame vs A3:
Like I said first we need to look at their portrayal to determine a winner, A3 stalemated the Hachibi and gave numerous shinobi of the alliance trouble despite them having knowledge on him, Kisame would never give that much trouble to war arc Naruto clone or not. Kisame on the other hand already admitted inferiority to Jiraiya who is weaker than SM Naruto and his rival is someone said to get in SM Naruto's way against Pain (even if you disagree with that SM Naruto is still generally portrayed as above Gai). SM Naruto would never be forced to use danger sensing to beat Kisame. So from a portrayal aspect A3 > Kisame.
However when it comes to Kisame we have a direct on-panel fight clearly showing us Kisame can be a bad match-up to certain characters that are above him in strength like Killer Bee (yes Killer Bee even without BM is still superior to Kisame because he is more dangerous and can beat more shinobi than Kisame can).
Now the question is what is the profile of the shinobi that Kisame is the ultimate hard-counter for?
1. wears a chakra shroud
2. fights mainly in CQC
3. has a ton of chakra to supply Kisame for healing and to empower himself (ironically both A3 and Bee have biju-level chakra)
A3 fits this nicely, you could argue V2 Bee and A3 are very similar in how they fight and thus Kisame would be able to replicate his performance against Bee.
So one could argue Kisame keeps soaking the damage and getting stronger while A3 gets weaker, and we know Kisame almost drained Bee who has the reserves of the entire Hachibi clean so A3 won't take much longer. A3 also is very straightforward and doesn't have many options. Kisame has also absorbed Raiton in canon too so the lightning armor isn't a problem.
However there are still problems with this view, one is that the portrayal of Nukite's strength could be argued to be above V2 Bee's Lariat and that Kisame wouldn't survive it, another is that we're still only assuming that Bee and A3 are similar enough that it wouldn't make a difference against Kisame while in reality any difference in CQC skill, reflexes, and more importantly the strength of Nukite could make enough of a difference that Kisame doesn't actually win. Another problem is that A3 supposedly has "Black Lightning" that we have to account for...
Overall, I think the more logical and fair conclusion would be to say A3 can potentially be in trouble against Kisame due to how he fights, but is more likely to come out on top due to his superior portrayal, unseen black lightning and any minor advantages he might have over Bee in CQC skill/speed/reflexes/physicality.
Hebi Sasuke vs Kisame:
In CQC Sasuke is faster, has sharingan, CS and survivability. Kisame's strength likely won't be a bigger factor than Sasuke's CQC snake ninjutsu, 3T genjutsu and CS amp.
Kisame's Suitons can be dodged or blocked by snake meatshields, giant snake summons or Manda. Kisame will be hard pressed to deal with both Manda and Sasuke which could leave him very open to subtle genjutsu (like Deidara), sudden CS amp, and snakes. If Sasuke is severely wounded he can use Oral Rebirth, he could use it even as a surprise attack like he did against Itachi. Kisame could outlast but Sasuke can use Kirin with no chakra left, so even that route is not guaranteed for Kisame.
Kirin, Manda, 3T genjutsu and CS2 give Sasuke the win. Basically Sasuke can match him directly whereas Kisame will be hard pressed against Sasuke's indirect tricks (genjutsu, CS, Oral Rebirth).
Sasuke is generally stronger as he has a Kage-level boss summon, an S-rank finisher that while requires some prep can be used with no chakra left, a Senjutsu boost and the powers of the white snake. Mid-level Akatsuki like Deidara are below a restricted Hebi Sasuke and restricted high kages like Sick Itachi can be pushed by him.
Kisame vs Deidara:
Kisame is much better in CQC but he isn't fast enough to completely prevent Deidara from reaching the air. Once in the air Deidara will pressure Kisame with C1/C2, Kisame can dive underwater to escape the explosions but Deidara can create Clay Fish which is big trouble for Kisame.
Kisame's offense will be shark missiles in order to reach Deidara but those can be dodged by his bird while Deidara counters with bombs. Daikodan could have enough aoe that Deidara can't dodge it but it isn't so fast that he can't match it with a C2 bomb that the shark can't absorb.
Deidara probably high-diffs, Kisame not being able to absorb the Clay screws him here. Although there is a chance Kisame could injure Deidara on the ground seeing as the distance is only 5 meters.
3T Itachi vs Kisame:
Could go either way, with full knowledge Kisame will try to avoid CQC and focus on long range ninjutsu while Itachi will try to do the opposite.
Really the match depends on who succeeds in pressuring the other into their range, which is a toss up. Kisame would destroy 3T Itachi with long range ninjutsu while Itachi is skilled and fast enough to finesse Kisame with his powerful 3T genjutsu in CQC that Kisame likely won't be able to break in time.
In terms of portrayal 3T Itachi shouldn't be underestimated; he could startle Orochimaru with his power (compare that to Orochimaru disrespecting PI Kakashi's power) and he was overwhelming Kakashi in PI (who was said to not be a low-diff for Kisame). Additionally Itachi's clone without MS beat IA Naruto who was said to have surpassed IA Kakashi.
Orochimaru vs Kisame:
There are three stages to Kisame's fights (although the first one might be skipped straight to the second like his Shoten did); first is on the ground (kinjutsu and occasional Suiton if water is available like against Asuma) on the lake/body of water (kinjutsu and more frequent Suiton like against team Gai and 7G Gai) and inside the waterdome (Bee).
If Kisame engages Orochimaru on the ground he will be overwhelmed quickly, Summons are a problem without ninjutsu, Orochimaru's sneak attacks are a problem (blindsiding KN4 post-TBB), bindingsnake glare is a problem (Hebi Sasuke subdued both partial-transformation Jugo and Suigetsu with it, while Orochimaru restrained a massive branch of the God Tree). On the lake he stands in a better position as Orochimaru's underground tactics and snakes will be tougher to land and he can dive underwater and try to dictate the battle from there.
Kisame is going to be constantly pressured from match start by snakes, Kusanagi, and poison (that he likely can't heal) while on land. If he finds room (likely unless he has no knowledge) to use his lake (or start with it like we've seen him do against team Gai) then he gets a breather. From there Orochimaru amps up the tempo with large summons that could likely swim (Manda 2 could swim) and Kisame gets overwhelmed; 1000 sharks is matched somewhat by 1000 snakes and Daikodan is blocked/meatshielded by Manda/Hydra/Rashomon, the rest of Orochimaru's jutsu (Kusanagi, Oral Rebirth, giant snakes, poison) trump Kisame's (shark bullet, water prison, feeding sharks (few in numbers) meaning Orochimaru is putting the pressure on Kisame on his own lake.
