Naruto: Wooing Tsunade from Day One!

Jiraiya walked out of the Hokage Building brimming with confidence. With determined strides, he made his way toward the Academy.

His first focus was on the students—they were young, adaptable, and ideal for training as reserve spies. These young talents would one day form the backbone of Konoha's Intelligence Division. However, for spies who could be deployed on missions in the near term, Jiraiya had other plans in mind.

Knowing the Academy's headmaster, Kawakaze, personally, he expected things to move more smoothly. He also understood that Tsunade's secret letter would only go so far. To someone like Kawakaze, it was little more than a formality. If Jiraiya needed assistance from Orochimaru or personnel from the Medical Department, he would have to make a personal appeal.

Before reaching the Academy, Jiraiya spotted a familiar figure approaching.

"Yo, Jiraiya. Where are you headed?" Kawakaze called out. Having just left the Academy, he had been planning to drop by the Hokage's Office to pass the time. Among Konoha's high-ranking officials, Kawakaze was undoubtedly the one with the most free time.

"You're still as free as ever," Jiraiya remarked knowingly. "Don't bother looking for Tsunade. Come with me to the Academy."

Jiraiya didn't need to guess where Kawakaze had been going.

"What's the point of going to the Academy?" Kawakaze asked, leaning closer to Jiraiya as they walked.

"It's like this..." Jiraiya began, explaining his plan to scout for potential recruits.

Kawakaze listened and then shook his head in disapproval. "Oh, you're really overthinking this! There won't be any good candidates at the Academy. You should head to the Anbu instead."

"There are still members of the old Root Division there," Kawakaze added, his eyes gleaming with interest. He was clearly eager to let Jiraiya stir up some trouble for Sakumo.