Chapter 44: Unplanned returns

She couldn't say this was what she was expecting when she agreed to help Anko out after seeing the usually energetic woman buried under a pile of paperwork due to being the proctor for the second exam. The one where, according to the rumor mill, Orochimaru finally showed his hand for the first time. The thought itself was still bittersweet; their leader had placed all of their safety over his own survival. It was something to be proud of. And yet that no one had managed to do a thing to stop the man that killed their Hokage felt like a poisoned wound that refused to close. Still, they moved onward. Konoha was a resilient village, and even if the Godaime hadn't been decided on yet, they were well on their path back to normalcy.

Vermillion eyes flickered towards the man walking by her side.

Asuma had certainly lost more than just a leader; however, the man was very much personifying that resiliency. Whether that was for his student's sake or his own, Kurenai couldn't be sure. If this was the way he'd chosen to cope with his loss, then the young woman would play along and offer her silent presence.

"But man, I'll really have to stick with window shopping for a while," the man sighed as he looked at a passing store.

"Huh?"

"Well," he winced, his hand reaching out to scratch his cheek. "Let's just say my wallet may be hurting for a bit...and Kakashi's is definitely happy."

"Wait...you betted against them?" Disbelief colored her words.

"Oh, come on, you know none of us truly expected all of our kids to make it to the finals." True enough, but none of her other coworkers had been a prodigious ANBU captain at 13. "He had Naruto for the gods' sake. And against a Teisho of all people!"

Shaking her head, the kunoichi bit back her laughter. Seriously, to bet against Kakashi's student had been a bad idea from the beginning. "They are the only team that man has ever passed. Plus, he runs them to the ground with their training; surely you've seen them racing all over the village."

"Yeah, doing D-ranks..."

"Yo!" Speak of the devil...Kakashi waved at them from in front of a dango shop. "Hey there, you two...you're so chummy." The man had t be smiling under the mask. "Are you on a date?"

"Don't be an idiot." Heat rushed to her cheeks on its own. "Anko asked me to buy some dango."

"What about you? What are you doing here?" Asuma rushed, a bit of a sad attempt to change the conversation. "I thought you didn't like sweets."

"Well, I came to buy something to put on a grave, so I figured I'd just meet with some people here while I was at it." Too pronounced, Kakashi's shake of his head was too evident, and his visible eye shifted towards the inside of the shop. "Sasuke and Kagome, actually."

A splash of red on pitch-black fabric caught her attention. Other than the shop's staff there were only two people inside. Both were wearing cloaks and hiding their faces...the information about Sandaime-sama's death had probably spread like wildfire; infiltrators were to be expected.

"That's a rare sight for you to be waiting for someone." A slight movement was all that was needed for her elbow to lightly connect with Asuma

"Mah, I can be on time once in a while." His lazy drawl was louder as he pointedly looked to his left. "Morning, Kagome-chan."

"Good morning, sensei...Kurenai-sensei and Asuma-sensei too." There was a slightly confused look on her face. Sasuke-kun followed behind her with a frown on her face. "I hope your day's been going well."

"Morning, Kagome-chan, we're just running an errand."

Azure eyes flickered to the table behind them, the Uchiha boy's gaze immediately following hers. Experience made sure that all the adults around kept their expressions from showing anything at the empty seats behind them, the ordered snacks and tea still in their place. So...those two were gone the instant the two clan heirs arrived.

"None of us like natto." The annoyed complaint was somewhat expected.

"Oh...really."

They may not have worked with the elite Copy Ninja, but it didn't take a genius to realize what his glare meant. Not allowing her gaze to harden, Kurenai looked back at the Higurashi heiress. The girl was sharp; she would undoubtedly notice something was amiss. The question here was...how close would she get?

"Well, we've got somewhere to be," the genjutsu specialist smiled, making sure to remain relaxed. "See you around."

Not willing to waste more time, the kunoichi allowed chakra to burst to her feet. Speeding in pursuit of the cloaked 'strangers' that had vanished in a blink. Asuma hot on her heels. A flicker of irritation rose inside her; they were calmly strolling by the river. Not a hint of their movements betrayed any kind of hurry. Looking to her side, she nodded at Asuma's unspoken question and stopped right in front of them.

"It's been so long..." The words were softly spoken, not worried at all. "Asuma...Kurenai."

"You're not from this village...what's your business here?" Asuma's glare hardened. "And yet, you could only know our names if you were Konoha shinobis."