Kisame will likely die before he gets off Daikodan or waterdome, I would say his chances of surviving until he gets them are about as equal as his chances of being killed off neg-diff in initial CQC exchange I.e unlikely. If he did manage to get them off Orochimaru can probably Oral Rebirth out of being grappled and drained, from being ripped by the sharks and right before he drowns to get a new pair of lungs. Orochimaru can probably still fight from a distance using Manda or other snakes, and if Yamata comes out there's not much Kisame can do to something bigger and stronger than Manda has eight separate giant heads, regen (presumably) and has Orochimaru himself inside of it to also fight.
Overall a low/mid diff fight for Orochimaru, if Orochimaru used more jutsu that were absorbable, or wasn't as indirect in his fighting style Kisame would have stood a better chance. Orochimaru is also smarter, more knowledgeable, more experienced, has more unknown jutsu hype, knows more elements, has a perfect score in genjutsu, etc. Plus Kisame said Jiraiya was stronger than him, with the wording indicating the reason is because he's a Sannin, and was said to not be able to defeat PI Kakashi scot-free (something like mid-diff-ish, you can argue it's higher but definitely not a low diff) whereas Orochimaru was so far above PI Kakashi that they were almost incomparable as indicated by Kakashi's reluctance to even face him (neg/low-diff)
Jiraiya vs Kisame:
Jiraiya is primarily a mid-long range fighter who relies on those ranges to deal damage and locations to set traps or activate jutsu and has large aoe techniques in combination with his summons that he can afford to use because of his stamina, he has SM on top which enhances all of the previously mentioned traits and the added bonus of also having short range as a much more steady option as well as a one-shot genjutsu.
Kisame is mainly a CQC fighter that can still operate in mid-range by using his suiton and long-range with his bigger guns/trump cards (Daikodan/1000 feeding sharks), his stamina coupled with his absorption and healing allow him to fight a prolonged battle however the absorption and healing are less reliable than his stamina since they depend on the opponent's fighting style to occur. He has no special defense, no extraordinary intelligence/knowledge and his basic ninjutsu is not versatile and he mainly depends on an anti-ninjutsu blast in the form of Daikodan and sometimes he fuses with his sword (most likely to capture but might use it to kill if need be?).
When we look at their portrayal, we know Kisame admitted inferiority and was almost killed by Toad Stomach, yes Jiraiya was advantaged because of the building for that specific jutsu but if Kisame was equal to or superior to Jiraiya at full power he wouldn't have struggled to survive even with that disadvantage against Jiraiya so easily. It’s a location advantage not a sharingan power up or something; it’s not like Jiraiya is a tier stronger when he’s in a building.
Kisame usually likes to engage in short range cqc first, or at best we can assume he'll use mid-range suitons after he supplies himself with the lake like against team Gai. Jiraiya on the other hand uses mid-range combat abilities. If Kisame decides to engage Jiraiya on land, he will either get killed or severely injured by Jiraiya's jutsu. Jiraiya's oil, Yomi Numa, Wild Lion's Mane etc are all a problem for Kisame who has nothing to rely on but his strength and cqc. Assuming Kisame starts with the lake he makes things easier for himself, but the problem is even Jiraiya's small toads have feats of sneaking up on shared vision (when Jiraiya got out of that small toad's mouth). Jiraiya's boss summons have large aoe that Kisame can't counter other than Daikodan and they can likely swim efficiently too, the toads can fight in CQC with their weapons or clear distances by jumping high or side-stepping like against Shukaku, a Biju-sized Gamayu Endan gets no answer from Kisame other than a well-timed Daikodan. 1000 sharks can be cleared by the toads aoe plus Jiraiya's attacks. Kisame is stronger than Gamabunta but he needs to focus on him to actually beat him and he’s still got Jiraiya to worry about.
The above is basically saying that Kisame is absolutely struggling against Base Jiraiya and one of his boss summons and needs his trump card to even survive realistically, this means that there is a chance the fight will end here before progressing into the “next stage” for Kisame (waterdome and fusion) by a blindside from Jiraiya; just like there was a chance before that Kisame would be defeated or injured on land before he decides to use his suitons.
This is an important point here because characters don’t start out with their stronger jutsu and instead pick up the pace, so there’s a chance that they will get defeated or injured before the fight escalates depending on the gap between the two characters or more specifically how strong their "casual" arsenal is.
Examples from the manga are when Orochimaru came out of Sasuke and used his Hydra, he was ready to engage Itachi with his Kusanagi (and presumably other snake powers he didn’t need his arms for) however he was stopped short before even engaging Itachi and sealed. If we’re being optimistic towards Itachi this implies a decent gap between him and Orochimaru in power, and if we’re being pessimistic this implies there’s a decent gap between their trump cards (Susano’o, Yamato), but the point is that there is a gap of strength that made one character die before he tried everything he had. Better yet look at Jiraiya vs Konan.
An example of injury would Asuma getting injured by Kisame before he really used Hien to its maximum effect nor used his Katons, and Asuma was going to be killed/incapacitated/injured further from Kisame’s water shark missile if not for Kakashi – Asuma’s cqc skill is high and he’s been praised for it so he could scratch Kisame with Hien but his other abilities pale in comparison and so does his portrayal which is why he was cast aside (or almost was) by Samehada shaving and shark missile respectively before he showed us everything he had.
Moving on, it's apparent that Kisame is outmatched and outgunned even in his lake both in direct combat and indirect combat (blindsides, numbers, distractions, traps) and all he has left is Samehada fusion which might help with surviving a few attacks but realistically Kisame can still be blindsided, dragged into an acid barrier, falls for a toad distraction, etc. The problem for him is Jiraiya’s attacks aren’t naturally easy to absorb and he’s still vulnerable even when fused, if he latches on to Jiraiya the latter might draw in NE and turn him to stone. The biggest problem is that Kisame might very well die before he fuses or more accurately before he decides to fuse; waterdome combo is more suited for shinobi like Killer Bee and Daikodan/1000 sharks are a more direct threat to shinobi than chasing and draining them.
There’s no need to get into SM Jiraiya vs Kisame because Kisame can’t realistically stop Jiraiya from reaching it if he wanted to since he isn’t nearly as versatile, smart or has what it takes to go through Jiraiya’s traps, and he can’t really last long against him. The feints SM Jiraiya against the 3 Pains in CQC would obliterate Kisame and so would COR and most of his attacks, worst of all Kisame can’t absorb any chakra since he’ll get turned to stone and Jiraiya being the more knowledgeable experienced shinobi might use that on Kisame.
