Old Man, Spill It!

Gen glanced pointedly at the pale Kakashi slumped on the bed, then met Jiraiya's gaze. "But Lord Jiraiya has more important duties. We can't impose. We'll just... pray we don't get ambushed again." He sighed dramatically. "And if we do? Well, it won't be your fault. Just our rotten luck..."

"..."

Jiraiya's eye twitched. Kid's got a tongue like poisoned kunai.

"Gen," Kakashi interjected weakly, sensing the tension, "I'll manage. Lord Jiraiya," he shifted focus, "tell us more about Orochimaru. I need specifics for my report."

"Right!" Gen fell silent, a subtle smirk playing at the corner of his lips as Jiraiya visibly relaxed.

"Not much beyond what I said," Jiraiya stroked his chin, brow furrowed. "This organization... a ghost. No name. No known members. But convincing Orochimaru to join? That screams power." He leaned forward. "My last solid lead placed him near Wave's main port. That's it."

"Elusive," Kakashi murmured.

"Wave Country again," Gen mused aloud, the timing deliberate. "Just like Itachi and Kisame. Funny, considering the Uchiha and Mist Swordsmen slaughtered each other in Whirlpool Country during the Third War..."

"Hmm?"

The implication hung heavy. Two bitter enemies, bound by blood feud and national loyalty... working side-by-side?

"It is strange they'd partner up," Gen pressed, feigning innocent curiosity. "A clan-slaying prodigy and a disgraced swordsman? Both proud. Both ruthless..." He let the observation sink in. "If they can cooperate... who else might be in this group?"

Gen's insinuation was a bomb.

Proud, antagonistic figures forced into cooperation… It painted a terrifying picture. Kakashi and Jiraiya exchanged grim looks. What kind of power could enforce such uneasy alliances?

"It... fits," Kakashi admitted, voice strained. "Their coordination earlier... too smooth for chance encounters. Combined with your intel, Lord Jiraiya..."

Jiraiya rubbed his temples, the weight of the revelation pressing down. "S-rank missing-nin... Itachi, Kisame, potentially Orochimaru... What in the Sage's name are they planning?"

"Nothing small," Gen stated the obvious. He saw Kakashi's [Exclusive Quest] flicker in his mind and seized the moment. "One more thing... Wave Country's proximity..."

"To the Land of Water," Kakashi finished, eyes sharpening.

"Exactly," Gen nodded. "Who hires an organization like that? Wave lacks the funds. Unless..." He paused, then dropped the name like a stone. "...it's someone like that Gato guy we almost liberated funds from..."

"Liberated?!" Jiraiya choked, whirling on Kakashi. "What the hell are you teaching this kid?!"

"Gen!" Kakashi groaned, pinching the bridge of his nose. That obsession again? "Forget Gato. His point stands – only entities like major villages or underworld kingpins could afford them."

"Which means..." Jiraiya's expression hardened with dawning realization, "...they're likely contracted by Kiri." His gaze turned distant, calculating risks.

"Lord Jiraiya," Gen cut in sharply, recognizing the dangerous resolve forming. "You're not thinking of going to Kiri alone?"

"Jiraiya-sama, don't!" Kakashi pushed himself up, urgency cutting through his fatigue. "If our suspicions are correct, Kiri is a trap! Isolated, surrounded by sea... escape routes are nonexistent!"

Gen nodded gravely, adding the final, morbid nail. "Sensei visits the Memorial Stone often enough already. We don't need another name added next year because someone charged blindly into the viper's nest."

"..." Jiraiya glared at Gen, the kid's bluntness stinging like salt in a wound. But the chilling logic was undeniable. The blood debt from past wars, a village shrouded in secrecy, plus a shadowy organization potentially harboring Sannin-level threats...

"Come back to Konoha with us, Lord Jiraiya," Gen pressed, his tone shifting to earnest concern under Kakashi's approving nod. "This is beyond solo reconnaissance. If Mist is involved, the village needs to know. They will mobilize resources."

"Gen's right," Kakashi added, his voice firm despite his weakness. "That organization's strength and composition demand a village-level response. Orochimaru and Itachi are Konoha's problems. The Hokage will act."

Jiraiya slumped, the fight draining out of him. Trapped between duty and his deep-seated aversion to Konoha's confines, the path forward was painfully clear.

"...Fine." The word came out in a long-suffering sigh. "Damn it all. Just when I thought I was out..." He ran a hand through his wild hair. "...they pull me back in. The price of freedom is steep, brat."

Relief washed over both Kakashi and Gen. Sending Jiraiya alone into the heart of potential enemy territory, surrounded by sea and possibly harboring multiple S-class killers? It was a suicide mission only the Shodai Hokage might have survived.

Mission accomplished!

Gen's goal was simple: get Jiraiya to witness the metaphorical "sakura blooming" back home. The elaborate manipulation of Kakashi and Jiraiya was necessary collateral.

Bonus points for stirring the pot for Obito. Kakashi's [Exclusive Quest] demanded opportunities.

If Jiraiya actually bumps into Obito in Kiri... Gen mused, curious about the timeline of Obito losing his grip on the Bloody Mist. Canon was vague, but signs pointed to Kisame's death and Itachi pairing with Kisame as turning points. Might just accelerate that quest...

As the thought formed, his system flashed:

[Side Quest: Jiraiya-san, The Sakuras Bloom in Your Homeland... – Complete!]

[Reward Acquired: Jiraiya's Sage Arts]

The old man finally coughed up the gold!

[New Main Quest: The Gathering Storm]

[Investigate the Akatsuki Organization]

Gen met Kakashi's weary but resolute gaze. A flicker of anticipation sparked beneath his calm exterior.

Phase one: Secure the Sage. Complete.

Phase two: Storm eyes... engage.