Bright crimson glared back at her from under the shadows of the straw hat still covering the young man's features. The unmistakable black magatamas surrounding the pupils were all she needed to know just who was standing in front of them.

"You!"

"Hmph," If there was tension in her partner's voice, it didn't compare to how it was now. "There's no mistake...Uchiha Itachi."

Everyone had known the Uchiha prodigy; everyone had been in awe and envy of the young shinobi's lightning speed in his promotions...even with the yeas that had passed, the sharingan was undeniable proof of his identity.

"Are they acquaintances of yours, Itachi-san? I suppose I should introduce myself as well." The second man was one she couldn't recognize. "I am Hoshigake Kisame, pleased to meet you, and hope to get to know you later."

"There's no later. I'm gonna take you down now!" Asuma growled.

"I've heard of you..." She needed to buy some time; hopefully, Kakashi would get here soon enough. "Hoshigake Kisame, a former Kirigakure shinobi. A nuke nin currently being sought by the land of Mizu...for charges such as assassination and subversive machinations against the state."

"You two are major felons that have bingo book rank S...Itachi, you've got guts to step foot in this village again after what you did." Her partner moved, taking a fighting stance.

"Asuma...Kurenai..." Uchiha Itachi spoke with the same unhurried pace. "Please, do not interfere...I don't want to kill you."

It was anger this time; that began to set her blood to boil. Kurenai had seen the aftermath of Itachi's actions first hand; it was hard not to notice how the Higurashi heiress' focus began t falter after being away from Sasuke-kun long enough. And the jounin had also seen the slight tension in the young boy whenever he came to pick Kagome-chan up, his mask less perfected when compared to his teammate. Those two kids had clearly gone through a special kind of hell, having to live through all that. And he...the one responsible for all of that was now leisurely speaking with them. Pretending to care about not hurting others.

"For someone who's committed parricide, that's an odd thing to say. Besides, there's no way you would just show up like this. Nonchalantly wearing clothes that don't look respectable for absolutely no reason..." Asuma was also clearly trying to buy time. "So, what are you after?"

Still with that infuriating slowness, the traitor's partner rose his hand to his bandaged weapon, placing it in front of him with a single swing, almost as if the whole thing was weightless. "He bothers me; shall I kill him?"

"Well, it doesn't seem like we'll be able to just walk out of the village without a fight, so..." Itachi shook his head slowly. "Just try not to overdo it. Your moves tend to attract attention."

"Understood."

For just an instant, time stopped.

And then, Asuma was in front of her, arms raised, blocking the claymore-sized sword with his trench knives. Their old teamwork strategies flashing back inside her mind; her hands weaved the seals in a rush, chakra flowing through her as the illusion made her disappear from their enemies' sight.

She had to make this perfect.

They said she was the best illusionist within Konoha, but that only ever happened after Uchiha Itachi was gone. Pushing back the urge to interfere with Asuma's confrontation, the young kunoichi focused on letting her chakra flow through the area. Genjutsu required her control to be as flawless as possible, and it was far more useful as a support or assassination skill. Besides, Asuma was no rookie; he should be able to handle himself while she weaved her trap.

"My long sword is called Samehada!" There was genuine joy on the blue-skinned rogue nin. "It means sharkskin! It doesn't slice." Blood sprayed from Asuma's shoulder, a pained groan escaping him. "It cuts you to ribbons!"

"Kurenai..." Despite it all, there was no panic in Asuma's voice. "What's taking you so long?"

Carefully constructed nets of chakra flew towards the invaders, forcing the images of her mind to become their realities. Immobilizing their movements as her thoughts were projected into their heads, tying them down with tendrils of illusionary wood before the young woman made her way to them.

Kisame was no doubt a threat, but it was the former Uchiha heir who set her nerves on edge. Gripping a kunai in her hand, she launched her attack...only for it to crash against the ground. The tree she'd conjured was now wrapped around her, trapping her.

"A weak genjutsu has no effect on me..." She could hear no inflection in his voice.

A reflection technique?

The sound of metal sliding out forced her head back to the present. She couldn't panic, not now. The sting of pain on her lip as she bit down, the metallic taste of her own blood barely shattered the illusion in time for her to dodge.

Adrenaline pushed her arms forward, an attempt to guard against a kick that was too precisely thrown.

"Kurenai!"

"Don't get distracted!"

"Impressive, Kurenai...however..." Shit, it was not just on genjutsu where she was outclassed. "It all ends now...for you, that is."