To conclude, Jiraiya needing Gamabunta and a few other jutsu might make this a mid-diff fight for him, but the fact that he is still not fighting with his full moveset and ignoring the power up SM gives him entirely I’m inclined to say it goes back down to low diff. This fits with the portrayal of these characters and takes into account their movesets.
To summarise the above: Jiraiya wins low difficulty against Kisame because:
1. Kisame could die or carry an injury before his big guns are out.
2. Jiraiya doesn't need SM to win.
3. Kisame needs his big guns to survive against Jiraiya's normal arsenal.
4. Kisame can't pressure Jiraiya enough to raise the difficulty.
5. Kisame can't reliably absorb/heal due to how Jiraiya fights.
Jiraiya vs Masters:
Jiraiya (unrestricted Jiraiya starting in base) is a solid high kage for me, SM Jiraiya (unrestricted Jiraiya starting in SM) is an above-average/strong high kage and Base Jiraiya is an average mid-kage. Either master is an average low kage.
A high-kage on average should have no trouble low-diffing a low-Kage, so two of them being defeated with high difficulty isn't a stretch. The issue here is the teamwork Gai and Kakashi possess and how much difference it will make and even more importantly that Jiraiya momentarily becomes a weak mid-kage or even arguably a strong low-Kage while prepping for SM so depending on how the fight goes and how aggressive the masters are Jiraiya might carry an injury or lose a limb as the cost of reaching SM.
Overall I give the edge to Jiraiya with extreme difficulty as a high-kage, once he reaches SM if he has a boss summon out (he should) the masters are walled unless Gai can pressure Jiraiya enough for a successful Kamui which I doubt given Jiraiya's numbers (clones/summons occupy one master, Jiraiyaoccupoes the other), superior stamina (infinite Senjutsu vs taxing gates) and ability to keep Gai in long-range (Gamayu Endan, Water Gunshots, Leaping huge distances).
Oro w/ET vs MS Sasuke:
I think Orochimaru is somewhere between MS Sasuke (strong high kage) and Hebi Sasuke (average mid-kage), Orochimaru is relative to another high-kage in SM Jiraiya (average high-kage), albeit slightly weaker - making Orochimaru a low high-kage.
MS Sasuke on average would defeat Orochimaru with somewhere between mid and high difficulty , it's not low because they're in the same tier, and it could be high because of match-up (Amaterasu resistance, etc).
Orochimaru then adds two Hokage levels to his power, the "Hokage" distinction implies they're not at the lowest levels of kage; so at worst they are not Entry-Kage level comparable to Chiyo, IA Kakashi/Naruto, but rather low-Kage comparable to Kisame, Mei and the Masters - at best they are mid-kage or higher.
Sasuke wil need to bulldoze through Orochimaru's summons and defenses in order to win, while simultaneously watching out for Mokuton, Suiton, Bringer of darkness that can trap kages and seems to not be broken even by partner method, among their other jutsu.
Another issue is actually putting all three Kage-levels down, Amaterasu seems to be a counter for Edo regen, however Hashirama could likely push the flames with Mokuton and Orochimaru Oral Rebirths out as per canon. Genjutsu is not much of a threat here because of the presence of three Kage-levels who can use partner method which is a canonical good counter against 3T genjutsu, we also saw Onoki bring a Kage back into the fight after Madara's genjutsu seemingly incapacitated him. Tsukiyomi would have been great here if Sasuke had it as it has the power to mind-control high-kages which would be a decent counter to Edo Tensei.
With the Edos not toying around like they were with Hiruzen, they probably could use more jutsu and with Orochimaru joining the fight Sasuke is gonna be hard pressed to find an opening for a sealing tag on the Edos, and an opening for Kirin for Orochimaru.
Orochimaru wins mid-diff, high diff at worst, eventually Sasuke runs out of chakra due to needing Susano'o so much to survive, or they find a way around his Susano'o while pressuring him/distracting him. These two outcomes are much more realistic than Sasuke soloing a high-kage + two low-kage minimum where his best jutsus are unlikely to overcome the numbers and counters they have and is needed for defense to not be overwhelmed.
Orochimaru w/ET general:
I think he only needs Edos for Danzō and the three paths. He clears the rest with varying difficulties without Edo Tensei.
Manda should be able to fight for a bit even if he's scratched, and he has the option of going underground to avoid Sasori's attacks, meanwhile Manda can cause heavy casualties to Sasori's puppets due to its strength and size. In addition Orochimaru himself seems to be immune to poison, and his Hydra overpowers Sasori's arsenal.
Close fight, Sasuke is crafty and dangerous but I think Orochimaru overall has the more powerful arsenal. Orochimaru has better mastery of the white snake power and Sasuke only has Kirin as an option to deal with Yamata. Neutral knowledge Orochimaru in a tough fight.
There are three stages to Kisame's fights; on the ground (kinjutsu and occasional Suiton if water is available like against Asuma) on the lake (kinjutsu and more frequent Suiton like against team Gai) and inside the waterdome (Bee).
Kisame on the ground will be overwhelmed quickly, Summons are a problem without ninjutsu, Orochimaru's sneak attacks are a problem, bindingsnake glare is a problem. On the lake he stands in a better position as Orochimaru's underground tactics and snakes will be tougher to land and he can dive underwater and try to dictate the battle from there.
Kisame is going to be constantly pressured from match start by snakes, Kusanagi, and poison while on land. If he finds room to use his lake (or start with it like we've seen him do against team Gai) then he gets a breather. From there Orochimaru amps up the tempo with large summons that could likely swim (Manda 2 could swim) and Kisame gets overwhelmed; 1000 sharks is matched somewhat by 1000 snakes and Daikodan is blocked/meatshielded by Manda/Hydra/Rashomon, the rest of Orochimaru's jutsu (Kusanagi, Oral Rebirth, giant snakes, poison) trump Kisame's (shark bullet, water prison, feeding sharks (few in numbers) meaning Orochimaru is putting the pressure on Kisame on his lake.
Orochimaru is also smarter, more knowledgeable, more experienced, has more unknown jutsu hype, knows more elements, has a perfect score in genjutsu, etc. Plus Kisame said Jiraiya was stronger than him, implying the reason is because he's a Sannin, and was compared to PI Kakashi favourably (something like mid-diff) whereas Orochimaru was so far above PI Kakashi that they were incomparable (neg/low-diff).
