Tears cascaded down Tsunade's face as she watched her old teammate and long-time friend disappear into the distance. Although he sounded his usual obnoxious and confident self, when he gave her one last thumbs-up, it did not seem like a "See you later!" to her; she knew, in the depths of her heart, that the gesture was meant as a final goodbye that he could not bring himself to utter aloud. "The Tale of Jiraiya the Gallant" would be coming to a close, and she was aware that he wanted the last chapter to portray him for the hero he truly was.
The Hokage could feel her heart ripping to shreds as she replayed the scenario over and over again, and despite only a few minutes having passed since Jiraiya's departure, regret weighed heavily on her conscious. She had been much too prideful to tell him what a significant person he had always been in her life, and…she had not been able to tell him she loved him. A fire was about to be extinguished for the sake of the village, and although Tsunade knew it was wrong of her, she found herself questioning whether the choice to let him go was one she wanted to live with.
When Fukasaku, an elder toad from Mount Myoboku who taught Jiraiya the art of senjutsu, arrived at the Hokage office with an encrypted message carved into his back and news of the toad sage's passing, Tsunade was not surprised but crippling sadness still overwhelmed her. She had never been good at gambling, and the loss of yet another man she loved was proof enough of that.
Once the initial sadness over her friend's death finally began subsiding and taking a backseat to her duties as the leader of the Village Hidden in the Leaves, a new challenge arose: how was she to break the tragic news to Naruto? Jiraiya had become family to the young jinchuriki, fulfilling his role as a god father as Minato asked him to. The Hokage felt sobs threatening to escape her throat once again at the thought of having to break Naruto's heart.
Fukasaku offered to tell the young man of his master's death, seeing how much Tsunade was struggling just over the thought of it. She felt weak taking the toad up on his offer, but she recognized that were she to attempt facing the boy she had come to view as a grandson with such awful news, she would breakdown all over again.
Naruto's reaction was just as the Hokage imagined it would be; he blamed her for Jiraiya's death in an attempt to redirect his sadness at the loss of a loved one into anger at the easiest target. She could not deny that she sent the toad sage to his death, but telling the young jinchuriki that was all she could manage to do. His words echoed throughout her mind long after he barged out of her office, although she had already managed to beat herself up about her decision more than anyone else ever could; he said, "If Pervy Sage had been the Fifth Hokage, he wouldn't have let Granny Tsunade take a risk like that…Never."
Once everyone cleared her office following the sad spectacle, Tsunade broke down into tears once again. Naruto's pain was evident in his eyes, and she felt as though she lost two important men in her life within a short time of each other—one to death and the other to her shitty gambling. Although Jiraiya told her not to, she had bet on him returning home after confronting the enemy, and this fact led her to believe that she truly was partially responsible for his untimely demise.
The morning following the heartbreaking day, Iruka found his way to the Hokage's office. He told her that he believed Naruto had calmed down upon being reminded that his master would not have wanted him to hurt over his death but to honor his life by taking on his will. She thanked the academy teacher for his efforts before dismissing him. As she sat alone, she secretly hoped that the knucklehead ninja would burst through her doors demanding a mission; she needed his unwavering optimism more than ever.
Some time passed before the young jinchuriki made his way into Tsunade's office again. Upon seeing him, there we so many things she wanted to say, but none of them seemed right. She could plead for his forgiveness or tell him that as a shinobi, he needed to learn to deal with death, but either way, it would not change what she had done or how he felt about it.
The Hokage was shocked when Naruto apologized to her, explaining that he realized she made the choice to allow his master to go not just for herself but also because it was Jiraiya's wish; he told her that, in the end, the toad sage decided his own fate, and it was no one's right to tarnish his heroic deeds by crying over him. Before the knucklehead ninja departed her office once more, not awaiting a reply from her, he gave her a smile and a thumbs up, and she swore that, for a split second, she saw her old friend himself standing in front of her.
"The Tale of Jiraiya the Gallant" had come to a close and left his loved ones wishing that there were more chapters to come. Tsunade realized, however, that this could not be; he was gone, and that was the end of it. Yet, as she saw Naruto off just as she had done Jiraiya, she felt no more sadness. Although she had never been particularly good at gambling, she found herself making a bet that she knew she would not lose in: Naruto would inherit the toad sage's will of fire, and as he continued to do justice to his old master, a new story would fill the void left in her life—"The Tale of Naruto Uzumaki".