Too fast, Itachi was far too fast, and her speed was simply no match for him..so this was the level of a genius...the prodigy among prodigies...

It was quite something to witness, the mask of an elite jounin as he pretended everything was fine while Kakashi-sensei led them through the streets, seemingly without any sort of direction. Look as she may, Kagome couldn't find any crack in it. She had felt it, however, a burst of chakra that lasted for less than a heartbeat. It happened so fast that the Higurashi heiress couldn't really pinpoint much of anything other than the fact that someone had been inside that dango shop.

Someone Kakashi-sensei was making a concerted effort to keep them away from.

She should know who that was...the thought kept circling inside her head, and the girl could almost feel an itch coming over her. The urge to follow whoever it was the other two jounins had to be tailing right now. Sasuke's grip in her hand tightened, both a comforting and a silent question. Forcing a smile to her, Kagome shook her head slightly.

Something was going on, but nothing was screaming danger at her.

"So, what's this about?" Finally, Sasuke broke the silence.

"Ah yes...first of all," their teacher's lazy drawl was the same as always. "What do you know about the person who took over Naruto's training for the Chuunin Selection Exam?"

"...Jiraiya-sama is known one of the great Sannin." Her answer was slow as she tried to figure out what was going on. "And from what Naruto-kun said, the person who fixed whatever it was Orochimaru did to that seal."

At this point, their teacher was more than well aware of how sharp her deductions tended to be. Pretending not to notice the relationship between those two things would only her look more suspicious. Showing some of her cards could be as smart as keeping them hidden.

"Right, guess I shouldn't be surprised you connected the dots." The man hadn't stopped walking, slowly guiding them to the center of the village. "Well, that same Jiraiya-sama has decided to offer Naruto a chance to continue with his training."

"And the problem here is?" Sasuke asked with a huff.

"Why would there be any problem?" The elite ninja's innocent tone fooled no one.

"Because if the moron was just taking on extra, we wouldn't be here." Irritation bled into the Uchiha's words.

"You're right." This time, the jounin didn't bother to hide his annoyed sigh. "Jiraiya-sama has been ordered to go and retrieve the person who is to become the next Hokage...and he'll take Naruto with him in his travels."

"What...?"

"And...how long will this journey take, Kakashi-sensei?"

She could feel it, the pressure tensing her muscle and worry gnawing at her entrails. A forceful shove of logic pushed back her anxiety. The apparent pervert was still one of the Sannins; he was one who took care of the Kyuubi seal. Their childhood friend would be in good hands...and if these hands were at the service of the same people who offered him and Itachi to the sacrificial block...well, the jinchuuriki was too useful. Getting rid of him when the boy had only ever shown loyalty to this rotten excuse of a village wouldn't make sense.

"Maaah, that I don't know." If Kagome didn't know any better, she'd say their teacher was simply bored. "The person they're gonna be looking for is not exactly easy to find."

"I see..." Kagome trailed off. "Is it safe to assume we'll be staying within the village until Naruto-kun either comes back or the teams get reassigned?"

"Most likely. Although, if that were to happen, someone else would need to be placed with us." It was a subtle reassurance to them. That at least the two of them wouldn't be separated. "Well, I just wanted to tell you that Naruto is probably already on his way, nothing more."

Without wasting even a second, the man vanished from the street. Had it not been for what happened earlier, the girl might have bought the excuse of Kakashi-sensei attempting to run away from their complaints at not being told before. Not that it made being notified that their best friend would be all but taken away right now was what she'd call a pleasant surprise. But at least the feeling that she was missing something important wouldn't be bothering her.

"Something is going on," Sasuke snorted. "Should we follow?"

Hesitating, the Higurashi heiress thought back to that fleeting feeling that lasted less than a heartbeat. For an instant, Kagome almost thought herself paranoid. The reactions of all of the jounins around them, however, had dispelled that option. It was nothing like the bad feeling she got during the day of the third phase of the exam, no dread pooling in her stomach.

"No..." Even if she felt no fear, all three teachers had reacted with controlled panic. Whatever it was, they wouldn't be able to move unsupervised at all. "Naruto-kun is probably already gone; it would be better to take advantage of it."

Stuck as they were likely to be for the next few days (if not weeks), they could use the time to delve into their research. While most of their leads had been hanging on the Hokage, they had realized there was one more thing they could work on.

Uchiha Shisui's apparent suicide.