Overall a low/mid diff fight for Orochimaru, if Orochimaru used more jutsu that were absorbable, or wasn't as indirect in his fighting style Kisame would have stood a better chance.
3T Itachi vs Deidara:
C1 can be dodged, C4 can be seen through and dodged as we've seen with Sasuke (he got caught due to being feinted which is unlikely to happen to Itachi).
C2 is 50/50 seeing as while it's faster and has larger aoe Deidara also had the advantage of the placed mines which were the main reason Sasuke struggled.
There's the possibility of Itachi closing the distance before Deidara takes to the air, and then there's 3T which Deidara has knowledge of and a supposed counter.
I would usually give the slight edge to Deidara due to C2 spam being more dangerous than Itachi's arsenal and Deidara having genjutsu resistance but with the distance here being 5 meters that's not guaranteed.
Itachi vs Minato
Itachi and Minato are similar in that they're both young geniuses who didn't live up to their potential, who both possess excellent reactions with instant/near-instant offense and defense (through MS and FTG). The issue for Itachi is that his MS in comparison to Minato costs much more chakra and has worse drawbacks which is the decider in this fight imo.
Minato's reactions and FTG mean Amaterasu and Totsuka are unlikely to land, they also mean Itachi can't corner him in CQC to land Tsukiyomi since Minato can keep teleporting.
With FTG-using KBs thrown in the mix and Minato's superior stamina it's a matter of time before Itachi is overwhelmed.
Minato also had very little panel time, at least in comparison to Itachi so he might have other stuff up his sleeve.
In terms of portrayal Minato beat Obito who Itachi couldn't beat in his lifetime when he had every reason to.
I heard there was another translation where it's said differently, but I don't know.
If not, you could and say that it wouldn't make sense that his power would be praised in relation to Itachi if the gap was significant, and that this piece of portrayal is more recent and should take precedence. Or you could say that the plethora of evidence showing Kisame being inferior to Itachi and Kishi not giving an explanation for this supposed sudden power-up of Kisame (the author could have had Kisame as someone who was hiding his true power or that he was playing weak or something like he made excuses for Hashirama like people didn't believe how strong he was, etc) points more towards Kisame being powerful just enough to be relevant to Itachi.
The issue is if Kisame did get retconned then all his past actions need to be explained (cucking to Jiraiya, saying Deidara was one of the stronger Akatsuki, etc), and since his introduction until his death he was built-up as Gai's rival, so did Gai get retconned too? Kisame being retconned to be much stronger than he was also can be argued to serve no purpose in the story as a side-villain and the author is unlikely to have an incentive to do that, and imp he probably didn't.
Kisame vs Kakuzu
Kisame wins in a tough fight or it could go either way, Kisame will need the lake to not be overwhelmed by the masks as that gives him ther advantage of diving underwater and the possibility of his 1000 sharks harrassing/killing the bears if the chance allows it. Otherwise Daikodan would completely fuck up whichever jutsu is launched at it and whichever hearts are caught in the aoe of the (now even bigger) shark will get killed. Kisame would struggle to breach Domu but iirc Kakuzu is stationary when it's active and he has to move at dome point, and in the waterdome a fused Kisame might get hit with Domu (if I'm wrong and Kakuzu can move freely while using it) but the same could be said about Killer Bee who could only manifest some tentacles but didn't, and Ki(Samehada) doesn't need to breach skin to absorb chakra.
Kimimaro vs Asuma
Tough one, Asuma was portrayed as decently stronger than his individual students in the war arc and is stated to be 'close in power' to Part I Kakashi - which would put him as a skilled/high Jonin since Kakashi is one of the strongest Jonin. Kimimaro on ther other hand was kept up with by the kids, however he could still easily subdue Jugo (I rank Jugo as average Jonin or lower at his best) but then again the gaps between Jonin levels is massive anyway. Kimimaro has some sketchy portrayal due to the implications of him being relevant in a Kage battle, being compared to Hebi Sasuke and being sick (so some of his hype might be referring to his stronger self). But even then those can be explained somewhat (Orochimaru meant absorbing his body then fighting Hiruzen rather than Kimimaro himself being there, being >> Jugo is not impressive when even Suigetsu could do it and Hebi Sasuke subdued both Suigetsu and Juugo effortlessly while Kimimaro only subdued Jugo).
I have Asuma mid-high diff by an extending Hien or his Katons, and he could probably outlast sick Kimi. Though I think it can be argued otherwise
We don't completely ignore them as that's unfair, however we work with the information available while making sure it doesn't contradict the character's and the jutsu's portrayed strength.
Daikodan is said to get bigger the bigger its target is, we saw it lose to Hirudora but the stress there was on Hirudora not having chakra rather than being the more powerful technique. That tells me that techniques (that have chakra) and are on Hirudora's destructive level would not overpower Daikodan's absorption. If Hirudora was too strong to be absorbed, Kishi would have had Gai overpower it directly, and there'd be no point in the whole "it's not made of chakra".
This is not to be confused with Daikodan's own firepower, as the whole idea of the technique (and absorption in general) is that it ignores firepower entirely (up to a certain point). Now the question is since Daikodan is an offensive projectile jutsu what is its actual firepower and how much damage does it do?
We know Daikodan is a much bigger version of the normal shark bullet, so based on that we can conclude its firepower is much stronger, but obviously its firepower is weaker than Hirudora's because the latter overpowered it.The shark bullet seems to be targeted/it chases the enemy rather than a straight line so maybe that also applies to the bigger version (which would be interesting if a shinobi were to dodge it he wouldn't get rid of it).
Other than that there clues like Daikodan's hype/portrayal as an absorption technique is not on the level of things like Preta path for example because the latter could absorb Senjutsu without problems and has better hype so the same way those characters/techniques aren't invincible so would Daikodan not be. Preta seemingly couldn't absorb solid material like Gaara's sand, so that puts in the question of whether the shark bullet can be blocked by solid ninjutsu. Daikodan is an offensive projectile meaning the end goal is to harm the enemy, based on common sense an average shinobi getting hit cleanly by Daikodan and surviving wouldn't make sense if his smaller shark creations could rip apart human flesh.
Yata made Itachi "invincible" and was called an "ultimate defense" while he had V4 Susano'o up, so one can make the argument that Yata is above V4 Susano'o durability (what's the point of Susano'o carrying a shield thats weaker than its body, and why would a shield that's weaker than its wielder's body be hyped up as an ultimate defense instead of that supposedly weaker body?).
By scaling the Totsuka was Orochimaru's downfall and something he seeked but couldn't find, Yata by hype is placed in that same category, meaning Yata > Orochimaru's defenses. For example Yata should outperform Orochimaru's Rashomon against KN4 TBB, and likely by a decent bit too. When it comes to things like Jinton for example it depends on which you believe has higher portrayal or is more valuable between Yata and Jinton, and Itachi's own portrayal in comparison to Onoki and how much their respective techniques account for their overall power (debatable but there's information to infer).
Frog Song can likely be countered by partner method, the author goes out of his way to highlight specific counters to powerful techniques. Tsukiyomi is immune to partner method and Kishi made sure to show us that when two PJ said it would one-shot them if it landed, and Naruto said everything happens in an instant so you can't break out. That didn't happen with Frog Song. You could say Senjutsu makes it hard to overpower but then it's a matter of Biju chakra vs Sage chakra. You could say the mechanism by which it works implies it's a one-shot once it happens since "it seals the mind and body" or that the partner (biju) would also be caught - those arguments aren't baseless but imo:
1. there is no incentive to believe it will one-shot; SM Jiraiya is not cleanly portrayed above Killer Bee.
2. the arguments for it being broken I feel are more supported by evidence rather than giving the benefit of the doubt to the sages.
Koto is more straightforward, we saw it can work on people on Edo Itachi's level but the issue is Shisui's portrayal isn't defined in the manga and there is very little information for us to conclude how strong he actually was. So this makes it difficult to rate how practical or to where a logical limit should be drawn for Koto.
Overall I think it's important to remember the practicality of these techniques; they first have to land on the opponent for this discussion to be needed (from a practical "who's stronger" perspective), Jiraiya has to prep SM and then prep frog, Itachi has to establish eye contact, Daikodan has to hit the target, Koto has to be cast etc. When we take these things into consideration they make the conclusion more likely to be close to the truth.
Jiraiya vs A3
Jiraiya vs A3:
Portrayal wise, KCM Naruto struggled to defeat A3, but his SM incarnation (which is weaker) defeated A3 with some knowledge advantage but it was only a clone and it was a straightforward defeat. SM Naruto was portrayed as superior to Jiraiya but not to the extent he'd lose to his clone. Jiraiya defeated Kisame and Konan quickly and in base and is portrayed superior to Hiruzen who's stated to be the strongest of the five kages. One might disagree and say Jiraiya won't stalemate the Hachibi but we can't ignore that Deidara (who's portrayed as so much weaker than Orochimaru who's Jiraiya relative to the extent he wouldn't make Orochimaru struggle) literally knocked out the three tails and several fodder shinobi could restrain the wild Hachibi (wild is an important distinction so we don't get carried away and apply all the feats of Bee to the Hachibi). If we say "Deidara just had the firepower it doesn't mean Jiraiya can do it" this implies it is a match up issue rather than an overall level of strength issue which can be easily turned around and used against A3's accomplishments (he only stalemated the Hachibi because of his stamina not because he's a match for him). What's more is that we've already seen Base Jiraiya defeat KN4 while technically he shouldn't have the firepower to do so. Overall all of Jiraiya's praise and hype puts him above A3 even if slightly.
How the fight goes down: we look at how they fight; A3 is a straightforward cqc fighter who engages in close range and relies on his strength, speed and durability to win while Jiraiya is a mid to long range fighter who relies on large aoe, traps and taking advantage of locations. So basically they are the opposite of each other. The fight will mostly be A3 trying to close the distance and kill Jiraiya in cqc while Jiraiya falls back and uses traps to slow A3 down/provide openings or his large aoe that isn't easily dodgeable.
In a neutral fight Jiraiya will start in base and have manga knowledge, even if we don't think Jiraiya knows about the lightning shroud and the Raikage's strong body (Tsunade did iirc) then Jiraiya still has the advantage here because Jiraiya has more abilities A3 doesn't know about than A3 has abilities Jiraiya doesn't knows about; this matters because throughout the course of the fight A3 who's straightforward will be figured out quickly as opposed to Jiraiya who can do dozens of things and fight in many different ways. Jiraiya will likely figure out A3's abilities and his strong body during the initial exchanges by using his mid-range attacks like Yomi Numa, FCD, Shadow manipulation etc and he likely won't be in danger because he doesn't prefer CQC anyway, from this point on Jiriaya will know if his arsenal in base is a match for A3 or if he needs SM. You might argue that Jiraiya shouldn't get enough time to figure all this out but we've literally seen the opposite happen to A3 against the alliance who had enough time to mount defenses that failed and gave them that knowledge. Jiraiya might not have fodders to support him but those fodders are nothing to Jiraiya in the first place.
Contrary to popular belief, Jiraiya can buy time for SM other than just Gamaken. He can set up dozens of traps like shadow manipulation, KB distractions, smoke bomb/toad diversions, Boss Summons leaping/jumping out of range while his detection barrier is active all together to reach SM. If we believe Jiraiya can't move while his hands are clasped for the ritual then that means it takes him very little time to reach SM (against Pain he was only perfectly still from the time Gamaken was falling until Gamaken reached the ground) and if we believe it takes him longer (i.e from the moment he clasped his hands and activated his barrier) then that means despite him taking longer to reach SM he can still move around freely. A3's problem here is that he's strong and durable but if the distractions are slowing him down he can't do much about them since he's pretty straightforward and doesn't have many options.
Once Jiraiya reaches SM, Frog Song definitively defeats A3 and now Jiraiya can do everything he did before to slow down the Raikage but much better since he has Senjutsu to enhance his base jutsu, new Senjutsu techniques (Geomon) and Ma and Pa who can target him with Futon to blow away the shroud (the Futon is dodgeable to A3 but them already knowing that would only use it after a distraction/blindside and we've seen A3 hit by Futon in canon). Blowing away the shroud might not be enough to weaken A3's durability enough so that Jiraiya can directly kill him, but it would make it easier to slow the Raikage even more than before and allow Frog Song to be executed. We must remember that in SM Jiraiya could escape shared vision and snag a body, A3 might be faster than the paths but he isn't as tough to deal with overall.
As for A3's speed it's is not so astronomical that Jiraiya will be overwhelmed by it if Dodai and those fodders didn't, and that's not an outlier because we've seen in the manga that faster characters tend to overwhelm slower characters after a while rather than right from the get-go:
1. Kurenai dodged Itachi's strike and blocked his kick, but was eventually overwhelmed and blindsided by Itachi's shunshin speed (when he went behind her without her knowing what happened).