A cousin to the main family, a prodigy in his own right that had been easily overshadowed by Itachi's outstanding talent. And Itachi's best friend. The teen had been the only person the then Uchiha heir had agreed to share their precious together-time with. He'd also been the only member of the Uchiha clan Kagome was allowed to use a family honorific. Shisui-nii had been an energetic contrast to Itachi's calm, but it had been a welcome, occasional addition to their afternoons.

Until he drowned.

Thinking about it now, it was after that incident that the other members of the clan began walking on eggshells around their prodigy. Not quite surprising, considering the files kept in code in the archives made it clear the elders didn't think the other teen's death had been a suicide. Since the other Uchiha had been assigned to keep an eye on the heir, it was only natural for them to make the leap and accuse Itachi of killing his best friend. And again, Kagome couldn't help but feel something was off about that explanation.

Oh, in paper, it sounded good. Shisui was tasked by the treasonous clan to spy on their key pawn, only to be discovered and killed by the prodigy in an effort to keep the village safe. But she remembered his pained silence during the funeral, the tension that filled him whenever he'd come back from a mission.

That Shisui-nii would be willing to betray his best friend just because of an order was yet another fact the girl couldn't quite come to terms with. Not once had she felt uncomfortable while in his presence, a sharp contrast to how she'd felt those last few days when alone with their official guardians. Would that grinning teen truly agree with such treason?...the potential possibilities of what had been the truth behind it were not nice to think about. But it couldn't be denied. Either Fugaku and the clan were right, and Itachi killed Shisui...or someone else had been the one to do it and pinned the blame on him instead. Judging the file's content, it was extremely unlike that someone from the Uchiha family was responsible for it. Yes, there was that one Sharingan-related jutsu that kept being referenced and wasn't mentioned anywhere in their library, but it wasn't nearly enough for it to be justifiable. Which only left...someone who was in the know of the coup d'etat and decided leaving Shisui alive was too risky.

Someone who could potentially be the next lead they needed to keep moving forward.

It would've had to be someone who had direct contact with Itachi. High enough in the hierarchy that the Uchihas wouldn't try spy on for fear of discovery and instant retaliation. But also someone who'd have a chance to notice the other Uchiha's involvement and could arrange a cover-up. Whatever it had been, the one thing that was clear was that suicide was not what happened.

"Let's go back home, then." Later, they could haunt Kakashi-sensei to find out what happened.

"Ah, Higurashi!" The overly chipper voice of Akitoki Hojo sent a shiver down her spine; spotting the package in his hands, it was all she could do not to cringe. "I've been looking for you for the last few days. I wanted to give you this after the...well, the funeral. By the time I was free, though you were already gone."

Ire was quick to flash in Sasuke's dark eyes even as his grip on her hand tightened to the point of it being painful. It was happening more and more often now, the moments of jealousy sparking intense reactions...it should bother her, worry her even. Instead, Kagome welcomed it. Because it was evident, as the Uchiha moved his hand to place it around her waist, that he would rather burn everything around him than let her go...and she'd happily lit the flames.

Whatever deity existed out there definitely seemed to hate his continued existence.

A crimson eye opened, immediately registering and copying the hand seals the blue-skinned foreigner was weaving to attack Asuma. Honestly, Hatake Kakashi just kept finding one demon after another, and all of them were a direct threat to his students. After spending so much time without ANBU-level missions, the jounin wasn't expecting to continue finding himself opposed to such high-level enemies. It would seem it all started thanks to his troublesome team. Well, nothing to be done about that; they'd passed the bell test and were his responsibility now.

Water rushed around him, intercepting the mirrored technique as his clone raced in front of Asuma, allowing him to jump behind the wanted Uchiha prodigy.

"Why are you here now?" The other man seemed to relax a little at his arrival.

"I know I asked you to do this for me..." This was not a good situation here. "But I guess I got a little worried..."

"Kage bunshins."

"Kakashi..."

Crimson locked into crimson, and he could feel the pressure of his stare piercing into his soul. The eyes of a real Sharingan user, of a genius with the technique the Copy Ninja had been gifted. He had to expect the worst if he wanted to have a chance.

"My, my, you're a surprise." The second Akatsuki seemed to be enjoying himself. "No wonder you stopped me...there is another with the eye. You must be Copy Ninja Kakashi, then."

"I'm the one who was surprised...catching the scent of suspicious folk at the tea house, and should it be...I never imagined it would be Uchiha Itachi and the scourge of Kirigakure, Hoshigake Kisame."

"Well, well, you even know my name. What an honor."

"I see, so that giant blade of yours belong to one of the Seven Ninja Swordsmen of Kirigagure, the Samehada." Perhaps Kakashi had taken on more than he could handle.

"Hehe, I heard that young Zabuza sparred with you." Funny, how the nuke nin didn't seem angry at that. "I'll cut you to ribbons."

"Drop it, Kisame."

This time, it was killing intent that seeped into the young man's voice, taking even his own partner by surprise...this was not what he'd expected of someone who'd gone on a rampage with his own family.

"If you spar with him head-on, you won't get away scot-free. And if you take too much time, you'll give other shinobi time to arrive." Once more, the Uchiha prodigy regained his calmness.

"But..."

"Do not forget our purpose..." It was as if Itachi could simply flip a switch and go from indifferent to murderous in a heartbeat. "You did not come here to suffer injuries."

"And, pray tell, what might that purpose be?" Letting them leave was not an option.

"We know what we're looking for is here..."

"Looking for?" For some reason, the Uchiha was answering his questions. "And what might you be looking for?"

"I..." the younger nuke nin trailed off... "Unlike Kisame, wouldn't take any time at all."

A threat and an offer all wrapped in one. He could look the other way, no, not even that. It was just about letting them pass. As long as Kakashi left this place dragging the other two jounins with him, Itachi would make sure to the other S-ranked rogue shinobi in check. Hell, they could even go and inform the council, just as long as they left without a fuss, giving them time to retreat or go into hiding. All implied in a calm, monotone voice.

This was the man that threatened all three of his brats.

They moved at the same time, his hands forming seals with as much speed as possible. Water rose around him, hiding him from just an instant, blocking the launched shuriken...and the suiton technique that almost pierced his defense.

Impressive, truly deserving of the praise the young man had received back in the day, to have such speed that even his Sharingan couldn't follow. Weaving signs with just one hand and using the other to throw decoys shuriken...this man was probably just as terrifyingly effective as Orochimaru was.

"Trust you, Kakashi, to have such a sharp sense of perception." Despite his words, the Copy Ninja couldn't hear any change in his voice as he vanished and reappeared right behind him. "The praise was well deserved."

Battle experience was a life-saver; water dripped from the wound on his clone. And yet, even as he swam out, and reached for his enemy's foot, Kakashi wondered if the prodigy had actually been caught off-guard at all. This was not yet the level of an ANBU commander, so... if Kakashi had the time to make a water clone, then...

"Nice, Kakashi." Shit, the others.

"Watch out, Kurenai!" He was running before he finished speaking, tackling Kurenai back. "This one is the bunshin!"

"Kakashi! Kurenai!"

The pain of the explosion hitting his back was almost enough to drown the noise itself. Rushing chakra to his wound, Kakashi forced himself to keep quiet. This would be nothing compared to what could've been...honestly, this was some serious bad luck...Kurenai and Asuma were two perfectly capable jounins, but the level of their enemies was simply too high. If the boy were to become serious, there was no way he could protect any of them.

"Kakashi!"

"Don't let your guard down..." he snapped at Asuma. "He's someone who rose to ANBU squad commander by the time he was 13."

"I can't believe he's this good."

"No...actually, he's better. He hasn't even begun to show his true strength." For the first time, genuine anger seemed to flicker in those crimson eyes at the Copy Ninja's words.

"Very impressive, that you who are not even of Uchiha blood have mastered the Sharingan this much. However, our body not being genetically adapted is not a match for that eye." That was something Kakashi already knew; even this much was starting to strain him all while there was not a single hint of exhaustion on the younger man. "Do you know why the Uchiha clan has been lauded and feared as the most powerful?

"Let me show you...my clan's true strength!"

It was a slow blink, deliberate, and Kakashi could see the chakra being sent towards his eyes...it couldn't be...could it? Kakashi had only ever heard about it, but...

"You two, don't look him in the eye!" He closed his own regular eye. "Listen closely, both of you, don't open your eyes no matter what...if you meet eyes with him right now, you'll be finished. Only another Sharingan can handle him now!"

"If one possessed the Sharingan...one can resist this Mangekyo to some extent." Itachi remained still, uncaring about a thing. "But you cannot break this special Sharingan jutsu...Tsukuyomi...only someone with kekkei genkai and a Sharingan can stop me."

"Sasuke..."

His world turned black.

Limbs immobilized, tied to a cross, black and white filled his vision, and he could only see a hundred copies about Uchiha Itachi surrounding him. Katana in hand. Slowly, the blade pierced, tearing through his flesh, pain rushing through him as his voice rose on its own.