2. V1 A was praised on panel of having speed that is >= Minato's but was being kept up with by Suigetsu and Jugo who could not only intercept him (interception feats usually aren't reliable, but this one in particular was highlighted by Shi as impressive) but block him too (Jugo). However they still eventually got overwhelmed by the speed (Juugo commenting on Raikage's speed and Raikage dodging him point blank and blindsiding him with shunshin+elbow).
A4 and A3 are both fast and durable, but A3's emphasis has always been on his durability (strongest body, tanks FRS, etc) while A4's was on his speed (fastest man, Minato's rival, Shi's commentary). More importantly, when A3's speed was emphasized it was through his reflexes to dodge FRS from close range rather than overwhelm his opponents with his speed, just like the emphasis on A4's durability was minor (surviving Chidori, Sasuke's sword bouncing off) rather than being emphasized as someone really tough to damage.
For Kisame vs A3 I said that Black Lightning might make a difference, but here I don't think it will. The reason for that is because A3 never bothered to use it against SM Naruto/the alliance shinobi which implies to me that people who are close to SM Naruto wouldn't have this jutsu make a difference against them either. In Kisame's case he is just much weaker than Jiraiya and Naruto so it's optimistic to assume that for him.
So yeah, Jiraiya wins with high difficulty.
Tsunade vs Hebi Sasuke
Tsunade vs Hebi Sasuke:
First we need to look and compare their portrayal to see who's likely to come out as the winner. For me Hebi Sasuke and Tsunade are on the same general level/tier and this is how I came to that conclusion:
The reason I think they're portrayed on the same level is that we know Jiraiya is portrayed above Tsunade because Shikaku said Sages are above anyone in the village, and Naruto had to surpass Jiraiya and not Tsunade to face Pain. This also fits with Naruto >/= Sasuke > Sakura theme and takes into consideration that her support abilities and accomplishments are included in her portrayal (so if she's on the same level as Orochimaru/Jiraiya with support/medical ninjutsu logically she would be below them without it (i.e fighting ability only). So we have:
Next, we know Jiraiya is portrayed as decently superior to people like Kisame (and therefore people around Kisame's level), while it's true Jiraiya had a location advantage in the hotel Kisame still shouldn't have been helpless if he was close in power to him. Kisame was portrayed as 7G Gai's rival (prolonged fight, trump cards were used, build-up since part I) who is relative to Kakashi. Kakashi up until the Pain arc thought Jiraiya's feats were "crazy". However we know that Kisame is still below Tsunade because he admitted inferiority to the Sannin collectively:
So now we have people solidly above Tsunade (Jiraiya, SM Naruto and people relative to them) and people solidly below Tsunade (mid-Akatsuki, Masters), the only question is who fits in and fills up Tsunade's tier? i.e which characters are portrayed as above mid-Akatsuki/Masters but still below SM Naruto/Jiraiya/MS Sasuke etc?
Hebi Sasuke already fought a mid-Akatsuki in Deidara, and had every disadvantage against him (no KI, match-up disadvantage (ironically people claim Sasuke had a match up advantage going against the author's words), Tobi laid the mines, genjutsu counter) yet Sasuke still won and the author literally had Sasuke say "even if Raiton didn't work I had a back up plan" as if to tell people "no you can't use Raiton as an excuse". Sasuke didn't use Kirin. Even from a story perspective this served as the "warm up" fight for Hebi Sasuke and for us to see a "glimpse" of his power before his actual real battle against Itachi. It's why Sasuke kept getting praised for his speed, sharingan, Raiton etc throughout the fight, Deidara was used to hype Sasuke.
Another way to look at it is that Sasuke had every disadvantage against Deidara and came out on top, meaning he's a level above him. Similar to how Itachi had every disadvantage against Hebi Sasuke (lack of KI, planned the fight, had to fight Orochimaru's hydra as well, etc), meaning Itachi was a level above him.
So now we have:
Other people you can fit in in Tsunade's tier are people portrayed below level 1 but above mid-Akatsuki and masters level: Like A3, A4, Hiruzen, Sasori etc. They might not be equal but they're comparable.
Now there is the issue of Karin telling Sasuke "Someone who beat Orochimaru shouldn't have struggled with the likes of Deidara" and Sasuke told her it was because Orochimaru was weakened. The thing is, we know why Sasuke "struggled" with Deidara: the author went out of his way to highlight that Sasuke had no KI, we saw Sasuke take damage and lose the ability to fly because of Tobi's interruption, we were directly told that Deidara is a bad match up for Sasuke, we found out Sasuke didn't use his trump card and we were told Sasuke still had a back up plan anyway. So all of these are clear reasons the author dedicated panels to highlight which show us why Sasuke struggled against Deidara. If Kishi wanted to portray Deidara as close to Hebi Sasuke he could have simply wrote the fight without those things, but he didn't and we shouldn't ignore that. Sasuke was informing Karin that his BoS version was lucky Orochimaru was sick, not that his Hebi version struggled against people Orochimaru wouldn't struggle against.
The point here is that there's no way Deidara (or those on his level) are on the same tier as Hebi Sasuke.
Excluding her support role, against the Susano'o clones Tsunade was portrayed as below Onoki (at least post-will) and comparable to A4 (he implied she was getting sloppy and he had one arm which points to his superiority but he still got caught by genjutsu which puts her back up there with him) and above Mei (who was getting overwhelmed).
Generally speaking they should be on the same level and comparable, the question is who should have the edge? If I had to choose I'll give a slight edge to Tsunade because I think it's slightly optimistic to assume Sasuke surpassed and can defeat a Sannin because his next power up the Mangekyo Sharingan is supposed to be equal to SM Naruto who has just surpassed the Sannin. The idea of Hebi Sasuke for me is that it is a bridge between Wind Arc Naruto and SM Naruto. Wind Arc Naruto is comparable at best to BoS Sasuke albeit weaker while SM Naruto is comparable to MS Sasuke. Hebi is in between these two stages and he ended up losing his Hebi powers as they were a red herring to the story and his development (Orochimaru and his powers are evil). So basically it doesn't make sense that there is a power up of Sasuke where he can defeat one Sannin and lose to the other two, what makes more sense is that he reached the minimum of Sannin-level and can give a really good fight to Tsunade but ultimately lose. I also don't think he'd do as well as Tsunade did against Madara even if most what she did was off-panel.