"In the Trukuyomi dreamscape, I completely control time, space, and even all substance." Again, the Uchiha's voice remained impassive. "For the next 72 hours...you will continually be pierced over and over again."

It lasted a second...it lasted an eternity...

Pain overwhelmed his senses, the feeling of his skin ripping apart, blood dripping from an ever-reopening wound. He couldn't breathe, not even scream. It wouldn't end, the pain, the hurt, his screams.

"What's wrong, Kakashi?!" Kurenai's voice finally registered.

"Keep your eyes shut!"

"What's going on?!" Asuma was clearly losing his patience. "One second that guy's talking, and the next second you hit the ground!"

One second...just one second, and even now, he could barely even breathe. Phantom pain made even keeping his balance above water was a struggle. His thoughts were jumbled, unfocused, and still...he was still breathing. Still standing. It would've been so easy to kill all of them once Kakashi was done for...so why?

"Hmph, after all that, the fool's spirit is still intact..." Kisame seemed genuinely surprised as he looked at his now heavily breathing partner. "Meanwhile, you've overused those eyes of yours...you know that's dangerous."

"This thing you seek..." He couldn't pass out, not yet. "Is it them?"

"...no..." Itachi's voice was still calm. "The legacy of Yondaime."

"Yondaime-sama's legacy...huh?" So, Jiraiya-sama had been right after all. It was a good thing Naruto was out of the village by now.

"Who are these guys?!" There was panic in Kurenai's question.

Was he supposed to be relieved? That it was only his sensei's son Itachi was after...or frustrated that it was only his whim that kept his other two kids alive...

Because it had become more than evident; that Kakashi's protection was just as useless as a monk's prayers.

"You're...not the only ones, are you?" He had to gain time, gain information. If only one of them made it out of this place. This had to be passed to whoever took over the village. "I know about you...you call yourselves the Akatsuki."

"Akatsuki?"

"Kisame!" Finally, Itachi was actually unsettled. "Change of plans, we're taking Kakashi. Make the other two disappear."

His body refused to move, his lungs struggled to take in air, and it was all he could do to follow Kisame's movements as he rushed to spell their damnation. There was no clever plan out of this one, it seemed...

Fuck...

If only he could get either of the people behind him out...if they could warn his children...

Familiar green appeared in front of him, kicking back the S-ranked criminal with an obnoxiously loud voice Kakashi felt relieved to hear for once...if Gai had called reinforcements...then at least part of this information would make it out.

The tension seemed to slide off his shoulders, the adrenaline he'd been relying on to keep standing slowly fading away, along with his strength. He could barely even feel the water rising as his chakra faltered, replacing the air that his lungs kept trying to obtain...it would be fine...his kids could still be protected.

A/N: So one thing that drives me absolutely crazy is the power scaling in canon, once Naruto Shippuden comes in a lot of the previous world building just gets ignored. It gets more than heavily implied that the new generations tended to be stronger than the previous ones (which makes sense, what with new jutsus being invented and the like) and to a degree we can see that happen up until the Pain arc, but once we get into the war arc all of that just kinda disappears. No one can really hold their own on one on one against the revived shinobis and the five Kages cannot last more than a minute against Madara. The Rasengan was supposed to be a Sannin level technique that only the Yondaime was able to learn but by that point in the story it's become sort of powerless needing Naruto make a dozen additions to it. Hell Madara ends up being so overpowered that at the ended it had to be basically Kaguya who stabs him in the back. And to beat her Sasuke and Naruto end up becoming reincarnations of what basically amounted to demigods.

All that is to say, to me the strongest human character would be Madara, followed by Pain and then we go down the list. Talking power level strictly (meaning ignoring whether or not any of them are capable of coming up with a winning strategy or them fighting together) then I would say Pain is still stronger than both Toga and Kimi, Kimi would be around around the Sannins but with the benefit of being younger and having more stamina and Toga in between those two levels. And yes, Itachi and Sesshoumaru would likely be around the same. That said this is just talking power levels strictly an actual fight could still go either way depending on the characters and circumstances. Like Shikamaru is definitely weaker than Inuyasha power level speaking but I think he could pull a win thanks to coming up with a good strategy and Inuyasha's character of not going full on at the start of a fight.

Also please feel free to ask any questions you may have since at times it actually helps me put things into perspective

As always thank you guys so much for reading and any and all review/comment/criticism is greatly appreciated.