Now we move on to how they fight: Hebi Sasuke is a close to mid-range fighter who relies on his swordsmanship and Raiton variants to damage the enemy, his Katons and snake hands/meatshields are used in close to mid-range for offense/defense and has access to high-level offensive and defensive techniques in the form of Oral Rebirth, Kirin, and his CS that while are very powerful they exhaust his chakra or require some time to set up. He also has access to a boss summon in Manda.
Tsunade is mainly a CQC fighter that relies on her top notch Taijutsu, paralyzing through Rashinsho, resilience, top notch regeneration, adeptness at evasion and most importantly her strength, her Byakugo increases all her stats on top of automatic regeneration and she has access to Katsuyu who is useful both in battle and as support although she is inconsistent in summoning it for battle. She also seems to have high stamina and a gravitation towards attrition battles.
How the fight goes down: First off we agreed their portrayal is close to each other meaning regardless of who wins it won't be without effort or without big jutsu being involved, so right off the bat Tsunade one-shotting Sasuke in the first CQC exchange or Sasuke beheading her with Chidori Eiso are out of the question. Tsunade will likely engage in CQC and so will Sasuke who will be at a disadvantage. The reason Tsunade will have the upper hand in CQC despite Sasuke's sharingan, emphasis on speed, CS2 amp, Raiton, kinjutsu is because her superior skill, much superior strength, Rashinsho, emphasis on evasion skill, resilience and durability which are overall a better and superior CQC toolkit than Sasuke's. Sasuke's skills will likely be relevant here for defensive purposes however, allowing him to survive her onslaught with his sharingan/speed/CS2 and gain some distance, at worst Sasuke wastes one Oral Rebirth but I doubt it. Her Byakugo is also a better enhancement than CS2 in CQC since not only does it boost her stats and make even much more dangerous due to her strength but it heals her from anything that doesn't kill her instantly from Sasuke in a swift fashion that barely slows her down. From there Sasuke will likely go for mid-range shurikens, Katons and using snakes which would be countered by Tsunade's strength/evasion and if not then by Byakugo which Tsunade would have activated by now due to knowing she'll need it to face someone with Orochimaru's powers and/or to handle Sasuke's Katon spam. At any rate like I said before their portrayal is close so Byakugo will definitely be activated before (if) she's killed.
At this point Sasuke would have realized that even if he were to go CS2 and attempt to kill Tsunade in CQC it likely won't work due to her strength/regen that he's seen before/is currently witnessing making his only remaining options genjutsu, Manda and Kirin.
When it comes to genjutsu and Tsunade, there are points in her favor and points that are in Sasuke's favor. In Sasuke's favor, we have seen him use genjutsu to land openings on Deidara and could (somewhat?) restrain Orochimaru. More importantly Sasuke has the ability to mind control summons and has a feat of doing just that to a Sannin boss summon no less. Some will say Sasuke only got Manda because he was distracted, Sasuke only controlled Manda for like a split second and only made him open his mouth which doesn't mean he can fully control his actions, controlling Manda cost Sasuke a lot of chakra, etc. But realistically speaking these are all excuses supported by zero evidence fro the manga or databooks, in fact the databook goes on to praise Sasuke for this skill and more importantly says that Sasuke displayed a glimpse of what Madara did when he controlled the Kyuubi i.e the reference for his feat was the feat of mind-controlling the Kyuubi (which obviously doesn't have any of those made up weaknesses).
In Tsunade's favor, we have to remember that Sasuke's genjutsu is not as strong as Itachi's and therefore less impactful, meaning Tsunade shouldn't struggle as much as Orochimaru to break it and risk losing a limb. Sasuke also doesn't tend to try and force eye contact in cqc as much as Itachi does and his genjutsu is mostly used for openings (likely because his genjutsu isn't as strong as Itachi's). Some optimistic assumptions for Tsunade would be her and Katsuyu sharing chakra/informing the other when genjutsu is used and then breaking it, but this is unlikely since I'm a firm believer in the idea that if the author highlights certain counters to a technique (like 3t) to hype it then we can't go and assume what other counters are just because the mechanism seems like it works, kind of like how Pain "constantly pumps chakra into the paths" but was never portrayed as immune to genjutsu. In Tsunade's defense however, we don't know how practical/successful would controlling Katusyu be, technically speaking if she's being occupied by Manda (which I'll get to next) then Sasuke might have an opening to genjutsu Katsuyu but the problem is Sasuke himself will be occupied with Tsunade and while this might mean the slug and her princess can't save each other from genjutsu (because each one is occupied fighting) it still likely isn't such a big factor since we established Sasuke's genjutsu isn't that dangerous looking at its portrayal and the fact that Sasuke may not have an opening to use it if Tsunade is charging him with Susano'o-busting, Magatama-tanking, Katon-swatting momentum. Another issue is that Sasuke doesn't have knowledge on any of Katsuyu's abilities so even if he's successful in controlling her it won't be that dangerous.
Manda and Katsuyu: By portrayal, Manda and Katsuyu are in the same league along with Gamabunta. Therefore logically speaking if we apply the deadlock the difficulty at which Katsuyu kills Manda should be about the same as the difficulty of Manda killing Gamabunta - so the common suggestion that Katsuyu "can't be killed by Manda, he can't do anything to her!" isn't true when Gamabunta could hold his own against Manda for a while. Also, Katsuyu in canon couldn't achieve that much dominance over Manda and Tsunade delivered the finishing blow; if Katsuyu could get rid of Manda that easily Manda wouldn't have occupied both summons and needed to be defeated by Tsunade.
Tsunade didn't opt to summon Katsuyu against Madara to help her fight, she only summoned her for support reasons, so did Sakura in the war arc. From the way the Madara fight and Tsunade's feats and portrayal in that fight were drawn, it doesn't seem like the author wants us to think that Tsunade was not fighting at full power. One could say this fits with Katsuyu's support abilities being so important implying that's what she's mainly used for. Tsunade did opt to summon Katsuyu against her fellow Sannin Orochimaru, but Orochimaru relies on summons anyway and that could be due to the summon deadlock. Even when Katsuyu was summoned.
However, a simple counter to the above within the context of this fight is that even if Tsunade wouldn't summon Katsuyu, she definitely will when Sasuke summons Manda anyway, and if Tsunade finds an opening against Manda she will one-shot the snake with her Byakugo-enhanced strength while Sasuke is gonna have more difficulty handling Katsuyu.
Now that we're past genjutsu and summons, at this point the likely outcome is that Manda gets killed by Tsunade or Katsuyu's acid while Katsuyu is de-summoned or remains on the battlefield while Tsunade heals from the injuries and Sasuke is fatigued from all the fighting and likely due to possibly having survived a punch from Tsunade due to Oral Rebirth, Sasuke used Oral Rebirth in an offensive manner against Itachi but he had the momentum then and it was part of his plan due to his knowledge, here the only thing he'll benefit from it is the extra life.
At this point the battle is over one of two ways, either Sasuke dies before he gets to set up Kirin from an incessant onslaught from the never-tiring Tsunade giving her a high difficulty win, or he manages to prep it. If he manages to prep it it would be weaker than what we saw against Itachi but still relevant enough to kill Tsunade, at this point Tsunade's only answer would be to have the Katsuyu that was already there (Katsuyu didn't de-summon since Sasuke presumably immediately went for Kirin) engulf her and protect her, this could work if we consider how durable Katsuyu is and that Kirin will be weaker than the one we saw, all on top of Tsunade's Byakugo. Or it could not work and Tsunade dies. However the problem with this is that the portrayal of Kirin specifically highlighted it's striking speed which implies most characters wouldn't get the chance to mount a defense, on the other hand one could argue the emphasis on it's striking speed is telling us "you can't dodge the aoe because it hits fast enough and big enough" not "you can't try to mount any defense of any shape" but that is too optimistic for Tsunade. If Tsunade is conveniently atop Katsuyu than that's lucky for her too.
With all that said though, I think it's more likely Sasuke doesn't get to set it off in the first place due to the incessant pressure he'll be getting from Tsunade that he didn't get from Itachi. If Itachi wasn't coughing blood, injured and wanted to kill Sasuke he wouldn't have gave him enough time to set up the Katons, jump up into the big stone, etc.
What really makes me lean towards Tsunade is the fact that Hebi Sasuke had two full on-panel one on one fights to show everything he had, Tsunade never had a one on one fight, was rusty and hemophobic in one fight and had a team and lots of off-panel performance in her other fight. At most we can say Sasuke can use some more minor snake abilities from Orochimaru but he's had his chances to showcase everything to use and he doesn't really have any hype to suggest important parts of his arsenal were not shown. Tsunade on the other hand has taught Shizune and Sakura how to use poisons offensively, participated in an entire war as a fighter before she became a medic, has been implied to be able to use medical ninjutsu offensively (against Orochimaru) and could have some small elemental jutsu here and there.
Imagine if the Deidara and Itachi fights were replaced with fights where Sasuke was rusty/had no will to fight/scared of blood and the other one in a team with five others where most of his on-panel showings are snapshots of CS2 Chidori through the opponent.
To conclude, it's a close battle but I lean towards Tsunade with high difficulty. Interestingly I had this fight as 50/50 not too long ago..
Jiraiya vs MS Sasuke:
MS Sasuke is portrayed stronger and has a stronger arsenal, he also matches up well against Jiraiya which is saying a lot since Jiraiya is so versatile and has so many options.
Snakes and genjutsu counter toads, Raiton counters Yomi Numa, Amaterasu counters any Katon, Susano'o blocks most Jiraiya's attacks, what's more is Jiraiya is dealing with someone who is trigger-happy with the MS, Jiraiya can only hope to sense and maybe do something about Amaterasu/Susano'o Arrows for so long before he's tagged or overwhelmed, MS genjutsu is still a problem and Jiraiya can't freely try to keep his distance with summons since Sasuke also has those in addition to flight.
Jiraiya loses even if he starts in SM, if he starts in base Sasuke wouldn't even need to resort to MS for a long portion of the fight since his base self is good enough a match-up against Jiraiya that he can afford to fight without MS for a while.
My opinion thread
Those within the same tier are not ordered but are not (necessarily) equal either. The tiers are ordered in an ascending manner; meaning tiers (not necessarily the order of ninja itself) get stronger as you read down. Don't mind the tier names towards the end, I had to make them up.
Part I Kabuto
Part I Kakashi
Immortals Arc Kakashi
Immortals Arc Naruto
Orochimaru w/o arms (host actively rejecting)
Orochimaru w/o arms (host not rejecting)
War Arc Sakura
Tsunade/4th Raikage/Gaara (War arc)
Healthy Orochimaru/Ōnoki (Will of Stone)
Danzō (no Koto)
Seven Swordsmen of the Mist
Healthy Orochimaru with PI Edo Tensei
KCM Naruto/EMS Sasuke (Kabuto fight)
The Legendary Sannin
Rinnegan Obito (no paths)
EMS Sasuke (Jūbito fight)
Bijū Mode Naruto
Bijū Mode Minato
Post-Jūbito EMS Sasuke
Rinnegan Obito (with Jinchūriki)
Jūbi Jinchūriki Madara
Some Elite Jonin could be Entry-Kage level (Darui, Kitsuchi, Hidan, boss summons), and some Entry-Kage could be Low-Kage (BoS Gaara, Chiyo, Manda 2.0).
Needing Bijū chakra to use Jutsu and "amped' Kisame
Kisame vs. Tsunade
More Kisame vs. Tsuande
Even more Kisame vs. Tsunade
Samehada vs. Daikōdan
Suirō Sameodori no Jutsu
A chakra eating dance! A giant prison of water amasses on the ground!
"Suiton Dai Bakusuishouha" covers the environment surrounding the enemy in one body of water, a gigantic water prison is created. The oppoent is shut away underwater, where breath is impossible, except for those who possesses the ninja sword Samehada and the ability to fuse with it to become a half-merman. The prey's movements are supplemented and taken away (I think, tough one). Samehada is aligned with ones body, than the opponents chakra and life are shaved away, the person is cornered by suffocation. Kisame's strong point is capturing someone alive with this Jutsu.
With Kisame in the middle, the water prison's movement is connected to his. To slip out of the large prison is not possible, liberated from the ground Kisame's movements become faster.
Sution Daikōdan no Jutsu
The shark's roar eats and shredded to pieces the enemy jutsu, while one's own power restores!!
A massive chakra bullet in the shape of a large shark, the Jutsu bursts towards the target it's aimed at. It has the ability to absorb the enemies chakra and change that into ones own power. The large shark stores the opponents chakra in it's belly, it's bottomless appetite is sated by it's fangs shredding the enemy to pieces
The opponent's and this jutsu clash, the chakra is eaten which results in a massive release.